桃条麦蛾性信息素5E-癸烯-1-醇及乙酸5E-癸烯酯的简便合成

doi:10.6023/cjoc201608011

有机化学 ›› 2017, Vol. 37 ›› Issue (4): 1046-1050.DOI: 10.6023/cjoc201608011 上一篇下一篇

研究简报

桃条麦蛾性信息素5E-癸烯-1-醇及乙酸5E-癸烯酯的简便合成

黄飞^a,b, 杨婉秋^c, 张玉顺^a, 姚赟^a

a. 云南大学化学科学与工程学院昆明 650091;
b. 昆明博鸿生物科技有限公司昆明 650501;
c. 昆明学院化学科学与技术系昆明 650214

收稿日期:2016-08-18 修回日期:2016-11-12 发布日期:2017-01-10
通讯作者: 陶云海 E-mail:cloudsea2000@163.com
基金资助:
国家自然科学基金（Nos.21362018，81460525）及云南省应用基础研究计划（No.2014FB117）资助项目.

Simple Synthesis of 5E-Decen-1-ol and 5E-Decenyl Acetate, the Sex Pheromone of Peach Twig Borer

Huang Fei^a,b, Yang Wanqiu^c, Zhang Yushun^a, Yao Yun^a

a. School of Chemistry Science and Engineering, Yunnan University, Kunming 650091;
b. Kunming Biohome Technology Co. Ltd., Kunming 650501;
c. Department of Chemical Science and Technology, Kunming University, Kunming 650214

Received:2016-08-18 Revised:2016-11-12 Published:2017-01-10
Contact: 10.6023/cjoc201608011 E-mail:cloudsea2000@163.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21362018, 81460525) and the Applied Basic Research Project of Yunnan Province (No. 2014FB117).

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摘要/Abstract

桃条麦蛾是危害果树的重要害虫之一，其性信息素主要成分为5E-癸烯-1-醇及乙酸5E-癸烯酯. 从丙烯醛出发，在钯催化下与乙炔加成得到5-溴-4E-戊烯醛，与甲氧基甲基三苯基氯化膦进行Wittig反应得到1E，5E/Z-1-溴-6-甲氧基己二烯，再与丁基溴化镁进行Kumada偶联反应得到1E/Z，5E-1-甲氧基癸二烯，水解得到5E-癸烯醛，再还原得到5E-癸烯-1-醇，最后酯化得到乙酸5E-癸烯酯.

关键词: 桃条麦蛾, 5E-癸烯-1-醇, 乙酸5E-癸烯酯, 信息素合成, Kumada偶联反应

Peach twig borer is one of the most serious pests, whose sex pheromone is 5E-decen-1-ol and 5E-decenyl acetate. Synthesis of both compounds was achieved from acrolein. Firstly, a tandem addition reaction of acrolein with acetylene in the presence of Pd(OAc)₂ gave 5-bromo-4E-pentenal, which reacted with the ylide prepared from (methoxymethyl)triphenyl- phodphonium chloride to afford (1E,5E/Z)-1-bromo-6-methoxyhexadiene. The compound was coupled with Grignard reagent, followed by hydrolysis and reduction to give 5E-decen-1-ol. Esterification of the alcohol afforded 5E-decenyl acetate.

Key words: peach twig borer, 5E-decen-1-ol, 5E-decenyl acetate, pheromone synthesis, Kumada cross-coupling

引用此文

黄飞, 杨婉秋, 张玉顺, 姚赟, 陶云海. 桃条麦蛾性信息素5E-癸烯-1-醇及乙酸5E-癸烯酯的简便合成[J]. 有机化学, 2017, 37(4): 1046-1050.

Huang Fei, Yang Wanqiu, Zhang Yushun, Yao Yun, Tao Yunhai. Simple Synthesis of 5E-Decen-1-ol and 5E-Decenyl Acetate, the Sex Pheromone of Peach Twig Borer[J]. Chin. J. Org. Chem., 2017, 37(4): 1046-1050.

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桃条麦蛾性信息素5E-癸烯-1-醇及乙酸5E-癸烯酯的简便合成

Simple Synthesis of 5E-Decen-1-ol and 5E-Decenyl Acetate, the Sex Pheromone of Peach Twig Borer

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