水稻螟虫信息素成分——13顺-十八碳烯醛等的合成

Syntheses of 13Z-Octadecenals——Sex pheromone Components of Both Rice Pests

标题化合物是水稻螟虫的信息素成分。从十二碳二醇出发,经单酯化和氧化得到乙酸12-氧代十二碳酯,经Wittig反应得到乙酸12顺-十七碳烯酯,再经水解和氧化得到12顺-十七碳烯醛,与甲氧基甲基三苯基氯化膦进行Wittig反应得到13顺-1-甲氧基十八碳-1,13-二烯,水解得到标题化合物,再经还原和乙酯化分别得到13顺-十八碳烯醇和乙酸13顺-十八碳烯酯。

The title compounds and so on are sex pheromone components of both rice pests.Synthesis of the compounds was achieved from 1,12-dodecanediol.Firstly,monoesterification and oxidation of 1,12-dodecanediol gave 12-oxododecyl acetate,which reacted with the ylide prepared from pentyltriphenylphodphonium bromide to afford 12Z-heptadecen-1-yl acetate.Hydrolysis and oxidation of the acetate gave 12Z-heptadecenal,which reacted with the ylide prepared from(Methoxymethyl)triphenylphodphonium chloride followed by hydrolysis to afford the title compound.Reduction of the title compound gave 13Z-octadecen-1-ol,which led to 13Z-octadecen-1-yl acetate by esterification.