1-(2,4-dinitrophenyl)-5-chloro-3-chloromethylpyrazole | 1100829-96-6

• 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-(2,4-dinitrophenyl)-5-chloro-3-chloromethylpyrazole
• 英文别名: 1-(2,4-Dinitrophenyl)-5-chloro-3-chloromethyl-pyrazole；5-chloro-3-(chloromethyl)-1-(2,4-dinitrophenyl)pyrazole
• CAS: 1100829-96-6
• 化学式: C₁₀H₆Cl₂N₄O₄
• 分子量: 317.088
• InChiKey: AAPCBOYQZVORID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2-dichlorovinyl chloromethyl ketone 2,4-dinitrophenylhydrazone 在 PPA 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以95%的产率得到1-(2,4-dinitrophenyl)-5-chloro-3-chloromethylpyrazole
  参考文献：
  名称：

  Distinguishing Features of reactions of 2-chloro-and 2,2-dichloro(bromo)vinyl ketones with alkyl-and arylhydrazines

  摘要：

  2-Chlorovinyl alkyl ketones react with alkylhydrazines to give mixtures of 1-R-3-R'- and 1-R-5-R'-pyrazoles: The 1-R-3-R'-pyrazoles form through the heterocyclization of 2-chlorovinyl ketone alkylhydrazones whereas in the heterocyclization into 1-R-5-R'-pyrazoles N1-alkyl-N2-(2-acylvinyl) hydrazines are involved. The regiospecific heterocyclization of 2-chloro- and 2,2-dichlorovinyl ketones with arylhydrazines and also of 2,2-dichloro(bromo) vinyl trifluoromethyl ketones with C alkylhydrazines into pyrazoles and 5-chloro(bromo)pyrazoles proceeds through a stage of haloenones hydrazones formation. The study of the structure of the obtained 1-alkyl-3(5)-alkylpyrazoles by means of two-dimenaional H-1 and C-13 NMR spectroscopy and GC-MS method made it possible to assign the proton and carbon signals of isomeric pyrazoles and to establish the diagnostic ions for the pair of 1,3- and 1,5-isomers.

  DOI：

  10.1134/s1070428008070129