化学学报 ›› 1980, Vol. 38 ›› Issue (6): 584-591. 上一篇    下一篇

研究简报

红铃虫性信息素 顺、顺-及顺、反-7、11-十六碳双烯-1-醇乙酸酯的合成

昆虫激素组1, 昆虫信息素组2   

  1. 1. 中国科学院上海有机化学研究所;
    2. 中国科学院上海昆虫研究所
  • 投稿日期:1978-06-20 发布日期:2013-06-03

SYNTHESIS OF THE PINK BOLLWORM SEX PHEROMONE, CIS, CIS-AND CIS, TRANS-7, 11-HEXADECADIENYL ACETATE

INSECT HORMONG GROUP1, INSECT SEX ATTRACTANT GROUP2   

  1. 1. Shanghai Institute of Organic Chemistry, Academia Sinica;
    2. Shanghai Entomological Institute, Academia Sinica
  • Received:1978-06-20 Published:2013-06-03

红铃虫[Pectinophora gossypiella(Saund.)]**是世界上许多地区棉花的主要害虫。在我国南方产棉区棉花因受红铃虫的危害,产量和质量每年损失较大。由于害虫对一般化学农药产生抗药性,以及农药在杀灭害虫的同时又伤害了天敌和其它益虫,对环境造成严重污染,因此人们正在寻找防治害虫的新方法。应用昆虫性信息素防治害虫即是其中的一个方法[1,2]。我们开展了红铃虫性信息素合成的研究。

The seg pheromones of pink bollworm,cis,cis-7,11-hegadecadienyl acetate (1) and cis,traps-7,11-hegadecadienyl acetate (2) were prepared as outlined in the Chinese text.Hydrogenation of acetylenic compound 8 over Lindlar catalyst or P-2 Ni gave the compound 4,while reduction of compound 3 with sodium in liquid ammonia gave the compound 5,Compound 4 and 5 were converted into the respective bromide 6 and 7 which were then separately coupled with 18 in the presence of n-butyl lithium and diglyme to afford 8 and 9.The triple bonds of 8 and 9 were again catalytically hydrogenated and.the 7HP-protecting groups were removed simultaneously on esterification with acetyl chloride and glacial acetic acid to furnish the desired products respectively,with‘purity of more than 93%.The overall yield is about 35%.Tha intermediate 18 was either prepared from the chloride 12a or the bromide 12b.