5-methyl-2-morpholino-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitrile | 851322-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methyl-2-morpholino-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitrile
• 英文别名: 3-methyl-6-morpholin-4-yl-2-oxo-3,4-dihydro-1H-pyridine-5-carbonitrile
• CAS: 851322-23-1
• 化学式: C₁₁H₁₅N₃O₂
• 分子量: 221.259
• InChiKey: SLEDKTQMMFOKSH-UHFFFAOYSA-N

物化性质

• 熔点：
  194-196 °C(Solv: ethanol (64-17-5))
• 沸点：
  443.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吗啉 、 2-methoxy-5-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carbonitrile 以 甲醇 为溶剂， 反应 24.0h， 以68%的产率得到5-methyl-2-morpholino-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitrile
  参考文献：
  名称：

  Cyclization of 5-Cyano-6-cyanoimino-3,4-dihydropyridin-2(1H)-ones with Amines

  摘要：

  The cyclization of 5-cyano-6-cyanoimino-3,4-dihydropyridin-2(1h)-ones with amines, leading to pyrido[2,3-d]pyrimidines, is studied. Four play all important role oil the direction of cyclization: (1) the planarity of the reaction area; (2) the cyclization proceeds by the nucleophilic attack of all amidine onto ail electrophilic group which call be either a cyano group or all alkylamidine; (3) the basicity of the amine plays all important role, the ionization Of the Substrate making more difficult the formation of the aforementioned amidine which is needed for the cyclization; and (4) the nucleophilic attack and the tautomerization of the cyclization product are processes which call occur practically Simultaneously, so that the electronic movement involved in the tautomerization process coincides with the one which happens In the nucleophilic attack, both processes promoting each other.

  DOI：

  10.3987/com-09-11860

文献信息

• Cyclization of 5-Cyano-6-cyanoimino-3,4-dihydropyridin-2(1H)-ones with Amines
  作者：José I. Borrell、Núria Mont、Francisco Carrión、Jordi Teixidó

  DOI：10.3987/com-09-11860

  日期：——

  The cyclization of 5-cyano-6-cyanoimino-3,4-dihydropyridin-2(1h)-ones with amines, leading to pyrido[2,3-d]pyrimidines, is studied. Four play all important role oil the direction of cyclization: (1) the planarity of the reaction area; (2) the cyclization proceeds by the nucleophilic attack of all amidine onto ail electrophilic group which call be either a cyano group or all alkylamidine; (3) the basicity of the amine plays all important role, the ionization Of the Substrate making more difficult the formation of the aforementioned amidine which is needed for the cyclization; and (4) the nucleophilic attack and the tautomerization of the cyclization product are processes which call occur practically Simultaneously, so that the electronic movement involved in the tautomerization process coincides with the one which happens In the nucleophilic attack, both processes promoting each other.