3-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)pyridine

• 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: 3-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)pyridine
• 英文别名: 3-(3-Benzyl-5-phenyltriazol-4-yl)pyridine；3-(3-benzyl-5-phenyltriazol-4-yl)pyridine
• 化学式: C₂₀H₁₆N₄
• 分子量: 312.374
• InChiKey: FWSWLYXJUQKPHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  溴甲苯 在 sodium azide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 3-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)pyridine
  参考文献：
  名称：

  乙二胺官能化纤维素上负载的铜（I）和钯纳米粒子可作为1,3-偶极环加成/直接芳基化序列的有效催化剂

  摘要：

  合成并表征了乙二胺功能化纤维素上担载的Pd的Cu（I）和纳米颗粒。发现合成的催化剂是通过可持续的1,3-偶极环加成/直接芳构化序列合成1,4,5-三取代的1,2,3-三唑的高效多相催化剂。催化剂可以通过简单的过滤容易地回收，并且可以重复使用至少五个循环而不会失去其活性。版权所有©2014 John Wiley＆Sons，Ltd.

  DOI：

  10.1002/aoc.3091

文献信息

• Palladium-Catalyzed Direct Arylations of 1,2,3-Triazoles with Aryl Chlorides using Conventional Heating
  作者：Lutz Ackermann、Rubén Vicente、Robert Born

  DOI：10.1002/adsc.200800016

  日期：2008.3.25

  Generally applicable, palladium-catalyzed direct arylations of 1,2,3-triazoles with aryl chlorides were accomplished through conventional heating at reaction temperatures of 105–120 °C. Thereby, intra- and intermolecular CH bond functionalizations were achieved with a variety of differently substituted chlorides as electrophiles, bearing numerous valuable functional groups.

  通常适用的是，通过在105-120°C的反应温度下进行常规加热来实现1,2,3-三唑与芳基氯化物的钯催化直接芳基化。因此，用各种不同取代的氯化物作为亲电子体，实现了分子内和分子间的CH键官能化，并带有许多有价值的官能团。
• Developing Bis(imino)acenaphthene-Supported <i>N</i>-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles
  作者：Li-Qun Hu、Rong-Li Deng、Yan-Fen Li、Cui-Jin Zeng、Dong-Sheng Shen、Feng-Shou Liu

  DOI：10.1021/acs.organomet.7b00784

  日期：2018.1.22

  On the basis of the strategy of developing highly efficient protocol for Pd-catalyzed cross-coupling reactions, a series of bulky bis(imino)acenaphthene (BIAN)-supported Pd-PEPPSI complexes were synthesized, characterized, and applied in direct arylation of azoles. The effect of backbone and N-moieties on NHCs was evaluated, and the reaction conditions were optimized. It was found that the bulky Pd-PEPPSI complexes could be successfully employed in cross-coupling of (hetero)aryl bromides with azoles at a low palladium loading of 0.5-0.05 mol % under aerobic conditions, demonstrating the ease of manipulation without glovebox and handling of solvents.
• Direct Pd-Catalyzed Arylation of 1,2,3-Triazoles
  作者：Stepan Chuprakov、Natalia Chernyak、Alexander S. Dudnik、Vladimir Gevorgyan

  DOI：10.1021/ol070697u

  日期：2007.6.1

  A highly efficient method for the synthesis of multisubstituted 1,2,3-triazoles via a direct Pd-catalyzed C-5 arylation has been developed.