有机化学 ›› 2009, Vol. 29 ›› Issue (11): 1840-1842. 上一篇    下一篇

研究简报

脯氨酰肼小分子催化的环己酮的直接α-硫代反应

程传玲   

  1. (郑州轻工业学院食品与生物工程学院 郑州 450002)
  • 收稿日期:2009-01-01 修回日期:2009-05-14 发布日期:2009-06-25
  • 通讯作者: 程传玲 E-mail:chuanlingcheng@163.com

Direct α-Sulfanylation Reaction of Cyclohexanone Catalyzed by Proline Hydrazide

Cheng, Chuanling   

  1. (School of Food and Biological Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002)
  • Received:2009-01-01 Revised:2009-05-14 Published:2009-06-25

研究了脯氨酰肼有机小分子催化环己酮的直接α-硫代反应. 考察了3种不同硫代试剂、9种溶剂、6种脯氨酰肼催化剂等对反应的活性和收率的影响. 结果表明, 硫代试剂、溶剂及催化剂的结构对反应的活性和反应收率均有较大的影响. 在优化条件下, 即以邻苯二甲酰亚胺为硫代试剂, 甲苯为溶剂, 脯氨酰肼1和4催化的环己酮的硫代反应活性比较高, 室温反应12 h, 收率达98%. 脯氨酰肼催化该类反应条件温和, 操作简单, 在药物合成中具有一定的应用潜力.

关键词: 脯氨酰肼, 有机小分子催化剂, 直接α-硫代反应

The direct α-sulfanylation reaction of cyclohexanone catalyzed by organocatalyst proline hydrazide was studied. The activities and yields of the reaction were researched through three different sulfanylating reagents, nine kinds of solvents as well as six catalysts of proline hydrazides, etc. The results showed that the activities and yields were effected by the sulfanylating reagents, solvents and the structure of the catalysts. Under the optimal reaction condition, namely using N-(phenylthio)succinimide as sulfanylating reagent and toluene as solvent, proline hydrazides 1 and 4 had higher catalytic activities to the reaction of the α-sulfanylation reaction. The yields of products were up to 98% after 12 h at room temperature. The reaction conditions catalyzed by proline hydrazide were mild and the operation was simple, which had some applica-tion to synthesis of drug.

Key words: proline hydrazide, organocatalyst, direct α-sulfanylation reaction

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