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.
出处
《高等学校化学学报》
CSCD
北大核心
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
关键词
增丝素
胂叶立德
昆虫
生长调节剂
Hydroprene
Arsonic Ylide
Stereoselectivity
Synthesis
