exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene | 187990-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene
• 英文别名: (1S,2S,6R,7R,8S,12R)-3,3,5,5-tetrafluoro-4,10-dioxatetracyclo[5.5.2.02,6.08,12]tetradec-13-ene
• CAS: 187990-62-1
• 化学式: C₁₂H₁₂F₄O₂
• 分子量: 264.22
• InChiKey: VMWRYXGZJLMMMU-UXAOAXNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene 在 palladium on activated charcoal 氢气 作用下， 反应 336.0h， 以20 mg的产率得到exo,exo-4,8-ethano-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene
  参考文献：
  名称：

  exo,exo-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms

  摘要：

  Unusual alkenes, exo,exo-4,8-etheno-1,1,3,3,5,5,7,7-octafluoro-2,6-dioxaperhydro-s-indacene (1) and exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene (2), as well as their nonfluorinated analogue 3 were synthesized. The structures of 1 and 3 have been determined in the solid state by X-ray crystallography and of all three compounds in solution by H-1, F-19, and C-13 NMR spectroscopy. The chemical. properties of compounds 1-3 were investigated and compared, The double bond in fluorinated polycycloalkenes 1 and 2 was found to be totally inert toward bromination, hydrogenenation, and oxidation with m-chloroperbenzoic acid and ozone. This is in contrast to nonfluorinated indacene 3, which behaves like a normal alkene, readily adds bromine and hydrogen, and reacts with oxidants. The only successful chemical transformation of I was achieved by treatment with Mn2O7, which led to oxirane 15 and rearranged pentacyclic acetal 16. An interesting skeletal rearrangement occurred in the course of bromination of 3 leading to bicyclic tetrabromo derivative 12. High chemical inertness of polyfluoroindacenes 1 and 2 has been attributed mainly to through-space electronic interactions of the double bond with proximal fluorine atoms.

  DOI：

  10.1021/jo962023v
• 作为产物：
  描述：

  (1S,2R,6S,7R,8R,12S)-9,9,11,11-tetrafluoro-4,10-dioxatetracyclo[5.5.2.02,6.08,12]tetradec-13-ene-3,5-dione 在 potassium hydrogensulfate 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene
  参考文献：
  名称：

  exo,exo-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms

  摘要：

  Unusual alkenes, exo,exo-4,8-etheno-1,1,3,3,5,5,7,7-octafluoro-2,6-dioxaperhydro-s-indacene (1) and exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene (2), as well as their nonfluorinated analogue 3 were synthesized. The structures of 1 and 3 have been determined in the solid state by X-ray crystallography and of all three compounds in solution by H-1, F-19, and C-13 NMR spectroscopy. The chemical. properties of compounds 1-3 were investigated and compared, The double bond in fluorinated polycycloalkenes 1 and 2 was found to be totally inert toward bromination, hydrogenenation, and oxidation with m-chloroperbenzoic acid and ozone. This is in contrast to nonfluorinated indacene 3, which behaves like a normal alkene, readily adds bromine and hydrogen, and reacts with oxidants. The only successful chemical transformation of I was achieved by treatment with Mn2O7, which led to oxirane 15 and rearranged pentacyclic acetal 16. An interesting skeletal rearrangement occurred in the course of bromination of 3 leading to bicyclic tetrabromo derivative 12. High chemical inertness of polyfluoroindacenes 1 and 2 has been attributed mainly to through-space electronic interactions of the double bond with proximal fluorine atoms.

  DOI：

  10.1021/jo962023v

文献信息

• <i>exo,exo</i>-4,8-Ethenopolyfluoro-2,6-dioxaperhydroindacenes. Unusual Alkenes Flanked with Fluorine Atoms
  作者：Wojciech Dmowski、Ireneusz Nowak、Przemysław Gluziński、Andrei Kemme

  DOI：10.1021/jo962023v

  日期：1997.3.1

  Unusual alkenes, exo,exo-4,8-etheno-1,1,3,3,5,5,7,7-octafluoro-2,6-dioxaperhydro-s-indacene (1) and exo,exo-4,8-etheno-1,1,3,3-tetrafluoro-2,6-dioxaperhydroindacene (2), as well as their nonfluorinated analogue 3 were synthesized. The structures of 1 and 3 have been determined in the solid state by X-ray crystallography and of all three compounds in solution by H-1, F-19, and C-13 NMR spectroscopy. The chemical. properties of compounds 1-3 were investigated and compared, The double bond in fluorinated polycycloalkenes 1 and 2 was found to be totally inert toward bromination, hydrogenenation, and oxidation with m-chloroperbenzoic acid and ozone. This is in contrast to nonfluorinated indacene 3, which behaves like a normal alkene, readily adds bromine and hydrogen, and reacts with oxidants. The only successful chemical transformation of I was achieved by treatment with Mn2O7, which led to oxirane 15 and rearranged pentacyclic acetal 16. An interesting skeletal rearrangement occurred in the course of bromination of 3 leading to bicyclic tetrabromo derivative 12. High chemical inertness of polyfluoroindacenes 1 and 2 has been attributed mainly to through-space electronic interactions of the double bond with proximal fluorine atoms.