3-((3-methoxyphenyl)(pyrrolidin-1-yl)methyl)-1H-indole | 1360151-13-8

• 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: 3-((3-methoxyphenyl)(pyrrolidin-1-yl)methyl)-1H-indole
• 英文别名: 3-[(3-methoxyphenyl)-pyrrolidin-1-ylmethyl]-1H-indole
• CAS: 1360151-13-8
• 化学式: C₂₀H₂₂N₂O
• 分子量: 306.407
• InChiKey: IWSUVDJJNVKZMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  四氢吡咯 、 吲哚 、 3-甲氧基苯甲醛 在 L-脯氨酸 作用下， 反应 6.0h， 以86%的产率得到3-((3-methoxyphenyl)(pyrrolidin-1-yl)methyl)-1H-indole
  参考文献：
  名称：

  l-Proline catalysed multicomponent synthesis of 3-amino alkylated indolesvia a Mannich-type reaction under solvent-free conditions

  摘要：

  已开发出一种高效的L-脯氨酸催化的一锅法合成3-氨基烷基吲哚，通过三组分Mannich反应，即在室温下无溶剂条件下的二级胺、醛和吲哚。对多种氨基酸（酸性、碱性和中性）进行了筛选，但最佳结果是使用L-脯氨酸。

  DOI：

  10.1039/c1gc16297g

文献信息

• Catalyst-free, Solvent-promoted and Scalable Multicomponent Synthesis of 3-Aminoalkylated Indoles via a Mannich-type Reaction
  作者：Jian-Fei Cao、Yan-Li Chen、Zhi Guan、Yan-Hong He

  DOI：10.5560/znb.2014-3313

  日期：2014.6.1

  A catalyst-free, solvent-promoted and scalable three-component Mannich-type reaction of indoles, aromatic aldehydes and secondary amines for the synthesis of 3-(1-dialkylaminoalkyl)-1H-indoles has been developed. The protocol provided a mild, simple and highly atom-economic alternative to prepare the title compounds, and the corresponding products could be obtained in good to excellent yields in most cases.

  为合成 3-(1-二烷基氨基烷基)-1H-吲哚，开发了一种无催化剂、溶剂促进和可扩展的吲哚、芳香醛和仲胺三组分曼尼希式反应。该方案为制备标题化合物提供了一种温和、简单且原子经济性高的替代方法，而且在大多数情况下都能以良好至极佳的收率获得相应的产物。
• 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.