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

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.

Peach twig borer is one of the most serious pests, whose sex pheromone is 5E-decen-l-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）-l-bromo-6-methoxyhexadiene. The compound was coupled with Grignard reagent, followed by hydrolysis and reduction to give 5E-decen-l-ol. Esterification of the alcohol afforded 5E-decenyl acetate.