S-phenyl 4-(phenylsulfanyl)benzothioate | 1047623-91-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: S-phenyl 4-(phenylsulfanyl)benzothioate
• 英文别名: S-phenyl 4-(phenylthio)benzothioate；S-phenyl 4-phenylsulfanylbenzenecarbothioate
• CAS: 1047623-91-5
• 化学式: C₁₉H₁₄OS₂
• 分子量: 322.452
• InChiKey: UUBHJCCJVDXTKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  S-苯基4-硝基苯硫代甲酸酯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以15%的产率得到S-phenyl 4-(phenylsulfanyl)benzothioate
  参考文献：
  名称：

  Kinetics of the reaction of substituted 4-nitrophenyl benzoates with benzenethiol in the presence of potassium carbonate in dimethylformamide

  摘要：

  The effect of the substituent nature on the rate and activation parameters of transesterification of a series of 4-nitrophenyl benzoates with benzenethiol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction method. In all cases, change of the Gibbs energy of activation is determined mainly by variation of the enthalpy of activation. 4-Nitrophenyl benzoates having electron-withdrawing substituents in the benzoyl fragment were found to fit an isokinetic relation with an isokinetic temperature beta of 318 K. Enthalpy-entropy compensation effect was observed in the reactions with all the examined 4-nitrophenyl benzoates. The relation between the reactivity and polarizability of nucleophilic center in S- and O-nucleophiles is discussed.

  DOI：

  10.1134/s1070428008040167

文献信息

• Pd-Catalyzed Thiocarbonylation with Stoichiometric Carbon Monoxide: Scope and Applications
  作者：Mia N. Burhardt、Rolf H. Taaning、Troels Skrydstrup

  DOI：10.1021/ol400138m

  日期：2013.2.15

  A general protocol for the Pd-catalyzed thiocarbonylation of aryl iodides with stoichiometric carbon monoxide has been established employing a catalytic system composed of Pd(OAc)(2) and DPEphos with low catalyst loading (1 mol %). Both electron-rich and -deficient aryl iodides proved effective for these couplings with aryl and alkyl thiols. The choice of the metal ligands and the solvent system was crucial for the efficiency and chemoselectivity of these transformations.