N-[(4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl]-N-methylbenzenamine | 1173282-86-4

• 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: N-[(4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl]-N-methylbenzenamine
• 英文别名: [(4-chlorophenyl)(5-methyloxy-1H-indol-3-yl)methyl]-methyl-phenyl-amine；[(4-chlorophenyl)-(5-methoxy-1H-indol-3-yl)-methyl]-methyl-phenyl-amine；N-((4-Chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl)-N-methylbenzenamine；N-[(4-chlorophenyl)-(5-methoxy-1H-indol-3-yl)methyl]-N-methylaniline
• CAS: 1173282-86-4
• 化学式: C₂₃H₂₁ClN₂O
• 分子量: 376.886
• InChiKey: DDJJTFBBMURVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  28.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醇 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 N-[(4-chlorophenyl)(5-methoxy-1H-indol-3-yl)methyl]-N-methylbenzenamine
  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

• 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。
• Efficient metal-free green syntheses of 4<i>H</i>-chromenes and 3-amino alkylated indoles using a reusable graphite oxide carbocatalyst under aqueous and solvent-free reaction conditions
  作者：Lenida Kyndiah、Fillip Kumar Sarkar、Ajay Gupta、Amarta Kumar Pal

  DOI：10.1039/d2nj00756h

  日期：——

  Graphite oxide (GO) was utilized for the one-pot three-component syntheses of pharmaceutically important 4H-chromenes and 3-amino alkylated indoles in water and solvent-free reaction conditions, respectively. Spectroscopic techniques such as FT-IR, XPS, SEM, TEM, SAED, EDX, PXRD, Raman, and TGA confirmed the formation and thermal stability of GO. These protocols provide green and sustainable reaction

  氧化石墨 (GO) 分别用于在水和无溶剂反应条件下一锅三组分合成药学上重要的 4 H-色烯和 3-氨基烷基化吲哚。FT-IR、XPS、SEM、TEM、SAED、EDX、PXRD、拉曼和 TGA 等光谱技术证实了 GO 的形成和热稳定性。这些协议提供了绿色和可持续的反应条件，包括优异的催化活性、良好的产品产率、催化剂的可重复使用性、高官能团耐受性和克级合成。此外，本方法排除了金属毒性、金属废物处理、产品中的金属污染以及挥发性有机溶剂的使用等问题。
• Catalyst-free, ethylene glycol promoted one-pot three component synthesis of 3-amino alkylated indoles via Mannich-type reaction
  作者：U. Chinna Rajesh、Rohit Kholiya、V. Satya Pavan、Diwan S. Rawat

  DOI：10.1016/j.tetlet.2014.03.112

  日期：2014.4

  A highly efficient and sustainable approach for the multi-component synthesis of biologically important 3-amino alkylated indoles has been investigated via Mannich-type reaction under catalyst-free, ethylene glycol as a recyclable promoting medium. The wide applicability of the present method was examined with various substrates viz substituted aldehydes, indoles and secondary amines. This method will be useful for a large scale synthesis of 3-amino alkylated indoles without the use of column chromatography. The present method provides higher environmental compatibility and sustainability factors such as smaller E-factor (0.433) and higher atom-economy (AE = 93.3%). (C) 2014 Elsevier Ltd. All rights reserved.
• 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.