1-(3-methylphenyl)-1H-indole-3-carbaldehyde

• 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-(3-methylphenyl)-1H-indole-3-carbaldehyde
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: LGBCXGLIDVULOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(3-methylphenyl)-1H-indole-3-carbaldehyde 、 二苯基乙炔 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 cesium pivalate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以71%的产率得到2-methyl-5,6-diphenylindolo[1,2-a]quinoline
  参考文献：
  名称：

  Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C–H Activation: A Facile Access to Diverse Indolo[1,2-a]quinolines

  摘要：

  The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh(III)-catalyzed C-H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo[1,2-a]quinoline structures. As illustrative examples, a concise three-step synthesis of indolo[1,2-a]quinoline-based sensitizers is accomplished that exhibits the potential of C-H activation in the construction of organic optoelectronic materials.

  DOI：

  10.1021/acs.orglett.5b01171
• 作为产物：
  描述：

  3-吲哚甲醛 、 间碘甲苯 在 copper(I) oxide 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以75%的产率得到1-(3-methylphenyl)-1H-indole-3-carbaldehyde
  参考文献：
  名称：

  New 1-arylindoles based serotonin 5-HT7 antagonists. Synthesis and binding evaluation studies

  摘要：

  Based on 5-HT1A and 5-HT7 ligand MR25003 scaffold, a new series of 1-aryl indole analogues were prepared and evaluated against 5-HT7 receptors. Modulations of aryl moieties provided a large number of new indolic derivatives. Most of compounds tested have displayed 5-HT7 affinity in the nanomolar range. Among them, 1-(naphthyl)indole derivative 3p (Ki (5-HT7) = 4.5 nM) showed also a good selectivity over 5-HT1A, 5-HT2A and 5-HT6 receptors. This compound was pharmacology characterized as an antagonist. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.055

文献信息

• Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C–H Activation: A Facile Access to Diverse Indolo[1,2-<i>a</i>]quinolines
  作者：Xingyan Liu、Xiaoyu Li、Hu Liu、Qiang Guo、Jingbo Lan、Ruilin Wang、Jingsong You

  DOI：10.1021/acs.orglett.5b01171

  日期：2015.6.19

  The aldehyde group has been developed for the first time as a traceless directing group to promote regioselective Rh(III)-catalyzed C-H activation/cyclization of indolyl aldehydes with alkynes. This protocol streamlines access to a variety of appealing indolo[1,2-a]quinoline structures. As illustrative examples, a concise three-step synthesis of indolo[1,2-a]quinoline-based sensitizers is accomplished that exhibits the potential of C-H activation in the construction of organic optoelectronic materials.
• New 1-arylindoles based serotonin 5-HT7 antagonists. Synthesis and binding evaluation studies
  作者：Charlène Sagnes、Guy Fournet、Grzegorz Satala、Andrzej J. Bojarski、Benoît Joseph

  DOI：10.1016/j.ejmech.2014.01.055

  日期：2014.3

  Based on 5-HT1A and 5-HT7 ligand MR25003 scaffold, a new series of 1-aryl indole analogues were prepared and evaluated against 5-HT7 receptors. Modulations of aryl moieties provided a large number of new indolic derivatives. Most of compounds tested have displayed 5-HT7 affinity in the nanomolar range. Among them, 1-(naphthyl)indole derivative 3p (Ki (5-HT7) = 4.5 nM) showed also a good selectivity over 5-HT1A, 5-HT2A and 5-HT6 receptors. This compound was pharmacology characterized as an antagonist. (C) 2014 Elsevier Masson SAS. All rights reserved.