2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-nitropyridine | 60639-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-nitropyridine
• 英文别名: 3-nitro-2-(3,5-dimethylpyrazol-1-yl)pyridine；2-(3,5-dimethylpyrazol-1-yl)-3-nitropyridine
• CAS: 60639-21-6
• 化学式: C₁₀H₁₀N₄O₂
• 分子量: 218.215
• InChiKey: WHYUYNMOCOSTEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-nitropyridine 以90%的产率得到
  参考文献：
  名称：

  BOUCHET P., BULL. SOC. CHIM. FRANCE , 1976, NO 5-6, PART. 2, 839-844

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-3-硝基吡啶 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-nitropyridine
  参考文献：
  名称：

  Synthesis and pharmacological activity of N-hetaryl-3(5)-nitropyridines

  摘要：

  Previously undescribed 2-, 4or 6-substituted hetaryl-3(5)-nitropyridines were synthesized by the interaction of a number of chlorosubstituted 3(5)-nitropyridines with some diazoles or 3-chloropyridazin-6one. In addition, pyrazolyl-3-nitropyridines were prepared by both the above method and cyclization of hydrazinopyridines, which, in turn, were synthesized by the treatment of chlorosubstituted 3-nitropyridines with hydrazine. It has been shown that these compounds have a moderate antibacterial activity against some pathogenic Gram-positive and Gram-negative bacteria (Staphylococcus aureus and Escherichia coli) and a strong protistocidal effect on protozoa species Colpoda steinii surpassing in this respect clinically used reference drugs.

  DOI：

  10.1134/s1068162015030048

文献信息

• An efficient route to polynitrogen-fused tricycles via a nitrene-mediated N–N bond formation under microwave irradiation
  作者：Coralie Nyffenegger、Eric Pasquinet、Franck Suzenet、Didier Poullain、Christian Jarry、Jean-Michel Léger、Gérald Guillaumet

  DOI：10.1016/j.tet.2008.07.055

  日期：2008.9

  The synthesis of unprecedented fused azaheterocyclic ring systems is described. Tricycles with either a central pyrazole or a triazole ring were obtained via a nitrene-mediated reaction of nitro bis(hetaryl) derivatives in the presence of triethylphosphite. The cyclization proceeded with complete chemoselectivity for the desired N–N bond formation and was completed within minutes under microwave activation

  描述了前所未有的稠合氮杂杂环系统的合成。在亚磷酸三乙酯存在下，通过硝基双（杂芳基）衍生物的硝基反应，可以得到带有中心吡唑环或三唑环的三环环。环化反应对所需的N–N键形成具有完全的化学选择性，并在微波激活下在数分钟内完成。关键的硝基自行车是使用Stille偶联或芳族亲核取代合成的。
• Inductive Heating with Magnetic Materials inside Flow Reactors
  作者：Sascha Ceylan、Ludovic Coutable、Jens Wegner、Andreas Kirschning

  DOI：10.1002/chem.201002291

  日期：2011.2.7

  can be performed under flow conditions by using inductively heated flow reactors. These include transfer hydrogenations, heterocyclic condensations, pericyclic reactions, organometallic reactions, multicomponent reactions, reductive cyclizations, homogeneous and heterogeneous transition‐metal catalysis. Silica‐coated iron oxide nanoparticles are stable under many chemical conditions and the silica shell

  涂有硅胶或钢珠的超顺磁性纳米粒子是用于流动反应器的新型固定床材料，可在流动条件下有效地加热感应场中的反应混合物。与常规加热和微波加热相比，研究了这些新型加热材料的范围和局限性。结果表明，就速率加速而言，感应加热可以与微波加热进行比较。还证明了通过使用感应加热的流动反应器，可以在流动条件下进行非常多种多样的不同反应。这些包括转移氢化，杂环缩合，周环反应，有机金属反应，多组分反应，还原环化，均相和非均相过渡金属催化。
• Synthesis and pharmacological activity of N-hetaryl-3(5)-nitropyridines
  作者：A. I. Klimenko、L. N. Divaeva、A. A. Zubenko、A. S. Morkovnik、L. N. Fetisov、A. N. Bodryakov

  DOI：10.1134/s1068162015030048

  日期：2015.7

  Previously undescribed 2-, 4or 6-substituted hetaryl-3(5)-nitropyridines were synthesized by the interaction of a number of chlorosubstituted 3(5)-nitropyridines with some diazoles or 3-chloropyridazin-6one. In addition, pyrazolyl-3-nitropyridines were prepared by both the above method and cyclization of hydrazinopyridines, which, in turn, were synthesized by the treatment of chlorosubstituted 3-nitropyridines with hydrazine. It has been shown that these compounds have a moderate antibacterial activity against some pathogenic Gram-positive and Gram-negative bacteria (Staphylococcus aureus and Escherichia coli) and a strong protistocidal effect on protozoa species Colpoda steinii surpassing in this respect clinically used reference drugs.
• BOUCHET P., BULL. SOC. CHIM. FRANCE <BSCF-AS>, 1976, NO 5-6, PART. 2, 839-844
  作者：BOUCHET P.

  DOI：——

  日期：——