1-(4-chlorophenyl)-5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole | 27293-99-8

• 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-(4-chlorophenyl)-5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole
• 英文别名: 1-(4-chloro-phenyl)-5-(4-methoxy-phenyl)-3-phenyl-1H-pyrazole；1-(p-Chlorphenyl)-5-(p-methoxyphenyl)-3-phenylpyrazol；1-(4-Chlorophenyl)-5-(4-methoxyphenyl)-3-phenylpyrazole
• CAS: 27293-99-8
• 化学式: C₂₂H₁₇ClN₂O
• 分子量: 360.843
• InChiKey: XZQXVPFVLPWYNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二硫代苯甲酸甲酯 在 sodium hydride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-(4-chlorophenyl)-5-(4-methoxyphenyl)-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  Cyclocondensation of Arylhydrazines with 1,3-Bis(het)arylmonothio-1,3-diketones and 1,3-Bis(het)aryl-3-(methylthio)-2-propenones: Synthesis of 1-Aryl-3,5-bis(het)arylpyrazoles with Complementary Regioselectivity

  摘要：

  Two efficient highly regioselective routes for the synthesis of unsymmetrically substituted 1-aryl-3,5-bis(het)arylpyrazoles with complementary regioselectivity starting from active methylene ketones have been reported. In the first protocol, the newly synthesized 1,3-bis(het)aryl-monothio-1,3-diketone precursors (prepared by condensation of active methylene ketones with het(aryl) dithioesters in the presence of sodium hydride) were reacted with arylhydrazines in refluxing ethanol under neutral conditions, furnishing 1-aryl-3,5-bis(het)arylpyrazoles 7, in which the het(aryl) moiety attached to the thiocarbonyl group of monothio-1,3-diketones is installed at the 3-position. In the second method, the corresponding 3-(methylthio)-1,3-bis(het)aryl-2-propenones (prepared in situ by base-induced alkylation of 1,3-monothiodiketones) were condensed with arylhydrazines in the presence of potassium tert-butoxide in. refluxing tert-butyl alcohol, yielding 1-aryl-3,5-bis(het)arylpyrazoles 9 with complementary regioselectivity (method A). The efficiency of this protocol was further improved by developing a one-pot, three-component procedure for the synthesis of pyrazoles 9, directly from active methylene ketones, by reacting in situ generated 3-(methylthio)-1,3-bis(het)aryl-2-propenones with arylhydrazines in the presence of sodium hydride (instead of potassium tert-butoxide as base). The structures and regiochemistry of newly synthesized pyrazoles were confirmed from their spectral and analytical data along with X-ray crystallographic data of three pairs of regioisomers.

  DOI：

  10.1021/jo400599e

文献信息

• Cross-coupling of 1-aryl-5-bromopyrazoles: regioselective synthesis of 3,5-disubstituted 1-arylpyrazoles
  作者：Xiao-jun Wang、Jonathan Tan、Karl Grozinger

  DOI：10.1016/s0040-4039(00)00704-8

  日期：2000.6

  The cross-coupling of 1-aryl-5-bromopyrazoles 4 with alkynes, vinyltins and arylboronic acids promoted by Pd(PPh3)(4) afforded unsymmetrical 3,5-disubstituted 1-arylpyrazoles 5-8 in excellent yields. 1-Aryl-5-bromopyrazoles 4 were prepared from their corresponding 1-arylpyrazolones 3 with PBr3 in refluxing acetonitrile. (C) 2000 Elsevier Science Ltd. All rights reserved.