经由胂叶立德立体有择合成仿保幼激素──增丝素（ZR－512）及其（2Z，4E）－异构体  

Stereoselective Synthesis of Hydroprene and Its(2Z, 4E)-Isomer via Arsonic Ylide

作　　者：刘天麟[1] 倪赤友[1] 谢文权[1] 李正名[1] 

机构地区：[1]南开大学元素有机化学研究所

出　　处：《高等学校化学学报》1994年第3期387-390,共4页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金

摘　　要：３－甲基－２－丁烯酸乙酯４经ＳｅＯ２反式氧化、还原、溴化得到关键中间体４－溴－３－甲基－（２Ｅ）－丁烯酸乙酯７．７与三苯基胂反应生成季８．二氢香茅醛与８在Ｋ＿２ＣＯ＿３－乙醇－微量水的存在下反应，得到（２Ｅ，４Ｅ）－３，７，１１－三甲基－２，４－十二碳二烯酸乙酯１ａ及其（２Ｚ，４Ｅ）－异构体１ｂ，产率７４％。该反应具有（４Ｅ）－立体选择性，同时Ｃ－２双键发生部分构型转化。The key intermediate ethyl 4-bromo-3-methyl-( 2E)-butenoate 7 was obtained from ethyl 3-methyl-2-butenoate 4 by a sequence of reactions:trans-oxidation(SeO2), reduction and bromination, Reaction of 7 and triphenylarsine gave the arsonium salt 8.Finally, reaction of 8 and dihydrocitronellal in the presence of K_2CO_3-C_2H_5OH-trace H_2O afforded hydroprene and its (2Z, 4E)-isomer in yield of 74%. The(4E)-selectivity and the partial inversion of C-2 double bond configuration happened in this reaction.

关 键 词：增丝素 胂叶立德 昆虫 生长调节剂 

分 类 号：TQ453.8[化学工程—农药化工]