3-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole | 1417450-06-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazole
• 英文别名: Trimethyl-[2-[(3-phenyl-1,2,4-triazol-1-yl)methoxy]ethyl]silane；trimethyl-[2-[(3-phenyl-1,2,4-triazol-1-yl)methoxy]ethyl]silane
• CAS: 1417450-06-6
• 化学式: C₁₄H₂₁N₃OSi
• 分子量: 275.426
• InChiKey: OUXBLGQOMJUGHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  间溴苯甲醚 、 3-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 为溶剂， 反应 18.0h， 以65%的产率得到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
• 作为产物：
  描述：

  溴苯 在 2,2-二甲基丁酸 、 butyl di-1-adamantylphosphine tetrafluoroborate 、 palladium diacetate 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 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