2-[2-Nitro-1-(4-nitrophenyl)ethyl]-1H-pyrrole | 1210053-73-8

• 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-[2-Nitro-1-(4-nitrophenyl)ethyl]-1H-pyrrole
• CAS: 1210053-73-8
• 化学式: C₁₂H₁₁N₃O₄
• 分子量: 261.237
• InChiKey: JAIXFOGBMIUNLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吡咯 、 1-硝基,2-(4-硝基苯基)-乙烯 在 montmorillonite K₁₀ 作用下， 反应 0.58h， 以89%的产率得到2-[2-Nitro-1-(4-nitrophenyl)ethyl]-1H-pyrrole
  参考文献：
  名称：

  蒙脱石 K10：无溶剂条件下吲哚和吡咯与硝基烯烃的 Friedel-Crafts 烷基化催化剂

  摘要：

  发现蒙脱石 K10 在无溶剂条件下有效地催化吲哚或吡咯与硝基烯烃的迈克尔加成。值得注意的是反应时间短、后处理简单和收率高。绿色催化剂可以重复使用三个运行，而收率没有显着变化。

  DOI：

  10.1080/00397910903219344

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。
• Post-modified anionic nano-porous metal–organic framework as a novel catalyst for solvent-free Michael addition reactions
  作者：Saeideh Beheshti、Ali Morsali

  DOI：10.1039/c4ra05226a

  日期：——

  By the strategy developed here, a novel application of anionic metal–organic frameworks as heterogeneous catalysts has been introduced. We have been able to prepare a cation exchanged anionic MOF as a new heterogeneous catalytic system for solvent-free Michael addition of pyrrole to electron-deficient β-nitrostyrenes. This catalyst was easily recovered and reused for at least six reaction cycles without a significant degradation in activity.

  通过这里开发的策略，介绍了一种阴离子金属有机框架作为异质催化剂的新应用。我们成功制备了一种经过阳离子交换的阴离子MOF，作为一种新型的异质催化系统，用于无溶剂的吡咯与电子缺陷β-硝基苯乙烯的迈克尔加成反应。该催化剂易于回收，并可在至少六个反应周期内重复使用，且活性没有显著降低。
• 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.
• 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.
• Montmorillonite K10: Catalyst for Friedel–Crafts Alkylation of Indoles and Pyrrole with Nitroalkenes Under Solventless Conditions
  作者：Li-Tao An、Li-Li Zhang、Jian-Ping Zou、Guang-Liang Zhang

  DOI：10.1080/00397910903219344

  日期：2010.6.16

  Montmorillonite K10 was found to catalyze the Michael addition of indoles or pyrrole with nitroalkenes efficiently under solventless condition. The short reaction time, simple workup, and excellent yields were noteworthy. The green catalyst could be reused for three runs without considerable variation in yield.

  发现蒙脱石 K10 在无溶剂条件下有效地催化吲哚或吡咯与硝基烯烃的迈克尔加成。值得注意的是反应时间短、后处理简单和收率高。绿色催化剂可以重复使用三个运行，而收率没有显着变化。