3-Cyano-4-methyl-6-oxo-piperidin-(2E)-ylidene-cyanamide | 103970-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 3-Cyano-4-methyl-6-oxo-piperidin-(2E)-ylidene-cyanamide
• 英文别名: 5-Cyano-6-cyanoimino-4-methyl-3,4-dihydro-2-pyridone；(3-cyano-4-methyl-6-oxopiperidin-2-ylidene)cyanamide
• CAS: 103970-26-9
• 化学式: C₈H₈N₄O
• 分子量: 176.178
• InChiKey: GDXYNRMAWQTKAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Cyano-4-methyl-6-oxo-piperidin-(2E)-ylidene-cyanamide 、 正丁胺 以 氯仿 为溶剂， 反应 70.0h， 以97%的产率得到4-amino-2-(butilamino)-5,6-dihydro-5-methylpyrido[2,3-d]pyrimidin-7(8H)-one
  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
• 作为产物：
  描述：

  Sodium;cyano-(3-cyano-4-methyl-6-oxopiperidin-2-yl)azanide 在 氢溴酸 作用下， 以 1,4-二氧六环 为溶剂， 以82%的产率得到2-amino-4-bromo-5,6-dihydro-5-methylpyrido<2,3-d>pyrimidin-7(8H)-one
  参考文献：
  名称：

  Teixido, Jordi; Borrell, Jose I.; Serra, Blanca, Heterocycles, 1999, vol. 50, # 2, p. 739 - 756

  摘要：

  DOI：

文献信息

• Teixido, Jordi; Borrell, Jose I.; Serra, Blanca, Heterocycles, 1999, vol. 50, # 2, p. 739 - 756
  作者：Teixido, Jordi、Borrell, Jose I.、Serra, Blanca、Matallana, Josep Lluis、Colominas, Carles、Carrion, Francisco、Pascual, Rosalia、Falco, Josep Lluis、Batllori, Xavier

  DOI：——

  日期：——
• 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.