1-F-Adamantyl trifluoroacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-F-Adamantyl trifluoroacetate
• 英文别名: (2,2,3,4,4,5,6,6,7,8,8,9,9,10,10-Pentadecafluoro-1-adamantyl) 2,2,2-trifluoroacetate
• 化学式: C₁₂F₁₈O₂
• 分子量: 518.102
• InChiKey: METDJTGQFDWQJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  1-F-Adamantyl trifluoroacetate 以 一氟三氯甲烷 为溶剂， 以0.45 g的产率得到F-adamantan-1-ol
  参考文献：
  名称：

  Highly Fluorinated Adamantanols:  Synthesis, Acidities, and Reactivities

  摘要：

  Aerosol direct fluorination of 1-adamantyl acetate produces F-1-adamantyl trifluoroacetate and 2-hydryl-F-1-adamantyl trifluoroacetate in a near 1:1 ratio. Hydrolyses of these two esters give the corresponding alcohols, F-adamantan-1-ol and 2-hydryl-F-adamantan-1-ol. 2-Hydryl-F-adamantan-2-ol is synthesized by LiAlH4 reduction of F-adamantanone, The acidities of these alcohols and the rates of their acetylation reactions were measured. A H-1 NMR study of their hydrogen bonding with t-BuOCH(3) is described.

  DOI：

  10.1021/jo9511096
• 作为产物：
  描述：

  1-乙酰氧基金刚烷 以 1,1,2-三氯乙烷 为溶剂， 以9.4%的产率得到1-F-Adamantyl trifluoroacetate
  参考文献：
  名称：

  Polarized C-H Groups as Novel Hydrogen-Bond Donors in Hydryl-F-alkyl Esters: Unequivocal Examples of the Pinchas Effect

  摘要：

  H-1 NMR and IR spectral evidence for a C-H...O hydrogen bonds in 1-[2-hydryl-F-adamantyl] trifluoroacetate and 1,3-[2-hydryl-F-adamantyl] bis(trifluoroacetate) are presented. Evidence indicating a three-center hydrogen bond in 1,3-[2-hydryl-F-adamantyl] bis-(trifluoroacetate) is also presented. Both compounds, despite otherwise normal H-1 NMR chemical shift displacements and carbonyl stretching frequency depressions, show strong increases in C-H stretching frequencies related to hydrogen-bond interactions (the ''Pinchas Effect'').

  DOI：

  10.1021/jo00112a021