perfluorocyclohex-1-enol | 63284-87-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: perfluorocyclohex-1-enol
• 英文别名: Nonafluorcyclohex-1-enol；Perfluorcyclohexenol-1；2,3,3,4,4,5,5,6,6-Nonafluoro-1-cyclohexen-1-ol；2,3,3,4,4,5,5,6,6-nonafluorocyclohexen-1-ol
• CAS: 63284-87-7
• 化学式: C₆HF₉O
• 分子量: 260.059
• InChiKey: XTVOKSIOOIFWEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  perfluorocyclohex-1-enol 在 水 、 溴 作用下， 生成 2-bromoperfluorocyclohexane-1,1-diol
  参考文献：
  名称：

  高氟酮的水合物和半缩酮形成的能量学

  摘要：

  已计算出一系列氟代酮的水合热为HF / 6-31G ** // 6-31G **，并且已测量了有关氟代酮与三氟乙醇形成半缩酮的平衡常数。发现这些反应在循环中比在相应的无环系统中明显更有利。量子力学计算表明，这种差异可以追溯到无环加合物中的位阻。

  DOI：

  10.1016/s0040-4039(96)02149-1
• 作为产物：
  描述：

  1-benzyloxyperfluorocyclohexene 在 硫酸 作用下， 生成 perfluorocyclohex-1-enol
  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.