2-(4-Chloro-phenyl)-4,6-dimethoxy-1H-indole | 827024-94-2

• 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-(4-Chloro-phenyl)-4,6-dimethoxy-1H-indole
• 英文别名: 2-(4-Chlorophenyl)-4,6-dimethoxy-1H-indole；2-(4-chlorophenyl)-4,6-dimethoxy-1H-indole
• CAS: 827024-94-2
• 化学式: C₁₆H₁₄ClNO₂
• 分子量: 287.746
• InChiKey: IGSYCDHTXOCIIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-Dimethoxy-2-(p-chlorophenyl)-ethanol 在 对甲苯磺酸 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 14.5h， 生成 2-(4-Chloro-phenyl)-4,6-dimethoxy-1H-indole
  参考文献：
  名称：

  Investigation and Application of Amphoteric α-Amino Aldehyde: An in Situ Generated Species Based on Heyns Rearrangement

  摘要：

  In situ generation of the reactive amphoteric a amino aldehyde with simple alpha-hydroxy ketones and phenyl amine-via Heyns rearrangement was proven to be feasible. Metal-free domino reactions based on this reactive intermediate were effectively used to afford important N-heterocycles including polysubstituted pyrroles, indoles, and quinoxalines conveniently. A simple starting material, water as the only byproduct, and diversity of the useful products will make this method greatly attractive for pharmaceutics.

  DOI：

  10.1021/acs.orglett.6b02133

文献信息

• Synthesis of activated 3-substituted indoles: an optimised one-pot procedure
  作者：Karin Pchalek、Ashley W. Jones、Monique M.T. Wekking、David StC. Black

  DOI：10.1016/j.tet.2004.10.060

  日期：2005.1

  3-Substituted-4,6-dimethoxyindoles can be synthesised in a one-pot procedure from 3,5-dimethoxyaniline and 2-haloketones in the presence of lithium bromide and sodium bicarbonate. (C) 2004 Elsevier Ltd. All rights reserved.
• Investigation and Application of Amphoteric α-Amino Aldehyde: An in Situ Generated Species Based on Heyns Rearrangement
  作者：Guangxun Li、Ling Tang、Hongxin Liu、Yingwei Wang、Gang Zhao、Zhuo Tang

  DOI：10.1021/acs.orglett.6b02133

  日期：2016.9.16

  In situ generation of the reactive amphoteric a amino aldehyde with simple alpha-hydroxy ketones and phenyl amine-via Heyns rearrangement was proven to be feasible. Metal-free domino reactions based on this reactive intermediate were effectively used to afford important N-heterocycles including polysubstituted pyrroles, indoles, and quinoxalines conveniently. A simple starting material, water as the only byproduct, and diversity of the useful products will make this method greatly attractive for pharmaceutics.