1-(4'-methoxybiphenyl-4-yl)-4-phenyl-1H-1,2,3-triazole | 1318079-63-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4'-methoxybiphenyl-4-yl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-[4-(4-Methoxyphenyl)phenyl]-4-phenyltriazole；1-[4-(4-methoxyphenyl)phenyl]-4-phenyltriazole
• CAS: 1318079-63-8
• 化学式: C₂₁H₁₇N₃O
• 分子量: 327.385
• InChiKey: XAVSSABUOLTKHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 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：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴苯基三氟硼酸钾 在 四(三苯基膦)钯 、 sodium azide 、 caesium carbonate 、 copper(I) bromide 、 N,N'-二甲基乙二胺 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 10.5h， 生成 1-(4'-methoxybiphenyl-4-yl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Efficient and rapid synthesis of regioselective functionalized potassium 1,2,3-triazoletrifluoroborates via 1,3-dipolar cycloaddition

  摘要：

  In this study, we present a previously unreported method of preparing regiospecific organo-[1,2,3]-triazol-1-aryl-trifluoroborates from haloaryltrifluoroborates via a one-pot 1,3-dipolar cycloaddition reaction. We found that the use of either electron-rich or electron-deficient haloaryltrifluoroborates led to the desired cycloaddition products with good to excellent yields. Furthermore, we successfully carried Out the cross-coupling reactions of the obtained triazoles with various aryl halides by means of the Suzuki-Miyaura reaction in the presence of 3 mol % of Pd(PPh(3))(4) catalyst in a 20% aqueous 1,4-dioxane solution at 100 degrees C; all these reactions yielded complete conversion to the corresponding products. Besides providing a high level of personnel safety, our highly versatile approach allows the preparation of functionalized organotrifluoborates containing 1,2,3-triazoles with retained functionality. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.126