4-amino-3-phenyl-2-oxo-2,3-dihydropyrimidine-5-carbaldehyde | 154867-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4-amino-3-phenyl-2-oxo-2,3-dihydropyrimidine-5-carbaldehyde
• 英文别名: 6-amino-2-oxo-1-phenylpyrimidine-5-carbaldehyde
• CAS: 154867-34-2
• 化学式: C₁₁H₉N₃O₂
• 分子量: 215.211
• InChiKey: RVPWJXSSWLSLHX-UHFFFAOYSA-N

物化性质

• 沸点：
  443.7±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.63
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  77.98
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-amino-3-phenyl-2-oxo-2,3-dihydropyrimidine-5-carbaldehyde 在 亚硝酸异戊酯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以10%的产率得到5-(dimethoxymethyl)-3-phenyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Syntheses with nitriles, XCV: Deamination of cytosine derivatives

  摘要：

  Treatment of 2-formyl-3-dimethylamino-propenenitrile (1a) and 2-ethoxycarbonyl-3-dimethylamino-propenenitrile (1b), resp., with substituted ureas led to the 2-cyano-3-ureidoacrylates 2, which can be cyclized under alkaline conditions to give 5-formyl-5-cyano-, and 5-alkoxycarbonyl-2-oxopyrimidine derivatives 3, 6, and 7. Reaction of 3 with isopentylnitrite gave a mixture of the deaminated and oxidized product 4 and the oxo derivative 5, which was acetalized during the separation step. Similar reaction with the alkoxycarbonyl derivatives 7 led to the formation of 1-alkyl-5-alkoxycarbonyl-pyrimidine-2,6-diones 8a-d.

  DOI：

  10.1007/bf00811761
• 作为产物：
  描述：

  2-formyl-3-(3-phenylureido)propenenitrile 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以35%的产率得到4-amino-3-phenyl-2-oxo-2,3-dihydropyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Synthesis with Nitriles: 92. Synthesis of 5-Formylcytosine Derivatives

  摘要：

  The reactivity of 3-dimethylamino-2-formylpropenenitrile (1) with various amino compounds is studied. Thus, condensation of 1 with anilines gives the corresponding azomethines (2a-c). Reaction of 1 with thiourea and guanidne resp., leads to 5-formylthiocytosine (3) and 2-amino-5-cyanopyrimidine (4). The 2-formyl-3-ureidopropenenitriles (5a-i) can be obtained by reaction of 1 with urea and substituted ureas. 5a-i can easily be cyclized to 3-substituted 5-formylcytosines (6-e). Condensation of 6 with aniline, benzylamine and phenylhydrazine leads to the azomethines (7a-i). Pyrido [ 2,3-d ] pyrimidine-6-carbonitriles (8a, 8b, Sd and 83) are obtained by reaction of 6 with malononitrile.

  DOI：

  10.3987/com-93-6416