1-p-tolyl-3H-pyrrolo[1,2-a]indole-2-carbaldehyde | 914983-16-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醛
• 英文名称: 1-p-tolyl-3H-pyrrolo[1,2-a]indole-2-carbaldehyde
• 英文别名: 3-(4-methylphenyl)-1H-pyrrolo[1,2-a]indole-2-carbaldehyde
• CAS: 914983-16-7
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: JIJHHQGMQDKTEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-p-tolyl-3H-pyrrolo[1,2-a]indole-2-carbaldehyde 以 氘代氯仿 为溶剂， 反应 24.0h， 生成 1-p-tolyl-9H-pyrrolo[1,2-a]indole-2-carbaldehyde
  参考文献：
  名称：

  TiCl₄/t-BuNH₂-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-a]indol-2-carbaldehydes

  摘要：

  [GRAPHICS]An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[ 1,2-a] indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multiactivity reagent: catalyst/Lewis acid/water scavenger. Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.

  DOI：

  10.1021/ol061872u
• 作为产物：
  描述：

  (1H-吲哚-2-基)(4-甲基苯基)甲酮 在 四丁基溴化铵 、 四氯化钛 sodium hydroxide 、 叔丁胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 1-p-tolyl-3H-pyrrolo[1,2-a]indole-2-carbaldehyde
  参考文献：
  名称：

  TiCl₄/t-BuNH₂-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-a]indol-2-carbaldehydes

  摘要：

  [GRAPHICS]An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[ 1,2-a] indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multiactivity reagent: catalyst/Lewis acid/water scavenger. Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.

  DOI：

  10.1021/ol061872u

文献信息

• TiCl₄/<i>t</i>-BuNH₂-Promoted Hydroamination/Annulation of δ-Keto-acetylenes:  Synthesis of Novel Pyrrolo[1,2-<i>a</i>]indol-2-carbaldehydes
  作者：Giorgio Abbiati、Alessandro Casoni、Valentina Canevari、Donatella Nava、Elisabetta Rossi

  DOI：10.1021/ol061872u

  日期：2006.10.1

  [GRAPHICS]An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[ 1,2-a] indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multiactivity reagent: catalyst/Lewis acid/water scavenger. Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.