1-(2-(methylthio)ethyl)-4-phenyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-(methylthio)ethyl)-4-phenyl-1H-1,2,3-triazole
• 化学式: C₁₁H₁₃N₃S
• 分子量: 219.31
• InChiKey: CZWVGWBYFMBARY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30.71
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  bis(η3-allyl-μ-chloropalladium(II)) 、 1-(2-(methylthio)ethyl)-4-phenyl-1H-1,2,3-triazole 、 silver tetrafluoroborate 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到(π-allyl)palladium chloride
  参考文献：
  名称：

  A new palladium(II)–allyl complex containing a thioether-triazole ligand as active catalyst in Suzuki–Miyaura reaction. Use of tetraalkylammonium salts as promoters: Influence of the salt anion and cation on the catalytic activity

  摘要：

  The novel cationic palladium-allyl complex [Pd(eta(3)-C3H5)(1-(2-(methylthio)ethyl)-4-phenyl-1H-1,2,3-triazole)](BF4) (2) is a precatalyst for the Suzuki-Miyaura reaction. Good turnover numbers are obtained in the reaction between different aryl bromides and phenylboronic acid in toluene with K2CO3 as the base. No reaction is instead observed with aryl chlorides due to catalyst decomposition to palladium black. Catalyst decomposition can be circumvented by adding tetraalkylammonium salts in the presence of which reasonably good reaction rates are obtained in the coupling of different aryl chlorides with phenylboronic acid. The beneficial effect of tetraalkylammonium salts is found to depend on the nature of the additive as well as the additive to substrate molar ratio. A systematic study allows to delineate the roles played by the cation and the anion of the promoter. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.05.028
• 作为产物：
  描述：

  1-azido-2-methylsulfanyl-ethane 、 苯乙炔 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以85%的产率得到1-(2-(methylthio)ethyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  A new palladium(II)–allyl complex containing a thioether-triazole ligand as active catalyst in Suzuki–Miyaura reaction. Use of tetraalkylammonium salts as promoters: Influence of the salt anion and cation on the catalytic activity

  摘要：

  The novel cationic palladium-allyl complex [Pd(eta(3)-C3H5)(1-(2-(methylthio)ethyl)-4-phenyl-1H-1,2,3-triazole)](BF4) (2) is a precatalyst for the Suzuki-Miyaura reaction. Good turnover numbers are obtained in the reaction between different aryl bromides and phenylboronic acid in toluene with K2CO3 as the base. No reaction is instead observed with aryl chlorides due to catalyst decomposition to palladium black. Catalyst decomposition can be circumvented by adding tetraalkylammonium salts in the presence of which reasonably good reaction rates are obtained in the coupling of different aryl chlorides with phenylboronic acid. The beneficial effect of tetraalkylammonium salts is found to depend on the nature of the additive as well as the additive to substrate molar ratio. A systematic study allows to delineate the roles played by the cation and the anion of the promoter. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.05.028