2-phenylsulfanylmethyl-3,3a,4,5,6,7-hexahydro-2H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-phenylsulfanylmethyl-3,3a,4,5,6,7-hexahydro-2H-indole
• 英文别名: 2-phenylsulfenylmethyl-3,3a,4,5,6,7-hexahydro-2H-indole；2-(phenylsulfanylmethyl)-3,3a,4,5,6,7-hexahydro-2H-indole
• 化学式: C₁₅H₁₉NS
• 分子量: 245.389
• InChiKey: ATJSQQVULGGPFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2'-丙烯基)环己酮肟 、 二苯二硫醚 在 2,6-dimethylbenzenesulfinyl chloride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2-phenylsulfanylmethyl-3,3a,4,5,6,7-hexahydro-2H-indole
  参考文献：
  名称：

  通过哈德逊反应生成亚胺基和环化亚胺的新方法。

  摘要：

  [化学式：见正文]已开发出一种温和的新合成程序，用于将亚氨基自由基原位生成和环化到侧链烯烃上，然后通过多种捕集试剂之一将所得碳自由基官能化。该方法的关键过程涉及在-50℃至室温下通过用容易获得的2，6-二甲基苯亚磺酰氯处理醛肟或酮肟来生产亚胺基（Hudson反应）。

  DOI：

  10.1021/ol990720e

文献信息

• Development of efficient new methodology for generation, cyclization and functional trapping of iminyl and amidyl radicals
  作者：Xichen Lin、Gerald D. Artman、Didier Stien、Steven M. Weinreb

  DOI：10.1016/s0040-4020(01)00878-x

  日期：2001.10

  New methodology has been devised for the generation and subsequent cyclization of iminyl and amidyl radicals under mild conditions. The process involves either the treatment of oximes with 2,6-dimethylbenzenesulfinyl chloride, or the treatment of hydroxamic acids with tert-butylsulfinyl chloride (-50 degreesC to rt), to give the corresponding nitrogen radicals, followed by cyclization onto pendant olefins. Radical traps such as diphenyl diselenide, diphenyl disulfide, and TEMPO can be used to terminate the cyclizations, thus introducing functionality that provides multiple options for further manipulation. In a more convenient procedure, both iminyl and amidyl radical cyclizations can be initiated using commercially available diethyl chlorophosphite which generally provides similar (with diphenyl disulfide and TEMPO) or significantly higher (with diphenyl diselenide) yields of products. (C) 2001 Elsevier Science Ltd. All rights reserved.