1-Butyne → (3E,11Z)-3,11-tetradecadienyl acetate

HRID 1944

반응식

HRID 1944 반응식
C#CCC.BrCCCCCCOC1CCCCO1.[C:19]([O:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29]/[CH:30]=[CH:31]\[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])(=[O:21])[CH3:20].O1CCCCC1OCCC#CCCC/C=C\C/C=C\CC.C(OCC/C=C/CCC/C=C\C/C=C\CC)(=O)C.C[Si](C)(C)OCCCCCCC/C=C\C/C=C\CC.O1CCCCC1OCCC/C=C\CCCCC>C(Cl)(Cl)(Cl)Cl>[C:19]([O:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]/[CH:33]=[CH:34]\[CH2:35][CH3:36])(=[O:21])[CH3:20]

참가 물질

9

반응물 7

HCID 78461-ButyneHCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyran2회HCID 9992319Tetradeca-3,8,11-trienyl acetate, (3E,8Z,11Z)-HCID 105387863E,8Z-Tetradecadienyl acetateHCID 10989926(8Z,11Z)-1-(tetrahydropyran-2-yloxy)-8,11-tetradecadien-3-yneHCID 67591886(4Z)-1-(tetrahydropyran-2-yloxy)-4-decene2회HCID 86752267(8Z,11Z)-trimethylsiloxy-8,11-tetradecadiene

생성물 1

HCID 86752266(3E,11Z)-3,11-tetradecadienyl acetate수율 15%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

Starting from 1-butyne and 1-bromo-6-(tetrahydropyran-2-yloxy)-hexane (22), the (3E,11Z)-3,11-tetradecadien-1-yl acetate (30) was prepared by a synthetic route similar to that used for the preparation of (3E,8Z)-3,8-tetradecadien-1-yl acetate (21), as depicted in the following scheme. ##STR18## The yield was 15% [17 mg; 96% isomeric purity (GC)] based on the starting material, 1-bromo-6-(tetrahydropyran-2-yloxy)hexane (22). 1H NMR (500 MHz) δ: 5.51 (dtt, J=15.1, 6.8, 6.8, 1.2, 1.5 Hz, 1H, =CH -3), 5.35 (m, 3H, CH=CH -4, 11, 12), 4.06 (t, J=6.8, 6.8 Hz, 2H, CH2 -1), 2.31 (dddt, J=1.2, 1.2, 6.8, 6.8, 6.8 Hz, 2H, CH2 -2), 2.05 (s, 3H, COCH3), 2.02 (m, 6H, CH2 -5, 10, 13), 1.36-1.24 (m, 6H, CH2 -6, 7, 8, 9), 0.95 (t, J=7.3, 7.6 Hz, 3H, CH3). 13 C NMR (100.6 MHz) δ: 171.1 (C=O), 133.6 (=CH-3), 131.6 (=CH-12), 129.3 (=CH-11), 125.0 (=CH-4), 64.1 (CH2 -1), 32.6 (CH2 -2), 31.9 (CH2 -6), 29.7 (CH2 -8), 29.3 (CH2 -7), 29.1 (CH2 -9), 29.0 (CH2 -10), 27.1 (CH2 -5), 21.0 (COCH3), 20.5 (CH2 -13), 14.4 (CH3 -14). MS [EI, m/z(%)] 192 (M+ -60, 6), 163 (6), 149 (9), 135 (12), 121 (16), 107 (16), 96 (28), 95 (37), 93 (25), 82 (50), 81 (60), 80 (35), 79 (36), 69 (33) 68 (64), 67 (97), 55 (45), 43 (100), 41 (67). IR (CCl4, cm-1) 3006 (=CH cis str), 1743 (C=O), 1238, 1036 (C--O), 969 (=CH trans wag). IR (gas phase, cm-1) 3012 (cis =C--H str), 2934 (CH2), 1761 (C=O), 1231, 1038 (--O--), 968 (=CH trans wag).

출처 및 근거

ORD 기록
ord-2f15776952b34a539da4eb150087740b
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728376

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