2,5-bis(1-(4-methoxyphenyl)-2-nitroethyl)-1H-pyrrole | 1246172-04-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,5-bis(1-(4-methoxyphenyl)-2-nitroethyl)-1H-pyrrole
• CAS: 1246172-04-2
• 化学式: C₂₂H₂₃N₃O₆
• 分子量: 425.441
• InChiKey: GSTUXMMBELCCCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.85
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  120.53
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  吡咯 、 1-(4-甲氧苯基)-2-硝基乙烯 在 silica gel 作用下， 反应 0.33h， 以89%的产率得到2,5-bis(1-(4-methoxyphenyl)-2-nitroethyl)-1H-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

• Silica Gel, an Effective Catalyst for the Reaction of Electron-Deficient Nitro-Olefins with Nitrogen Heterocycles
  作者：Abdullah M. A. Shumaila、Radhika S. Kusurkar

  DOI：10.1080/00397910903340694

  日期：2010.8.31

  The reaction of electron-deficient olefins with nitrogen heterocycles such as pyrrole and indole was examined in the presence of silica gel at room temperature under stirring at solvent-free conditions. It was found that silica gel is an effective catalyst for this conjugate addition. This work resulted in the formation of monosubstituted pyrroles selectively as a major product except in a few cases

  缺电子烯烃与氮杂环如吡咯和吲哚的反应在硅胶存在下在室温下在无溶剂条件下搅拌下进行了检查。发现硅胶是这种共轭加成的有效催化剂。这项工作导致选择性地形成单取代的吡咯作为主要产物，但在少数情况下双取代的吡咯也作为副产物形成。因此，建立了一种简单、快速、高效、环境友好且无溶剂的方法。
• Catalyst free conjugate addition of indoles and pyrroles to nitro alkenes under solvent free condition (SFC): an effective greener route to access 3-(2-nitro-1-phenylethyl)-1H-indole and 2-(2-nitro-1-phenylethyl)-1H-pyrrole derivatives
  作者：Pateliya Mujjamil Habib、Veerababurao Kavala、Chun-Wei Kuo、Mustafa J. Raihan、Ching-Fa Yao

  DOI：10.1016/j.tet.2010.05.104

  日期：2010.8

  Catalyst free conjugate addition of reactive hetero aromatics (pyrrole and indoles) to nitro alkenes under solvent free condition is described. This method provides several advantages, such as operational simplicity, solvent-free conditions and good yields of products. Also it is environmentally friendly and more cost effective alternative to existing protocols. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.
• 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.