2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoic acid
• 英文别名: 2-(4-Phenyltriazol-1-yl)benzoic acid；2-(4-phenyltriazol-1-yl)benzoic acid
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: MFJFBWNLROGDCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoic acid 在 ammonium peroxydisulfate 、 potassium acetate 、 silver nitrate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以78%的产率得到3-phenyl-5H-benzo[d][1,2,3]triazolo[5,1-b][1,3]oxazin-5-one
  参考文献：
  名称：

  Silver-Catalyzed Intramolecular C(5)–H Acyloxylation of 1,4-Di­substituted 1,2,3-Triazoles

  摘要：

  报道了银催化的1,4-二取代-1,2,3-三唑酸的直接内酯化反应，通过C(5)–H乙酰氧化作用。该方法提供了一种简洁高效的途径，以在室温下获得良好至优良产率的内酯-融合三唑衍生物。

  DOI：

  10.1055/s-0036-1588779
• 作为产物：
  描述：

  2-(4-phenyl-1H-1,2,3-triazol-1-yl)phenylmethanol 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以90%的产率得到2-(4-phenyl-1H-1,2,3-triazol-1-yl)benzoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of phenyl-1H-1,2,3-triazole derivatives as anti-inflammatory agents

  摘要：

  Rapid and efficient synthesis of a phenyl-1H-1,2,3-triazole library enabled cost-effective biological testing of a range of novel non-steroidal anti-inflammatory drugs with potential for improved drug efficacy and toxicity profiles. Anti-inflammatory activities of the phenyl-1H-1,2,3-triazole analogs synthesized in this report were assessed using the xylene-induced ear edema model in mice. At least four analogs, 2a, 2b, 2c, and 4a, showed more potent effects than the reference anti-inflammatory drug diclofenac at the same dose of 25 mg/kg. To explore relationships between the structural properties of phenyl-1H-1,2,3-triazole analogs and their anti-inflammatory activities in xylene-induced ear edema, comparative molecular field analysis was performed, and pharmacophores showing good anti-inflammatory activities were identified based on an analysis of contour maps obtained from comparative molecular field analysis. The anti-inflammatory effect on the molecular level was tested by the expression of tumor necrosis factor-alpha induced COX-2 using Western blots. Because the addition of the analog 2c caused the expression change of TNF-alpha induced COX-2, the molecular binding mode between 2c and COX-2 was elucidated using in silico docking. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.01.003

文献信息

• One-pot synthesis of 1,4-disubstituted 1,2,3-triazoles from nitrobenzenes
  作者：Fen Zhao、Zhen Chen、Kai Xie、Rui Yang、Yu-Bo Jiang

  DOI：10.1016/j.cclet.2015.09.021

  日期：2016.1

  Abstract A facile synthesis of 1,4-disubstituted 1,2,3-triazoles was achieved from nitrobenzenes and terminal alkynes under mild conditions. The reactions were successful for nitrobenzenes and terminal alkynes bearing various functionalities, from which the 1,2,3-triazole derivatives were smoothly synthesized through a four-step one-pot sequence.

  摘要在温和的条件下，由硝基苯和末端炔烃轻松合成了1,4-二取代的1,2,3-三唑。对于具有各种功能的硝基苯和末端炔烃，反应是成功的，通过四步一锅法平稳地合成了1,2,3-三唑衍生物。
• 一种1,4-二取代-1,2,3-三氮唑衍生物的制备 方法
  申请人：昆明理工大学

  公开号：CN104945339B

  公开（公告）日：2017-11-10

  本发明公开一种1,4‑二取代‑1,2,3‑三氮唑衍生物的制备方法，属于有机合成中间体技术领域；本发明采用廉价易得的硝基化合物为原料，在室温条件下先与还原剂发生还原反应，接着依次与亚硝酸钠及叠氮钠分别发生氧化及叠氮化反应，再与炔在碘化亚铜催化下反应生成1,4‑二取代‑1,2,3‑三氮唑衍生物，所涉及的四步反应连续操作，中间产物不需分离；本方法具有成本低、反应效率高、操作便利等优点，有望应用于工业化生产；所合成的化合物含有1,2,3‑三唑环结构单元，可应用于有机合成中间体及药物的合成与修饰，亦为药物筛选提供新颖而有效的合成方法。
• Pd-catalyzed selective decarboxylation/C–H activation coupling of aryl acid with thiazole and oxazole directed by 1,2,3-triazole
  作者：Xinyuan Ma、Yaowen Liu、Kai Xie、Yubo Jiang

  DOI：10.1016/j.tetlet.2018.08.055

  日期：2018.10

  An efficient palladium-catalyzed selective decarboxylation/C–H activation coupling of aryl acid with thiazole and oxazole under the assistance of 1,2,3-triazole ring were developed. This work provides an effective access to build functionalized 1,2,3-triazoles bearing thiazole and oxazole moieties. This method has good substrate compatibility to compose a series of selective heterocyclic compounds

  在1,2,3-三唑环的帮助下，开发了一种有效的钯催化的选择性酸脱羧/ CH活化活化芳基酸与噻唑和恶唑的偶联反应。这项工作为构建带有噻唑和恶唑基团的功能化1,2,3-三唑提供了有效途径。该方法具有良好的底物相容性，可以以中等至良好的产率组成一系列选择性杂环化合物。
• Synthesis of 2-(1,2,3-Triazolyl)benzamide Derivatives by a Copper(I)-Catalyzed Multicomponent Reaction
  作者：Abdulhakim Hayeebueraheng、Benyapa Kaewmee、Vatcharin Rukachaisirikul、Juthanat Kaeobamrung

  DOI：10.1002/ejoc.201701316

  日期：2017.12.8

  The copper-catalyzed multicomponent reaction of 2-iodobenzamides, NaN3 and terminal alkynes for the synthesis of 2-(1,2,3,-triazolyl)benzamide derivatives was achieved in a one-step process and short period of time under mild reaction condition. The transformations consisted of C(aryl)-N bond formation and azide-alkyne cycloadditon. The absence of an external base was found to be crucial in determining

  2-碘代苯甲酰胺、NaN3和末端炔烃的铜催化多组分反应合成2-(1,2,3,-三唑基)苯甲酰胺衍生物是在温和反应条件下一步法、短时间完成的. 转化包括 C(芳基)-N 键形成和叠氮化物-炔烃环加成。发现不存在外部碱对于确定优选的反应途径至关重要。
• Microwave-Assisted Click Chemistry Synthesis of 1,2,3-Triazoles from Aryldiazonium Silica Sulfates in Water
  作者：Amin Zarei、Leila Khazdooz、Abdol Hajipour、Hamidreza Aghaei、Ghobad Azizi

  DOI：10.1055/s-0032-1316783

  日期：——

  Abstract A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles is studied by in situ generation of aryl azides via the reaction of aryldiazonium silica sulfates and sodium azide, followed by coupling with a terminal alkyne in the presence of copper catalyst. These reactions are carried out in water under mild and heterogeneous conditions without using any additional ligands

  摘要 通过芳基重氮二氧化硅硫酸盐和叠氮化钠的反应原位生成芳基叠氮化物，然后在存在下与末端炔烃偶联，研究了微波辅助点击化学合成1,4-二取代的1,2,3-三唑的方法。铜催化剂。这些反应在温和和非均质条件下于水中进行，无需使用任何其他配体。 通过芳基重氮二氧化硅硫酸盐和叠氮化钠的反应原位生成芳基叠氮化物，然后在存在下与末端炔烃偶联，研究了微波辅助点击化学合成1,4-二取代的1,2,3-三唑的方法。铜催化剂。这些反应在温和和非均质条件下于水中进行，无需使用任何其他配体。