2-bromo-1-[(E)-7-phenylhept-6-en-4-ynyl]-1H-indole-3-carboxaldehyde | 568571-19-7

• 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: 2-bromo-1-[(E)-7-phenylhept-6-en-4-ynyl]-1H-indole-3-carboxaldehyde
• 英文别名: 2-bromo-1-[(E)-7-phenylhept-6-en-4-ynyl]indole-3-carbaldehyde
• CAS: 568571-19-7
• 化学式: C₂₂H₁₈BrNO
• 分子量: 392.295
• InChiKey: OFPHTSBCDVTGSN-VZUCSPMQSA-N

物化性质

• 沸点：
  563.0±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2-bromo-1-[(E)-7-phenylhept-6-en-4-ynyl]-1H-indole-3-carboxaldehyde 在 palladium diacetate 、 sodium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 3-[(E)-β-styryl]-5,6-dihydro-4H-indolo[3,2,1-ij]-1,6-naphthyridine
  参考文献：
  名称：

  Synthesis of Annulated γ-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes

  摘要：

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.

  DOI：

  10.1021/jo0343228
• 作为产物：
  描述：

  E-styryl iodide 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 27.0h， 生成 2-bromo-1-[(E)-7-phenylhept-6-en-4-ynyl]-1H-indole-3-carboxaldehyde
  参考文献：
  名称：

  Synthesis of Annulated γ-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes

  摘要：

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.

  DOI：

  10.1021/jo0343228

文献信息

• Synthesis of Annulated <i>γ</i>-Carbolines and Heteropolycycles by the Palladium-Catalyzed Intramolecular Annulation of Alkynes
  作者：Haiming Zhang、Richard C. Larock

  DOI：10.1021/jo0343228

  日期：2003.6.1

  A variety of N-substituted 2-bromo-1H-indole-3-carboxaldehydes incorporating an alkyne-containing tether on the indole nitrogen have been converted to the corresponding tert-butylimines, which have been subjected to palladium-catalyzed intramolecular iminoannulation, affording various gamma-carboline derivatives with an additional ring fused across the 4- and 5-positions in good to excellent yields. When the tethered carbon-carbon triple bond is terminal or substituted with a triethylsilyl group, the iminoannulation generates a tert-butyl-gamma-carbolinium salt as the major product. The palladium-catalyzed intramolecular annulations of N-substituted 2-bromo-1H-indole-3-carboxaldehyde, methyl 2-iodo-1H-indole-3-carboxylate, and 2-iodo-3-phenyl-1H-indole containing a phenylpentynyl tether produce the corresponding heteropolycycles in moderate to good yields.