5-ethoxycarbonyl-6-methyl-4-cyclohexyl-3,4-dihydropyrimidin-2(1H)-one | 1262942-59-5

• 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: 5-ethoxycarbonyl-6-methyl-4-cyclohexyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: ethyl (4R)-4-cyclohexyl-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1262942-59-5
• 化学式: C₁₄H₂₂N₂O₃
• 分子量: 266.34
• InChiKey: OUEAJWSKZFZMMI-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 尿素 、 环己烷基甲醛 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68%的产率得到5-ethoxycarbonyl-6-methyl-4-cyclohexyl-3,4-dihydropyrimidin-2(1H)-one
  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%).