1-(p-chlorophenyl)-2-(n-hexyl)-1H-indole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(p-chlorophenyl)-2-(n-hexyl)-1H-indole
• 英文别名: 1-(4-Chlorophenyl)-2-hexylindole
• 化学式: C₂₀H₂₂ClN
• 分子量: 311.854
• InChiKey: AEZIBSNEYKCHGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-溴-2-辛-1-炔-1-基苯 、 对氯苯胺 在 copper(l) iodide 、 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以70%的产率得到1-(p-chlorophenyl)-2-(n-hexyl)-1H-indole
  参考文献：
  名称：

  General and Efficient Indole Syntheses Based on Catalytic Amination Reactions

  摘要：

  Highly flexible and efficient syntheses of the indole backbone are presented starting from o-alkynylhaloarenes. These transformations proceed via a palladium- or a copper-catalyzed amination reaction and a subsequent cyclization reaction in good to excellent yields. Furthermore. a multicatalytic one-pot indole synthesis starting from o-chloroiodobenzene is viable using a single catalyst consisting of an N-heterocyclic carbene palladium complex and Cul.

  DOI：

  10.1021/ol047649j

文献信息

• General and Efficient Indole Syntheses Based on Catalytic Amination Reactions
  作者：Lutz Ackermann

  DOI：10.1021/ol047649j

  日期：2005.2.1

  Highly flexible and efficient syntheses of the indole backbone are presented starting from o-alkynylhaloarenes. These transformations proceed via a palladium- or a copper-catalyzed amination reaction and a subsequent cyclization reaction in good to excellent yields. Furthermore. a multicatalytic one-pot indole synthesis starting from o-chloroiodobenzene is viable using a single catalyst consisting of an N-heterocyclic carbene palladium complex and Cul.
• Copper-Catalyzed<i>N</i>-Arylation/Hydroamin(d)ation Domino Synthesis of Indoles and its Application to the Preparation of a Chek1/KDR Kinase Inhibitor Pharmacophore
  作者：Lutz Ackermann、Sebastian Barfüßer、Harish K. Potukuchi

  DOI：10.1002/adsc.200900004

  日期：2009.5

  Abstractmagnified imageInexpensive copper catalysts allow for efficient syntheses of N‐aryl‐, N‐acyl‐, or N‐H‐(aza)indoles starting from ortho‐alkynylbromoarenes. The broad scope of this domino N‐arylation/hydroamin(d)ation process is highlighted by the synthesis of highly functionalized indoles, as well as of a Chek1/KDR inhibitor pharmacophore.