6-methyl-4-(5-nitro-2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid benzyl ester | 433964-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-methyl-4-(5-nitro-2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid benzyl ester
• 英文别名: benzyl 4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 433964-36-4
• 化学式: C₁₉H₁₇N₃O₆
• 分子量: 383.36
• InChiKey: XYVCEXHVCKXTFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  134
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  乙酰丙酮苄酯 、 5-硝基水杨醛 、 尿素 在 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以60%的产率得到6-methyl-4-(5-nitro-2-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step

  摘要：

  A new efficient approach for the synthesis of functionalized dihydro-pyrimido[4,3-d]coumarins is described. Use of benzyl- or tert-butyl acetoacetate and various salicyl aldehydes in typical Biginelli multicomponent reactions provides esters that can be easily deprotected to yield the corresponding hydroxy acids. Annelation of the latter leads to the target dihydro-pyrimido[4,3-d]coumarins. Formation of some unexpected oxo-bridged tetrahydro-pyrimidines is also described. Spectral properties of the synthesized dihydro-pyrimido[4,3-d]coumarins indicate the necessity to revisit some compounds previously reported as products of direct one-pot Biginelli condensation involving 4-hydroxycoumarin as dicarbonyl component. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.088

文献信息

• Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step
  作者：Mihaela Matache、Cristian Dobrota、Niculina D. Bogdan、Ioana Dumitru、Lavinia L. Ruta、Codruta C. Paraschivescu、Ileana C. Farcasanu、Ion Baciu、Daniel P. Funeriu

  DOI：10.1016/j.tet.2009.05.088

  日期：2009.8

  A new efficient approach for the synthesis of functionalized dihydro-pyrimido[4,3-d]coumarins is described. Use of benzyl- or tert-butyl acetoacetate and various salicyl aldehydes in typical Biginelli multicomponent reactions provides esters that can be easily deprotected to yield the corresponding hydroxy acids. Annelation of the latter leads to the target dihydro-pyrimido[4,3-d]coumarins. Formation of some unexpected oxo-bridged tetrahydro-pyrimidines is also described. Spectral properties of the synthesized dihydro-pyrimido[4,3-d]coumarins indicate the necessity to revisit some compounds previously reported as products of direct one-pot Biginelli condensation involving 4-hydroxycoumarin as dicarbonyl component. (C) 2009 Elsevier Ltd. All rights reserved.