(4S)-3,4-dihydro-5-isocyanato-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-1H-pyrimidine-2-one | 143317-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-3,4-dihydro-5-isocyanato-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-1H-pyrimidine-2-one
• CAS: 143317-27-5
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: CHDDAGJXZMPZHW-KRWDZBQOSA-N

物化性质

• 沸点：
  455.9±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.98
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  10-十一烯-1-醇 、 (4S)-3,4-dihydro-5-isocyanato-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-1H-pyrimidine-2-one 以 甲苯 为溶剂， 反应 3.0h， 以48%的产率得到(4S)-3,4-dihydro-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-5-<(10-undecenyloxy)carbonyl>amino-1H-pyrimidin-2-one
  参考文献：
  名称：

  Synthesis and reactions of biginelli compounds −5. Facile preparation and resolution of a stable 5-dihydropyrimidinecarboxylic acid.

  摘要：

  The synthesis of enantiomerically pure 5-dihydropyrimidinecarboxylic acids 7a,b is described. Condensation of benzyl acetoacetate with methylurea and 2-naphthaldehyde gave Biginelli compound 3b, which after methylation and removal of the benzyl group led to racemic acid 5b. Fractional crystallization of diastereomeric alpha-methylbenzylammonium salts 6a,b followed by acidification provided the desired optically pure carboxylic acids 7a,b. Conversion of 7a,b to carboxylic acid azides 8a,b, followed by Curtius rearrangement and reaction with 10-undecenol led to chiral urethanes 10a,b. The absolute stereochemistry of acids 7a,b was established by X-ray analysis of diastereomeric alpha-methylbenzylammonium-carboxylate 6c.

  DOI：

  10.1016/s0040-4020(01)88301-0
• 作为产物：
  描述：

  1,2,3,4-tetrahydro-1,6-dimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid benzylester 在 palladium on activated charcoal 、 甲苯 sodium azide 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二甲基亚砜 、 丙酮 、 甲苯 、 paraffin 为溶剂， 60.0 ℃ 、300.0 kPa 条件下， 反应 5.75h， 生成 (4S)-3,4-dihydro-5-isocyanato-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-1H-pyrimidine-2-one
  参考文献：
  名称：

  Synthesis and reactions of biginelli compounds −5. Facile preparation and resolution of a stable 5-dihydropyrimidinecarboxylic acid.

  摘要：

  The synthesis of enantiomerically pure 5-dihydropyrimidinecarboxylic acids 7a,b is described. Condensation of benzyl acetoacetate with methylurea and 2-naphthaldehyde gave Biginelli compound 3b, which after methylation and removal of the benzyl group led to racemic acid 5b. Fractional crystallization of diastereomeric alpha-methylbenzylammonium salts 6a,b followed by acidification provided the desired optically pure carboxylic acids 7a,b. Conversion of 7a,b to carboxylic acid azides 8a,b, followed by Curtius rearrangement and reaction with 10-undecenol led to chiral urethanes 10a,b. The absolute stereochemistry of acids 7a,b was established by X-ray analysis of diastereomeric alpha-methylbenzylammonium-carboxylate 6c.

  DOI：

  10.1016/s0040-4020(01)88301-0