[(cyclohexyl)(1H-indol-3-yl)methyl]-methyl-phenyl-amine | 1173282-78-4

• 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: [(cyclohexyl)(1H-indol-3-yl)methyl]-methyl-phenyl-amine
• 英文别名: N-[cyclohexyl(1H-indol-3-yl)methyl]-N-methylaniline
• CAS: 1173282-78-4
• 化学式: C₂₂H₂₆N₂
• 分子量: 318.462
• InChiKey: NNVUSVKUZOXTBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 、 环己甲醇 在 Iron(III) nitrate nonahydrate 、 2,2,6,6-四甲基哌啶氧化物 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 生成 [(cyclohexyl)(1H-indol-3-yl)methyl]-methyl-phenyl-amine
  参考文献：
  名称：

  Iron mediated one pot three component synthesis of 3-substituted indoles via aerobic iminium ion formation

  摘要：

  An efficient and economical method was developed for the synthesis of 3 substituted indoles by a highly efficient one-pot three component coupling reaction of substituted or unsubstituted benzyl alcohol, N-methyl aniline or pyrrolidine, and indoles or substituted indoles. (C) 2015 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2015.12.047

文献信息

• Micelle promoted multicomponent synthesis of 3-amino alkylated indoles via a Mannich-type reaction in water
  作者：Atul Kumar、Maneesh Kumar Gupta、Mukesh Kumar、Deepti Saxena

  DOI：10.1039/c2ra22428c

  日期：——

  An efficient micelle promoted one-pot synthesis of 3-amino alkylated indoles has been developed via a three-component Mannich-type reaction from secondary amines, aldehydes and indoles in water under mild reaction conditions. In this Mannich-type reaction, micelles stabilize iminium ions, which undergo a nucleophilic addition of the indole to give 3-amino alkylated indoles in very good yields.

  在温和的反应条件下，通过仲胺、醛和吲哚在水中的三组分曼尼希式反应，开发出了一种高效的胶束促进的单锅合成 3-氨基烷基化吲哚的方法。在这种曼尼希式反应中，胶束稳定了铵离子，铵离子与吲哚发生亲核加成反应，从而以非常高的产率得到 3-氨基烷基化吲哚。
• Zwitterionic-Type Molten Salt: A Mild and Efficient Organocatalyst for the Synthesis of 3-Aminoalkylated Indoles via Three-Component Coupling Reaction
  作者：Alakananda Hajra、Dhiman Kundu、Avik Bagdi、Adinath Majee

  DOI：10.1055/s-0030-1259940

  日期：2011.5

  A general and efficient method has been developed for the synthesis of 3-aminoalkylated indoles by a three-component coupling of indoles, aldehydes, and amines in the presence of a catalytic amount of zwitterionic-type molten salt under solvent-free conditions. The non-hazardous experimental procedure, mild reaction conditions, and the reusability of the catalyst are the notable advantages of the present

  在催化量的两性离子型熔盐存在下，在无溶剂条件下，通过吲哚、醛和胺的三组分偶联，开发了一种通用且有效的合成 3-氨基烷基化吲哚的方法。本方法的显着优点是无危险的实验程序、温和的反应条件和催化剂的可重复使用性。
• One-pot three-component coupling reaction: solvent-free synthesis of novel 3-substituted indoles catalyzed by PMA–SiO2
  作者：P. Srihari、Vinay K. Singh、Dinesh C. Bhunia、J.S. Yadav

  DOI：10.1016/j.tetlet.2009.02.176

  日期：2009.7

  Solvent-free PMA–SiO2-catalyzed synthesis of 3-substituted indole derivatives by a one-pot three-component coupling reaction between aldehyde, N-methyl aniline and indole is described.

  描述了无溶剂的PMA-SiO 2催化醛，N-甲基苯胺和吲哚之间的一锅三组分偶联反应，合成了3-取代的吲哚衍生物。
• Bromodimethylsulfonium bromide (BDMS)-catalyzed multicomponent synthesis of 3-aminoalkylated indoles
  作者：Deepak K. Yadav、Rajesh Patel、Vishnu P. Srivastava、Geeta Watal、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2010.08.065

  日期：2010.10

  Bromodimethylsulfonium bromide (BDMS)-catalyzed three-component coupling reaction between indoles, aldehydes, and N-alkylanilines is reported to access substituted 3-aminoalkylated indoles at room temperature in high yields (82-96%) within 1.5-3.5 h. The salient features of this protocol are the simplicity of the procedure, the ready accessibility of the catalyst, its cost effectiveness, and higher yields in relatively short reaction times. (C) 2010 Elsevier Ltd. All rights reserved.