4-(1-苯基-5-对甲苯基-1H-吡唑-3-基)-苯甲酸甲酯 | 1014625-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(1-苯基-5-对甲苯基-1H-吡唑-3-基)-苯甲酸甲酯
• 英文名称: 4-(1-phenyl-5-p-tolyl-1H-pyrazol-3-yl)-benzoic acid methyl ester
• CAS: 1014625-49-0
• 化学式: C₂₄H₂₀N₂O₂
• 分子量: 368.435
• InChiKey: OKJAVEJQIPBSRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  44.12
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (E)-2-(4-methylphenyl)-1-nitroethene 、 p-carbomethoxybenzaldehyde phenylhydrazone 以 乙二醇 为溶剂， 反应 16.0h， 生成 4-(1-苯基-5-对甲苯基-1H-吡唑-3-基)-苯甲酸甲酯
  参考文献：
  名称：

  Regioselective Synthesis of 1,3,5-Tri- and 1,3,4,5-Tetrasubstituted Pyrazoles from N-Arylhydrazones and Nitroolefins

  摘要：

  [GRAPHICS]Two general protocols are developed for the regioselective synthesis of 1,3,5-tri- and 1,3,4,5-tetrasubstituted pyrazoles by the reaction of electron-deficient N-arylhydrazones with nitroolefins. Studies on the stereochemistry of the key pyrazolidine intermediate suggest a stepwise cycloaddition mechanism.

  DOI：

  10.1021/jo7026195

文献信息

• Synthesis, Anti-inflammatory, Analgesic and Antipyretic Activity of Novel 1,3,5-Trisubstituted Pyrazole Derivatives
  作者：THATAVARTHI PADMINI、BIGALA RAJ KAMAL

  DOI：10.14233/ajchem.2019.21781

  日期：2019.5.25

  A novel series of 1,3,5-trisubstituted pyrazole derivatives were synthesized by the cycloaddition reaction between the electron rich N-substituted aryl hydrazones and nitro-olefins. Different N-substituted aryl hydrazones (1a-j) on reacting with 4-methyl-β-nitrostyrene (2) in ethylene glycol or trifluoroethanol-trifluoro acetic acid mixture (for acid stable hydrazones) at 120 ºC, yielded various 1,3,5-trisubstituted pyrazoles (3a-j). The final products were characterized by spectral analysis using Mass, NMR and IR spectroscopy. All the products were assessed for their anti-inflammatory, analgesic and antipyretic activities on Swiss albino rats. All the compounds (3a-j) exhibited noteworthy defence against inflammation, nociception and hyperthermia. Compounds (3e and 3h) disclosed better antiinflammatory, analgesic and antipyretic activities while compound 3c had highest anti-inflammatory activity compared to the standard nimesulide.

  一系列的1,3,5-三取代吡唑衍生物通过电子富集的N-取代芳基腙和硝基烯烃的环加成反应合成。不同的N-取代芳基腙(1a-j)与4-甲基-β-硝基苯乙烯(2)在乙二醇或三氟乙醇-三氟乙酸混合物(用于酸稳定的腙)中于120°C反应，生成各种1,3,5-三取代吡唑(3a-j)。最终产物通过质谱、核磁共振和红外光谱进行了表征分析。所有产物在瑞士白鼠上进行了抗炎、镇痛和退热活性评估。所有化合物(3a-j)表现出显著的抗炎、镇痛和退热活性。化合物(3e和3h)表现出更好的抗炎、镇痛和退热活性，而化合物3c的抗炎活性最高，超过了标准药物尼美舒利。