(R)-3-(5-(1-(呋喃-2-基)-2-硝基乙基)-1H-吡咯-2-基)-1-苯基丙烷-1-酮 | 1011711-96-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (R)-3-(5-(1-(呋喃-2-基)-2-硝基乙基)-1H-吡咯-2-基)-1-苯基丙烷-1-酮
• 英文名称: (R)-3-(5-(1-(furan-2-yl)-2-nitroethyl)-1H-pyrrol-2-yl)-1-phenylpropan-1-one
• 英文别名: 3-{5-[1-(2-furyl)-2-nitroethyl]-1H-pyrrol-2-yl}-1-phenylpropan-1-one；3-[5-[(1R)-1-(furan-2-yl)-2-nitroethyl]-1H-pyrrol-2-yl]-1-phenylpropan-1-one
• CAS: 1011711-96-8
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: IHUMTDMZCMASAB-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  91.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-糠酰)-2-硝基乙烯 、 1-phenyl-3-(1H-pyrrol-2-yl)propan-1-one 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 6.0h， 以94%的产率得到(R)-3-(5-(1-(呋喃-2-基)-2-硝基乙基)-1H-吡咯-2-基)-1-苯基丙烷-1-酮
  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

• 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.