桃小食心虫性信息素——（Z）-7-二十碳烯-11-酮的简便合成
收稿日期: 2014-01-13
修回日期: 2014-03-16
网络出版日期: 2014-04-01
基金资助
云南大学理（工）科校级科研（No.2011YB12）及云南省教育厅基金（No.2011Y112）资助项目.
Simple Synthesis of (Z)-7-Eicosen-11-one- the Sex Pheromone of Peach Fruit Moth
Received date: 2014-01-13
Revised date: 2014-03-16
Online published: 2014-04-01
Supported by
Project supported by the Science and Technology Foundation of Yunnan University (No. 2011YB12) and the Foundation of Yunnan Province Department of Education (No. 2011Y112).
桃小食心虫是危害最大的果树害虫之一，其性信息素主要成分为（Z）-7-二十碳烯-11-酮. 从2，3-二氢呋喃出发，经酸水解得到4-羟基丁醛，与正庚基三苯基溴化磷制备的Wittig试剂反应得到（Z）-4-十一碳烯-1-醇，经氧化得到（Z）-4-十一碳烯醛，再经格氏加成得到（Z）-7-二十碳烯-11-醇，氧化后得到目标产物.
关键词： 桃小食心虫; （Z）-7-二十碳烯-11-酮; 信息素合成; Wittig反应; 格氏加成
杨晓梅 , 张玉顺 , 姚赟 , 陶云海 . 桃小食心虫性信息素——（Z）-7-二十碳烯-11-酮的简便合成[J]. 有机化学, 2014 , 34(7) : 1458 -1461 . DOI: 10.6023/cjoc201401021
Peach fruit moth is one of the most serious pests, whose sex pheromone is (Z)-7-eicosen-11-one. Synthesis of the compound was achieved from 2,3-dihydrofuran. Firstly, acidic hydrolysis of 2,3-dihydrofuran gave 4-hydroxybutanal, which reacted with the ylide prepared from heptyltriphenylphosphonium bromide to afford (Z)-4-undecen-1-ol. The alcohol was oxidated followed by Grignard addition and further oxidation to give the target product.
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