1,2,3,4-tetrahydro-1,6-dimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid benzylester | 143317-16-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4-tetrahydro-1,6-dimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid benzylester
• 英文别名: Benzyl 3,4-dimethyl-6-naphthalen-2-yl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• CAS: 143317-16-2
• 化学式: C₂₄H₂₂N₂O₃
• 分子量: 386.45
• InChiKey: JTIDVMXRZJPWEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 甲苯 、 paraffin 为溶剂， 25.0~60.0 ℃ 、300.0 kPa 条件下， 反应 5.0h， 生成 1,2,3,4-tetrahydro-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid
  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：

  乙酰丙酮苄酯 、 2-萘甲醛 、 N-甲基脲 在 L-酒石酸 作用下， 以 甲醇 为溶剂， 以70%的产率得到1,2,3,4-tetrahydro-1,6-dimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid benzylester
  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

文献信息

• Synthesis and reactions of biginelli compounds −5. Facile preparation and resolution of a stable 5-dihydropyrimidinecarboxylic acid.
  作者：C.Oliver Kappe、Georg Uray、Peter Roschger、Wolfgang Lindner、Christoph Kratky、Walter Keller

  DOI：10.1016/s0040-4020(01)88301-0

  日期：1992.1

  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.