3-methyl-1-phenyl-4-acetylhydrazono-2-pyrazoline-5-one | 133636-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-methyl-1-phenyl-4-acetylhydrazono-2-pyrazoline-5-one
• 英文别名: 4-ethanehydrazonoyl-5-methyl-2-phenyl-4H-pyrazol-3-one
• CAS: 133636-19-8
• 化学式: C₁₂H₁₄N₄O
• 分子量: 230.269
• InChiKey: ITZWWVYNPLTOKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  71.05
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-methyl-1-phenyl-4-acetylhydrazono-2-pyrazoline-5-one 在 tetraphosphorus decasulfide 、 一水合肼 、 三氯氧磷 作用下， 以 吡啶 、 乙醇 为溶剂， 反应 3.0h， 生成 4-Methyl-1-phenyl-3-(1H-pyrazol-4-yl)-1,6-dihydro-pyrazolo[3,4-c]pyrazole
  参考文献：
  名称：

  Studies in the Vilsmeier-Haack reaction, part VII: Synthesis and reaction of 3-methyl-1-phenyl-4-acetyl hydrazono 2-pyrazoline-5-one(-5-thione)

  摘要：

  The keto (thio) tautomers 1-4 of the hydrazono pyrazolone, thiopyrazolone derivatives underwent simultaneous diformylation, chlorination (desulphurization) and ring closure under Vilsmeier reaction conditions giving the pyrazolo[3,4-c]pyrazole aminoacroleins (5,6). Treatment of 5 and/or 6 with proper reagents afforded the corresponding pyrazolo[3,4-c]pyrazoles with different heterocyclic systems at the 3-position.The structures of these compounds were confirmed by elemental analysis, IR and H-1-NMR spectroscopy. All synthesized compounds have been screened in vitro for their antibacterial activities against a number of Gram-positive and Gram-negative bacteria.

  DOI：

  10.1007/bf00809252
• 作为产物：
  描述：

  4-乙酰基-5-甲基-2-苯基-2,4-二氢-3H-吡唑-3-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以70%的产率得到3-methyl-1-phenyl-4-acetylhydrazono-2-pyrazoline-5-one
  参考文献：
  名称：

  Studies in the Vilsmeier-Haack reaction, part VII: Synthesis and reaction of 3-methyl-1-phenyl-4-acetyl hydrazono 2-pyrazoline-5-one(-5-thione)

  摘要：

  The keto (thio) tautomers 1-4 of the hydrazono pyrazolone, thiopyrazolone derivatives underwent simultaneous diformylation, chlorination (desulphurization) and ring closure under Vilsmeier reaction conditions giving the pyrazolo[3,4-c]pyrazole aminoacroleins (5,6). Treatment of 5 and/or 6 with proper reagents afforded the corresponding pyrazolo[3,4-c]pyrazoles with different heterocyclic systems at the 3-position.The structures of these compounds were confirmed by elemental analysis, IR and H-1-NMR spectroscopy. All synthesized compounds have been screened in vitro for their antibacterial activities against a number of Gram-positive and Gram-negative bacteria.

  DOI：

  10.1007/bf00809252