[(1H-indol-3-yl)-phenylmethyl]-methyl-phenyl-amine | 1173282-71-7

• 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: [(1H-indol-3-yl)-phenylmethyl]-methyl-phenyl-amine
• 英文别名: N-(3-indolyl-(phenyl)methyl)-N-methylaniline；N-((1H-Indol-3-yl)(phenyl)methyl)-N-methylbenzenamine；N-[1H-indol-3-yl(phenyl)methyl]-N-methylaniline
• CAS: 1173282-71-7
• 化学式: C₂₂H₂₀N₂
• 分子量: 312.414
• InChiKey: VEJUJYWYFTTZCE-UHFFFAOYSA-N

物化性质

• 熔点：
  145-147 °C
• 沸点：
  518.5±45.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  苯甲醇 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 [(1H-indol-3-yl)-phenylmethyl]-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 Synthesis of 3-[(<i>N</i>-Alkylanilino)(aryl)methyl]indoles via a Transition Metal Assisted Three-Component Condensation at Room Temperature
  作者：Goutam Brahmachari、Suvankar Das

  DOI：10.1002/jhet.1909

  日期：2014.8

  A simple and highly efficient protocol for the one-pot synthesis of a series of 3-[(N-alkylanilino)(aryl)methyl]indoles has been developed based on low-cost and environmentally benign zirconium oxychloride octahydrate and copper chloride dihydrate catalysts via three-component condensation between indoles, aromatic aldehydes, and N-alkylanilines at room temperature under neat condition. Mild reaction

  基于低成本，环境友好的八水合氯氧化锆和二水合氯化铜催化剂，开发了一种简单高效的协议，可以一锅合成一系列3-[（N-烷基苯胺基）（芳基）甲基]吲哚。室温，纯净条件下，吲哚，芳族醛和N-烷基苯胺之间的三组分缩合反应。温和的反应条件，操作简便，原子经济性高，在相对较短的反应时间内具有良好的收率，使用低成本和环境友好的催化剂是该协议的主要特征。
• A Facile Synthesis of 3-[(N-Alkylanilino)(aryl)methyl]indoles Using TCT¹
  作者：Biswanath Das、Jayprakash Kumar、Avula Kumar、Kongara Damodar

  DOI：10.1055/s-0029-1218637

  日期：2010.3

  Three component reaction of indoles, benzaldehydes, and N-alkylanilines in the presence of 2,4,6-trichloro-1,3,5-triazine (TCT) afforded the corresponding 3-[(N-alkylanilino)(aryl)methyl]indoles at room temperature in high yields (87-95%) within 1 to 2.5 hours.

  在2,4,6-三氯-1,3,5-三嗪（TCT）存在下，吲哚、苯甲醛和N-烷基苯胺的三元反应在室温下1至2.5小时内以高收率（87-95%）生成相应的3-[(N-烷基苯胺基)(芳基)甲基]吲哚。
• Cellulose–Sulfonic Acid: An Efficient, Recyclable, and Biodegradable Solid Acid Catalyst for the Synthesis of 3-Aminoalkylindoles
  作者：S. Satyanarayana、K. Praveen Kumar、P. Lakshmi Reddy、R. Narender、G. Narasimhulu、B. V. Subba Reddy

  DOI：10.1246/cl.130370

  日期：2013.9.5

  Three-component coupling (3CC) of indoles, aldehydes, and N-alkylanilines has been accomplished using a catalytic amount of cellulose–sulfonic acid under mild reaction conditions to furnish the 3-a...

  在温和的反应条件下，使用催化量的纤维素-磺酸完成了吲哚、醛和 N-烷基苯胺的三组分偶联 (3CC)，以提供 3-a...