1-hydroxyperfluorocyclobut-1-ene | 60838-91-7

• 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: 1-hydroxyperfluorocyclobut-1-ene
• 英文别名: perfluorocyclobut-1-enol；Perfluorcyclobutenol-1；1-Hydroxy-2,3,3,4,4-pentafluorcyclobutenon；2,3,3,4,4-Pentafluorocyclobutene-1-ol；2,3,3,4,4-pentafluorocyclobuten-1-ol
• CAS: 60838-91-7
• 化学式: C₄HF₅O
• 分子量: 160.043
• InChiKey: QEMVKVZSPRCQRJ-UHFFFAOYSA-N

物化性质

• 沸点：
  51.8±40.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2906199090

反应信息

• 作为反应物：
  描述：

  1-hydroxyperfluorocyclobut-1-ene 在 氢氧化钾 作用下， 生成 2,4,4-Trifluor-3-hydroxy-cyclobuten-1-on
  参考文献：
  名称：

  Bekker,R.A. et al., Doklady Chemistry, 1977, vol. 235, # 1, p. 370 - 373

  摘要：

  DOI：
• 作为产物：
  描述：

  (2,3,3,4,4-Pentafluorocyclobuten-1-yl)oxymethylbenzene 在 盐酸 作用下， 以 various solvent(s) 为溶剂， 反应 0.02h， 以95%的产率得到1-hydroxyperfluorocyclobut-1-ene
  参考文献：
  名称：

  新型酮-烯醇系统：环丁烷衍生物

  摘要：

  3H-全氟双环[2.2.0]hexan-2-one (3) 已由六氟苯合成并与其烯醇形式 (4) 平衡。在四氯化碳 Ke/k = 0.07 ± 0.01 (25 °C) 中，但在路易斯碱性溶剂（例如乙腈、乙醚和四氢呋喃）中，由于烯醇作为氢键供体的强度，因此在平衡状态下只能检测到烯醇。在该酮-烯醇系统的单环对应物 2H-全氟环丁酮 (1) 和全氟环丁-1-烯醇 (2) 中，烯醇更稳定。在平衡条件下，在所有检测的介质（包括四氯化碳）中都检测不到酮。在不受阻碍和未共轭的烯醇中，2 和 4 相对于它们的酮比任何其他已报道的更稳定。从头算量子力学计算支持以下结论：酮的不稳定，

  DOI：

  10.1021/ja952998h

文献信息

• Functionalization of saturated fluorocarbons with and without light
  作者：Xudong Chen、David M. Lemal

  DOI：10.1016/j.jfluchem.2006.06.005

  日期：2006.9

  Photochemical transformation of saturated fluorocarbons into tetrabutylammonium enolates has been improved, and a method employing ketyls as reductants has been developed that accomplishes the same chemistry without light. Enolates have been isolated as enol methyl ethers, from which they can be efficiently regenerated with tetrabutylammonium iodide. In other cases, enolates have been isolated as the

  饱和碳氟化合物向烯丙基四丁基铵的光化学转化已经得到改善，并且已经开发出使用酮基作为还原剂的方法，该方法无需光照即可完成相同的化学反应。烯醇酸酯已经被分离为烯醇甲基醚，可以用碘化四丁基铵从烯醇甲基醚有效地再生它们。在其他情况下，烯醇盐已被分离为相应的酮或稳定的烯醇。氟碳LUMO能量与其反应性相关，并作为选择酮基的指南。讨论了该化学方法在氟聚合物表面改性中的用途。
• Energetics of hydrate and hemiketal formation for highly fluorinated ketones
  作者：Patrick E. Lindner、David M. Lemal

  DOI：10.1016/s0040-4039(96)02149-1

  日期：1996.12

  Heats of hydration for a series of fluoroketones have been calculated at the HF/6-31G **//6-31G ** level, and equilibrium constants for hemiketal formation with trifluoroethanol have been measured for a related series. These reactions were found to be considerably more favorable in cyclic than in corresponding acyclic systems. Quantum mechanical calculations indicate that this difference can be traced

  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。
• 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.
• Novel Keto-Enol Systems
  作者：Ricardo A. Correa、Patrick E. Lindner、David M. Lemal

  DOI：10.1021/ja00102a059

  日期：1994.11
• Bekker,R.A. et al., Doklady Chemistry, 1976, vol. 231, p. 700 - 703
  作者：Bekker,R.A. et al.

  DOI：——

  日期：——