摘要
从简单原料乙炔出发,通过炔对丙烯醛的加成反应得到7-溴代-(4Z,6E)-庚二烯醛,再经乙二醇保护、Pd催化偶联、水解、Wittig反应和还原等步骤,立体选择性地得到松毛虫性信息素(5Z,7E)-十二碳二烯醇,其结构通过IR,NMR和MS等技术得到确认.
Sexpheromone of Dendrolimus Spp. is composed of (5Z, 7E)-5,7-Dodecadien-1-ol(1) and its acetate and propionate. At first 7-bromo-(4Z, 6E)-heptadien-1-al(2) was stereoselectively synthesized by the tandem addition reaction of acrolein with acetylene in the presence of Pd(OAc)_2. Novel stereoselective synthesis of (5Z, 7E)-5,7-Dodecadien-1-ol was achieved in five steps, using palladium-catalyzed coupling reaction of 7-bromo-(4Z, 6E)-4,6-heptadiene-1-al ethylene acetal from production of the above aldehyde with Grignard reagent as the key step. The structures of all the compounds were confirmed by IR, NMR and MS spectra.
出处
《高等学校化学学报》
SCIE
EI
CAS
CSCD
北大核心
2005年第6期1072-1075,共4页
Chemical Journal of Chinese Universities
基金
云南省自然科学基金(批准号:2000B006M)资助.
