5-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazole | 1417450-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazole
• 英文别名: 1-(Oxan-2-yl)-5-phenyl-1,2,4-triazole；1-(oxan-2-yl)-5-phenyl-1,2,4-triazole
• CAS: 1417450-01-1
• 化学式: C₁₃H₁₅N₃O
• 分子量: 229.282
• InChiKey: OMHBETWHLZAYCA-UHFFFAOYSA-N

物化性质

• 沸点：
  419.9±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazole 在 盐酸 、 palladium diacetate 、 potassium carbonate 、 三甲基丙酮酸 、 正丁基二(1-金刚烷基)膦 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 生成 3-(4-methoxyphenyl)-4-methyl-5-phenyl-4H-1,2,4-triazole
  参考文献：
  名称：

  C–H Bonds as Ubiquitous Functionality: Preparation of Multiple Regioisomers of Arylated 1,2,4-Triazoles via C–H Arylation

  摘要：

  We describe a general approach for the synthesis of complex aryl 1,2,4-triazoles. The electronic character of the C-H bonds and the triazole ring allows for the regioselective C-H arylation of 1-alkyl- and 4-alkyltriazoles under catalytic conditions. We have also developed the SEM and THP switch as well as trans-N-alkylation, which enable sequential arylation of the triazole ring to prepare 3,5-diaryltriazoles. This new strategy provides rapid access to a variety of arylated 1,2,4-triazoles and well complements existing cyclization methods.

  DOI：

  10.1021/jo3021677
• 作为产物：
  描述：

  溴苯 、 1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazole 在 palladium diacetate 、 sodium t-butanolate 、 正丁基二(1-金刚烷基)膦 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以90%的产率得到5-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazole
  参考文献：
  名称：

  C–H Bonds as Ubiquitous Functionality: Preparation of Multiple Regioisomers of Arylated 1,2,4-Triazoles via C–H Arylation

  摘要：

  We describe a general approach for the synthesis of complex aryl 1,2,4-triazoles. The electronic character of the C-H bonds and the triazole ring allows for the regioselective C-H arylation of 1-alkyl- and 4-alkyltriazoles under catalytic conditions. We have also developed the SEM and THP switch as well as trans-N-alkylation, which enable sequential arylation of the triazole ring to prepare 3,5-diaryltriazoles. This new strategy provides rapid access to a variety of arylated 1,2,4-triazoles and well complements existing cyclization methods.

  DOI：

  10.1021/jo3021677