2-(1-cyclohexyl-2-nitroethyl)-1H-pyrrole | 1174172-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(1-cyclohexyl-2-nitroethyl)-1H-pyrrole
• 英文别名: (S)-2-(1-cyclohexyl-2-nitroethyl)-1H-pyrrole；2-[(1S)-1-cyclohexyl-2-nitroethyl]-1H-pyrrole
• CAS: 1174172-59-8
• 化学式: C₁₂H₁₈N₂O₂
• 分子量: 222.287
• InChiKey: IAHZWOZZPQSPBL-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  吡咯 、 2-硝基乙烯基环己烷 在 chiral dinuclear zinc catalyst 4 A molecular sieve 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2-(1-cyclohexyl-2-nitroethyl)-1H-pyrrole 、 2-(1-cyclohexyl-2-nitroethyl)-1H-pyrrole
  参考文献：
  名称：

  Asymmetric Friedel−Crafts Alkylation of Pyrroles with Nitroalkenes Using a Dinuclear Zinc Catalyst

  摘要：

  The catalytic enantioselective and atom economic Friedel-Crafts alkylation of pyrroles with nitroalkenes under mild reaction conditions using a dinuclear zinc catalyst is reported. The versatility of the reaction is demonstrated by the conversion of a number of differentially substituted nitroalkenes with differentially substituted pyrroles. Tandem addition reactions to form 2,5-disubstituted pyrroles are also demsonstrated. All pyrrole alkylations have been carried out without using N-protecting groups, which also enhances the efficiency by which substituted pyrroles may be synthesized. The reactions result in good yields and excellent enantioselectivities.

  DOI：

  10.1021/ja711080y

文献信息

• Asymmetric Friedel–Crafts reaction of N-heterocycles and nitroalkenes catalyzed by imidazoline–aminophenol–Cu complex
  作者：Naota Yokoyama、Takayoshi Arai

  DOI：10.1039/b904275j

  日期：——

  Catalytic asymmetric Friedel–Crafts reaction of pyrrole with nitroalkenes was smoothly catalyzed by newly synthesized nitro-substituted imidazoline–aminophenol (1b)–Cu complex to give the adduct with up to 92% ee.

  新合成的硝基取代咪唑啉–氨基苯酚 (1b)–铜复合物顺利催化了吡咯与硝基烯烃的催化不对称Friedel–Crafts反应，产物的对映体过量达到92%。
• Enantioselective Michael Addition of Pyrroles with Nitroalkenes in Aqueous Media Catalyzed by a Water-Soluble Catalyst
  作者：Yang Gui、Yanan Li、Jianan Sun、Zhenggen Zha、Zhiyong Wang

  DOI：10.1021/acs.joc.8b01141

  日期：2018.7.20

  A new water-soluble catalytic system was developed and used in an enantioselective Michael addition of pyrroles with nitroalkenes in water to afford nitroethylpyrrole derivatives with both excellent yields and ee values.

  开发了一种新的水溶性催化系统，并将其用于吡咯与硝基烯烃在水中的对映选择性迈克尔加成反应，从而获得具有优异收率和ee值的硝基乙基吡咯衍生物。