5-(4-methoxyphenyl)-1-methyl-4-nitro-1H-pyrazole | 1584233-58-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-methoxyphenyl)-1-methyl-4-nitro-1H-pyrazole
• 英文别名: 5-(4-Methoxyphenyl)-1-methyl-4-nitropyrazole
• CAS: 1584233-58-8
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: QKZVQIURZHYBIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-methoxyphenyl p-toluenesulfonate 、 1-甲基-4-硝基吡唑 在 palladium diacetate 、 caesium carbonate 、 cesium pivalate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以77%的产率得到5-(4-methoxyphenyl)-1-methyl-4-nitro-1H-pyrazole
  参考文献：
  名称：

  Palladium Catalyzed Arylation and Benzylation of Nitroarenes Using Aryl Sulfonates and Benzyl Acetates

  摘要：

  Pd-catalyzed arylation or benzylation of nitroazoles using aryl sulfonates or benzyl acetates is described. Electronically varied aryl tosylates and mesylates, as well as benzyl acetates, afford the arylated and benzylated products. Arylation of nitrobenzene is also reported. The relative rate for the arylation of halides is greater than that of tosylates using the reported reaction parameters. These studies enhance the scope of electrophiles for nitroarene arylations and benzylations, which was hitherto limited to the use of halide electrophiles.

  DOI：

  10.1021/acs.joc.7b00550

文献信息

• C-H Arylation of Nitroimidazoles and Nitropyrazoles Guided by the Electronic Effect of the Nitro Group
  作者：Haeun Jung、Seri Bae、Ha-Lim Jang、Jung Min Joo

  DOI：10.5012/bkcs.2014.35.10.3009

  日期：2014.10.20

  palladium-catalyzed C–H arylation reaction of nitroimidazoles and nitropyrazoles was developed using aryl bromides as arene donors. The electron-withdrawing effect of the nitro group allows for direct C–H arylation reactions of the nitro diazoles with high regioselectivity under mild conditions. The new C–H arylation approach is thus complementary to nucleophilic substitution reactions, enabling the preparation

  使用芳基溴化物作为芳烃供体，开发了钯催化的硝基咪唑和硝基吡唑的 C-H 芳基化反应。硝基的吸电子效应使硝基二唑在温和条件下具有高区域选择性的直接 C-H 芳基化反应。因此，新的 C-H 芳基化方法与亲核取代反应互补，能够制备复杂的硝唑化合物。
• Regioselective and Guided C–H Activation of 4-Nitropyrazoles
  作者：Viktor O. Iaroshenko、Ashot Gevorgyan、Olena Davydova、Alexander Villinger、Peter Langer

  DOI：10.1021/jo4025418

  日期：2014.4.4

  A divergent and regioselective approach to 5-aryl-4-nitro-1H-pyrazoles was developed by guided transition-metal-catalyzed arylation of 4-nitro-1H-pyrazoles. This method provides a convenient tool for the functionalization of the pharmacologically relevant pyrazole scaffold. The scope and limitations of the methodology were studied.