2-[1-(3,4-dimethoxyphenyl)-2-nitroethyl]-1H-pyrrole | 1210053-72-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[1-(3,4-dimethoxyphenyl)-2-nitroethyl]-1H-pyrrole
• CAS: 1210053-72-7
• 化学式: C₁₄H₁₆N₂O₄
• 分子量: 276.292
• InChiKey: MQAVYBZMFGSLCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(3,4-dimethoxyphenyl)-2-nitroethyl]-1H-pyrrole 在 氢气 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 15.25h， 生成 2-benzyl-4-phenyl-7-(3,4-dimethoxyphenyl)-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：

  吡咯 、 1,2-dimethoxy-4-(2-nitro-vinyl)-benzene 在 silica gel 作用下， 反应 3.0h， 以83%的产率得到2-[1-(3,4-dimethoxyphenyl)-2-nitroethyl]-1H-pyrrole
  参考文献：
  名称：

  硅胶，缺电子硝基烯烃与氮杂环反应的有效催化剂

  摘要：

  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。

  DOI：

  10.1080/00397910903340694

文献信息

• Microwave-Assisted Conjugate Addition of Pyrrole on Electron-Deficient Nitro-Olefins
  作者：Radhika S. Kusurkar、Nabil A. H. Alkobati

  DOI：10.1080/00397910903458025

  日期：2010.1.14

  Michael addition of pyrrole to -nitrovinyl compounds were carried out using microwave methodology. Monosubstituted pyrroles were obtained selectively in a major amount. Formation of novel product obtained during one of the reactions was explained by the double addition to nitrostyrene.
• 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。
• 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.