benzyl 1,6-dimethyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 60750-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl 1,6-dimethyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid benzyl ester；Benzyl 1,6-dimethyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate；benzyl 3,4-dimethyl-2-oxo-6-phenyl-1,6-dihydropyrimidine-5-carboxylate
• CAS: 60750-24-5
• 化学式: C₂₀H₂₀N₂O₃
• 分子量: 336.39
• InChiKey: AMNUHHIUBSEOIK-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  542.9±50.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  benzyl 1,6-dimethyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 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 2.0h， 生成 1,2,3,4-四氢-1,3,6-三甲基-2-氧代-4-苯基-5-嘧啶羧酸
  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 、 苯甲醛 、 N-甲基脲 在 ytterbium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以36%的产率得到benzyl 1,6-dimethyl-4-phenyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  微波辅助溶液相合成二氢嘧啶C5酰胺和酯

  摘要：

  以多步骤顺序生成多官能化的二氢嘧啶-5-羧酸酰胺和酯，其中集成了多种使能和高通量技术，例如自动化或并行微波合成，使用聚合物支持的试剂，氟合成和纯化策略以及连续流动氢化系统。通过苄基或烯丙基β-酮酯与醛和脲/硫脲的Biginelli多组分缩合，然后进行合适的苄基或烯丙基脱保护策略，可通过两步获得关键的二氢嘧啶-5-羧酸中间体。使用聚合物负载的偶联剂，用胺对酸核进行进一步官能化，或者使用光延化学，通过醇对醇进行进一步官能化，分别提供所需的酰胺或酯。

  DOI：

  10.1016/j.tet.2005.12.061

文献信息

• ZIGEUNER G.; KNOPP C.; BLASCHKE H., MONATSH. CHEM. <MOCH-AP>, 1976, 107, NO 3, 587-603
  作者：ZIGEUNER G.、 KNOPP C.、 BLASCHKE H.

  DOI：——

  日期：——
• Microwave-assisted solution phase synthesis of dihydropyrimidine C5 amides and esters
  作者：Bimbisar Desai、Doris Dallinger、C. Oliver Kappe

  DOI：10.1016/j.tet.2005.12.061

  日期：2006.5

  Multifunctionalized dihydropyrimidine-5-carboxylic amides and esters are generated in a multistep sequence integrating a variety of enabling and high throughput technologies such as automated or parallel microwave synthesis, the use of polymer-supported reagents, fluorous synthesis and purification strategies, and a continuous flow hydrogenation system. The key dihydropyrimidine-5-carboxylic acid intermediates

  以多步骤顺序生成多官能化的二氢嘧啶-5-羧酸酰胺和酯，其中集成了多种使能和高通量技术，例如自动化或并行微波合成，使用聚合物支持的试剂，氟合成和纯化策略以及连续流动氢化系统。通过苄基或烯丙基β-酮酯与醛和脲/硫脲的Biginelli多组分缩合，然后进行合适的苄基或烯丙基脱保护策略，可通过两步获得关键的二氢嘧啶-5-羧酸中间体。使用聚合物负载的偶联剂，用胺对酸核进行进一步官能化，或者使用光延化学，通过醇对醇进行进一步官能化，分别提供所需的酰胺或酯。
• 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.