Pesticide Chemistry Department, Taiwan Agricultural Chemical and Toxic Substances Research Institute (TACTRI), Taiwan R.O.C..
J Chem Ecol. 1992 Feb;18(2):95-103. doi: 10.1007/BF00993745.
An alternative synthesis of (Z)-3-dodecen-1-y1 (E)-2-butenoate without use of carcinogenic ethylene oxide and HMPA is described. By coupling of the tetrahydropyranyl (THP) ether of 3-butyn-1-ol with 1-bromooctane with sodamide in liquid ammonia, 12-(2-tetrahydropyranyloxy)-9-dodecyne was obtained; subsequent hydrolysis and semihydrogenation afforded (Z)-3-dodecen-1-ol. The alcohol was then reacted with crotonyl chloride to give the desired crotonate with a total yield of 29.8%. Males of sweet-potato weevil,Cylas formicarius were strongly attracted to the synthetic sex pheromone. The attraction from the dispenser of polyethylene tube was better than the attraction from the dispenser of rubber septum in the field.
本文描述了一种不使用致癌的环氧乙烷和六甲基磷酰胺（HMPA）合成（Z）-3-十二烯-1-基（E）-2-丁烯酸酯的方法。通过在液氨中用氨基钠将 3-丁炔-1-醇的四氢吡喃（THP）醚与 1-溴辛烷偶联，得到了 12-（2-四氢吡喃基氧基）-9-十二炔；随后进行水解和半氢化得到（Z）-3-十二烯-1-醇。然后将该醇与巴豆酰氯反应，以总收率 29.8%得到所需的巴豆酸盐。甘薯象甲雄虫对合成性信息素具有强烈的吸引力。在野外，聚乙烯管分配器的吸引力优于橡胶隔垫分配器的吸引力。
