(2S,4R)-N-hydroxy-N-(perfluorophenyl)pyrrolidine-2-carboxamide | 1262942-40-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4R)-N-hydroxy-N-(perfluorophenyl)pyrrolidine-2-carboxamide
• 英文别名: (2S,4R)-4-hydroxy-N-(2,3,4,5,6-pentafluorophenyl)pyrrolidine-2-carboxamide
• CAS: 1262942-40-4
• 化学式: C₁₁H₉F₅N₂O₂
• 分子量: 296.197
• InChiKey: OYEPEIYNWFAGHB-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  benzyl (2S,4R)-4-hydroxy-2-[(2,3,4,5,6-pentafluorophenyl)carbamoyl]pyrrolidine-1-carboxylate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (2S,4R)-N-hydroxy-N-(perfluorophenyl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Enantioselective Organocatalytic Biginelli Reaction: Dependence of the Catalyst on Sterics, Hydrogen Bonding, and Reinforced Chirality

  摘要：

  From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).

  DOI：

  10.1021/jo101717m

文献信息

• Enantioselective Organocatalytic Biginelli Reaction: Dependence of the Catalyst on Sterics, Hydrogen Bonding, and Reinforced Chirality
  作者：Satyajit Saha、Jarugu Narasimha Moorthy

  DOI：10.1021/jo101717m

  日期：2011.1.21

  From a systematic investigation involving the synthesis of a series of catalysts and screening studies, the organocatalyst 16, which is sterically hindered, contains a strong hydrogen-bonding site, and is endowed with reinforced chirality, is shown to promote the Biginelli cyclocondensation of aromatic as well as aliphatic aldehydes with ethyl acetoacetate and urea in a remarkably high enantioselectivity (ee ca. 94-99%).