5H-tridecafluoro-heptan-4-one | 2546-28-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5H-tridecafluoro-heptan-4-one
• 英文别名: 3-Hydro-perfluor-heptan-4-on；1,1,1,2,2,3,3,5,6,6,7,7,7-Tridecafluoroheptan-4-one
• CAS: 2546-28-3
• 化学式: C₇HF₁₃O
• 分子量: 348.064
• InChiKey: VLSWXVMRCGODDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4H-tridecafluoro-4-methoxy-hept-3-ene 在 硫酸 作用下， 反应 22.0h， 生成 5H-tridecafluoro-heptan-4-one
  参考文献：
  名称：

  Fluoro Ketones. II. Reactions with Trialkyl Phosphites

  摘要：

  DOI：

  10.1021/jo01030a051

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.
• Fluoro Ketones. II. Reactions with Trialkyl Phosphites
  作者：D. W. Wiley、H. E. Simmons

  DOI：10.1021/jo01030a051

  日期：1964.7