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马尾松毛虫(Dendralimus punctatus Walker)是中国南方马尾松林的一种毁灭性害虫。通过Wittig缩合反应合成了马尾松毛虫性信息素的三个活性组分:顺,反-5,7-十二碳双烯-1-醇(Ⅰ),顺,反-5,7-十二碳双烯-1-基乙酸酯(Ⅱ)和顺,反-5,7-十二碳双烯-1-基丙酸酯(Ⅲ)。Wittig反应是在六甲基磷酰三胺溶剂中,以正丁基锂作碱完成的。经气相色谱分析,主要产物是颇,反异构体和反,反异构体的混合物,两者的比例约为91:9。用二甲基亚砜代替六甲基磷酰三胺作溶剂时,产物中顺,反与反,反异构体的比例约75:25。
Dendralimus punctatus Walker is a devastating pest in the Pinus massoniana forest in southern China. The three active components of sex pheromone of Dendrolimus punctatus were synthesized by Wittig condensation reaction: cis, trans-5,7-dodecanedien-1-ol (Ⅰ), cis, trans- 1-yl acetate (II) and cis, trans-5,7-dodecadien-1-yl propionate (III). Wittig reaction is in hexamethylphosphoric triamide solvent, with n-butyl lithium as a base to complete. By gas chromatography, the main products are quite, anti-isomers and anti-and anti-isomer mixture, the ratio of the two is about 91: 9. When dimethylsulfoxide was used as a solvent in place of hexamethylphosphoric triamide, the ratio of cis, trans, trans and trans isomers in the product was about 75:25.