1-butyl-3-propyl-1H-pyrazole | 1100829-44-4

• 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-butyl-3-propyl-1H-pyrazole
• 英文别名: 1-butyl-3-propylpyrazole
• CAS: 1100829-44-4
• 化学式: C₁₀H₁₈N₂
• 分子量: 166.266
• InChiKey: YODDFVGWHJFWRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  1,1-二丁基肼 、 1-chlorohex-1-en-3-one 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以60%的产率得到1-butyl-3-propyl-1H-pyrazole
  参考文献：
  名称：

  1-Alkylpyrazoles and 1-alkyl-5-chloropyrazoles from halovinyl ketones and 1,1-dialkylhydrazines

  摘要：

  Regioselective heterocyclization of alkyl 2-chloro- and 2,2-dichlorovinyl ketones with 1,1-dialkylhydrazines to 1,3-dialkyl-1H-pyrazoles and 1,3-dialkyl-5-chloro-1H-pyrizoles involves intermediate formation of the corresponding dialkylhydrazones. Fragmentation pattern of chlorine-containing pyrazoles, 3-chloromethyl-1-methyl-1H-pyrazole and 5-chloro-1-methyl-3-propyl-1H-pyrazole, depends on the position of the halogen atom.

  DOI：

  10.1134/s1070428008080150

文献信息

• Distinguishing Features of reactions of 2-chloro-and 2,2-dichloro(bromo)vinyl ketones with alkyl-and arylhydrazines
  作者：G. V. Bozhenkov、V. A. Savosik、L. I. Larina、L. V. Klyba、E. R. Zhanchipova、A. N. Mirskova、G. G. Levkovskaya

  DOI：10.1134/s1070428008070129

  日期：2008.7

  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.
• Ratio of 1,3- and 1,5-dialkyl-substituted pyrazoles obtained from chlorovinyl alkyl ketones and alkylhydrazines, 3(5)-pyrazoles and alkyl bromides
  作者：A. V. Popov、E. V. Rudyakova、L. I. Larina、V. A. Kobelevskaya、G. G. Levkovskaya

  DOI：10.1134/s1070428014110190

  日期：2014.11

  Unsymmetrically substituted 1,3- and 1,5-dialkylpyrazoles and 1,3-dialkyl-5-chloropyrazoles were prepared. 2-Chlorovinyl ketones react with C-1-C-8-alkylhydrazines along two routes giving mixtures of 1-R'-3-R- and 1-R'-5-R-pyrazoles with the prevalence of 1,3-isomer. The proportion of 3-substituted 1-alkylpyrazole in the isomers mixture grows from 60 to 94-97% with growing length of the alkyl chain in the hydrazine. The alkylation of 1-unsubstituted 3(5)-alkylpyrazoles with alkyl bromides afforded predominantly (by 16-50%) 1,3-disubstituted pyrazoles. 1,3-Dialkyl-5-chloropyrazoles form from 2,2-dichlorovinyl alkyl ketones and functionalized alkylhydrazines. It was suggested to synthesize 1,3-dialkyl-substituted pyrazoles by dechlorination of unsymmetrically substituted 1,3-dialkyl-5-chloropyrazoles in the presence of complex nickel catalyst and water as the proton source.