N-((3-indolyl)(4-nitrophenyl)methyl)-N-methylaniline | 1173282-76-2

• 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: N-((3-indolyl)(4-nitrophenyl)methyl)-N-methylaniline
• 英文别名: N-[1H-indol-3-yl-(4-nitrophenyl)methyl]-N-methylaniline
• CAS: 1173282-76-2
• 化学式: C₂₂H₁₉N₃O₂
• 分子量: 357.412
• InChiKey: GSJLZCVFTLMTPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  27
• 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：
  64.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 以 甲苯 为溶剂， 生成 N-((3-indolyl)(4-nitrophenyl)methyl)-N-methylaniline
  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。
• One-pot Solvent Free Synthesis of Some Tert-indolylmethane Amine Derivatives by Fe(HSO₄)₃as a Recyclable Catalyst
  作者：Mohammad Rahimizadeh、Hossein Eshghi、Majid Mokaber-Esfahani、Mostafa Gholizadeh

  DOI：10.1002/jccs.201400192

  日期：2014.11

  Solvent‐free synthesis of 3‐substituted indole derivatives by a one‐pot three‐component coupling reaction between aldehyde, N‐alkyl aniline and indole by Fe(HSO4)3 catalyzed is described. The noticeable features of this protocol are the simplicity of the procedure, easy synthesized, recyclable and inexpensive catalyst, no organic solvent and high yields in relatively short reaction times.

  描述了通过Fe（HSO 4）3催化的醛，N-烷基苯胺和吲哚之间的一锅三组分偶联反应，无溶剂合成3-取代的吲哚衍生物。该方案的显着特征是操作简单，易于合成，可回收且廉价的催化剂，无有机溶剂且在相对较短的反应时间内具有较高的收率。