ANNEXE 1 : SPECTRES DE RÉSONANCE MAGNÉTIQUE NUCLÉAIRE DES PROTONS ET DES CARBONES-13
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1 AEXE 1 : SPECTRES DE RÉSACE MAGÉTIQUE UCLÉAIRE DES PRTS ET DES CARBES
2 3,4-Bis(méthoxycarbonyl)-2-méthyl-5-(pent-4 -ényl)-1-phényl-1h-pyrrole (82). Ph 2 C C 2 123
3 Acide 2-(-benzoyl--méthylamino)oct-7-énoïque (87a). Ph H 124
4 Acide (87b). (Z)-2-(-acétyl--méthylamino)-7-(,-diéthylcarbamoyl)hept-6-énoïque H Et 2 125
5 Acide 2-(-benzoyl--phénylamino)hept-6-énoïque (87c). H 126
6 Zwittérion (rac-89a). Ph H 127
7 Zwittérion (rac-89b). H CEt 2 128
8 2-(-t-Butoxycarbonyl--méthylamino)acétate d éthyle (91). Et 129
9 6-hydroxy-,-diéthylhex-2-énamide H Et 2 130
10 6-iodohex-1-ène (92). I 131
11 (Z)-6-Iodo-,-diéthylhex-2-énamide (93). Et 2 I 132
12 2-(-t-Butoxycarbonyl--méthylamino)oct-7-énoate d éthyle (94). Et 133
13 (Z)-2-(-t-Butoxycarbonyl--méthylamino)-7-(,-diéthylcarbamoyl)hept-6-énoate d éthyle (95). t-bu Et Et 2 134
14 2-(-Benzoyl--méthyl)aminooct-7-énoate d éthyle (96). Ph Et 135
15 (Z)-2-(-Acétyl--méthyl)amino-7-(,-diéthylcarbamoyl)hept-6-énoate (97). d éthyle Et Et 2 136
16 5-iodopent-1-ène (101). I 137
17 Acide 6-t-butyldiméthylsilanyloxyhex-2-ynoïque H TBDMS 138
18 6-t-Butyldiméthylsilanyloxy-,-diéthylhex-2-ynamide (104). Et 2 TBDMS 139
19 (Z)-6-t-Butyldiméthylsilanyloxy-,-diéthylhex-2-énamide (105). Et 2 TBDMS 140
20 (-Benzoyl--phénylamino)acétate d éthyle (108). 141
21 2-(-Benzoyl--phénylamino)hept-6-énoate d éthyle (109). 142
22 3,4-Bis(méthoxycarbonyl)-1,5-diphényl-2-(pent-4 -ényl)-1h-pyrrole (112). Ph Ph 2 C C 2 143
23 2-phényl-2-[-phényl--(hex-5 -énoyl)amino]acétate de méthyle Ph 144
24 Acide 2-phényl-2-[-phényl--(hex-5 -énoyl)amino]acétique (113). Ph H 145
25 rac-(1-méthyl-2-phénylhexahydrocyclopenta[b]pyrrol-6a-yl)méthanol (rac-117). H Ph H 146
26 rac-(1-méthyl-2-phényloctahydroindol-7a-yl)méthanol (rac-118). H Ph H 147
27 1-Méthyl-2-phényl-1,4,5,6-tétrahydrocyclopenta[b]pyrrole (123). Ph 148
28 Acide 2-[-(4-méthoxyphényl)--(hex-5 -énoyl)amino]propanoïque (130). H 149
29 -(4 -Méthoxyphényl)hex-5-énamide (133). H 150
30 3,4-Bis(méthoxycarbonyl)-2-méthyl-5-(pent-4 -ényl)-1-(4 -méthoxyphényl)-1hpyrrole (137). 2 C C 2 151
31 -Phénylhex-5-énamide (138). H 152
32 -Méthylaminophénylacétate de méthyle (145). Ph H 153
33 2-[-Méthyl--(hex-5 -énoyl)amino]phénylacetate de méthyle (146). Ph 154
34 Acide 2-[-méthyl--(hex-5 -énoyl)amino]phénylacétique (147). Ph H 155
35 3,4-Bis(méthoxycarbonyl)-2-phényl-5-(pent-4 -ényl)-1-méthyl-1h-pyrrole (151). Ph 2 C C 2 156
36 (Z/E)-2-[-(6 -chlorohex-5 -énoyl)--phénylamino]propanoate de méthyle Cl 157
37 Acide 2-[-(6 -chlorohex-5 -énoyl)--phénylamino]propanoïque (152). Cl H 158
38 2-[-(6 -diéthylcarbamoylhex-5 -énoyl)--phénylamino]propanoate de méthyle 159
39 Acide (154). (Z)-2-[-(6 -diéthylcarbamoylhex-5 -énoyl)--phénylamino]propanoïque H 160
40 (E)-2-[-(6 -itrohex-5 -énoyl)-phénylamino]propanoate de méthyle (155)
41 Acide 2-{-[5 -(2,2 -diméthyl-4,6 -dioxo-[1,3]dioxan-5 -ylidène)pentanoyl]-phénylamino}propanoïque (157). de suivi de réaction. H 162
42 Acide 5-benzyloxypentanoïque Bn H 163
43 5-Benzyloxy--phénylpentanamide (159). Bn H 164
44 2-[-(5 -benzyloxypentanoyl)--phénylamino]propanoate de méthyle Bn 165
45 2-[-(5 -hydroxy)pentanoyl--phénylamino]propanoate de méthyle (177). H 166
46 2-[-(5 -xo)pentanoyl--phénylamino]propanoate de méthyle (160). 167
47 2-(5 -Chloropent-4 -ényl)-3,4-di(méthoxycarbonyl)-5-méthyl-1-phényl-1hpyrrole (163). Ph 2 C C 2 Cl 168
48 2-{-[6 -(-Méthoxy--méthylcarbamoyl)hex-5 -énoyl]-phénylamino}propanoate de méthyle (164). 169
49 t-butylhex-5-ynyloxydiméthylsilane TBDMS 170
50 Acide 7-t-butyldiméthylsilanyloxyhept-2-ynoïque (167). H TBDMS 171
51 7-t-butyldiméthylsilanyloxy-,-diéthylhept-2-ynamide TBDMS 172
52 Acide 6-(,-diéthylcarbamoyl)hex-5-ynoïque (168). H 173
53 2-[-(6 -Diéthylcarbamoylhex-5 -ynoyl)--phénylamino]propanoate de méthyle (172). 174
54 ,-Diéthyl-2-méthyl-1-phényl-1,4,5,6-tétrahydrocyclopenta[b]pyrrole-3-carbamide (175). Ph Et 2 C 175
55 Acide 2-[-(5 -hydroxypentanoyl)--phénylamino]propanoïque (178). H H 176
56 Acide 2-[-(5 -oxopentanoyl)--phénylamino]propanoïque (179). H 177
57 Z/E 2-[-(6 -méthoxyhex-5 -énoyl)--phénylamino]propanoate de méthyle 178
58 Acide 2-[-(6 -méthoxyhex-5 -énoyl)--phénylamino]propanoïque (190). H 179
59 2-(5 -Méthoxypent-4 -ényl)-3,4-bis(méthoxycarbonyl)-5-méthyl-1-phényl-1hpyrrole (193). Ph 2 C C 2 180
60 2-[-(Hex-5-ynoyl)-phénylamino]propanoate de méthyle (196). 181
61 Acide 2-]-(Hex-5 -ynoyl)-phénylamino]propanoïque (197). H 182
62 Acide 2-[-(6 -Diéthylcarbamoylhex-5 -ynoyl)--phénylamino]propanoïque (207). H 183
63 2-[-(6-diéthylcarbamoyl-5-méthylhex-5-énoyl)--phénylamino]propanoate méthyle de Et 2 C 184
64 Acide 2-[-(6-diéthylcarbamoyl-5-méthylhex-5-énoyl)--phénylamino]propanoïque (210). Et 2 C H 185
65 AEXE 2 : CRDÉES DE DIFFRACTI DES RAYS-X DU CMPSÉ
66 Experimental : The crystals were grown by slow evaporation of a CH 2 Cl 2 :2-Propanol (25:75) solution at room temperature. ne single crystal of 0.20 X 0.30 X 0.50 mm 3 was mounted using a glass fiber on the goniometer at 198(2) K. Data were collected on an Enraf-onius CAD-4 automatic diffractometer at the Université de Sherbrooke using ω scans. The DIFRAC (1) program was used for centering, indexing, and data collection. ne standard reflection was measured every 100 reflections, no intensity decay was observed during data collection. The data were reduced with RCVAX (2), solved using SHELXS-97 (3) and refined by full-matrix least squares on F 2 with SHELXL-97 (4). The non-hydrogen atoms were refined anisotropically, except for C16 on the disordered hydroxyl group. The hydrogen atoms were placed at idealized calculated geometric position and refined isotropically using a riding model. The hydroxyl group was disordered on two geometric sites, a fractional population analysis was use to refine. nly the major component with 52% occupation is shown for clarity. (1) H.D. Flack, E. Blanc and D. Schwarzenbach (1992), J. Appl. Cryst., 25, (2) E.J. Gabe, Y. Le Page, J.-P. Charland, F.L. Lee, and P.S. White, (1989) J. Appl. Cryst., 22, (3) G. M. Sheldrick, SHELXS-97, G.M. Sheldrick, University of Göttingen, Germany, 1997, Release (4) G. M. Sheldrick, SHELXL-97, G.M. Sheldrick, University of Göttingen, Germany, 1997, Release
67 Table 1. Crystal data and structure refinement for 118. Identification code ma3045 Empirical formula C16 H23 Formula weight Temperature 198(2) K Wavelength Å Crystal system Tetragonal Space group p42/n Unit cell dimensions a = (10) Å α= 90. b = (10) Å β= 90. c = 7.090(2) Å γ = 90. Volume (8) Å 3 Z 8 Density (calculated) Mg/m 3 Absorption coefficient mm -1 F(000) 1072 Crystal size 0.5 x 0.3 x 0.2 mm 3 Theta range for data collection 3.12 to Index ranges 0<=h<=24, 0<=k<=24, 0<=l<=8 Reflections collected 2346 Independent reflections 2346 [R(int) = ] Completeness to theta = % Absorption correction Empirical Max. and min. transmission and Refinement method Full-matrix least-squares on F 2 Data / restraints / parameters 2346 / 0 / 176 Goodness-of-fit on F Final R indices [I>2sigma(I)] R1 = , wr2 = R indices (all data) R1 = , wr2 = Extinction coefficient (4) Largest diff. peak and hole and e.å
68 Table 2. Atomic coordinates ( x 10 4 ) and equivalent isotropic displacement parameters (Å 2 x 10 3 ) for 118. U(eq) is defined as one third of the trace of the orthogonalized U ij tensor. x y z U(eq) C(1) -572(2)6637(2) 5795(6) 59(1) C(2) -951(3)6326(2) 7188(6) 68(1) C(3) -1647(3)6266(3) 7003(7) 76(2) C(4) -1962(3)6483(3) 5380(8) 77(2) C(5) -1589(3)6786(3) 3987(8) 84(2) C(6) -900(2)6855(2) 4187(7) 68(1) C(7) 177(2)6728(2) 5960(6) 61(1) C(8) 608(2)6251(2) 4704(6) 65(1) C(9) 1056(2)5860(2) 6123(5) 61(1) C(10) 1141(2)6369(2) 7766(5) 55(1) C(11) 747(2)5195(3) 6716(6) 70(1) C(12) 1060(3)4896(2) 8472(7) 80(2) C(13) 1011(3)5393(2) 10094(6) 70(1) C(14) 1364(3)6045(2) 9596(6) 65(1) C(15) 313(3)7196(3) 9129(6) 81(2) (1) 448(2)6626(2) 7896(4) 57(1) C(16) 1673(6)6996(6) 7274(19) 57(2) (1) 2328(3)6702(3) 7123(7) 67(2) C(16') 1604(7)6846(6) 7126(19) 57(2) (1') 1756(4)7399(4) 8432(8) 85(3) 189
69 Table 3. Bond lengths [Å] and angles [ ] for 118. C(1)-C(6) 1.387(6) C(1)-C(2) 1.393(6) C(1)-C(7) 1.517(6) C(2)-C(3) 1.407(7) C(3)-C(4) 1.383(7) C(4)-C(5) 1.380(7) C(5)-C(6) 1.396(6) C(7)-(1) 1.490(5) C(7)-C(8) 1.567(6) C(8)-C(9) 1.560(6) C(9)-C(11) 1.529(7) C(9)-C(10) 1.558(6) C(10)-C(16') 1.409(13) C(10)-(1) 1.485(5) C(10)-C(14) 1.518(6) C(10)-C(16) 1.685(12) C(11)-C(12) 1.517(6) C(12)-C(13) 1.524(6) C(13)-C(14) 1.529(6) C(15)-(1) 1.465(5) C(16)-(1) 1.444(13) C(16')-(1') 1.476(14) C(6)-C(1)-C(2) 117.7(4) C(6)-C(1)-C(7) 119.7(4) C(2)-C(1)-C(7) 122.6(4) C(1)-C(2)-C(3) 120.9(5) C(4)-C(3)-C(2) 120.3(5) C(5)-C(4)-C(3) 119.1(5) C(4)-C(5)-C(6) 120.5(5) C(1)-C(6)-C(5) 121.4(5) (1)-C(7)-C(1) 114.5(4) (1)-C(7)-C(8) 103.8(3) C(1)-C(7)-C(8) 115.4(4) C(9)-C(8)-C(7) 104.9(3) 190
70 C(11)-C(9)-C(10) 114.2(3) C(11)-C(9)-C(8) 112.5(4) C(10)-C(9)-C(8) 102.5(4) C(16')-C(10)-(1) 113.6(6) C(16')-C(10)-C(14) 111.8(7) (1)-C(10)-C(14) 111.8(3) C(16')-C(10)-C(9) 106.0(6) (1)-C(10)-C(9) 99.8(3) C(14)-C(10)-C(9) 113.0(4) C(16')-C(10)-C(16) 7.8(9) (1)-C(10)-C(16) 110.2(5) C(14)-C(10)-C(16) 108.0(5) C(9)-C(10)-C(16) 113.8(5) C(12)-C(11)-C(9) 113.7(4) C(11)-C(12)-C(13) 109.6(4) C(12)-C(13)-C(14) 110.8(4) C(10)-C(14)-C(13) 115.2(4) C(15)-(1)-C(10) 118.7(4) C(15)-(1)-C(7) 112.0(4) C(10)-(1)-C(7) 109.4(3) (1)-C(16)-C(10) 106.6(7) C(10)-C(16')-(1') 116.4(9) Symmetry transformations used to generate equivalent atoms: 191
71 Table 4. Anisotropic displacement parameters (Å 2 x 10 3 )for 118. The anisotropic displacement factor exponent takes the form: -2π 2 [ h 2 a* 2 U h k a* b* U 12 ] U 11 U 22 U 33 U 23 U 13 U 12 C(1) 64(3) 62(3)51(2) -5(2) -2(2) -2(2) C(2) 73(3) 76(3)55(3) 5(2) 5(2) -6(2) C(3) 85(4) 79(4)64(3) 2(3) 12(3) -22(3) C(4) 71(3) 76(4)83(4) 8(3) -2(3) -11(3) C(5) 76(4) 101(4) 77(3) 14(3) -19(3) -8(3) C(6) 71(3) 74(3)59(3) 16(2) -2(2) -17(2) C(7) 60(3) 75(3)48(2) -4(2) 0(2) 2(2) C(8) 83(3) 69(3)44(2) -7(2) 4(2) -2(2) C(9) 51(3) 92(4)42(2) -8(2) 2(2) 13(2) C(10) 62(3) 62(3)41(2) 2(2) 11(2) -1(2) C(11) 69(3) 83(4)57(3) -15(3) 0(2) 3(3) C(12) 120(5) 48(3)71(3) 6(2) 2(3) -21(3) C(13) 78(3) 79(3)53(2) 8(2) -7(2) -3(3) C(14) 88(4) 64(3)43(2) -3(2) -1(2) -11(2) C(15) 97(4) 102(4) 45(2) -20(3) -1(3) 1(3) (1) 67(2) 62(2)42(2) 1(2) 1(2) 0(2) (1) 84(5) 65(4)50(3) 3(3) -1(3) -9(3) (1') 125(7) 98(6)31(3) -26(3) 6(4) -50(5) 192
72 Table 5. Hydrogen coordinates ( x 10 4 ) and isotropic displacement parameters (Å 2 x 10 3 ) for 118. x y z U(eq) H(2) H(3) H(4) H(5) H(6) H(7) H(8A) H(8B) H(9) H(11A) H(11B) H(12A) H(12B) H(13A) H(13B) H(14A) H(14B) H(15A) H(15B) H(15C) H(16A) H(16B) H(1) H(16C) H(16D) H(1')
73 Table 6. Torsion angles [ ] for 118. C(6)-C(1)-C(2)-C(3) -3.0(7) C(7)-C(1)-C(2)-C(3) 178.4(4) C(1)-C(2)-C(3)-C(4) 3.6(8) C(2)-C(3)-C(4)-C(5) -2.9(8) C(3)-C(4)-C(5)-C(6) 1.9(9) C(2)-C(1)-C(6)-C(5) 2.0(7) C(7)-C(1)-C(6)-C(5) (5) C(4)-C(5)-C(6)-C(1) -1.5(9) C(6)-C(1)-C(7)-(1) 166.3(4) C(2)-C(1)-C(7)-(1) -15.2(6) C(6)-C(1)-C(7)-C(8) -73.3(6) C(2)-C(1)-C(7)-C(8) 105.2(5) (1)-C(7)-C(8)-C(9) 5.3(5) C(1)-C(7)-C(8)-C(9) (4) C(7)-C(8)-C(9)-C(11) 93.5(4) C(7)-C(8)-C(9)-C(10) -29.7(5) C(11)-C(9)-C(10)-C(16') 162.2(7) C(8)-C(9)-C(10)-C(16') -75.8(7) C(11)-C(9)-C(10)-(1) -79.5(4) C(8)-C(9)-C(10)-(1) 42.4(4) C(11)-C(9)-C(10)-C(14) 39.4(5) C(8)-C(9)-C(10)-C(14) 161.4(4) C(11)-C(9)-C(10)-C(16) 163.1(6) C(8)-C(9)-C(10)-C(16) -74.9(6) C(10)-C(9)-C(11)-C(12) -47.4(5) C(8)-C(9)-C(11)-C(12) (4) C(9)-C(11)-C(12)-C(13) 56.9(6) C(11)-C(12)-C(13)-C(14) -59.0(6) C(16')-C(10)-C(14)-C(13) (7) (1)-C(10)-C(14)-C(13) 68.4(5) C(9)-C(10)-C(14)-C(13) -43.4(5) C(16)-C(10)-C(14)-C(13) (5) C(12)-C(13)-C(14)-C(10) 53.9(6) C(16')-C(10)-(1)-C(15) -59.4(8) C(14)-C(10)-(1)-C(15) 68.3(5) 194
74 C(9)-C(10)-(1)-C(15) (4) C(16)-C(10)-(1)-C(15) -51.9(6) C(16')-C(10)-(1)-C(7) 70.9(7) C(14)-C(10)-(1)-C(7) (4) C(9)-C(10)-(1)-C(7) -41.6(4) C(16)-C(10)-(1)-C(7) 78.4(6) C(1)-C(7)-(1)-C(15) -76.4(5) C(8)-C(7)-(1)-C(15) 157.0(4) C(1)-C(7)-(1)-C(10) 149.8(4) C(8)-C(7)-(1)-C(10) 23.1(5) C(16')-C(10)-C(16)-(1) -61(7) (1)-C(10)-C(16)-(1) (6) C(14)-C(10)-C(16)-(1) 59.1(8) C(9)-C(10)-C(16)-(1) -67.3(9) (1)-C(10)-C(16')-(1') 69.8(11) C(14)-C(10)-C(16')-(1') -58.0(11) C(9)-C(10)-C(16')-(1') 178.4(8) C(16)-C(10)-C(16')-(1') 4(6) Symmetry transformations used to generate equivalent atoms: 195
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