欧洲葡萄花翅小卷蛾性信息素7E,9Z-十二碳二烯乙酸酯的简便合成  

Simple Synthesis of 7E,9Z-dodecadien-1-yl Acetate, The Sex Pheromone of European Grapevine Moth

作　　者：张海瑞 黄飞 张玉顺[1] 陶云海[1,2] ZHANG Hai-rui;HUANG Fei;ZHANG Yu-shun;TAO Yun-hai(School of Chemistry Science and Engineering,Yunnan University,Kunming 650091,China;Kunming Biohome Technology Co.,Ltd.,Kunming 650501,China)

机构地区：[1]云南大学化学科学与工程学院,云南昆明650091 [2]昆明博鸿生物科技有限公司,云南昆明650501

出　　处：《合成化学》2020年第2期138-142,共5页Chinese Journal of Synthetic Chemistry

基　　金：国家自然科学基金资助项目(21362018,81460525);云南省应用基础研究计划项目(2014FB117)。

摘　　要：欧洲葡萄花翅小卷蛾的性信息素主要成分为7E,9Z-十二碳二烯乙酸酯。从1,5-二溴戊烷出发,制成格氏试剂后与甲醛发生格氏加成反应得到1,7-庚二醇,单酯化得到7-羟基庚醇乙酸酯,氧化得到7-氧代庚醇乙酸酯,与(2,2-二甲氧基乙基)三苯基溴化膦进行Wittig反应并水解得到9-氧代-7E-壬烯乙酸酯,再与正丙基三苯基溴化膦进行Wittig反应合成了7E,9Z-十二碳二烯乙酸酯,总产率13%,其结构经1H NMR和13C NMR确证。European grapevine moth is one of the most serious pests, whose sex pheromone is 7E,9Z-dodecadien-1-yl acetate. A simple synthesis of this sex pheromone was reported using 1,5-dibromopentane as material. Firstly, the Grignard reagent prepared from 5-dibromopentane was reacted with formaldehyde to afford heptane-1,7-diol. Monoesterification of the diol following oxidation gave 7-oxoheptyl acetate. The aldehyde reacted with the ylide prepared from(2,2-dimethoxyethyl)triphenylphosphonium bromide, followed by hydrolysis to provide 9-oxo-7E-nonen-1-yl acetate. The Wittig reaction of the aldehyde with propyltriphenylphosphonium bromide provided the target product, with total yield of 13%. The target product was confirmed by 1H NMR and 13C NMR.

关 键 词：欧洲葡萄花翅小卷蛾 7E 9Z-十二碳二烯乙酸酯 信息素 合成 加成反应 WITTIG反应 

分 类 号：O623.624[理学—有机化学] O626[理学—化学]