N-((1H-indol-3-yl)(3-nitrophenyl)methyl)-N-methylbenzenamine | 1314029-55-4

• 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-((1H-indol-3-yl)(3-nitrophenyl)methyl)-N-methylbenzenamine
• 英文别名: N-[1H-indol-3-yl-(3-nitrophenyl)methyl]-N-methylaniline
• CAS: 1314029-55-4
• 化学式: C₂₂H₁₉N₃O₂
• 分子量: 357.412
• InChiKey: SEIMEJUTESNORB-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 、 间硝基苯甲醛 、 N-甲基苯胺 在 ferric hydrogen sulfate 作用下， 以 neat (no solvent) 为溶剂， 反应 2.0h， 以96%的产率得到N-((1H-indol-3-yl)(3-nitrophenyl)methyl)-N-methylbenzenamine
  参考文献：
  名称：

  Fe（HSO4）3作为可循环利用催化剂的单锅无溶剂合成某些叔吲哚基甲烷胺衍生物

  摘要：

  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。

  DOI：

  10.1002/jccs.201400192

文献信息

• 3-Substitued indoles: One-pot synthesis and evaluation of anticancer and Src kinase inhibitory activities
  作者：V. Kameshwara Rao、Bhupender S. Chhikara、Amir Nasrolahi Shirazi、Rakesh Tiwari、Keykavous Parang、Anil Kumar

  DOI：10.1016/j.bmcl.2011.05.010

  日期：2011.6

  An efficient and economical method was developed for the synthesis of 3-substituted indoles by one-pot three-component coupling reaction of a substituted or unsubstituted benzaldehyde, N-methylaniline, and indole or N-methylindole using Yb(OTf)(3)-SiO2 as a catalyst. All the synthesized compounds were evaluated for inhibition of cell proliferation of human colon carcinoma (HT-29), human ovarian adenocarcinoma (SK-OV-3), and c-Src kinase activity. The 4-methylphenyl (4o and 4p) and 4-methoxyphenyl (4q) indole derivatives inhibited the cell proliferation of SK-OV-3 and HT-29 cells by 70-77% at a concentration of 50 mu M. The unsubstituted phenyl (4d) and 3-nitrophenyl (4l) derivatives showed the inhibition of c-Src kinase with IC50 values of 50.6 and 58.3 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• A convenient one-pot three component synthesis of 3-aminoalkylated indoles catalyzed by 3-chlorophenylboronic acid
  作者：Santosh V. Goswami、Prashant. B. Thorat、Vijay N. Kadam、Sachin A. Khiste、Sudhakar R. Bhusare

  DOI：10.1016/j.cclet.2013.03.024

  日期：2013.5

  An efficient protocol was developed for the synthesis of 3-aminoalkylated indoles using 3-chlorophenylboronic acid as a catalyst under ambient temperature conditions. The three-component reaction of indoles, aromatic aldehydes and N-methyl aniline offered corresponding 3-aminoalkylated indoles in excellent yields. This protocol presents some remarkable features such as mild reaction conditions, simple workup procedure and excellent yields. (C) 2013 Sudhakar R. Bhusare. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• 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。