dimethyl 2,5-dihydro-4,6-diphenylpyridazine-3,5-dicarboxylate | 847225-80-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: dimethyl 2,5-dihydro-4,6-diphenylpyridazine-3,5-dicarboxylate
• 英文别名: dimethyl 3,5-diphenyl-1,4-dihydropyridazine-4,6-dicarboxylate
• CAS: 847225-80-3
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: CZBXYIATCFJSSI-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  494.7±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2,5-dihydro-4,6-diphenylpyridazine-3,5-dicarboxylate 在 盐酸 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以94%的产率得到dimethyl 4,6-diphenyl-1,4-dihydropyridazine-3,5-dicarboxylate
  参考文献：
  名称：

  Prototropic isomerization of dihydropyridazinecarboxylic and dihydropyridazinedicarboxylic acid esters

  摘要：

  3,5-Disubstituted 1,4-dihydropyridazine-4-carboxylic and 4,6-disubstituted 2,5-dihydropyridazine-3,5-dicarboxylic acid esters undergo isomerization into 2,5-dihydropyridazine-4-carboxylate and 1,4-dihydropyridazine-3,5-dicarboxylate derivatives, respectively, by the action of a catalytic amount of a mineral acid or strong base at 20 degrees C. The transformation may be regarded as prototropic rearrangement, and it includes two consecutive 1,2-hydride shifts. The direction of the isomerization is determined by higher thermodynamic stability of the isomer containing a beta-aminoacrylate fragment.

  DOI：

  10.1134/s1070428012030177
• 作为产物：
  描述：

  重氮乙酸甲酯 、 methyl 2,3-diphenyl-2-cyclopropene-1-carboxylate 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 以84%的产率得到dimethyl 2,5-dihydro-4,6-diphenylpyridazine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of 4,6-Disubstituted Dimethyl Pyridazine-3,5-dicarboxylates

  摘要：

  Dimethyl pyridazine-3,5-dicarboxylates were synthesized by reaction of substituted 2-cyclopropenecarboxylates with methyl diazoacetate, followed by oxidation of the resulting 1,4-dihydropyridazine-4,6-dicarboxylates.

  DOI：

  10.1023/b:rujo.0000045199.21494.c7

文献信息

• Prototropic isomerization of dihydropyridazinecarboxylic and dihydropyridazinedicarboxylic acid esters
  作者：V. V. Razin、M. E. Yakovlev、V. A. Vasin

  DOI：10.1134/s1070428012030177

  日期：2012.3

  3,5-Disubstituted 1,4-dihydropyridazine-4-carboxylic and 4,6-disubstituted 2,5-dihydropyridazine-3,5-dicarboxylic acid esters undergo isomerization into 2,5-dihydropyridazine-4-carboxylate and 1,4-dihydropyridazine-3,5-dicarboxylate derivatives, respectively, by the action of a catalytic amount of a mineral acid or strong base at 20 degrees C. The transformation may be regarded as prototropic rearrangement, and it includes two consecutive 1,2-hydride shifts. The direction of the isomerization is determined by higher thermodynamic stability of the isomer containing a beta-aminoacrylate fragment.
• Synthesis of 4,6-Disubstituted Dimethyl Pyridazine-3,5-dicarboxylates
  作者：M. E. Yakovlev、V. V. Razin

  DOI：10.1023/b:rujo.0000045199.21494.c7

  日期：2004.7

  Dimethyl pyridazine-3,5-dicarboxylates were synthesized by reaction of substituted 2-cyclopropenecarboxylates with methyl diazoacetate, followed by oxidation of the resulting 1,4-dihydropyridazine-4,6-dicarboxylates.