exo,exo-4,8-ethano-2,6-dioxaperhydro-s-indacene | 129258-14-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: exo,exo-4,8-ethano-2,6-dioxaperhydro-s-indacene
• 英文别名: 4,8-Ethano-3a,4,4a,5,7,7a,8,8a-octahydro-1H,3H-benzo<1,2-c:4,5>difuran
• CAS: 129258-14-6
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: QEAYIHOQKPBMGW-KUDAMMAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-syn,3-syn,5-syn,6-syn-tetrakis(hydroxymethyl)bicyclo[2.2.2]octane 在 三甲基氯硅烷 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以99%的产率得到exo,exo-4,8-ethano-2,6-dioxaperhydro-s-indacene
  参考文献：
  名称：

  Atzkern, Hermann; Koehler, Frank H.; Mueller, Reinhard, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1990, vol. 45, # 3, p. 329 - 343

  摘要：

  DOI：

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.