2,5-bis(2-phenyl-1-aminoethyl)pyrrole | 1309577-42-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-bis(2-phenyl-1-aminoethyl)pyrrole
• 英文别名: 2-[5-(2-amino-1-phenylethyl)-1H-pyrrol-2-yl]-2-phenylethanamine
• CAS: 1309577-42-1
• 化学式: C₂₀H₂₃N₃
• 分子量: 305.423
• InChiKey: UJVOUIUHECYDFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.8
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,5-bis(2-phenyl-1-aminoethyl)pyrrole 在 5% Pd(II)/C(eggshell) 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 生成 1,8-diphenyl-4,5-di(4-nitrophenyl)-9H-dipyrido-[4,3-b;3',4'-d]pyrrole
  参考文献：
  名称：

  Diastereoselective synthesis of tetrasubstituted-octahydro-3,6-diazacarbazoles and tetrasubstituted-3,6-diazacarbazoles via double Pictet–Spengler reaction

  摘要：

  Pictet-Spengler condensation of 2,5-bis(2-phenyl-1-aminoethyl)pyrrole using glacial acetic acid afforded only one diastereomer of unreported tetrasubstituted-octahydro-3,6-diazacarbazoles. These were readily dehydrogenated to tetrasubstituted-3,6-diazacarbazoles. The stereoselectivity in the Pictet-Spengler reaction has been demonstrated using single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.060
• 作为产物：
  描述：

  2,5-bis(2-nitro-1-phenylethyl)-1H-pyrrole 在 氢气 作用下， 以 甲醇 为溶剂， 以92%的产率得到2,5-bis(2-phenyl-1-aminoethyl)pyrrole
  参考文献：
  名称：

  Diastereoselective synthesis of tetrasubstituted-octahydro-3,6-diazacarbazoles and tetrasubstituted-3,6-diazacarbazoles via double Pictet–Spengler reaction

  摘要：

  Pictet-Spengler condensation of 2,5-bis(2-phenyl-1-aminoethyl)pyrrole using glacial acetic acid afforded only one diastereomer of unreported tetrasubstituted-octahydro-3,6-diazacarbazoles. These were readily dehydrogenated to tetrasubstituted-3,6-diazacarbazoles. The stereoselectivity in the Pictet-Spengler reaction has been demonstrated using single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.060

文献信息

• Diastereoselective synthesis of tetrasubstituted-octahydro-3,6-diazacarbazoles and tetrasubstituted-3,6-diazacarbazoles via double Pictet–Spengler reaction
  作者：Abdullah M.A. Shumaila、Vedavati G. Puranik、Radhika S. Kusurkar

  DOI：10.1016/j.tetlet.2011.03.060

  日期：2011.5

  Pictet-Spengler condensation of 2,5-bis(2-phenyl-1-aminoethyl)pyrrole using glacial acetic acid afforded only one diastereomer of unreported tetrasubstituted-octahydro-3,6-diazacarbazoles. These were readily dehydrogenated to tetrasubstituted-3,6-diazacarbazoles. The stereoselectivity in the Pictet-Spengler reaction has been demonstrated using single crystal X-ray analysis. (C) 2011 Elsevier Ltd. All rights reserved.