1,3-<2-Hydryl-F-adamantyl> bis(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: 1,3-<2-Hydryl-F-adamantyl> bis(trifluoroacetate)
• 英文别名: [2,2,3,4,4,6,6,7,8,8,9,10,10-Tridecafluoro-5-(2,2,2-trifluoroacetyl)oxy-1-adamantyl] 2,2,2-trifluoroacetate
• 化学式: C₁₄HF₁₉O₄
• 分子量: 594.129
• InChiKey: WGWRJUYZBPTQDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  23

反应信息

• 作为反应物：
  描述：

  1,3-<2-Hydryl-F-adamantyl> bis(trifluoroacetate) 生成 2-Hydryl-F-adamantan-1,3-diol
  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
• 作为产物：
  描述：

  1,3-二羟基金刚烷二乙酸酯 以 1,1,2-三氯乙烷 为溶剂， 以5%的产率得到1,3-<2-Hydryl-F-adamantyl> bis(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

文献信息

• Polarized C-H Groups as Novel Hydrogen-Bond Donors in Hydryl-F-alkyl Esters: Unequivocal Examples of the Pinchas Effect
  作者：James L. Adcock、Huqiu Zhang

  DOI：10.1021/jo00112a021

  日期：1995.4

  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'').