3H-perfluoro-1,3-dimethylcyclohexene | 817579-06-9

• 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: 3H-perfluoro-1,3-dimethylcyclohexene
• 英文别名: 1,3,3,4,4,5,5-Heptafluoro-2,6-bis(trifluoromethyl)cyclohexene
• CAS: 817579-06-9
• 化学式: C₈HF₁₃
• 分子量: 344.075
• InChiKey: VATUYHRJXKNOLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3H-perfluoro-1,3-dimethylcyclohexene 在 1,8-双二甲氨基萘 作用下， 以 氘代乙腈 为溶剂， 生成 perfluoro-1,3-dimethylcyclohex-1-en-3-yl anion
  参考文献：
  名称：

  Synthesis, Basicity, and Dynamics of a Perfluorocyclohexenyl Anion

  摘要：

  Electron transfer to perfluoro-1,3-dimethylcyclohexane in moist THF has yielded two quite different products. Tetrabutylammonium iodide irradiated with ultraviolet light gives a tetrabutylammonium enolate, but potassium fluorenone ketyl affords a cyclohexenyl anion. This allylic anion was isolated as its conjugate acid, a rather strong carbon acid. Ring inversion in the anion, measured by F-19 NMR line shape analysis, is characterized by these activation parameter values: AH(+/-) = 8.84 +/-0.14 kcal/mol and DeltaS(+/-) = 0.81 +/- 0.6 cal mol(-1) K-1.

  DOI：

  10.1021/jo040246c
• 作为产物：
  描述：

  全氟-1,3-二甲基环己烷 在 9-芴酮 、 硫酸 、 四丁基溴化铵 、 氢化钾 作用下， 以 四氢呋喃 、 三甘醇二甲醚 为溶剂， 反应 8.0h， 生成 3H-perfluoro-1,3-dimethylcyclohexene
  参考文献：
  名称：

  Synthesis, Basicity, and Dynamics of a Perfluorocyclohexenyl Anion

  摘要：

  Electron transfer to perfluoro-1,3-dimethylcyclohexane in moist THF has yielded two quite different products. Tetrabutylammonium iodide irradiated with ultraviolet light gives a tetrabutylammonium enolate, but potassium fluorenone ketyl affords a cyclohexenyl anion. This allylic anion was isolated as its conjugate acid, a rather strong carbon acid. Ring inversion in the anion, measured by F-19 NMR line shape analysis, is characterized by these activation parameter values: AH(+/-) = 8.84 +/-0.14 kcal/mol and DeltaS(+/-) = 0.81 +/- 0.6 cal mol(-1) K-1.

  DOI：

  10.1021/jo040246c

文献信息

• Synthesis, Basicity, and Dynamics of a Perfluorocyclohexenyl Anion
  作者：Xudong Chen、David M. Lemal

  DOI：10.1021/jo040246c

  日期：2004.11.1

  Electron transfer to perfluoro-1,3-dimethylcyclohexane in moist THF has yielded two quite different products. Tetrabutylammonium iodide irradiated with ultraviolet light gives a tetrabutylammonium enolate, but potassium fluorenone ketyl affords a cyclohexenyl anion. This allylic anion was isolated as its conjugate acid, a rather strong carbon acid. Ring inversion in the anion, measured by F-19 NMR line shape analysis, is characterized by these activation parameter values: AH(+/-) = 8.84 +/-0.14 kcal/mol and DeltaS(+/-) = 0.81 +/- 0.6 cal mol(-1) K-1.