1-[(E)-4,4-dichloro-3-oxobut-2-en-1-yl]-3,5-dimethyl-1H-pyrazole | 1151391-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-[(E)-4,4-dichloro-3-oxobut-2-en-1-yl]-3,5-dimethyl-1H-pyrazole
• 英文别名: 1-[(e)-4,4-Dichloro-3-oxobut-1-en-1-yl]-3,5-dimethyl-1h-pyrazole；(E)-1,1-dichloro-4-(3,5-dimethylpyrazol-1-yl)but-3-en-2-one
• CAS: 1151391-59-1
• 化学式: C₉H₁₀Cl₂N₂O
• 分子量: 233.097
• InChiKey: JTKMAPXVSKPNJW-ONEGZZNKSA-N

物化性质

• 熔点：
  67 °C(Solvent: Water)
• 沸点：
  231.6±40.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-二甲基吡唑 、 1,1,4-trichlorobut-3-en-2-one 以 苯 为溶剂， 以68%的产率得到1-[(E)-4,4-dichloro-3-oxobut-2-en-1-yl]-3,5-dimethyl-1H-pyrazole
  参考文献：
  名称：

  Unusual reaction of chloroacetyl chloride with 1,2-dichloroethene. Synthesis and properties of 2-chlorovinyl dichloromethyl ketone

  摘要：

  The reaction of chloroacetyl chloride with 1,2-dichloroethene in the presence of AlCl3 unexpectedly led to the formation of (E)-1,1,4-trichlorobut-3-en-2-one whose structure was proved by H-1 and C-13 NMR, IR, and mass spectra and independent synthesis. A probable reaction scheme was proposed, which involves transformation of initially formed 1,2,4-trichloro-3-oxobutan-2-yl cation by the action of AlCl3. The high reactivity of the vinylic halogen atom in (E)-1,1,4-trichlorobut-3-en-2-one was demonstrated by its reactions with nitrogen-centered nucleophiles (triethylamine, aniline, 3,5-dimethyl-1H-pyrazole) and sodium sulfide. These reactions involved only the C-Cl bond in the vinyl fragment and afforded (4,4-dichloro-3-oxobut-2-en-1-yl)triethylammonium chloride, 1,1-dichloro-4-phenylaminobut-3-en-2-one, 1-(4,4-dichloro-3-oxobut-2-en-1-yl)-3,5-dimethyl-1H-pyrazole, and 4,4'-thiobis(1,1-dichlorobut-3-en-2-one), respectively. The reaction of 1,1,4-trichlorobut-3-en-2-one with benzylhydrazine gave a mixture of 1,3- and 1,5-disubstituted pyrazoles.

  DOI：

  10.1134/s1070428008120038