1-ethyl-6-hydroxy-5-((3-methoxyphenyl) diazenyl)-4-methyl-2-oxo-1,2-dihydropyridine -3-carbonitrile | 881069-36-9

• 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: 1-ethyl-6-hydroxy-5-((3-methoxyphenyl) diazenyl)-4-methyl-2-oxo-1,2-dihydropyridine -3-carbonitrile
• 英文别名: 5-(3-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone
• CAS: 881069-36-9
• 化学式: C₁₆H₁₆N₄O₃
• 分子量: 312.328
• InChiKey: OMLFWHOXXXKLRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.97
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  间氨基苯甲醚 、 1-乙基-1,2-二氢-6-羟基-4-甲基-2-氧代-3-吡啶氰 在 盐酸 、 sodium nitrite 、 potassium hydroxide 作用下， 以 水 为溶剂， 反应 4.5h， 以67%的产率得到1-ethyl-6-hydroxy-5-((3-methoxyphenyl) diazenyl)-4-methyl-2-oxo-1,2-dihydropyridine -3-carbonitrile
  参考文献：
  名称：

  On the structures of 5-(4-, 3- and 2-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone: An experimental and theoretical study

  摘要：

  In this work, a combined experimental and theoretical study on the structures of methoxy substituted 5-phenylazo-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridones has been reported. The dyes under the investigation have been thoroughly characterized. X-ray single-crystal analysis shows that 5-(4-methoxyphenylazo)-3-cyano-1-ethyl-6-hydroxy-4-methyl-2-pyridone crystallizes in the hydrazone form. Quantum chemical calculations of energies, geometrical structure and vibrational wavenumbers of the investigated dyes have been performed using density functional theory. The optimized geometrical parameters obtained by density functional theory calculations are in good conformity with the single-crystal data. The fundamental vibrational wavenumbers, as well as their intensities have been calculated and a good agreement between observed and scaled calculated wavenumbers has been achieved. Stability of the molecule arising from hyperconjugative interactions and charge delocalization has been analyzed using natural bond orbital analysis. Vibrational, nuclear magnetic resonance and natural bond orbital analysis confirm that the prepared dyes exist in the hydrazone tautomeric form in the solid state and dimethyl sulfoxide solution. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.dyepig.2014.01.007