2-(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)ethanamine | 1269020-03-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)ethanamine
• CAS: 1269020-03-2
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: LYCZDAMZPDXVLC-UHFFFAOYSA-N

物化性质

• 熔点：
  94-96 °C(Solvent: Ligroine)
• 沸点：
  394.2±37.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)ethanamine 、 苯甲醛 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.25h， 以61%的产率得到2-benzyl-4-phenyl-7-(4-methoxyphenyl)-1H-pyrrolo[3,2-c]pyridine
  参考文献：
  名称：

  Synthesis of tetrahydro-5-azaindoles and 5-azaindoles using Pictet–Spengler reaction—appreciable difference in products using different acid catalysts

  摘要：

  Pictet-Spengler condensation of 2-(aryl)-2-(1H-pyrrol-2-yl)ethanamines using conventional acid catalysts like TMSCl or TFA resulted in the formation of substituted 5-azaindoles involving a tandem one pot four steps reaction sequence. By contrast use of glacial acetic acid furnished the targeted tetrahydro-5-azaindoles in diastereoselective manner. These were readily dehydrogenated to 5-azaindoles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.003
• 作为产物：
  描述：

  2-(1'-(4''-methoxyphenyl)-2'-nitroethyl)-1H-pyrrole 在 氢气 作用下， 以 甲醇 为溶剂， 以91%的产率得到2-(4-methoxyphenyl)-2-(1H-pyrrol-2-yl)ethanamine
  参考文献：
  名称：

  Synthesis of tetrahydro-5-azaindoles and 5-azaindoles using Pictet–Spengler reaction—appreciable difference in products using different acid catalysts

  摘要：

  Pictet-Spengler condensation of 2-(aryl)-2-(1H-pyrrol-2-yl)ethanamines using conventional acid catalysts like TMSCl or TFA resulted in the formation of substituted 5-azaindoles involving a tandem one pot four steps reaction sequence. By contrast use of glacial acetic acid furnished the targeted tetrahydro-5-azaindoles in diastereoselective manner. These were readily dehydrogenated to 5-azaindoles. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.12.003

文献信息

• Synthesis of tetrahydro-5-azaindoles and 5-azaindoles using Pictet–Spengler reaction—appreciable difference in products using different acid catalysts
  作者：Abdullah M.A. Shumaila、Vedavati G. Puranik、Radhika S. Kusurkar

  DOI：10.1016/j.tet.2010.12.003

  日期：2011.2

  Pictet-Spengler condensation of 2-(aryl)-2-(1H-pyrrol-2-yl)ethanamines using conventional acid catalysts like TMSCl or TFA resulted in the formation of substituted 5-azaindoles involving a tandem one pot four steps reaction sequence. By contrast use of glacial acetic acid furnished the targeted tetrahydro-5-azaindoles in diastereoselective manner. These were readily dehydrogenated to 5-azaindoles. (C) 2010 Elsevier Ltd. All rights reserved.