2-formyl-3-(3-allylureido)propenenitrile | 154867-27-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2-formyl-3-(3-allylureido)propenenitrile
• 英文别名: 1-(2-cyano-3-oxoprop-1-enyl)-3-prop-2-enylurea
• CAS: 154867-27-3
• 化学式: C₈H₉N₃O₂
• 分子量: 179.178
• InChiKey: RDAZTMKZUZQNOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.08
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81.99
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-formyl-3-(3-allylureido)propenenitrile 在 溶剂黄146 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 4-amino-3-allyl-5-phenylaminomethylenepyrimidin-2(3H)-one
  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
• 作为产物：
  描述：

  烯丙基脲 、 (2E)-3-(二甲基氨基)-2-甲酰基丙烯腈 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以58%的产率得到2-formyl-3-(3-allylureido)propenenitrile
  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