| 8,9-环氧苧烯的合成 |
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| 引用本文： | 杨始刚,龚雪丽,张欣慰. 8,9-环氧苧烯的合成[J]. 化学通报, 2006, 69(11): 857-860 |
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| 作者姓名： | 杨始刚 龚雪丽 张欣慰 |
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| 作者单位： | 上海应用技术学院化工系,上海,200235;上海应用技术学院化工系,上海,200235;上海应用技术学院化工系,上海,200235 |
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| 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。
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| 关 键 词： | 1-甲基-4-乙酰基-1-环己烯 Diels-Alder反应 锍叶立德 8 9-环氧苧烯 1 8-对盖二烯-10-醇 |
| 收稿时间： | 2006-05-29 |
| 修稿时间： | 2006-05-292006-07-19 |
Synthesis of 8,9-Epoxylimonene |
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| Yang Shigang,Gong Xueli,Zhang Xinwei. Synthesis of 8,9-Epoxylimonene[J]. Chemistry, 2006, 69(11): 857-860 |
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| Authors: | Yang Shigang Gong Xueli Zhang Xinwei |
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| Affiliation: | Department of Chemical Engineering, Shanghai Institute of Technology, Shanghai 200235 |
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| Abstract: | 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. Dimethyloxosulfonium methylide interacted with the carbonyl of mentioned product to give enantiomeric 8,9-epoxylimonene. The over yield was 56%. 8,9-Epoxylimonene 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 characterised by IR,NMR and MS. |
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| Keywords: | 4-Acetyl-1-methyl-1-cyclohexene Diels-Alder reaction Dimethyloxosulfonium methylide 8 9-Epoxy-limonene 1 8-p-menthdiene-10-ol |
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