Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view.
|
|
- Elisabeth Gilmore
- 5 years ago
- Views:
Transcription
1 Supplementary Figure S1 X-ray crystallographic structure of (C)-(-)-6. (a) ORTEP drawing of (C)-(-)-6 at probability ellipsoids of 50%: tope view. (b) Side view. All hydrogen atoms are omitted for clarity. S1
2 Supplementary Figure S2 Bowl depths of (a) (C)-(-)-6 and (b) sumanene. The bowl depths were measured between the centroid of central benzene ring and that of focused atoms. S2
3 Supplementary Figure S3 Optimized bowl structure of compound (C)-(-)-1 by DFT calculation (B3LYP/6-311+G (d, p). (a) Side view. (b) Top view. Cartesian coordinates are listed in Supplementary Table S3. E (RB3LYP) = a.u.; Zero-point correction = a.u.; Sum of electronic and zero-point energy E bowl = a.u. S3
4 Supplementary Figure S4 Optimized flat structure of compound 1 corresponding to the transitional state of the bowl inversion with one imaginary frequency by DFT calculation (B3LYP/6-311+G (d, p). (a) Side view. (b) Top view. Cartesian coordinates are listed in Supplementary Table S4. E (RB3LYP) = a.u.; Zero-point correction = a.u.; Sum of electronic and zero-point energy E flat = a.u. The calculated bowl inversion energy ΔE = E flat E bowl = ( ) = 39.9 kcal/mol. S4
5 Supplementary Figure S5 CD and UV-Vis spectra of compound 6 in CH 2 Cl 2 ( M). S5
6 Supplementary Figure S6 (a) 1 H and (b) 13 C NMR spectra of compound 4. S6
7 Supplementary Figure S7 (a) 1 H and (b) 13 C NMR spectra of compound 7. S7
8 Supplementary Figure S8 (a) 1 H and (b) 13 C NMR spectra of compound 8. S8
9 Supplementary Figure S9 (a) 1 H and (b) 13 C NMR spectra of compound 5. S9
10 Supplementary Figure S10 (a) 1 H and (b) 13 C NMR spectra of compound (C)-(-)-1. S10
11 Supplementary Figure S11 (a) 1 H and (b) 13 C NMR spectra of compound (C)-(-)-6. S11
12 Supplementary Tables Supplementary Table S1 Screening of oxidative aromatization from compound 5 to (C)-(-)-1 by using different oxidants. a,b Determined by 1 H NMR using of mesitylene as an internal standard; c Microwave assisted reaction; d Isolated yield by PTLC. DDQ=2,3-dichloro-5,6-dicyano-1,4-benzoquinone. S12
13 Supplementary Table S2 Screening of oxidative aromatization from compound 5 to (C)-(-)-1 by using of trityl cationic reagents. Entry a Oxidant Base Yield/% b 1 Ph 3 CPF Ph 3 CB(C 6 F 5 ) 4 - < 5 3 Ph 3 COH-TFA c Ph 3 CBF Ph 3 CBF 4 i-pr 2 EtN < 5 6 Ph 3 CBF 4 Proton sponge d < 5 7 Ph 3 CBF 4 pyridine 0 8 Ph 3 CBF 4 2,6-lutidine 40 9 e Ph 3 CBF 4 DTBMP f g Ph 3 CBF 4 DTBMP 73 h a The reactions were carried out in anhydrous CH 2 Cl 2 at 25 C for 12 h by using of 900 mol% oxidant and 330 mol% base (if used). b NMR yield using mesitylene as an internal standard. c TFA = trifluoroacetic acid. d Proton sponge = N,N,N,N -tetramethyl-1,8- naphthalenediamine. e The reaction took 3 days for completion. f DTBMP = 2,6-di-tert- butyl-4-methylpyridine. g 600 mol% Ph 3 CBF 4 and 800 mol% DTBMP were used and the reaction was completed within 8 h. h Isolated yield. S13
14 Supplementary Table S3 Cartesian Coordinates of compound (C)-(-)-1 by DFT calculation (B3LYP/6-311+G (d, p)). Center Number Atom Type Coordinates (Angstroms) X Y Z 1 C C C C C C C N C C C N C C C N C C C C C H H H S14
15 25 H H H S S S C H H H C H H H C H H H S15
16 Supplementary Table S4 Cartesian Coordinates of flat 1 by DFT calculation (B3LYP/6-311+G (d, p)). Center Number Atom Type Coordinates (Angstroms) X Y Z 1 C C C C C C C N C C C N C C C N C C C C C H H H H S16
17 26 H H S S S C H H H C H H H C H H H S17
18 Supplementary Methods Nomenclature of chiral buckybowls Official stereodescriptor system for the absolute configuration of chiral buckybowls has not been established yet. In this paper, we use the stereodescriptor system based on fullerene nomenclature described as C or A Another system was proposed by L. T. Scott described as M or P 31. Bowl inversion kinetic equation where a is the initial concentration of (C)-(-)-1 assigned as 1, and x is the concentration of (A)-(+)-1 at time t. Synthesis and characterization of compound 4 to 5. (1aS,3aR,4aS,6aR,7aS,9aR)-2,5,8-tris(4-methoxybenzyl)-1a,2,3a,4,4a,5,6a,7,7a,8-decahydro -1H-2,5,8-triazatricyclopenta[def,jkl,pqr]triphenylene-3,6,9(9aH)-trione (4) S18
19 A mixture of 3 (1.36 g, 2.0 mmol) in AcOH (140 ml) and conc. HCl (50 ml) was heated to 60 o C for 4 h. After cooling, the mixture was evaporated to afford white solid, which was then dissolved in anhydrous DMF (100 ml). To the solution was added DIPEA (7 ml, 40.0 mmol) and the solution was cooled to 0 o C under Ar atmosphere. Then FDPP (6.9 g, 18.0 mmol) in DMF (25 ml) was added. After addition, the mixture was stirred at 0 o C, 10 o C, 20 o C and 30 o C for 1 h, respectively, and then heated to 60 o C for 2 h. Evaporation of DMF afforded a residue and 1 M NaOH solution (150 ml) was added. The mixture was extracted with CH 2 Cl 2 (3 100 ml) and the combined organic layer was washed with brine, dried over Na 2 SO 4, filtered, and evaporated. The crude product was purified by silica gel chromatography (5-10% MeOH/CH 2 Cl 2 ). The resulting tan solid was stirred with EtOAc (20 ml) for 10 min and filtered, washed with EtOAc (3 5 ml) and dried to give compound 4 as an off-white solid (0.80 g, 59%). [ ] : (c = 1.0, CHCl 3); mp: >250 o C (decomp.); IR (KBr): 2934, 1635, 1512, 1439, 1400, 1302, 1248, 1176, 1032, 817 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): 7.27 (d, J = 8.4 Hz, 6H), 6.87 (d, J = 8.4 Hz, 6H), 5.51 (d, J = 14.6 Hz, 3H), (m, 3H), (m, 3H), 3.80 (s, 9H), 3.70 (d, J = 14.6 Hz, 3H), (m, 3H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ): 170.1, 159.1, 141.0, 139.4, 129.8, 128.5, 114.1, 60.4, 55.2, 46.0, 43.9, 42.8; HRMS (EI) m/z Calcd for C 42 H 39 N 3 O 6 (M + ): ; Found: (1aS,3aR,4aS,6aR,7aS,9aR)-2,5,8-tris(4-methoxybenzyl)-1a,2,3a,4,4a,5,6a,7,7a,8-decahydro -1H-2,5,8-triazatricyclopenta[def,jkl,pqr]triphenylene-3,6,9(9aH)-trithione (7) S19
20 A solution of compound 4 (0.19 g, mmol) and Lawesson s reagent (0.564 g, mmol) in dichloroethane (10 ml) was loaded into a microwave instrument vial (10-20 ml). The vial was evacuated and flushed with argon and sealed. The mixture was irradiated with stirring at a fixed temperature of 160 o C for 40 min on a Biotage Initiator microwave apparatus. Upon completion of the reaction time, the vial was cooled with a stream of air and opened. The mixture was purified by silica gel column chromatography (0-5% EtOAc/CH 2 Cl 2 ) to afford compound 7 (0.187 g, 92%). [ ] : (c = 1.0, CHCl 3); mp: > 250 o C (decomp.); IR (KBr): 2937, 1612, 1510, 1412, 1251, 1175, 1035, 814 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): 7.41 (d, J = 8.6 Hz, 6H), 6.90 (d, J = 8.6 Hz, 6H), 6.83 (d, J = 14.6 Hz, 3H), (m, 3H), (m, 3H), 4.10 (d, J = 14.6 Hz, 3H), 3.81 (s, 9H), (m, 3H), (m, 3H); 13 C NMR (100 MHz, CDCl 3 ): 201.5, 159.8, 140.4, 138.5, 129.9, 127.1, 114.6, 62.4, 55.5, 52.5, 52.4, 47.8; HRMS (EI) m/z Calcd for C 42 H 39 N 3 O 3 S 3 (M + ): ; Found: (1aS,3aR,4aS,6aR,7aS,9aR)-1a,2,3a,4,4a,5,6a,7,7a,8-decahydro-1H-2,5,8-triazatricyclopent a[def,jkl,pqr]triphenylene-3,6,9(9ah)-trithione (8) A solution of compound 7 (310 g, mmol) in TFA (10 ml) was loaded in a microwave instrument vial (10-20 ml) and sealed. The solution was irradiated with stirring at a fixed temperature of 100 o C for 2 h on a microwave apparatus. On completion of the reaction time S20
21 the vial was cooled with a stream of air and opened. Some white precipitation was observed. After evaporation of TFA, to the resulting solid was added CH 2 Cl 2 and the mixture was stirred for 10 min. The white solid was collected by filtration and washing with CH 2 Cl 2 (3 5 ml) to afford pure compound 8 (138 mg, 88%). [ ] : (c = 0.2, DMSO); mp: > 260 o C (decomp.); IR (KBr): 3268, 2998, 2867, 1647, 1506, 1312, 1145, 1077, 802, 736, 707 cm -1 ; 1 H NMR (400 MHz, DMSO-d 6 ): 10.6 (br s, 3H), (m, 3H), (m, 3H), (m, 3H), (m, 3H); 13 C NMR (100 MHz, DMSO-d 6 ): 202.2, 140.8, 138.9, 58.7, 50.2, 45.5; HRMS (EI) m/z Calcd for C 18 H 15 N 3 S 3 (M + ): ; Found: (1aS,3aR,4aS,6aR,7aS,9aR)-3,6,9-tris(methylthio)-1a,3a,4,4a,6a,7,7a,9a-octahydro-1H-2,5,8 -triazatricyclopenta[def,jkl,pqr]triphenylene (5) To a suspension of compound 8 (260 mg, mmol) and K 2 CO 3 (974 mg, 7.06 mmol) in DMF (60 ml) was added MeI (1.34 ml, 21.5 mmol). The mixture was stirred for 4 h at ambient temperature. DMF was removed by evaporation (< 45 o C) and to the residue was partitioned H 2 O (10 ml) and CH 2 Cl 2 (30 ml). The aqueous layer was extracted twice with CH 2 Cl 2 (10 ml). The combined organic layer was washed with brine (20 ml), dried over Na 2 SO 4, filtered, and evaporated. The residue was purified by PTLC (7% EtOAc/CH 2 Cl 2 ) to give compound 5 as a white solid (228 mg, 79%). [ ] : (c = 1.0, CHCl 3); mp: > 260 o C (decomp.); IR (KBr): 2958, 2925, 2876, 1645, 1582, 1438, 1296, 1124, 1040, 1005, 938 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): 5.14 (ddd, J = 7.5, 7.5, 7.5 Hz, 3H), 3.78 (ddd, J = 8.0, 8.0, 8.0 Hz, 3H), 3.40 (ddd, J = , 8.0 Hz, 3H), 1.55 (ddd, J = 13.1, 8.4, 8.4 Hz, 3H); 13 C NMR (100 MHz, CDCl 3 ): 167.0, 142.8, 140.2, 65.0, 44.3, 43.8, 12.4; HRMS (EI) m/z Calcd for C 21 H 21 N 3 S 3 (M + ): ; Found: S21
A Sumanene-based Aryne, Sumanyne
A Sumanene-based Aryne, Sumanyne Niti Ngamsomprasert, Yumi Yakiyama, and Hidehiro Sakurai* Division of Applied Chemistry, Graduate School of Engineering, Osaka University, 2-1 Yamadaoka, Suita, Osaka 565-0871
More informationDomino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes
Domino reactions of 2-methyl chromones containing an electron withdrawing group with chromone-fused dienes Jian Gong, Fuchun Xie, Wenming Ren, Hong Chen and Youhong Hu* State Key Laboratory of Drug Research,
More informationThe First Asymmetric Total Syntheses and. Determination of Absolute Configurations of. Xestodecalactones B and C
Supporting Information The First Asymmetric Total Syntheses and Determination of Absolute Configurations of Xestodecalactones B and C Qiren Liang, Jiyong Zhang, Weiguo Quan, Yongquan Sun, Xuegong She*,,
More informationSupporting Information for
Page of 0 0 0 0 Submitted to The Journal of Organic Chemistry S Supporting Information for Syntheses and Spectral Properties of Functionalized, Water-soluble BODIPY Derivatives Lingling Li, Junyan Han,
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Rh 2 (Ac) 4 -Catalyzed 2,3-Migration of -rrocenecarboxyl -Diazocarbonyl
More informationFacile Multistep Synthesis of Isotruxene and Isotruxenone
Facile Multistep Synthesis of Isotruxene and Isotruxenone Jye-Shane Yang*, Hsin-Hau Huang, and Shih-Hsun Lin Department of Chemistry, National Taiwan University, Taipei, Taiwan 10617 jsyang@ntu.edu.tw
More informationSYNTHESIS OF A 3-THIOMANNOSIDE
Supporting Information SYNTHESIS OF A 3-THIOMANNOSIDE María B Comba, Alejandra G Suárez, Ariel M Sarotti, María I Mangione* and Rolando A Spanevello and Enrique D V Giordano Instituto de Química Rosario,
More informationSupporting Information. (1S,8aS)-octahydroindolizidin-1-ol.
SI-1 Supporting Information Non-Racemic Bicyclic Lactam Lactones Via Regio- and cis-diastereocontrolled C H insertion. Asymmetric Synthesis of (8S,8aS)-octahydroindolizidin-8-ol and (1S,8aS)-octahydroindolizidin-1-ol.
More informationSupporting Information
Supporting Information (Tetrahedron. Lett.) Cavitands with Inwardly and Outwardly Directed Functional Groups Mao Kanaura a, Kouhei Ito a, Michael P. Schramm b, Dariush Ajami c, and Tetsuo Iwasawa a * a
More informationSupporting Material. 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials
Supporting Material 2-Oxo-tetrahydro-1,8-naphthyridine-Based Protein Farnesyltransferase Inhibitors as Antimalarials Srinivas Olepu a, Praveen Kumar Suryadevara a, Kasey Rivas b, Christophe L. M. J. Verlinde
More informationElectronic Supplementary Information (ESI)
Electronic Supplementary Information (ESI) A thin-layered chromatography plate prepared from naphthalimide-based receptor immobilized SiO 2 nanoparticles as a portable chemosensor and adsorbent for Pb
More informationSupporting Text Synthesis of (2 S ,3 S )-2,3-bis(3-bromophenoxy)butane (3). Synthesis of (2 S ,3 S
Supporting Text Synthesis of (2S,3S)-2,3-bis(3-bromophenoxy)butane (3). Under N 2 atmosphere and at room temperature, a mixture of 3-bromophenol (0.746 g, 4.3 mmol) and Cs 2 C 3 (2.81 g, 8.6 mmol) in DMS
More informationSupporting Information. Cells. Mian Wang, Yanglei Yuan, Hongmei Wang* and Zhaohai Qin*
Electronic Supplementary Material (ESI) for Analyst. This journal is The Royal Society of Chemistry 2015 Supporting Information Fluorescent and Colorimetric Probe Containing Oxime-Ether for Pd 2+ in Pure
More informationSupporting Information
Supporting Information Total Synthesis of (±)-Grandilodine B Chunyu Wang, Zhonglei Wang, Xiaoni Xie, Xiaotong Yao, Guang Li, and Liansuo Zu* School of Pharmaceutical Sciences, Tsinghua University, Beijing,
More informationSynthesis of Glaucogenin D, a Structurally Unique. Disecopregnane Steroid with Potential Antiviral Activity
Supporting Information for Synthesis of Glaucogenin D, a Structurally Unique Disecopregnane Steroid with Potential Antiviral Activity Jinghan Gui,* Hailong Tian, and Weisheng Tian* Key Laboratory of Synthetic
More informationSupporting Information. BODIPY-based Ratiometric Fluorescent Probe for Sensitive and Selective Sensing of Cyanide Ion
Supporting Information BODIPY-based Ratiometric Fluorescent Probe for Sensitive and Selective Sensing of Cyanide Ion Jingtuo Zhang, a Shilei Zhu, a Loredana Valenzano, a Fen-Tair Luo, b and Haiying Liu*
More informationSupporting Information
Supporting Information Wiley-VCH 2008 69451 Weinheim, Germany Concise Stereoselective Synthesis of ( )-Podophyllotoxin by Intermolecular Fe III -catalyzed Friedel-Crafts Alkylation Daniel Stadler, Thorsten
More informationSupplementary Information (Manuscript C005066K)
Supplementary Information (Manuscript C005066K) 1) Experimental procedures and spectroscopic data for compounds 6-12, 16-19 and 21-29 described in the paper are given in the supporting information. 2)
More informationAn Efficient Total Synthesis and Absolute Configuration. Determination of Varitriol
An Efficient Total Synthesis and Absolute Configuration Determination of Varitriol Ryan T. Clemens and Michael P. Jennings * Department of Chemistry, University of Alabama, 500 Campus Dr. Tuscaloosa, AL
More informationReduction-free synthesis of stable acetylide cobalamins. Table of Contents. General information. Preparation of compound 1
Electronic Supporting Information Reduction-free synthesis of stable acetylide cobalamins Mikołaj Chromiński, a Agnieszka Lewalska a and Dorota Gryko* a Table of Contents General information Numbering
More informationSupplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol.
Tetrahedron Letters 1 Pergamon TETRAHEDRN LETTERS Supplementary Material for: Unexpected Decarbonylation during an Acid- Mediated Cyclization to Access the Carbocyclic Core of Zoanthenol. Jennifer L. Stockdill,
More informationSupplementary Information
Supplementary Information C aryl -C alkyl bond formation from Cu(ClO 4 ) 2 -mediated oxidative cross coupling reaction between arenes and alkyllithium reagents through structurally well-defined Ar-Cu(III)
More informationFormal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis
Formal Total Synthesis of Optically Active Ingenol via Ring-Closing Olefin Metathesis Kazushi Watanabe, Yuto Suzuki, Kenta Aoki, Akira Sakakura, Kiyotake Suenaga, and Hideo Kigoshi* Department of Chemistry,
More informationAn unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP)
This journal is The Royal Society of Chemistry 213 Supplementary Information for An unexpected highly selective mononuclear zinc complex for adenosine diphosphate (ADP) Lei Shi, Ping Hu, Yanliang Ren and
More informationIndium Triflate-Assisted Nucleophilic Aromatic Substitution Reactions of. Nitrosobezene-Derived Cycloadducts with Alcohols
Supporting Information Indium Triflate-Assisted ucleophilic Aromatic Substitution Reactions of itrosobezene-derived Cycloadducts with Alcohols Baiyuan Yang and Marvin J. Miller* Department of Chemistry
More informationBlock: Synthesis, Aggregation-Induced Emission, Two-Photon. Absorption, Light Refraction, and Explosive Detection
Electronic Supplementary Information (ESI) Luminogenic Materials Constructed from Tetraphenylethene Building Block: Synthesis, Aggregation-Induced Emission, Two-Photon Absorption, Light Refraction, and
More informationSupporting Information. Identification and synthesis of impurities formed during sertindole
Supporting Information Identification and synthesis of impurities formed during sertindole preparation I. V. Sunil Kumar* 1, G. S. R. Anjaneyulu 1 and V. Hima Bindu 2 for Address: 1 Research and Development
More informationSUPPORTING INFORMATION. A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore
SUPPORTING INFORMATION A Sensitive and Selective Ratiometric Near IR Fluorescent Probe for Zinc Ions Based on Distyryl-Bodipy Fluorophore Serdar Atilgan,, Tugba Ozdemir, and Engin U. Akkaya * Department
More informationSupporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2002
Supporting Information for Angew. Chem. Int. Ed. Z50016 Wiley-VCH 2002 69451 Weinheim, Germany Total Synthesis of (±)-Wortmannin Takashi Mizutani, Shinobu Honzawa, Shin-ya Tosaki, and Masakatsu Shibasaki*
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2012 Subcellular Localization and Activity of Gambogic Acid Gianni Guizzunti,* [b] Ayse Batova, [a] Oraphin Chantarasriwong,
More informationSilver-catalyzed decarboxylative acylfluorination of styrenes in aqueous media
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supporting Information Silver-catalyzed decarboxylative acylfluorination of styrenes in aqueous
More informationSupporting Information
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2017 Supporting Information Direct copper-catalyzed oxidative trifluoromethylthiolation
More informationCu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines. and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary
Cu-Catalyzed Synthesis of 3-Formyl imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines by Employing Ethyl Tertiary Amines as Carbon Sources Changqing Rao, Shaoyu Mai and Qiuling Song* Institute of Next
More informationSupporting Information. DBU-Mediated Metal-Free Oxidative Cyanation of α-amino. Carbonyl Compounds: Using Molecular Oxygen as the Oxidant
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information DBU-Mediated Metal-Free Oxidative Cyanation of α-amino
More information1G (bottom) with the phase-transition temperatures in C and associated enthalpy changes (in
Supplementary Figure 1. Optical properties of 1 in various solvents. UV/Vis (left axis) and fluorescence spectra (right axis, ex = 420 nm) of 1 in hexane (blue lines), toluene (green lines), THF (yellow
More informationElectronic Supplementary Material
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Material A Novel Functionalized Pillar[5]arene: Synthesis, Assembly
More informationSupporting Information
Intramolecular hydrogen-bonding activation in cysteines. New effective radical scavenging Luisa Haya, a Iñaki Osante, b Ana M. Mainar, a Carlos Cativiela, b Jose S. Urieta*,a a Group of Applied Thermodynamics
More informationSupplementary Materials
Supplementary Materials ORTHOGOALLY POSITIOED DIAMIO PYRROLE- AD IMIDAZOLE- COTAIIG POLYAMIDES: SYTHESIS OF 1-(3-SUBSTITUTED-PROPYL)-4- ITROPYRROLE-2-CARBOXYLIC ACID AD 1-(3-CHLOROPROPYL)-4- ITROIMIDAZOLE-2-CARBOXYLIC
More informationEfficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene
Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene Seyoung Choi and Sangho Koo* Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, 449-728, Korea. E-mail:
More informationSynthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene
Supporting Information for Synthesis and nucleophilic aromatic substitution of 3- fluoro-5-nitro-1-(pentafluorosulfanyl)benzene Javier Ajenjo 1, Martin Greenhall 2, Camillo Zarantonello 2 and Petr Beier
More informationSupporting Information. for. Angew. Chem. Int. Ed. Z Wiley-VCH 2003
Supporting Information for Angew. Chem. Int. Ed. Z53001 Wiley-VCH 2003 69451 Weinheim, Germany 1 Ordered Self-Assembly and Electronic Behavior of C 60 -Anthrylphenylacetylene Hybrid ** Seok Ho Kang 1,
More informationStructural Elucidation of Sumanene and Generation of its Benzylic Anions
Structural Elucidation of Sumanene and Generation of its Benzylic Anions idehiro Sakurai, Taro Daiko, iroyuki Sakane, Toru Amaya, and Toshikazu irao Department of Applied Chemistry, Graduate School of
More informationSupplementary Note 2. Synthesis of compounds. Synthesis of compound BI Supplementary Scheme 1: Synthesis of compound BI-7273
Supplementary ote 2 Synthesis of compounds Synthesis of compound I-7273 H HMe 2 *HCl aac, AcH 4 7 ah(ac) 3 ah, MeI CH 2 Pd 2 (dba) 3, KAc, X-Phos 1,4-dioxane 5 6 8 + Pd(dppf) *CH 2 a 2 C 3 DMF I-7273 (2)
More informationSynthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain
rganic Lett. (Supporting Information) 1 Synthetic Studies on Norissolide; Enantioselective Synthesis of the Norrisane Side Chain Charles Kim, Richard Hoang and Emmanuel A. Theodorakis* Department of Chemistry
More informationMaksim A. Kolosov*, Olesia G. Kulyk, Elena G. Shvets, Valeriy D. Orlov
1 Synthesis of 5-cinnamoyl-3,4-dihydropyrimidine-2(1H)-ones Supplementary Information Maksim A. Kolosov*, lesia G. Kulyk, Elena G. Shvets, Valeriy D. rlov Department of organic chemistry, V.N.Karazin Kharkiv
More informationSupporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A
Fuerst et al. Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers: Approaches to Diazonamide A S1 Supporting Information for Synthesis of C(3) Benzofuran Derived Bis-Aryl Quaternary Centers:
More informationhydroxyanthraquinones related to proisocrinins
Supporting Information for Regiodefined synthesis of brominated hydroxyanthraquinones related to proisocrinins Joyeeta Roy, Tanushree Mal, Supriti Jana and Dipakranjan Mal* Address: Department of Chemistry,
More informationLight-Controlled Switching of a Non- Photoresponsive Molecular Shuttle
Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South
More informationSupporting Information. Application of the Curtius rearrangement to the synthesis of 1'- aminoferrocene-1-carboxylic acid derivatives
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018 Supporting Information Application
More informationAppendix A. Supplementary Information. Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Appendix A Supplementary Information Design, synthesis and photophysical properties of 8-hydroxyquinoline-functionalized
More informationSUPPORTING INFORMATION
SUPPRTING INFRMATIN A Direct, ne-step Synthesis of Condensed Heterocycles: A Palladium-Catalyzed Coupling Approach Farnaz Jafarpour and Mark Lautens* Davenport Chemical Research Laboratories, Chemistry
More informationCompound Number. Synthetic Procedure
Compound Number 1 2 3 4 5 Synthetic Procedure Compound 1, KY1220, (Z)-5-((1-(4-nitrophenyl)-1H-pyrrol-2-yl)methylene)-2-thioxoimidazolidin-4-one was purchased from Chemdiv, Catalog #3229-2677, 97% HPLC
More informationSupporting Information for. An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization
Supporting Information for An Approach to Tetraphenylenes via Pd-Catalyzed C H Functionalization Hang Jiang, Yu Zhang, Dushen Chen, Bo Zhou, and Yanghui Zhang * Department of Chemistry, and Shanghai Key
More informationdichloropyrimidine (1.5 g, 10.1 mmol) in THF (10 ml) added at -116 C under nitrogen atmosphere.
Supporting Information Experimental The presence of atropisomerism arising from diastereoisomerism is indicated in the 13 C spectra of the relevant compounds with the second isomer being indicated with
More informationSynthesis and Use of QCy7-derived Modular Probes for Detection and. Imaging of Biologically Relevant Analytes. Supplementary Methods
Synthesis and Use of QCy7-derived Modular Probes for Detection and Imaging of Biologically Relevant Analytes Supplementary Methods Orit Redy a, Einat Kisin-Finfer a, Shiran Ferber b Ronit Satchi-Fainaro
More informationFacile Synthesis of Flavonoid 7-O-Glycosides
Facile Synthesis of Flavonoid 7-O-Glycosides Ming Li, a Xiuwen Han, a Biao Yu b * a State Key Laboratory of Catalyst, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
More informationSynthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition
Synthesis of fluorophosphonylated acyclic nucleotide analogues via Copper (I)- catalyzed Huisgen 1-3 dipolar cycloaddition Sonia Amel Diab, Antje Hienzch, Cyril Lebargy, Stéphante Guillarme, Emmanuel fund
More informationSupporting Information
Supporting Information Silver-Mediated Oxidative Trifluoromethylation of Alcohols to Alkyl Trifluoromethyl Ethers Jian-Bo Liu, Xiu-Hua Xu, and Feng-Ling Qing Table of Contents 1. General Information --------------------------------------------------------------------------2
More informationRed Color CPL Emission of Chiral 1,2-DACH-based Polymers via. Chiral Transfer of the Conjugated Chain Backbone Structure
Electronic Supplementary Material (ESI) for Polymer Chemistry. This journal is The Royal Society of Chemistry 2015 Red Color CPL Emission of Chiral 1,2-DACH-based Polymers via Chiral Transfer of the Conjugated
More informationSupporting Information
Supporting Information Tuning Supramolecular Structure and Functions of Peptide bola-amphiphile by Solvent Evaporation-Dissolution Anhe Wang,, Lingyun Cui,, Sisir Debnath, Qianqian Dong, Xuehai Yan, Xi
More informationSupporting information. An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling
Supporting information An improved photo-induced fluorogenic alkene-tetrazole reaction for protein labeling X. Shang, 1 R. Lai, 1,3 X. Song, 1 H. Li, 1,3 W. Niu, 2 and J. Guo 1 * 1. Department of Chemistry,
More informationSupporting Information
Supporting Information In Situ Ratiometric Quantitative Tracing Intracellular Leucine Aminopeptidase Activity via an Activatable Near- Infrared Fluorescent Probe Kaizhi Gu, Yajing Liu, Zhiqian Guo,*,,#
More informationHow to build and race a fast nanocar Synthesis Information
How to build and race a fast nanocar Synthesis Information Grant Simpson, Victor Garcia-Lopez, Phillip Petemeier, Leonhard Grill*, and James M. Tour*, Department of Physical Chemistry, University of Graz,
More informationSupporting Information
Supporting Information Syntheses and characterizations: Compound 1 was synthesized according to Scheme S-1. Scheme S-1 2 N N 5 i N 4 P Et Et iii N 6 ii P Et Et iv v, vi N N i) Fmoc-Su, DIPEA, Acetone;
More informationSUPPLEMENTARY INFORMATION
Supplementary Method Synthesis of 2-alkyl-MPT(R) General information (R) enantiomer of 2-alkyl (18:1) MPT (hereafter designated as 2-alkyl- MPT(R)), was synthesized as previously described 1, with some
More informationA Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones. Jin-Quan Yu, a and E. J.
A Mild, Catalytic and Highly Selective Method for the Oxidation of α,β- Enones to 1,4-Enediones Jin-Quan Yu, a and E. J. Corey b * a Department of Chemistry, Cambridge University, Cambridge CB2 1EW, United
More informationSupporting Information for
Electronic Supplementary Material (ES) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016 Supporting nformation for BODPY-Containing
More informationSynthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed. Cascade Trifluoromethylation/Cyclization of. 2-(3-Arylpropioloyl)benzaldehydes
Supporting Information to Synthesis of Trifluoromethylated Naphthoquinones via Copper-Catalyzed Cascade Trifluoromethylation/Cyclization of 2-(3-Arylpropioloyl)benzaldehydes Yan Zhang*, Dongmei Guo, Shangyi
More informationChiral Sila[1]ferrocenophanes
Supporting Information Thermal Ring-Opening Polymerization of Planar- Chiral Sila[1]ferrocenophanes Elaheh Khozeimeh Sarbisheh, Jose Esteban Flores, Brady Anderson, Jianfeng Zhu, # and Jens Müller*, Department
More informationBranching of poly(adp-ribose): Synthesis of the Core Motif
Branching of poly(adp-ribose): Synthesis of the Core Motif Hans A. V. Kistemaker, Herman S. Overkleeft, Gijsbert A. van der Marel,* and Dmitri V. Filippov* Supporting information Table of contents Experimental
More informationwith EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15
2. A solution of Rhodamine B (14.2 g, 30.0 mmol) in CH 2 Cl 2 (40 ml) was treated with EDCI (5.73 g, 30.0 mmol) for 10 min. Bromoethylamine hydrobromide (6.15 g, 30.0 mmol) and TEA (4.21 ml, 3.03 g, 30.0
More informationHighly stereocontrolled synthesis of trans-enediynes via
Supporting Information for Highly stereocontrolled synthesis of trans-enediynes via carbocupration of fluoroalkylated diynes Tsutomu Konno*, Misato Kishi, and Takashi Ishihara Address: Department of Chemistry
More informationPhotooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins
S1 Photooxidations of 2-(γ,ε-dihydroxyalkyl) furans in Water: Synthesis of DE-Bicycles of the Pectenotoxins Antonia Kouridaki, Tamsyn Montagnon, Maria Tofi and Georgios Vassilikogiannakis* Department of
More informationAll solvents and reagents were used as obtained. 1H NMR spectra were recorded with a Varian
SUPPLEMETARY OTE Chemistry All solvents and reagents were used as obtained. 1H MR spectra were recorded with a Varian Inova 600 MR spectrometer and referenced to dimethylsulfoxide. Chemical shifts are
More informationPost-Synthetic Approach for the Synthesis of 2 -O-Methyldithiomethyl-Modified Oligonucleotides Responsive to Reducing Environment
Supplementary Information Post-Synthetic Approach for the Synthesis of 2 -O-Methyldithiomethyl-Modified Oligonucleotides Responsive to Reducing Environment Yosuke Ochi, Osamu Nakagawa, Katsunori Sakaguchi,
More informationEffect of Conjugation and Aromaticity of 3,6 Di-substituted Carbazole On Triplet Energy
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) for Effect of Conjugation and Aromaticity of 3,6 Di-substituted
More informationSupporting Information for
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017 Supporting Information for
More informationHalogen halogen interactions in diiodo-xylenes
Electronic Supplementary Material (ESI) for CrystEngComm. This journal is The Royal Society of Chemistry 2016 Electronic Supplementary Information (ESI) for CrystEngComm. This journal is The Royal Society
More informationOscillating Emission of [2]Rotaxane Driven by Chemical Fuel
Oscillating Emission of [2]Rotaxane Driven by Chemical Fuel Amit Ghosh, a Indrajit Paul, a Matthias Adlung, b Claudia Wickleder, b Michael Schmittel*,a a Center of Micro- and Nanochemistry and Engineering,
More informationSupporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline
Supporting information for A simple copper-catalyzed two-step one-pot synthesis of indolo[1,2-a]quinazoline Chunpu Li 1,2, Lei Zhang 2, Shuangjie Shu 2 and Hong Liu* 1,2 Address: 1 Department of Medicinal
More informationStraightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol
S1 Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2010 Straightforward Synthesis of Enantiopure (R)- and (S)-trifluoroalaninol Julien
More informationSupporting Information
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2013 Tuning the Lewis Acidity of Boranes in rustrated Lewis Pair Chemistry: Implications for the Hydrogenation of Electron-Poor
More informationTetrahydrofuran (THF) was distilled from benzophenone ketyl radical under an argon
SUPPLEMENTARY METHODS Solvents, reagents and synthetic procedures All reactions were carried out under an argon atmosphere unless otherwise specified. Tetrahydrofuran (THF) was distilled from benzophenone
More informationTriazabicyclodecene: an Effective Isotope. Exchange Catalyst in CDCl 3
Triazabicyclodecene: an Effective Isotope Exchange Catalyst in CDCl 3 Supporting Information Cyrille Sabot, Kanduluru Ananda Kumar, Cyril Antheaume, Charles Mioskowski*, Laboratoire de Synthèse Bio-rganique,
More informationSupporting Information
Supporting Information SmI 2 -Mediated Carbon-Carbon Bond Fragmentation in α-aminomethyl Malonates Qiongfeng Xu,, Bin Cheng, $, Xinshan Ye,*, and Hongbin Zhai*,,,$ The State Key Laboratory of Natural and
More informationSupplementary Table 1. Small molecule screening data
Supplementary Table 1. Small molecule screening data Category Parameter Description Assay Type of assay Cell-based Target Primary measurement Key reagents Assay protocol PS1/BACE1 interaction Detection
More informationSupporting information
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 205 A simple and greener approach
More informationSupporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Supporting Information TEMPO-catalyzed Synthesis of 5-Substituted Isoxazoles from Propargylic
More informationSignificant improvement of dye-sensitized solar cell. performance by a slim phenothiazine based dyes
Significant improvement of dye-sensitized solar cell performance by a slim phenothiazine based dyes Yong Hua, a Shuai Chang, b Dandan Huang, c Xuan Zhou, a Xunjin Zhu, *a,d Jianzhang Zhao, c Tao Chen,
More informationSupporting Information. for. Advances in the synthesis of functionalised. pyrrolotetrathiafulvalenes
Supporting Information for Advances in the synthesis of functionalised pyrrolotetrathiafulvalenes Luke J. O Driscoll, Sissel S. Andersen, Marta V. Solano, Dan Bendixen, Morten Jensen, Troels Duedal, Jess
More informationStabilisation of small mono- and bimetallic gold-silver nanoparticles by calix[8]arene derivatives
Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 208 Supplementary Information Stabilisation
More informationSupplementary Table S1: Response evaluation of FDA- approved drugs
SUPPLEMENTARY DATA, FIGURES AND TABLE BIOLOGICAL DATA Spheroids MARY-X size distribution, morphology and drug screening data Supplementary Figure S1: Spheroids MARY-X size distribution. Spheroid size was
More informationChia-Shing Wu, Huai-An Lu, Chiao-Pei Chen, Tzung-Fang Guo and Yun Chen*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Supporting Information Water/alcohol soluble electron injection material containing azacrown ether groups: Synthesis, characterization
More informationMolecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe
Supporting Information for Molecular Imaging of Labile Iron(II) Pools in Living Cells with a Turn-on Fluorescent Probe Ho Yu Au-Yeung, Jefferson Chan, Teera Chantarojsiri and Christopher J. Chang* Departments
More informationSupporting Information for:
Supporting Information for: Photoenolization of 2-(2-Methyl Benzoyl) Benzoic Acid, Methyl Ester: The Effect of The Lifetime of the E Photoenol on the Photochemistry Armands Konosonoks, P. John Wright,
More informationSupplementary Material. Ionic liquid iodinating reagent for mild and efficient iodination of. aromatic and heteroaromatic amines and terminal alkynes
Supplementary Material onic liquid iodinating reagent for mild and efficient iodination of aromatic and heteroaromatic amines and terminal alkynes Mahboobe Nouzarian 1, Rahman Hosseinzadeh 1,*, and Hamid
More informationSupporting Information for Sonogashira Hagihara reactions of halogenated glycals. Experimental procedures, analytical data and NMR spectra
Supporting Information for Sonogashira Hagihara reactions of halogenated glycals Dennis C. Koester and Daniel B. Werz* Address: Institut für Organische und Biomolekulare Chemie, Georg-August-Universität
More informationElectronic Supplementary Information for. Biomimetic aerobic oxidative hydroxylation of arylboronic acids to phenols catalysed by a flavin derivative
Electronic Supplementary Material (ESI) for Organic. This journal is The Royal Society of Chemistry 2014 Electronic Supplementary Information for Biomimetic aerobic oxidative hydroxylation of arylboronic
More informationSupporting Information
Supporting Information Synthesis of 2-Benzazepines from Benzylamines and MBH Adducts Under Rhodium(III) Catalysis via C(sp 2 ) H Functionalization Ashok Kumar Pandey, a Sang Hoon Han, a Neeraj Kumar Mishra,
More informationSupporting Information
Supporting Information Organocatalytic Enantioselective Formal Synthesis of Bromopyrrole Alkaloids via Aza-Michael Addition Su-Jeong Lee, Seok-Ho Youn and Chang-Woo Cho* Department of Chemistry, Kyungpook
More information