ethyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)benzoate | 1417450-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)benzoate
• 英文别名: Ethyl 3-[2-(2-trimethylsilylethoxymethyl)-1,2,4-triazol-3-yl]benzoate；ethyl 3-[2-(2-trimethylsilylethoxymethyl)-1,2,4-triazol-3-yl]benzoate
• CAS: 1417450-04-4
• 化学式: C₁₇H₂₅N₃O₃Si
• 分子量: 347.489
• InChiKey: CLRSITUSCNGQES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.43
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(三甲基硅烷基)乙氧甲基氯 在 butyl di-1-adamantylphosphine tetrafluoroborate 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 三甲基丙酮酸 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 34.0h， 生成 ethyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)benzoate
  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

文献信息

• C–H Bonds as Ubiquitous Functionality: Preparation of Multiple Regioisomers of Arylated 1,2,4-Triazoles via C–H Arylation
  作者：Jung Min Joo、Pengfei Guo、Dalibor Sames

  DOI：10.1021/jo3021677

  日期：2013.1.18

  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.