2-[1-(2-furyl)-2-nitroethyl]-1H-pyrrole | 1182279-96-4

• 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-(2-furyl)-2-nitroethyl]-1H-pyrrole
• 英文别名: (R)-2-(1-(furan-2-yl)-2-nitroethyl)-1H-pyrrole；2-((1R)-2-nitro-1-furylethyl)-1H-pyrrole；2-[(1R)-1-(furan-2-yl)-2-nitroethyl]-1H-pyrrole
• CAS: 1182279-96-4
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: UCBBBMGAQZYYOQ-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡咯 、 1-(2-糠酰)-2-硝基乙烯 在 (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 以90%的产率得到2-[1-(2-furyl)-2-nitroethyl]-1H-pyrrole
  参考文献：
  名称：

  Chiral Bro̷nsted Acid-Catalyzed Asymmetric Friedel−Crafts Alkylation of Pyrroles with Nitroolefins

  摘要：

  A highly efficient Friedel-Crafts reaction of pyrroles with nitroolefins by a chiral phosphoric acid was realized. With 5 mol % of catalyst, reactions conducted at rt afforded the 2-substituted or 2,5-disubstituted pyrroles in up to 94% ee for a wide range of substrates.

  DOI：

  10.1021/jo9013029

文献信息

• A heterotrimetallic Pd–Sm–Pd complex for asymmetric Friedel–Crafts alkylations of pyrroles with nitroalkenes
  作者：Guoqi Zhang

  DOI：10.1039/c2ob25074h

  日期：——

  Catalytic asymmetric Friedel–Crafts alkylations of pyrroles and nitroalkenes were carried out by using a novel heterotrimetallic Pd–Sm–Pd catalyst based on a simple chiral ligand 1, to give the adducts with high yields and up to 93% ee.

  采用一种基于简单手性配体1的新型异三金属Pd–Sm–Pd催化剂，进行了吡咯和硝基烯烃的催化不对称Friedel–Crafts烷基化反应，获得了高产率和高达93%的对映体过剩。
• 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。
• Asymmetric Friedel−Crafts Alkylation of Pyrroles with Nitroalkenes Using a Dinuclear Zinc Catalyst
  作者：Barry M. Trost、Christoph Müller

  DOI：10.1021/ja711080y

  日期：2008.2.1

  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.