4-O-ethyl 5-O-methyl 3,6-dimethyl-1,4-dihydropyridazine-4,5-dicarboxylate | 202980-61-8

• 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: 4-O-ethyl 5-O-methyl 3,6-dimethyl-1,4-dihydropyridazine-4,5-dicarboxylate
• CAS: 202980-61-8
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: PRTHTBBIFKAFCC-UHFFFAOYSA-N

物化性质

• 沸点：
  323.3±52.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  4-O-ethyl 5-O-methyl 3,6-dimethyl-1,4-dihydropyridazine-4,5-dicarboxylate 在 phenyltrimethylammonium tribromide 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到3,6-Dimethyl-pyridazine-4,5-dicarboxylic acid 4-ethyl ester 5-methyl ester
  参考文献：
  名称：

  Novel and Convenient Synthesis of 1,4-Dihydropyridazines and Pyridazines from Aminocarbonylazoalkenes

  摘要：

  1-直接翻译成中文： 未取代的1,4-二氢吡嗪在温和条件下通过氨基羰基偶氮烯与β-三羰基化合物的反应，以良好至优异的产率获得。在室温下处理未取代的1,4-二氢吡嗪与苯基三甲基铵三溴化物，直接高产率地得到了相应的吡嗪衍生物。

  DOI：

  10.1055/s-1997-1042
• 作为产物：
  描述：

  (1R,5R,6R)-1,4-Dimethyl-2,3-diaza-bicyclo[3.1.0]hex-3-ene-2,5,6-tricarboxylic acid 2,5-diethyl ester 6-methyl ester 在 sodium hydroxide 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.42h， 生成 4-O-ethyl 5-O-methyl 3,6-dimethyl-1,4-dihydropyridazine-4,5-dicarboxylate
  参考文献：
  名称：

  Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4H,5H)-Cyclopropylpyrazole Derivatives

  摘要：

  1-Aminocarbonyl-1,2-diaza-1,3-butadienes with beta-tri- or beta-dicarbonyl compounds containing at least two keto functions give 1,4-dihydropyridazines, while hydrazone 1,4-adducts are obtained in the case of compounds containing one or no keto function. 1,4-Dihydropyridazines are transformed into pyridazines. The same substrates with 3-phenoxypentane-2,4-dione afford pyridazines. Surprisingly, 1-alkoxycarbonyl-1,2-diaza-1,3-butadiene with methyl 2-acetylacetoacetate produce 1-alkoxycarbonyl-4,5(4H,5H)-(alkoxycarbonylcyclopropyl)pyrazoles deriving from 1-alkoxycarbonyl-1,2-dihydropyridazine intermediates by ring contraction. These pyrazole derivatives with acetic acid show ring expansion to 1-alkoxycarbonyl-1,4-dihydropyridazines that can be converted into 1,4-dihydropyridazines with sodium hydroxide. 1-Alkoxycarbonyl-4,5(4H, 5H)-(alkoxycarbonylcyclopropyl)pyrazoles or 1-alkoxycarbonyl-1,4-dihydropyridazines with trifluoroacetic acid provide 1-aminopyrroles via 1-alkoxycarbonyl-1,4-dihydropyridazine intermediates in the case of pyrazoles. The X-ray crystal structure of 1-tert-butoxycarbonyl-3,5-dimethyl-4-methoxycarbonyl-4,5(4H,5H)-(methoxycarbonylcyclopropyl)-1H-pyrazole was determined.

  DOI：

  10.1021/jo9816515