4-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]pyridine | 217499-16-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]pyridine
• CAS: 217499-16-6
• 化学式: C₁₄H₁₀FN₃
• 分子量: 239.252
• InChiKey: XYZRUIZJLLLEOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 4-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]pyridine 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以85.2%的产率得到1-benzoyl-3-(4-pyridyl)-5-(4-fluorophenyl)pyrazole
  参考文献：
  名称：

  SYNTHESIS AND ANTI-MICROBIAL ACTIVITIES OF 1,3,5-TRISUBSTITUTED-PYRAZOLE DERIVATIVES CONTAINING A PYRIDYL MOIETY

  摘要：

  Claisen condensation of ethyl isonicotinate with different acetophenones gave the corresponding pyridyl-beta-diketones, while the treatment with hydrazine hydrate yielded 3,5-disubstituted-1H-pyrazoles, which then converted 1,3,5-trisubstituted-pyrazole derivatives containing a pyridyl moiety by N-acylation with acyl chloride. The structures of all newly synthesized compounds are established by FTIR, H-1 NMR, mass spectroscopy and elemental analysis, and in the case of compound 2e, analyzed by single-crystal X-ray diffraction further. The anti-microbial activities of the title compounds have been tested by disc diffusion method against Escherichia coli, Staphylococcus aureus, Pyricularia oryzae and Rhizoctnia solani. The results showed that compounds 3c and 4c exhibited good inhibitory activity against all the tested organisms.

  DOI：

  10.4067/s0717-97072015000100018
• 作为产物：
  描述：

  4-(3-(4-fluorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-yl)pyridine 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以56%的产率得到4-[3-(4-fluorophenyl)-1H-pyrazol-5-yl]pyridine
  参考文献：
  名称：

  非对称3,5-双（杂）芳族吡唑的模块化Sydnone环加成/ Suzuki-Miyaura交叉偶联策略

  摘要：

  4-卤代壬烯与1-卤代炔烃的[3 + 2]偶极环加成反应可直接访问3,5-dihalopyrazoles，这是用于通过位点选择性Pd催化的交叉选择性修饰非对称3,5-取代吡唑衍生物的有价值的支架。偶联反应。例如，在PMP保护的吡唑核的C-5和C-3位置上灵活引入不同的（杂）芳基取代基是通过与各种硼酸的顺序反应以一锅操作实现的。

  DOI：

  10.1021/ol101087j

文献信息

• A Modular Sydnone Cycloaddition/Suzuki−Miyaura Cross-Coupling Strategy to Unsymmetrical 3,5-Bis(hetero)aromatic Pyrazoles
  作者：Thierry Delaunay、Pierre Genix、Mazen Es-Sayed、Jean-Pierre Vors、Nuno Monteiro、Geneviève Balme

  DOI：10.1021/ol101087j

  日期：2010.8.6

  The [3 + 2] dipolar cycloaddition of 4-halosydnones with 1-haloalkynes opens a straightforward access to 3,5-dihalopyrazoles, valuable scaffolds for the elaboration of unsymmetrically 3,5-substituted pyrazole derivatives via site-selective Pd-catalyzed cross-coupling reactions. For instance, the flexible introduction of different (hetero)aryl substituents at the C-5 and C-3 positions of the PMP-protected

  4-卤代壬烯与1-卤代炔烃的[3 + 2]偶极环加成反应可直接访问3,5-dihalopyrazoles，这是用于通过位点选择性Pd催化的交叉选择性修饰非对称3,5-取代吡唑衍生物的有价值的支架。偶联反应。例如，在PMP保护的吡唑核的C-5和C-3位置上灵活引入不同的（杂）芳基取代基是通过与各种硼酸的顺序反应以一锅操作实现的。
• Facile Access to 3,5-Dihalogenated Pyrazoles by Sydnone Cycloaddition and their Versatile Functionalization by Pd-Catalyzed Cross-Coupling Processes
  作者：Thierry Delaunay、Mazen Es-Sayed、Jean-Pierre Vors、Nuno Monteiro、Geneviève Balme

  DOI：10.1002/ejoc.201100119

  日期：2011.7

  The 1,3-dipolar cycloaddition of diversely N-substituted 4-iodosydnones with 3-halopropiolates produces easily separable mixtures of dihalogenated pyrazolylcarboxylic esters at a preparative scale level, with the 3,5-dihalogenopyrazole regioisomers always predominating. Further decarboxylation of the major isomers provided the corresponding 3,5-dihalogenopyrazoles with a free C-4 position. These were

  不同 N-取代的 4-碘代炔酮与 3-卤代丙炔酸酯的 1,3-偶极环加成在制备规模水平上产生易于分离的二卤化吡唑基羧酸酯混合物，其中 3,5-二卤代吡唑区域异构体始终占主导地位。主要异构体的进一步脱羧提供相应的具有游离 C-4 位的 3,5-二卤代吡唑。这些被发现是通过位点选择性 Pd 催化交叉偶联反应制备不对称 1,3,5-三取代吡唑衍生物的有价值的支架。值得注意的是，在吡唑核的 C-5 和 C-3 位置灵活且选择性地引入不同的（杂）芳基、乙烯基或烷基取代基可以通过与各种硼化合物的顺序 Suzuki 型反应来实现。此外，
• SYNTHESIS AND ANTI-MICROBIAL ACTIVITIES OF 1,3,5-TRISUBSTITUTED-PYRAZOLE DERIVATIVES CONTAINING A PYRIDYL MOIETY
  作者：DUN-JIA WANG、HUA LIU、YAN-FANG KANG、YAN-JUN HU、XIAN-HONG WEI

  DOI：10.4067/s0717-97072015000100018

  日期：——

  Claisen condensation of ethyl isonicotinate with different acetophenones gave the corresponding pyridyl-beta-diketones, while the treatment with hydrazine hydrate yielded 3,5-disubstituted-1H-pyrazoles, which then converted 1,3,5-trisubstituted-pyrazole derivatives containing a pyridyl moiety by N-acylation with acyl chloride. The structures of all newly synthesized compounds are established by FTIR, H-1 NMR, mass spectroscopy and elemental analysis, and in the case of compound 2e, analyzed by single-crystal X-ray diffraction further. The anti-microbial activities of the title compounds have been tested by disc diffusion method against Escherichia coli, Staphylococcus aureus, Pyricularia oryzae and Rhizoctnia solani. The results showed that compounds 3c and 4c exhibited good inhibitory activity against all the tested organisms.