(4S)-1,2,3,4-tetrahydro-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid | 143317-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S)-1,2,3,4-tetrahydro-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid
• 英文别名: (4S)-1,3,6-trimethyl-4-naphthalen-2-yl-2-oxo-4H-pyrimidine-5-carboxylic acid
• CAS: 143317-22-0
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: RQCMFUYCUVLOPB-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S)-1,2,3,4-tetrahydro-1,3,6-trimethyl-4-(2-naphthyl)-2-oxo-5-pyrimidinecarboxylic acid 在 sodium azide 、 三乙胺 作用下， 以 二甲基亚砜 、 丙酮 、 甲苯 为溶剂， 反应 3.75h， 生成 (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 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 (4S)-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

文献信息

• Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases
  作者：Oliver P. Kleidernigg、C.Oliver Kappe

  DOI：10.1016/s0957-4166(97)00214-0

  日期：1997.6

  The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual enantiomers could be achieved with at least one CSP with alpha-values ranging from 1.10 to 8.67. (C) 1997 Elsevier Science Ltd.
• 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.