5-chloro-2-phenyl-3-(p-tolylthio)-1H-indole | 1285494-91-8

• 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: 5-chloro-2-phenyl-3-(p-tolylthio)-1H-indole
• 英文别名: 5-chloro-3-(4-methylphenyl)sulfanyl-2-phenyl-1H-indole
• CAS: 1285494-91-8
• 化学式: C₂₁H₁₆ClNS
• 分子量: 349.884
• InChiKey: AFRQNKLGSHAJRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  41.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-氯-2-(苯基乙炔基)苯胺 、 对甲苯二硫醚 在 copper(l) iodide 、 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以79%的产率得到5-chloro-2-phenyl-3-(p-tolylthio)-1H-indole
  参考文献：
  名称：

  Copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides for one-step synthesis of 3-sulfenylindoles and 3-selenylindoles

  摘要：

  The copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides has been achieved under mild reaction conditions using the weak base Cs2CO3 in combination with air oxidant, providing a convenient and efficient method for synthesis of 3-sulfenylindoles and 3-selenylindoles, including complex products bearing two attached 3-sulfenylindole rings. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.052

文献信息

• Microwave assisted metal-/oxidant-free cascade electrophilic sulfenylation/5-endo-dig cyclization of 2-alkynylanilines to generate diversified 3-sulfenylindoles
  作者：Shivani Sharma、Ramdas S. Pathare、Sukanya、Antim K. Maurya、Bhagyashree Goswami、Vijai K. Agnihotri、Devesh M. Sawant、Ram T. Pardasani

  DOI：10.1016/j.tetlet.2017.08.046

  日期：2017.10

  A metal-/oxidant-free sustainable protocol for the synthesis of 3-sulfenylindoles based on electrophilic cyclization of 2-alkynylanilines has been developed under microwave irradiation. Herein, catalytic amount of iodine and stoichiometric amount of sulfonyl hydrazides were employed as catalyst and electrophiles respectively to induce the 5-endo-dig cyclization of 2-alkynylanilines. This strategy allows a wide substrate scope, demonstrates good functional group tolerance, utilizes easily available reagents and overcome multistep synthesis. (C) 2017 Elsevier Ltd. All rights reserved.