N-(1,12-dicarba-closo-dodecaboran-2-yl)trifluoroacetamide | 1254975-68-2

• 英文名称: N-(1,12-dicarba-closo-dodecaboran-2-yl)trifluoroacetamide
• CAS: 1254975-68-2
• 化学式: C₄H₁₂B₁₀F₃NO
• 分子量: 255.251
• InChiKey: IESKJSQUHSIJOP-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：

  N-(1,12-dicarba-closo-dodecaboran-2-yl)trifluoroacetamide 在 NaOH 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以76%的产率得到2-NH2-1.12-C2B10H11
  参考文献：
  名称：

  Novel Approach to Aminocarboranes by Mild Amidation of Selected Iodo-carboranes

  摘要：

  A mild protocol for the palladium-catalyzed Buchwald-Hartwig amidation of icosahedral carboranes is described. Employing 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (1) as a ligand and K3PO4 as a base, benzamide, trifluoroacetamide, acetamide, and formamide were coupled to a series of mono- and di-iodo carboranes furnishing the respective carborane derivatives in good to excellent yields. Subsequent base-mediated saponification of the trifluoroacetamide derivatives was shown to provide the free aminocarboranes. The structures of N-(1,7-dicarba-closo-dodecaboran-9-y1)benzamide (8a), N-(1,7-dicarba-closo-dodecaboran-9-yl)trifluoroacetamide (8b), N-(1,12-dicarba-closo-dodecaboran-2-yl)benzamide (10a), N-(1,2-dicarba-closo-dodecaboran-9-yl)benzamide (12a), N-(1,2-dicarba-closo-dodecaboran-9-yl)acetamide (12c), N-(1,2-dicarba-closo-dodecaboran-9-yl)formamide (12d), N-(1,2-dicarba-closo-dodecaboran-3-yl)benzamide (13a), N,N'-(1,7-dicarba-closo-dodecaboran-9,10-diyl)dibenzamide (15a), and N,N'-(1,7-dicarba-closo-dodecaboran-9,10-diyl)bis(trifluoroacetamide) (15b) have been established through X-ray single-crystal diffraction studies.

  DOI：

  10.1021/ic101620h
• 作为产物：
  描述：

  2-iodo-closo-1,12-dodecaborane 、 2,2,2-三氟乙酰胺 在 K₃PO₄ 、 2-Cy₂P-2-(N,N-dimethylamino)biphenyl 、 tris(dibenzylideneacetone)dipalladium 作用下， 以 四氢呋喃 为溶剂， 生成 N-(1,12-dicarba-closo-dodecaboran-2-yl)trifluoroacetamide
  参考文献：
  名称：

  Novel Approach to Aminocarboranes by Mild Amidation of Selected Iodo-carboranes

  摘要：

  A mild protocol for the palladium-catalyzed Buchwald-Hartwig amidation of icosahedral carboranes is described. Employing 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl (1) as a ligand and K3PO4 as a base, benzamide, trifluoroacetamide, acetamide, and formamide were coupled to a series of mono- and di-iodo carboranes furnishing the respective carborane derivatives in good to excellent yields. Subsequent base-mediated saponification of the trifluoroacetamide derivatives was shown to provide the free aminocarboranes. The structures of N-(1,7-dicarba-closo-dodecaboran-9-y1)benzamide (8a), N-(1,7-dicarba-closo-dodecaboran-9-yl)trifluoroacetamide (8b), N-(1,12-dicarba-closo-dodecaboran-2-yl)benzamide (10a), N-(1,2-dicarba-closo-dodecaboran-9-yl)benzamide (12a), N-(1,2-dicarba-closo-dodecaboran-9-yl)acetamide (12c), N-(1,2-dicarba-closo-dodecaboran-9-yl)formamide (12d), N-(1,2-dicarba-closo-dodecaboran-3-yl)benzamide (13a), N,N'-(1,7-dicarba-closo-dodecaboran-9,10-diyl)dibenzamide (15a), and N,N'-(1,7-dicarba-closo-dodecaboran-9,10-diyl)bis(trifluoroacetamide) (15b) have been established through X-ray single-crystal diffraction studies.

  DOI：

  10.1021/ic101620h