5-(3-methoxyphenyl)-3-phenyl-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-1,2,4-triazole | 1417450-07-7

• 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-(3-methoxyphenyl)-3-phenyl-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-1,2,4-triazole
• 英文别名: 2-[[5-(3-Methoxyphenyl)-3-phenyl-1,2,4-triazol-1-yl]methoxy]ethyl-trimethylsilane；2-[[5-(3-methoxyphenyl)-3-phenyl-1,2,4-triazol-1-yl]methoxy]ethyl-trimethylsilane
• CAS: 1417450-07-7
• 化学式: C₂₁H₂₇N₃O₂Si
• 分子量: 381.55
• InChiKey: JXDZWFJIIVYQGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-methoxyphenyl)-3-phenyl-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-1,2,4-triazole 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以90%的产率得到3-(3-methoxyphenyl)-5-phenyl-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
• 作为产物：
  描述：

  5-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole 在 butyl di-1-adamantylphosphine tetrafluoroborate 、 palladium diacetate 、 potassium carbonate 、 三甲基丙酮酸 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 5-(3-methoxyphenyl)-3-phenyl-1-((2-(trimethylsilyl)ethoxy)-methyl)-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