3-hydroheptafluoro-2-butanone | 85093-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-hydroheptafluoro-2-butanone
• 英文别名: 3-hydroperfluoro-2-butanone；1,1,1,3,4,4,4-Heptafluorobutan-2-one
• CAS: 85093-76-1
• 化学式: C₄HF₇O
• 分子量: 198.04
• InChiKey: MTTVUQDONWTDRR-UHFFFAOYSA-N

物化性质

• 沸点：
  34-35 °C
• 密度：
  1.520±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-hydroheptafluoro-2-butanone 以 氨 为溶剂， 生成 2-hydroxy-2-amino-3-hydroperfluorobutane
  参考文献：
  名称：

  Saloutina, L. V.; Zapevalov, A. Ya.; Kolenko, I. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2019 - 2024

  摘要：

  DOI：
• 作为产物：
  描述：

  (E/Z)-perfluoro-2-buten-2-ol 在 N-甲基吡咯烷酮 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 生成 3-hydroheptafluoro-2-butanone
  参考文献：
  名称：

  Perfluorinated Cyclic and Acyclic Keto−Enol Systems:  A Remarkable Contrast

  摘要：

  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.

  DOI：

  10.1021/ja963788n

文献信息

• 3-Hydroperfluoro-2-butanone and its reactions
  作者：L. V. Saloutina、A. Ya. Zapevalov、M. I. Kodess、I. P. Kolenko、L. S. German

  DOI：10.1007/bf00958424

  日期：1982.11
• SALOUTINA, L. V.;ZAPEVALOV, A. YA.;KODESS, M. I.;KOLENKO, I. P.;GERMAN, L+, IZV. AN CCCP. CEP. XIM., 1982, N 11, 2615
  作者：SALOUTINA, L. V.、ZAPEVALOV, A. YA.、KODESS, M. I.、KOLENKO, I. P.、GERMAN, L+

  DOI：——

  日期：——
• SALOUTINA L. V.; ZAPEVALOV A. YA.; KOLENKO I. P., ZH. ORGAN. XIMII, 22,(1986) N 11, 2250-2256
  作者：SALOUTINA L. V.、 ZAPEVALOV A. YA.、 KOLENKO I. P.

  DOI：——

  日期：——
• Saloutina, L. V.; Zapevalov, A. Ya.; Kolenko, I. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 11, p. 2019 - 2024
  作者：Saloutina, L. V.、Zapevalov, A. Ya.、Kolenko, I. P.

  DOI：——

  日期：——
• 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.