Citation: Huang Fei, Yang Wanqiu, Zhang Yushun Yushun, Yao Yun, Tao Yunhai. Simple Synthesis of 5E-Decen-1-ol and 5E-Decenyl Acetate, the Sex Pheromone of Peach Twig Borer[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 1046-1050. doi: 10.6023/cjoc201608011 shu

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

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

Corresponding author: Tao Yunhai, cloudsea2000@163.com
Received Date: 18 August 2016
Revised Date: 12 November 2016

Fund Project: the National Natural Science Foundation of China 21362018the National Natural Science Foundation of China 81460525the Applied Basic Research Project of Yunnan Province 2014FB117

Figures(3)

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