Dimethyl 3,6-dimethyl-1,4-dihydropyridazine-4,5-dicarboxylate | 202980-59-4

• 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: Dimethyl 3,6-dimethyl-1,4-dihydropyridazine-4,5-dicarboxylate
• CAS: 202980-59-4
• 化学式: C₁₀H₁₄N₂O₄
• 分子量: 226.232
• InChiKey: WFEKFUKOYJXWGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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 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94%的产率得到3,6-Dimethyl-pyridazine-4,5-dicarboxylic acid dimethyl 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：

  (E)-methyl 2-((E)-4-methoxy-4-oxobut-2-en-2-yl)diazenecarboxylate 在 sodium hydroxide 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 Dimethyl 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

文献信息

• Novel and Convenient Synthesis of 1,4-Dihydropyridazines and Pyridazines from Aminocarbonylazoalkenes
  作者：Orazio Attanasi、Paolino Filippone、Chiara Fiorucci、Fabio Mantellini

  DOI：10.1055/s-1997-1042

  日期：——

  1-Unsubstituted 1,4-dihydropyridazines have been obtained in good to excellent yields by reaction of aminocarbonylazoalkenes with β-tricarbonyl compounds under mild conditions. Treatment at room temperature of 1-unsubstituted 1,4-dihydropyridazines with phenyltrimethylammonium tribromide directly afforded the relevant pyridazine derivatives in high yield.

  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。
• Reaction of Some 1,2-Diaza-1,3-butadienes with Activated Methine Compounds. A Straightforward Entry to 1,4-Dihydropyridazine, Pyridazine, and 4,5(4<i>H</i>,5<i>H</i>)-Cyclopropylpyrazole Derivatives
  作者：Orazio A. Attanasi、Paolino Filippone、Chiara Fiorucci、Elisabetta Foresti、Fabio Mantellini

  DOI：10.1021/jo9816515

  日期：1998.12.1

  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.