4-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)benzonitrile | 1111662-41-9

• 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-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)benzonitrile
• 英文别名: 1-benzyl-5-(4-cyanoyphenyl)-4-phenyl-1H-1,2,3-triazole；4-(3-Benzyl-5-phenyltriazol-4-yl)benzonitrile；4-(3-benzyl-5-phenyltriazol-4-yl)benzonitrile
• CAS: 1111662-41-9
• 化学式: C₂₂H₁₆N₄
• 分子量: 336.396
• InChiKey: OLVBXNURERLZTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 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：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  对氯苯甲腈 、 1-苄基-4-苯基-1,2,3-噻唑 在 palladium diacetate 、 potassium carbonate 、 三环己基膦 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以71%的产率得到4-(1-benzyl-4-phenyl-1H-1,2,3-triazol-5-yl)benzonitrile
  参考文献：
  名称：

  使用常规加热，钯催化1,2,3-三唑与芳基氯化物的直接芳基化

  摘要：

  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。

  DOI：

  10.1002/adsc.200800016

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。
• Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles
  作者：Fang Wei、Haoyu Li、Chuanling Song、Yudao Ma、Ling Zhou、Chen-Ho Tung、Zhenghu Xu

  DOI：10.1021/acs.orglett.5b01342

  日期：2015.6.5

  A Cu/Pd-catalyzed, three-component click reaction of azide, alkyne, and aryl halide has been developed. By using this Cu/Pd transmetalation relay catalysis, a variety of 1,4,5-trisubstituted 1,2,3-triazoles were quickly assembled in one step in high yields with complete regioselectivity, just like assembling Lego bricks. Notably, different from the well-established CuAAC click reactions only working on terminal alkynes, this reaction offers an alternative solution for the problem of the click reaction of internal alkynes.
• 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 C-H Arylation of Heteroarenes with Aryl Chlorides by Using an Abnormal N-Heterocyclic-Carbene-Palladium Catalyst
  作者：Jasimuddin Ahmed、Samaresh Chandra Sau、Sreejyothi P、Pradip Kumar Hota、Pavan K. Vardhanapu、Gonela Vijaykumar、Swadhin K. Mandal

  DOI：10.1002/ejoc.201601218

  日期：2017.2.3

  Herein, we report a versatile catalytic system for the direct C–H arylation of heteroarenes with activated aryl chloride substrates. The catalyst works successfully for a variety of heteroarenes and aryl chloride coupling partners under very low catalyst-loading conditions. We have successfully performed the direct C–H arylations of 1-methylpyrrole, 1-methylindole, furan, thiophene, furfural, and N-benzyl-1

  在这里，我们报告了一种多功能催化系统，用于杂芳烃与活化的芳基氯底物的直接 C-H 芳基化。该催化剂在非常低的催化剂负载条件下成功地用于各种杂芳烃和芳基氯偶联伙伴。我们已经成功地进行了 1-甲基吡咯、1-甲基吲哚、呋喃、噻吩、糠醛和 N-苄基-1,2,3-三唑与芳基氯伙伴的直接 C-H 芳基化反应，收率良好，且不使用任何添加剂. 此外，我们使用这种催化过程开发了克级肌肉松弛剂丹曲林的一锅合成方案。此外，本催化系统可用于在一锅中进行连续芳基化。