1-benzyl-5-(naphthalen-2-yl)-4-phenyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-5-(naphthalen-2-yl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-5-naphthalen-2-yl-4-phenyltriazole；1-benzyl-5-naphthalen-2-yl-4-phenyltriazole
• 化学式: C₂₅H₁₉N₃
• 分子量: 361.446
• InChiKey: XOQXRDSVGJOIEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴萘 、 苯乙炔 、 苄基叠氮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 copper(l) chloride 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到1-benzyl-5-(naphthalen-2-yl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Cu/Pd-Catalyzed, Three-Component Click Reaction of Azide, Alkyne, and Aryl Halide: One-Pot Strategy toward Trisubstituted Triazoles

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.5b01342

文献信息

• Copper-Catalyzed Decarboxylative Cycloaddition of Propiolic Acids, Azides, and Arylboronic Acids: Construction of Fully Substituted 1,2,3-Triazoles
  作者：Xiang-Xiang Wang、Yangchun Xin、Yi Li、Wen-Jin Xia、Bin Zhou、Rui-Rong Ye、Ya-Min Li

  DOI：10.1021/acs.joc.9b03285

  日期：2020.3.6

  A copper-catalyzed decarboxylative cycloaddition of propiolic acids, azides, and arylboronic acids is described. The present reaction provides an efficient and convenient method for the synthesis of various fully substituted 1,2,3-triazoles from readily available starting materials. A possible mechanism is proposed.

  描述了丙酸，叠氮化物和芳基硼​​酸的铜催化的脱羧环加成。本反应为从容易获得的起始原料合成各种完全取代的1,2,3-三唑提供了一种有效而方便的方法。提出了一种可能的机制。
• 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.