2H-perfluorocyclohexanone | 63284-88-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2H-perfluorocyclohexanone
• 英文别名: 2H-Perfluorocyclohexanon；2,2,3,3,4,4,5,5,6-Nonafluorocyclohexan-1-one
• CAS: 63284-88-8
• 化学式: C₆HF₉O
• 分子量: 260.059
• InChiKey: YGFNDLJUTZXPSO-UHFFFAOYSA-N

物化性质

• 沸点：
  104.7±40.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2H-perfluorocyclohexanone 在 水 作用下， 生成 heptafluoro-1-hidroxycyclohexene-3-on
  参考文献：
  名称：

  Fluorine-containing keto-enolic systems of the cyclohexane series

  摘要：

  DOI：

  10.1007/bf00941100
• 作为产物：
  描述：

  十氟环己烯 生成 2H-perfluorocyclohexanone
  参考文献：
  名称：

  Fluorine-containing keto-enolic systems of the cyclohexane series

  摘要：

  DOI：

  10.1007/bf00941100

文献信息

• Perfluorinated Cyclic and Acyclic Keto−Enol Systems:  A Remarkable Contrast
  作者：Patrick E. Lindner、David M. Lemal

  DOI：10.1021/ja963788n

  日期：1997.4.1

  Recent reports from this laboratory have revealed that highly fluorinated 4- and 5-membered-ring enols are comparable in stability to, or more stable thermodynamically than, the corresponding ketones, even in non-Lewis-basic media. Work on perfluorinated keto-enol systems has now been extended to 2H-perfluorocyclohexanone plus its enol and to a series of acyclic analogues. In carbon tetrachloride, K-E/K = 0.33 (22 degrees C) for the six-ring system, but only enol is detectable in Lewis-basic solvents. This shift is attributable to strong hydrogen-bond formation between the enol and Lewis base. A perfluoroenol has been shown to form significantly stronger hydrogen bonds than the potent hexafluoroisopropyl alcohol. Acyclic systems (e.g., 3H-perfluoro-2-butanone and its enol) contrast sharply with the cyclic, as no enol is detectable at equilibrium even in powerfully Lewis-basic media. Ab initio quantum mechanical calculations indicate that it is principally the enols, not the ketones, that are responsible for the difference between the two types of keto-enol systems, i.e. acyclic perfluoroenols are strongly destabilized relative to cyclic counterparts.
• Fluorine-containing keto-enolic systems of the cyclohexane series
  作者：R. A. Bekker、V. Ya. Popkova

  DOI：10.1007/bf00941100

  日期：1978.12