摘要
６－溴－２－己酮在Ｌｉ２ｃｕＣｌ４催化下与γ－溴代巴豆酸甲酯进行格氏偶联，合成了蜂王物质９－羰基－（Ｅ）－２－癸烯酸（９－ＯＤＡ），将其还原得到另一蜂王物质９－羟基－（Ｅ）－２－癸烯酸（９－ＨＤＡ）。该法是合成９－ＯＤＡ和９－ＨＤＡ的新路线。
This paper discribes a novel synthesis of 9-oxo-(E)-2-decenoic acid(9-ODA)and 9-hydrox-y-(E)-2-decenoic acid(9-HDA),which are the main components of honeybee's feromones.The critical step is the cross-coupling with Li2CuCl4 catalyst between the Grignard reagent of 6-bromo-hexan-2-one ethylene ketal prepared from ethyl acetoacetate and γ-bromocrotonate.After the coupling product is hydrolyzed,“Queen Substance”9-ODA is obtained.The overall yield besed on 6-bromohexan-2-one is 50.4%.The other queen substance 9-HDA is obtained by reduction of 9-ODA with NaBH4.The yield is 88%.
出处
《合成化学》
CAS
CSCD
1996年第2期131-136,共6页
Chinese Journal of Synthetic Chemistry
关键词
蜂王物质
羰基
癸烯酸
羟基
激素
s:Queen substance,9-Oxo-(E)-2-decenoic acid,9-Hydroxy-(E)-2-decenoic acid,Grignard coupling.
