N-butyl-5-chloro-1H-indole-2-carboxamide

• 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-butyl-5-chloro-1H-indole-2-carboxamide
• 化学式: C₁₃H₁₅ClN₂O
• 分子量: 250.728
• InChiKey: HZNLABYUBBSRTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-butyl-5-chloro-1H-indole-2-carboxamide 在 lithium aluminium tetrahydride 作用下， 以 1,4-二氧六环 为溶剂， 以774 mg的产率得到N-[(5-chloro-1H-indol-2-yl)methyl]butan-1-amine
  参考文献：
  名称：

  Synthesis of Heteroarylogous 1H-Indole-3-carboxamidines via a Three-Component Interrupted Ugi Reaction

  摘要：

  A novel one-pot multicomponent synthesis of heteroarylogous 1H-indole-3-carboxamidines starting from readily available N-alkyl-N-(1H-indol-2-ylmethyl) amines, isocyanides, and carbonyl compounds is reported. The strategy exploits the ability of the indole nucleus to interrupt the classical Ugi reaction, by intercepting the nascent nitrilium ion.

  DOI：

  10.1055/s-0034-1378921
• 作为产物：
  描述：

  5-氯吲哚-2-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-butyl-5-chloro-1H-indole-2-carboxamide
  参考文献：
  名称：

  Synthesis of Heteroarylogous 1H-Indole-3-carboxamidines via a Three-Component Interrupted Ugi Reaction

  摘要：

  A novel one-pot multicomponent synthesis of heteroarylogous 1H-indole-3-carboxamidines starting from readily available N-alkyl-N-(1H-indol-2-ylmethyl) amines, isocyanides, and carbonyl compounds is reported. The strategy exploits the ability of the indole nucleus to interrupt the classical Ugi reaction, by intercepting the nascent nitrilium ion.

  DOI：

  10.1055/s-0034-1378921

文献信息

• A domino approach to pyrazino- indoles and pyrroles using vinyl selenones
  作者：Martina Palomba、Luca Sancineto、Francesca Marini、Claudio Santi、Luana Bagnoli

  DOI：10.1016/j.tet.2018.10.044

  日期：2018.12

  Herein we disclose an efficient and flexible approach to biologically relevant 3,4-dihydropyrazino[1,2-alpha] indol-1(2H)ones and 3,4-dihydropyrrolo[1,2-alpha]pyrazin-1(2H)ones through a domino Michael/intra-molecular nucleophilic substitution pathway using potassium hydroxide in dichloromethane. Variously substituted vinyl selenones and 1H-indole-2-carboxamides or 1H-pyrrole-2-carboxamides have been employed with success in chemo and regio-selective processes. The introduction of an amino acid portion on the amidic function is well tolerated without racemization. (C) 2018 Elsevier Ltd. All rights reserved.