摘要
以异戊二烯、甲基乙烯基酮为原料,氯化铝为催化剂,经Diels-Alder反应,合成得到1-甲基-4-乙酰基-1-环己烯,再用锍叶立德对羰基环氧化,专一地得到消旋体8,9-环氧烯,两步反应总得率为56%。从8,9-环氧烯出发,进一步合成得到萜类香料1,8-对二烯-10-醇和4-(4-甲基-3-环己烯-1-基)-4-戊烯醛。所有产物的结构经IR、NMR和MS证实。
Isoprene reacted with methyl vinyl ketone in the presence of Lewis acid to form the Diels-Alder reaction product 1-methyl-4-acetyl-1-cyclohexene. Dimcthyloxosulfonium methylide interacted with the carbonyl of mentioned product to give enantiomeric 8, 9-epoxylimonenc. The over yield was 56%. 8,9-Epoxylirnonene underwent rearrangement in presence of aluminum isopropoxylate to give 1,8-p-menthdiene-10-ol, which after transetherification with vinyl ethyl ether and Claisen rearrangement, afforded 4-（4-methyl-3-cyclohexen-1-yl）-4-pentenal. All of the products were charactefised by IR,NMR and MS.
出处
《化学通报》
CAS
CSCD
北大核心
2006年第11期857-860,共4页
Chemistry
基金
上海市教委科学基金资助项目(050Z17)
