4,6-dimethyl-1-(4-nitro-benzylidenamino)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile | 1562-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-dimethyl-1-(4-nitro-benzylidenamino)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
• 英文别名: 4,6-Dimethyl-1-(4-nitro-benzylidenamino)-2-oxo-1,2-dihydro-pyridin-3-carbonitril；4,6-dimethyl-1-{[(E)-(4-nitrophenyl)methylidene]amino}-2-oxo-1,2-dihydropyridine-3-carbonitrile；4,6-dimethyl-1-[(E)-(4-nitrophenyl)methylideneamino]-2-oxopyridine-3-carbonitrile
• CAS: 1562-11-4
• 化学式: C₁₅H₁₂N₄O₃
• 分子量: 296.285
• InChiKey: YASIPATWVIQSKT-RQZCQDPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4,6-dimethyl-1-(4-nitro-benzylidenamino)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile 生成 对硝基苯甲腈 、 3-氰基-4,6-二甲基-2-羟基吡啶
  参考文献：
  名称：

  Pyrolysis of aminonitriles, cyanohydrazones, and cyanoacetamides. Part I. Elimination reaction of 1-arylmethyleneamino-1,2-dihydro-4,6-dimethyl-2-oxopyridine-3-carbonitriles and substituted benzaldehyde cyanoacetylhydrazones

  摘要：

  Pyrolysis of the Schiff bases of 1-arylmethyleneamino-1,2-dihydro-4,6-dimethyl-2-oxopyridine-3-carbonitriles (1-5) has been studied. These compounds eliminate via a six-membered transition state to produce substituted benzonitriles and 2-hydroxy-4,6-dimethylpyridine-3-carbonitrile. These eliminations are unimolecular First-order reactions. The kinetic data gave a good correlation with sigma(0) values of the substituents on the aryl group with rho = 0.83 at 520 K. Utilization of the pyrolytic reaction in synthesis of various benzonitriles is considered, and mechanistic information has been obtained by comparing the kinetic data and product analysis of the Schiff bases with their open-chain substituted benzaldehyde cyanoacetylhydrazones (6-9) analogues. (C) 1996 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1996)28:10<741::aid-kin4>3.0.co;2-n
• 作为产物：
  描述：

  3-氰基-4,6-二甲基-2-羟基吡啶 在 乙醇 、 溶剂黄146 作用下， 生成 4,6-dimethyl-1-(4-nitro-benzylidenamino)-2-oxo-1,2-dihydro-pyridine-3-carbonitrile
  参考文献：
  名称：

  Ried; Meyer, Chemische Berichte, 1957, vol. 90, p. 2841,2846

  摘要：

  DOI：

文献信息

• Ried; Meyer, Chemische Berichte, 1957, vol. 90, p. 2841,2846
  作者：Ried、Meyer

  DOI：——

  日期：——
• Pyrolysis of aminonitriles, cyanohydrazones, and cyanoacetamides. Part I. Elimination reaction of 1-arylmethyleneamino-1,2-dihydro-4,6-dimethyl-2-oxopyridine-3-carbonitriles and substituted benzaldehyde cyanoacetylhydrazones
  作者：Nouria A. Al-Awadi、Mohamed H. Elnagdi、Tommy Mathew、Ibrahim El-Gamry、Mervat Abdel Khalik

  DOI：10.1002/(sici)1097-4601(1996)28:10<741::aid-kin4>3.0.co;2-n

  日期：——

  Pyrolysis of the Schiff bases of 1-arylmethyleneamino-1,2-dihydro-4,6-dimethyl-2-oxopyridine-3-carbonitriles (1-5) has been studied. These compounds eliminate via a six-membered transition state to produce substituted benzonitriles and 2-hydroxy-4,6-dimethylpyridine-3-carbonitrile. These eliminations are unimolecular First-order reactions. The kinetic data gave a good correlation with sigma(0) values of the substituents on the aryl group with rho = 0.83 at 520 K. Utilization of the pyrolytic reaction in synthesis of various benzonitriles is considered, and mechanistic information has been obtained by comparing the kinetic data and product analysis of the Schiff bases with their open-chain substituted benzaldehyde cyanoacetylhydrazones (6-9) analogues. (C) 1996 John Wiley & Sons, Inc.