ethyl 5-benzoyl-4-hydroxy-3-methyl-6-phenyl-2-thiooxohexahydropyrimidine-4-carboxylate

• 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: ethyl 5-benzoyl-4-hydroxy-3-methyl-6-phenyl-2-thiooxohexahydropyrimidine-4-carboxylate
• 英文别名: ethyl (4S,5S,6R)-5-benzoyl-4-hydroxy-3-methyl-6-phenyl-2-sulfanylidene-1,3-diazinane-4-carboxylate
• 化学式: C₂₁H₂₂N₂O₄S
• 分子量: 398.483
• InChiKey: JGZKDPCOFCXOPN-WWMYMODYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-苯基-2,4-二氧丁酸乙酯 、 苯甲醛 、 N-甲硫脲 在 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到ethyl 5-benzoyl-4-hydroxy-3-methyl-6-phenyl-2-thiooxohexahydropyrimidine-4-carboxylate
  参考文献：
  名称：

  Acyl pyruvates as synthons in the Biginelli reaction

  摘要：

  Chlorotrimethylsilane-promoted Biginelli-type reaction of ethyl 2,4-dioxo-4-phenylbutanoate, benzaldehyde, and various (thio)ureas is explored. The outcome of the reaction depends on the structure of the (thio)urea used and is strongly affected by the acceptor electronic properties of the COOEt substituent in the molecule of the starting beta-dicarbonyl compound. The di- and tetrahydropyrimidine derivatives obtained possess two functional groups with orthogonal reactivity, and thus represent promising building blocks for drug discovery. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.06.032

文献信息

• Acyl pyruvates as synthons in the Biginelli reaction
  作者：Sergey V. Ryabukhin、Andrey S. Plaskon、Semen S. Bondarenko、Eugeniy N. Ostapchuk、Oleksandr O. Grygorenko、Oleg V. Shishkin、Andrey A. Tolmachev

  DOI：10.1016/j.tetlet.2010.06.032

  日期：2010.8

  Chlorotrimethylsilane-promoted Biginelli-type reaction of ethyl 2,4-dioxo-4-phenylbutanoate, benzaldehyde, and various (thio)ureas is explored. The outcome of the reaction depends on the structure of the (thio)urea used and is strongly affected by the acceptor electronic properties of the COOEt substituent in the molecule of the starting beta-dicarbonyl compound. The di- and tetrahydropyrimidine derivatives obtained possess two functional groups with orthogonal reactivity, and thus represent promising building blocks for drug discovery. (C) 2010 Elsevier Ltd. All rights reserved.