(1-prop-2-ynyl-1H-indol-2-yl)-p-tolyl-methanone | 914983-09-8

• 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: (1-prop-2-ynyl-1H-indol-2-yl)-p-tolyl-methanone
• 英文别名: (4-Methylphenyl)-(1-prop-2-ynylindol-2-yl)methanone；(4-methylphenyl)-(1-prop-2-ynylindol-2-yl)methanone
• CAS: 914983-09-8
• 化学式: C₁₉H₁₅NO
• 分子量: 273.334
• InChiKey: SJMCSXMENKEAKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• 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-prop-2-ynyl-1H-indol-2-yl)-p-tolyl-methanone 在 四氯化钛 叔丁胺 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以75%的产率得到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 Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.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
• 作为产物：
  描述：

  1H-吲哚-2-羰酰氯 在 palladium diacetate 、 四丁基溴化铵 sodium hydroxide 、 potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 (1-prop-2-ynyl-1H-indol-2-yl)-p-tolyl-methanone
  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 Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.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.