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

HRID 1944

反应方程式

HRID 1944 反应方程式
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]

参与物

9

反应物 7

HCID 78461-丁炔HCID 1038602-(6-溴己氧基)四氢吡喃2 次HCID 9992319(3E,8Z,11Z)- 十四碳三烯乙酸酯HCID 10538786反-3,顺-8-十四碳三烯乙酸酯HCID 10989926(8Z,11Z)-1-(tetrahydropyran-2-yloxy)-8,11-tetradecadien-3-yneHCID 67591886(4Z)-1-(tetrahydropyran-2-yloxy)-4-decene2 次HCID 86752267(8Z,11Z)-trimethylsiloxy-8,11-tetradecadiene

产物 1

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

试剂、催化剂与溶剂 1

HCID 5943四氯化碳溶剂

实验过程

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).

来源与证据

ORD记录
ord-2f15776952b34a539da4eb150087740b
来源数据集
uspto-grants-1998_03
专利号
US05728376

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