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

doi:10.6023/cjoc201608011

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 1046-1050.DOI: 10.6023/cjoc201608011 Previous Articles Next Articles

Notes

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).

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

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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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