ethyl 4-(3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 4-(3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-(1-phenyl-3-p-tolyl-1H-pyrazol-4-yl)pyrimidine-5-carboxylate；ethyl 6-methyl-4-[3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-methyl-4-[3-(4-methylphenyl)-1-phenylpyrazol-4-yl]-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₄H₂₄N₄O₃
• 分子量: 416.48
• InChiKey: CUKVPBMGMWCMMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 尿素 、 1-苯基-3-对甲苯-1H-吡唑-4-甲醛 在 phospho-tungstic acid 、 phosphotungstic acid 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以74%的产率得到ethyl 4-(3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  磷钨酸促进的新型4-吡唑基-2-氧代-1,2,3,4-四氢嘧啶的合成

  摘要：

  使用吡唑醛，乙酰乙酸乙酯和尿素进行磷钨酸（一种Keggin型杂多酸催化的Biginelli反应），合成了新颖的4-吡唑基-2-氧代-1,2,3,4-四氢嘧啶-嘧啶。

  DOI：

  10.1002/jhet.5570420518

文献信息

• Synthesis of novel 4-pyrazolyl-2-oxo-1,2,3,4-tetrahydropyrimidines promoted by phosphotungstic acid
  作者：Ganesabaskaran Sivaprasad、Paramasivan T. Peramal

  DOI：10.1002/jhet.5570420518

  日期：2005.7

  Phosphotungstic acid, a keggin's type heteropoly acid catatalysed Biginelli reaction was carried out using pyrazole aldehyde, ethyl acetoacetate and urea to synthesis novel 4-pyrazolyl -2-oxo-1,2,3,4-tetrahydropy- rimidines.

  使用吡唑醛，乙酰乙酸乙酯和尿素进行磷钨酸（一种Keggin型杂多酸催化的Biginelli反应），合成了新颖的4-吡唑基-2-氧代-1,2,3,4-四氢嘧啶-嘧啶。
• 4-Functionally Substituted 3-Heterylpyrazoles: XIII. 3-Aryl(heteryl)-4-(4-pyrazolyl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones)
  作者：M. K. Bratenko、V. A. Chornous、M. V. Vovk

  DOI：10.1007/s11178-005-0127-9

  日期：2005.1

  Cyclocondesation of 3-aryl(heteryl)pyrazole-4-carbaldehydes with ethyl acetoacetate and urea (thiourea) in the presence of FeCl3 · 6H2O afforded 3-aryl(heteryl)-4-(4-pyrazolyl)-1,2,3,4-tetrahydropyrimidin-2-ones(thiones).

  3-芳基(杂基)吡唑-4-甲醛与乙酰乙酸乙酯和脲(硫脲)在FeCl3·6H2O存在下环缩合得到3-芳基(杂基)-4-(4-吡唑基)-1,2,3， 4-四氢嘧啶-2-酮（硫酮）。
• Novel dihydropyrimidines as a potential new class of antitubercular agents
  作者：Amit R. Trivedi、Vimal R. Bhuva、Bipin H. Dholariya、Dipti K. Dodiya、Vipul B. Kataria、Viresh H. Shah

  DOI：10.1016/j.bmcl.2010.08.046

  日期：2010.10

  A small library of 30 dihydropyrimidines was synthesized and evaluated for their in vitro antitubercular activity against Mycobacterium tuberculosis H(37)Rv. Two compounds, ethyl 4-[3-(4-fluorophenyl)-1-phenyl- 1H-pyrazol-4-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5 carboxylate 4a and ethyl 4-[3-(4-nitrophenyl)- 1-phenyl-1H-pyrazol-4-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 4d were found to be the most active compounds in vitro with MIC of 0.02 mu g/mL against MTB and were more potent than isoniazid. (C) 2010 Elsevier Ltd. All rights reserved.
• Sarasija; Ashok; Sudershan, Indian Journal of Heterocyclic Chemistry, 2015, vol. 24, # 3, p. 349 - 352
  作者：Sarasija、Ashok、Sudershan、Shivaraj

  DOI：——

  日期：——