1-mercapto-2-methoxycarbonyl-o-carborane | 237755-00-9

• 英文名称: 1-mercapto-2-methoxycarbonyl-o-carborane
• CAS: 237755-00-9
• 化学式: C₄H₁₄B₁₀O₂S
• 分子量: 234.33
• InChiKey: GISVHBGWSOBEDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2,6-双(溴甲基)吡啶 、 1-mercapto-2-methoxycarbonyl-o-carborane 在 水 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 以90%的产率得到2,6-bis(2'-methoxycarbonyl-1',2'-carboranyl-1'-thiomethyl)pyridine
  参考文献：
  名称：

  Synthesis of Pyridine NS₂ Ligands Incorporating 1-Methoxycarbonyl-2-thio(o-carborane). Are They a Route to “Carboranethiophene” Compounds?

  摘要：

  Facilitated benzothiophene condensation has been successfully achieved in pyridinedithia(S-phenyl)-substituted compounds, by complexation with Pd(II). In this work, the phenyl fragment in 2,6-bis(2'-methoxycarbonyl-phenylthiomethyl)pyridine is replaced by o-carborane. This moiety is often treated as a three-dimensional aromatic system, thus it was worthwhile to see their comparative behavior toward Pd(II). To perform the reaction the new compound 2,6-bis(2'-methoxycarbonyl-1',2'-carboranyl-1'-thiomethyl)pyridine has been synthesized. Its complexation behavior toward Pd(II), using an alcohol as a solvent, induces the cluster's partial degradation and the reduction of Pd(II) to Pd(0). The reaction of the partially degraded ligand, [2,6-bis(7'-methoxycarbonyl-7',8'-carboranyl-7'-thiomethyl) pyridine](2-) with Pd(II) leads to a dinuclear species, where the ligand acts in a bidentate mode. One of the ligand's arms in the complex is uncoordinated and free. This result is supported by ME (MALDI-TOFF) and H-1 NMR variable-temperature studies.

  DOI：

  10.1021/ic9716060
• 作为产物：
  描述：

  2-methoxycarbonyl-o-carborane 、 sulfur 以 乙醚 为溶剂， 以27%的产率得到1-mercapto-2-methoxycarbonyl-o-carborane
  参考文献：
  名称：

  Synthesis of Pyridine NS₂ Ligands Incorporating 1-Methoxycarbonyl-2-thio(o-carborane). Are They a Route to “Carboranethiophene” Compounds?

  摘要：

  Facilitated benzothiophene condensation has been successfully achieved in pyridinedithia(S-phenyl)-substituted compounds, by complexation with Pd(II). In this work, the phenyl fragment in 2,6-bis(2'-methoxycarbonyl-phenylthiomethyl)pyridine is replaced by o-carborane. This moiety is often treated as a three-dimensional aromatic system, thus it was worthwhile to see their comparative behavior toward Pd(II). To perform the reaction the new compound 2,6-bis(2'-methoxycarbonyl-1',2'-carboranyl-1'-thiomethyl)pyridine has been synthesized. Its complexation behavior toward Pd(II), using an alcohol as a solvent, induces the cluster's partial degradation and the reduction of Pd(II) to Pd(0). The reaction of the partially degraded ligand, [2,6-bis(7'-methoxycarbonyl-7',8'-carboranyl-7'-thiomethyl) pyridine](2-) with Pd(II) leads to a dinuclear species, where the ligand acts in a bidentate mode. One of the ligand's arms in the complex is uncoordinated and free. This result is supported by ME (MALDI-TOFF) and H-1 NMR variable-temperature studies.

  DOI：

  10.1021/ic9716060