应用化学 ›› 2009, Vol. 26 ›› Issue (6): 667-670.

• 研究论文 • 上一篇    下一篇

无气味的1-(1, 3-二噻-2-亚基)丙酮作有效的1, 3-丙二硫醇替代试剂的缩硫醛/酮化反应

于海丰   

  1. 鞍山师范学院化学系
  • 收稿日期:2008-06-05 修回日期:2008-08-19 出版日期:2009-06-10 发布日期:2009-06-10
  • 通讯作者: 于海丰

Thioacetalization Reaction of Odorless 1-(1, 3-dithian-2-ylidene)

  • Received:2008-06-05 Revised:2008-08-19 Published:2009-06-10 Online:2009-06-10

摘要:

在常温1-(1, 3-二噻-2-亚基)丙酮1f是无气味的、稳定的白色固体,它易通过易制备的3-(1, 3-二噻-2亚基)-2, 4-戊二酮1b的酸性条件下的脱乙酰化反应制得,产率为86%。在MeCOCl/MeOH体系中,在常温和回流条件下,1f能作为有效的1, 3-丙二硫醇替代试剂与醛和酮进行缩硫醛/酮化反应,高产率(86-99%)合成1, 3-二噻烷衍生物。与已报道的硫醇替代试剂1a-e相比,在缩硫醛/酮化反应中1f是活性最好的1, 3-丙二硫醇替代试剂。

关键词: 2-(1, 3-二噻-2-亚基)丙酮, 代硫醇试剂, 缩硫醛/酮化反应, 2-(1, 3-二噻-2-亚基)丙酮, 代硫醇试剂, 缩硫醛/酮化反应

Abstract:

1-(1, 3-dithian-2-ylidene)propan-2-one 1f, which is odorless and steady white crystal at room temperature, was prepared readily in 86% yield via decarbonylation of 3- (1, 3-Dithian-2-ylidene)-pentane-2,4-Dione 1b under acidic condition. Thioacetalization reactions of odorless 1-(1, 3-dithian-2-ylidene)propan-2-one as efficient 1, 3-propandithiol equivalent with selected aldehydes and ketones were carried out at room and reflux temperature in the present of MeCOCl in MeOH, and 1, 3-dithiane derivatives were obtained in excellent yield (86-99%). Compared with reported 1a-e, 1f is regarded as optimal 1, 3- propandithiol equivalent in thioacetalization reaction.

Key words: 1-(1, 3-dithian-2-ylidene)propan-2-one, thiol equivalents, thioacetalization reaction.

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