ethyl (4R)-6-methyl-2-oxo-4-(4-phenylmethoxyphenyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate | 1262942-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl (4R)-6-methyl-2-oxo-4-(4-phenylmethoxyphenyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1262942-54-0
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: BDLDWINBPRHBMI-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 乙酰乙酸乙酯 、 尿素 在 2,3,4,5,6-五氟苯甲酸 、 tritylamine trifluoracetate 、 (2S,4R)-4-tosylamido-N-(2,4,6-triphenyl)pyrrolidine-2-carboxamide 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 96.75h， 以66%的产率得到ethyl (4R)-6-methyl-2-oxo-4-(4-phenylmethoxyphenyl)-3,4-dihydro-1H-pyrimidine-5-carboxylate
  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%).