2-Bromo-2,3,3,4,4,5,5-heptafluoro-cyclopentanone | 180690-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-2,3,3,4,4,5,5-heptafluoro-cyclopentanone
• 英文别名: 2-Bromo-2,3,3,4,4,5,5-heptafluorocyclopentan-1-one
• CAS: 180690-70-4
• 化学式: C₅BrF₇O
• 分子量: 288.947
• InChiKey: NGTJUMDGAQPSJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  2,2,2-三氟乙醇 、 2-Bromo-2,3,3,4,4,5,5-heptafluoro-cyclopentanone 在 N-甲基吡咯烷酮 作用下， 以 二氯甲烷 为溶剂， 生成 2-Bromo-2,3,3,4,4,5,5-heptafluoro-1-(2,2,2-trifluoro-ethoxy)-cyclopentanol
  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-benzoxyperfluorocyclopentene 在 硫酸 、 水 、 溴 作用下， 以 氘代氯仿 为溶剂， 反应 0.58h， 生成 2-Bromo-2,3,3,4,4,5,5-heptafluoro-cyclopentanone
  参考文献：
  名称：

  Highly Fluorinated Cyclopentanones and Their Enols

  摘要：

  2H-Perfluorocyclopentanone (Ik) and its enol (le) have been independently synthesized and equilibrated. In carbon tetrachloride, the enol is the only detectable form at equilibrium. In addition to its high relative stability, this enol displays interesting reactivity, including reversible bromination and hydrolysis reactions. Replacing the vinyl fluorine of le with hydrogen changes the relative enol stability dramatically as the enol is only present to the extent of 13% in carbon tetrachloride under equilibrating conditions. In Lewis basic solvents, however, the enol is the only detectable form because of its strength as a hydrogen bond donor. Quantum mechanical calculations on both systems suggest that ketone destabilization, but not enol stabilization, by fluorination is responsible for the remarkable relative stability of the enols.

  DOI：

  10.1021/jo9602940

文献信息

• Highly Fluorinated Cyclopentanones and Their Enols
  作者：Patrick E. Lindner、David M. Lemal

  DOI：10.1021/jo9602940

  日期：1996.1.1

  2H-Perfluorocyclopentanone (Ik) and its enol (le) have been independently synthesized and equilibrated. In carbon tetrachloride, the enol is the only detectable form at equilibrium. In addition to its high relative stability, this enol displays interesting reactivity, including reversible bromination and hydrolysis reactions. Replacing the vinyl fluorine of le with hydrogen changes the relative enol stability dramatically as the enol is only present to the extent of 13% in carbon tetrachloride under equilibrating conditions. In Lewis basic solvents, however, the enol is the only detectable form because of its strength as a hydrogen bond donor. Quantum mechanical calculations on both systems suggest that ketone destabilization, but not enol stabilization, by fluorination is responsible for the remarkable relative stability of the enols.
• 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。