一种高效的超声辅助含共轭烯炔醇和共轭烯炔酮体系的脂肪酸酯的锌还原反应。
An efficient ultrasound-assisted zinc reduction of fatty esters containing conjugated enynol and conjugated enynone systems.
作者信息
Lie Ken Jie M S, Mustafa J, Pasha M K
机构信息
Department of Chemistry, University of Hong Kong, Hong Kong.
出版信息
Lipids. 1998 Sep;33(9):941-5. doi: 10.1007/s11745-998-0291-x.
Reduction of methyl 8-hydroxy-11-E/Z-octadecen-9-ynoate (1) with zinc in either aqueous n-propanol or water under concomitant ultrasound irradiation furnished a mixture of methyl 8-hydroxy-9Z,11E-octadecadienoate (3a) and methyl 8-hydroxy-9Z,11Z-octadecadienoate (3b) (96% yield). Reduction of methyl 8-oxo-11-E/Z-octadecen-9-ynoate (2) under similar conditions gave methyl 8-oxo-10-Z-octadecenoate exclusively (4, 70%). The latter compound was epoxidized and converted to a C18 furanoid fatty ester (6, methyl 8,11-epoxy-8,10-octadecadienoate) in 70% yield.
在水相正丙醇或水中，伴随超声辐射用锌还原8-羟基-11-E/Z-十八碳-9-炔酸甲酯（1），得到8-羟基-9Z,11E-十八碳二烯酸甲酯（3a）和8-羟基-9Z,11Z-十八碳二烯酸甲酯（3b）的混合物（产率96%）。在类似条件下还原8-氧代-11-E/Z-十八碳-9-炔酸甲酯（2），仅得到8-氧代-10-Z-十八碳烯酸甲酯（4，产率70%）。后一种化合物被环氧化，并以70%的产率转化为一种C18呋喃型脂肪酸酯（6，8,11-环氧-8,10-十八碳二烯酸甲酯）。
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