1-phenyl-3-methyl-4-chloropyrazole | 591233-95-3

• 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-methyl-4-chloropyrazole
• 英文别名: 3-methyl-1-phenyl-4-chloropyrazole；4-chloro-3-methyl-1-phenylpyrazole
• CAS: 591233-95-3
• 化学式: C₁₀H₉ClN₂
• 分子量: 192.648
• InChiKey: YVFZRALOSKFFAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  3,4-二氯-3-丁烯-2-酮 、 苯肼 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以77%的产率得到1-phenyl-3-methyl-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。
• [EN] PYRAZOLOPYRIMIDINES AS INHIBITORS OF GLUCOCORTICOID RECEPTOR TRANSLOCATION<br/>[FR] PYRAZOLOPYRIMIDINES UTILISÉES EN TANT QU'INHIBITEURS DE LA TRANSLOCATION DU RÉCEPTEUR DES GLUCOCORTICOÏDES
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2016123392A2

  公开（公告）日：2016-08-04

  Provided herein are compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of Glucocorticoid Receptor (GR) translocation. Furthermore, the subject compounds and compositions are useful for the treatment of diseases involved in the hypothalamic-pituitary-adrenal (HPA) axis.