5-phenyl-1-(p-tolyl)-4-(trimethylsilyl)-1H-1,2,3-triazole | 1338916-45-2

• 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-(p-tolyl)-4-(trimethylsilyl)-1H-1,2,3-triazole
• 英文别名: Trimethyl-[1-(4-methylphenyl)-5-phenyltriazol-4-yl]silane；trimethyl-[1-(4-methylphenyl)-5-phenyltriazol-4-yl]silane
• CAS: 1338916-45-2
• 化学式: C₁₈H₂₁N₃Si
• 分子量: 307.47
• InChiKey: MAAOPGUACTWYQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 在 盐酸 、 水 、 sodium nitrite 作用下， 以 水 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 33.0h， 生成 5-phenyl-1-(p-tolyl)-4-(trimethylsilyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Metal-Free 1,5-Regioselective Azide-Alkyne [3+2]-Cycloaddition

  摘要：

  Abstract[3+2]‐cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5‐disubstituted‐4‐(trimethyl‐silyl)‐1H‐1,2,3‐triazoles. The formation of the 1,5‐isomer is highly favored in this metal‐free cycloaddition, which could be proven by 1D selective NOESY and X‐ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5‐isomer. The described method provides a simple alternative protocol to metal‐catalyzed “click chemistry” procedures, widening the scope for regioselective heavy‐metal‐free synthetic applications.

  DOI：

  10.1002/asia.201100404

文献信息

• Metal-Free 1,5-Regioselective Azide-Alkyne [3+2]-Cycloaddition
  作者：Florian Kloss、Uwe Köhn、Burkhard O. Jahn、Martin D. Hager、Helmar Görls、Ulrich S. Schubert

  DOI：10.1002/asia.201100404

  日期：2011.10.4

  Abstract[3+2]‐cycloaddition reactions of aromatic azides and silylated alkynes in aqueous media yield 1,5‐disubstituted‐4‐(trimethyl‐silyl)‐1H‐1,2,3‐triazoles. The formation of the 1,5‐isomer is highly favored in this metal‐free cycloaddition, which could be proven by 1D selective NOESY and X‐ray investigations. Additionally, DFT calculations corroborate the outstanding favoritism regarding the 1,5‐isomer. The described method provides a simple alternative protocol to metal‐catalyzed “click chemistry” procedures, widening the scope for regioselective heavy‐metal‐free synthetic applications.