螺55十一烷-酮的合成.PDF

1996 7 　　　　　 29　 4 　　　　　　　 　　　　　　　 Jul. 1996 JOURNAL OF TIAN JIN UNIVERSITY Vol. 29　No. 4 [5. 5]-3- 冯亚青 张晓东 ()　　　() 　　　研究了螺 [5. 5]十一烷-3-酮新的合成路线,即环己酮 1经环氧化生成 1-氧杂螺 [2. 5]辛 烷 2; 2再与路易斯酸作用发生 重排生成甲酰环己酮 3; 3与甲基乙烯酮在酸的催化下经迈克尔 加成反应得到 1-螺 [5. 5]十一烯-3-酮 4; 最后经加 生成目的产物螺 [5. 5]十一烷-3-酮 5,总收率 为 28. 9% ,反应步骤少、操作简单 . : [5. 5]-3-,, : O626 INVESTIGATION ON SYNTHESIS OF SPIRO [5. 5] -3- UNDECANE ONE Feng Yaqing Zhang Xiaodong ( Dept. of Applied Che istry)　　 ( Phar aceutical Factory) 　　Abst act　 A new routine concerning the synthesis of spiro [5. 5]undecan-3-one is proposed. Firstly, the epoxidation of cyclohexanone 1 produces 1-oxaspiro [2. 5]octane 2. By the action of Lewis acid, thehydrogen rearrange ent is achieved, yielding cyclohexyl for aldehyde 3. Further- ore, with the catalysis of acid the Michael addition reaction of cyclohexyl for aldehyde with [5. 5] -1- -3 4. , [5. 5] - ethyl vinyl ketone leads to the spiro undecene one Finally the spiro undecane 3-one is obtained in virtue of the hydrogenation 5. The overall yield was 28. 9% . : [5. 5] -3- , , Key wo ds spiro undecane one hydrogen rearrange ent Michacl addition reaction 　　, . , . [1] 　　[5. 5]-3- , [2, 3] [4] , : ,、、、、 , [5. 5]-3- 5. 1994 5 20. 1994 8 31. 　* 　 1957, , , . 1957, . , . , . Born in fe D associate prof 　 29 4　　　　　　　:[5. 5]+ -3-