(1H-indol-2-yl)-thiophen-3-yl-methanone | 914983-06-5

• 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: (1H-indol-2-yl)-thiophen-3-yl-methanone
• 英文别名: 1H-indol-2-yl(thiophen-3-yl)methanone
• CAS: 914983-06-5
• 化学式: C₁₃H₉NOS
• 分子量: 227.287
• InChiKey: JLXSMWCSTYIHDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1H-indol-2-yl)-thiophen-3-yl-methanone 在 四丁基溴化铵 、 四氯化钛 sodium hydroxide 、 叔丁胺 作用下， 以 氘代氯仿 、 甲苯 为溶剂， 反应 32.0h， 生成 1-thiophen-3-yl-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 Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.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：

  3-噻吩硼酸 、 1H-吲哚-2-羰酰氯 在 palladium diacetate potassium carbonate 、 三(邻甲基苯基)磷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以74%的产率得到(1H-indol-2-yl)-thiophen-3-yl-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 Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.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

• Palladium-Catalyzed Domino C,N-Coupling/Carbonylation/Suzuki Coupling Reaction: An Efficient Synthesis of 2-Aroyl-/Heteroaroylindoles
  作者：Martin Arthuis、Renée Pontikis、Jean-Claude Florent

  DOI：10.1021/ol901875z

  日期：2009.10.15

  A convenient one-pot synthesis of 2-aroylindoles using a domino palladium-catalyzed C,N-coupling/carbonylation/C,C-coupling sequence is described. The reaction involved easily prepared 2-gem-dibromovinylanilines and boronic acids under carbon monoxide. Optimized reaction conditions allowed the construction of a wide variety of highly functionalized 2-aroyl-/heteroaroylindoles in satisfactory yields

  描述了使用多米诺钯催化的C，N偶联/羰基化/ C，C偶联序列方便地一锅合成2-芳基吲哚。所涉及的反应容易地制备2-偕- dibromovinylanilines和硼酸下一氧化碳。优化的反应条件允许以令人满意的产率构建各种高度官能化的2-芳酰基-/杂芳酰基吲哚。