methyl 3,5-diphenyl-1,4-dihydropyridazine-4-carboxylate | 60220-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: methyl 3,5-diphenyl-1,4-dihydropyridazine-4-carboxylate
• 英文别名: 3,5-diphenyl-1,4-dihydro-pyridazine-4-carboxylic acid methyl ester
• CAS: 60220-49-7
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: VMHRFUYNUAEIMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3,5-diphenyl-1,4-dihydropyridazine-4-carboxylate 在 potassium permanganate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以95%的产率得到6,6 dimethyl-3-(3-hydroxypropyl)thio-1-(thiazol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one
  参考文献：
  名称：

  Synthesis of Substituted Methyl Pyridazine-4-carboxylates via Cycloaddition of Diazomethane to 2,3-Disubstituted 2-Cyclopropenecarboxylic Acids

  摘要：

  A three-step procedure has been developed for the synthesis of 3,5-disubstituted methyl pyridazine-4-carboxylates from accessible 2,3-disubstituted 2-cyclopropenecarboxylates. In the first step, cyclopropene derivatives react with diazomethane to give adducts having 2,3-diazabicyclo[3.1.1]hex-2-ene structure. The regio- and stereoselectivity of the cycloaddition has been determined. The second step is isomerization of the bicyclic adducts into 1,4-dihydropyridazine derivatives by the action of sodium methoxide. Finally, oxidation with potassium permanganate yields the target pyridazine-4-carboxylates.

  DOI：

  10.1023/b:rujo.0000045198.22692.97
• 作为产物：
  描述：

  methyl (1R,5S,6R)-1,5-diphenyl-2,3-diazabicyclo[3.1.0]hex-2-ene-6-carboxylate 以90%的产率得到
  参考文献：
  名称：

  KOMENDANTOV M. I.; BEKMUXAMETOV R. R.; NOVINSKIJ V. G., ZH. ORGAN. XIMII , 1976, 12, HO 4, 801-805

  摘要：

  DOI：

文献信息

• Synthesis of Substituted Methyl Pyridazine-4-carboxylates via Cycloaddition of Diazomethane to 2,3-Disubstituted 2-Cyclopropenecarboxylic Acids
  作者：V. V. Razin、M. E. Yakovlev、K. V. Shataev、S. I. Selivanov

  DOI：10.1023/b:rujo.0000045198.22692.97

  日期：2004.7

  A three-step procedure has been developed for the synthesis of 3,5-disubstituted methyl pyridazine-4-carboxylates from accessible 2,3-disubstituted 2-cyclopropenecarboxylates. In the first step, cyclopropene derivatives react with diazomethane to give adducts having 2,3-diazabicyclo[3.1.1]hex-2-ene structure. The regio- and stereoselectivity of the cycloaddition has been determined. The second step is isomerization of the bicyclic adducts into 1,4-dihydropyridazine derivatives by the action of sodium methoxide. Finally, oxidation with potassium permanganate yields the target pyridazine-4-carboxylates.
• KOMENDANTOV M. I.; BEKMUXAMETOV R. R.; NOVINSKIJ V. G., ZH. ORGAN. XIMII <ZORK-AE>, 1976, 12, HO 4, 801-805
  作者：KOMENDANTOV M. I.、 BEKMUXAMETOV R. R.、 NOVINSKIJ V. G.

  DOI：——

  日期：——