1-phenyl-3-propyl-4-chloropyrazole | 1088492-21-0

• 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-phenyl-3-propyl-4-chloropyrazole
• 英文别名: 3-propyl-1-phenyl-4-chloropyrazole；4-chloro-1-phenyl-3-propylpyrazole
• CAS: 1088492-21-0
• 化学式: C₁₂H₁₃ClN₂
• 分子量: 220.702
• InChiKey: KZGANUIDWPNFCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1,2-dichlorovinyl propyl ketone phenylhydrazone 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到1-phenyl-3-propyl-4-chloropyrazole
  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

文献信息

• One-stage procedure of synthesis of highly reactive α-chloro-β-ketoacetals. 4-chloropyrazoles from α-chloro-β-ketodimethoxyacetals
  作者：G. V. Bozhenkov、V. A. Savosik、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428008020024

  日期：2008.2

  Conditions were developed where the reaction of alkyl 1,2-dichlorovinyl ketones with alcohols and 1,2-dihydroxybenzenes led to the formation of the corresponding open-chain and cyclic α-chloro-β-ketoacetals. The reaction of α-chloro-β-alkylketodimethoxyacetals with alkyl-, benzyl-, and arylhydrazines resulted in 1,3-substituted 4-chloropyrazoles in 70–90% yields demonstrating that primarily formed 2,2-dimethoxy-1-chloroethyl alkyl ketones hydrazones underwent heterocyclization.

  开发了一些条件，使得烷基1,2-二氯乙烯酮与醇和1,2-二羟基苯的反应生成相应的开放链和环状α-氯-β-酮乙缩醛。α-氯-β-烷基酮二甲氧基乙缩醛与烷基、苄基和芳基肼的反应生成了1,3-取代的4-氯吡唑，产率为70-90%，表明主要生成的2,2-二甲氧基-1-氯乙基烷基酮肼类化合物发生了杂环化反应。