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

HRID 1944

反応式

HRID 1944 の反応式
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]

参加物

9

反応物 7

HCID 78461-ButyneHCID 1038602-[(6-bromohexyl)oxy]tetrahydro-2H-pyran2 回HCID 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-decene2 回HCID 86752267(8Z,11Z)-trimethylsiloxy-8,11-tetradecadiene

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

出典と根拠

ORDレコード
ord-2f15776952b34a539da4eb150087740b
出典データセット
uspto-grants-1998_03
特許番号
US05728376

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