2-(1'-(4''-methoxyphenyl)-2'-nitroethyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(1'-(4''-methoxyphenyl)-2'-nitroethyl)-1H-pyrrole
• 英文别名: 2-[1-(4-methoxyphenyl)-2-nitroethyl]-1H-pyrrole
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: GELXULNFWLSFGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 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：
  70.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  吡咯 、 4-甲氧基-β-硝基苯乙烯 在 氨基磺酸 作用下， 反应 4.0h， 以91%的产率得到2-(1'-(4''-methoxyphenyl)-2'-nitroethyl)-1H-pyrrole
  参考文献：
  名称：

  在无溶剂条件下，氨基磺酸催化吲哚和吡咯的迈克尔加成到缺电子的硝基烯烃中

  摘要：

  氨基磺酸（SA）在无溶剂条件下有效催化吲哚和吡咯的迈克尔加成至硝基烯烃，从而以良好或优异的收率得到相应的迈克尔加成物。

  DOI：

  10.1016/j.tetlet.2007.04.011

文献信息

• I2-catalyzed Michael addition of indole and pyrrole to nitroolefins
  作者：Chunchi Lin、Jianming Hsu、M.N.V. Sastry、Hulin Fang、Zhijay Tu、Ju-Tsung Liu、Yao Ching-Fa

  DOI：10.1016/j.tet.2005.09.038

  日期：2005.12

  generate indolyl nitroalkane 5 and pyrrolyl nitroalkane 7 in high yields using β-nitrostyrene and indole/pyrrole at room temperature in the presence of catalytic amount of iodine is reported. The short reaction times and high yields of product are noteworthy. Molecular iodine promoted Michael addition is operationally simple and efficient method compared to the known Lewis acids or rare earth metal

  报道了一种在室温下在催化量的碘存在下使用β-硝基苯乙烯和吲哚/吡咯的高产率生成吲哚基硝基烷5和吡咯基硝基烷7的简便有效的方法。值得注意的是反应时间短，产品产率高。与已知的路易斯酸或稀土金属催化剂相比，分子碘促进的迈克尔加成是操作简单有效的方法，可以高产率产生不同的吲哚基/吡咯基硝基烷。
• Enantioselective and Regioselective Friedel-Crafts Alkylation of Pyrroles with Nitroalkenes Catalyzed by a Tridentate Schiff Base-Copper Complex
  作者：Fengfeng Guo、Dalu Chang、Guoyin Lai、Tao Zhu、Shunshun Xiong、Sujing Wang、Zhiyong Wang

  DOI：10.1002/chem.201102206

  日期：2011.9.26

  On a (pyr)role: A mild and highly efficient catalytic system has been developed for the asymmetric Friedel–Crafts alkylation of pyrroles with nitroalkenes (see scheme). High yields, and excellent enantioselectivities and regioselectivities were obtained for a broad range of substrates. The synthetic utility of this methodology and mechanistic studies involving a novel, negative, nonlinear effect are

  在（吡咯）上：已开发出温和高效的催化体系，用于吡咯与硝基烯烃的不对称Friedel-Crafts烷基化反应（请参见方案）。对于宽范围的底物，获得了高产率，优异的对映选择性和区域选择性。还介绍了这种方法的综合效用和涉及新颖，负面，非线性效应的机理研究。
• Microwave-Assisted Addition of Pyrroles to Electron-Deficient Olefins: A Rapid Entry to<i>C</i>-Alkyl Pyrroles
  作者：Zhuang-Ping Zhan、Wen-Zhen Yang、Rui-Feng Yang

  DOI：10.1055/s-2005-872688

  日期：——

  A general procedure for the Michael addition of pyrroles with electron-deficient olefins using silica gel supported reagent under microwave irradiation, has been developed. This new method is fast, efficient, environmentally benign and solvent-free. A catalytic amount of BiCl 3 is employed for moderately bulk electron-deficient olefins.

  已经开发了在微波辐射下使用硅胶支持的试剂将吡咯与缺电子烯烃迈克尔加成的一般程序。这种新方法快速、高效、环保且无溶剂。催化量的 BiCl 3 用于中等体积的缺电子烯烃。
• 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。
• 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。