1-Fluoro-4-iodocubane | 167496-66-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1-Fluoro-4-iodocubane
• CAS: 167496-66-4
• 化学式: C₈H₆FI
• 分子量: 248.039
• InChiKey: XDBOYKWHIDEWGQ-UHFFFAOYSA-N

物化性质

• 沸点：
  235.1±40.0 °C(Predicted)
• 密度：
  2.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Fluoro-4-iodocubane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 反应 2.0h， 以88%的产率得到fluorocubane
  参考文献：
  名称：

  Synthesis and 19F and 13C NMR Studies of a Series of 4-Substituted Fluorocubanes: Resonance Dependence of 19F Chemical Shifts in a Saturated System

  摘要：

  The substituent chemical shifts and the carbon-fluorine coupling constants of a range of 4-substituted cubyl fluorides in solvents of varying polarity are presented. Least squares regressional analysis of the data indicates that the fluorine probe, while being somewhat less sensitive to field effects as a result of the low polarizability of the cubane C-F bond, nevertheless responds in the ''reverse'' manner in agreement with precedents established in other alicyclic systems. The dependence of (1)J(CF) upon electronegativity has been interpreted as evidence for the occurrence of sigma-induction over four bonds, the longest reported to date. Significantly, resonance parameters are found to be very important in describing the effect of substituents on both the fluorine chemical shifts and the magnitude of the one-bond and four-bond C-13-F-19 coupling constants. This represents one of the rare occasions that resonance effects have been observed in a fully saturated system in the ground state. A possible mechanism by which these resonance effects may be transmitted is presented.

  DOI：

  10.1021/jo00121a059
• 作为产物：
  描述：

  4-Fluorocubane-1-carboxylic acid 在 lead(IV) acetate 、 碘 作用下， 以 苯 为溶剂， 反应 3.0h， 以90%的产率得到1-Fluoro-4-iodocubane
  参考文献：
  名称：

  Synthesis and 19F and 13C NMR Studies of a Series of 4-Substituted Fluorocubanes: Resonance Dependence of 19F Chemical Shifts in a Saturated System

  摘要：

  The substituent chemical shifts and the carbon-fluorine coupling constants of a range of 4-substituted cubyl fluorides in solvents of varying polarity are presented. Least squares regressional analysis of the data indicates that the fluorine probe, while being somewhat less sensitive to field effects as a result of the low polarizability of the cubane C-F bond, nevertheless responds in the ''reverse'' manner in agreement with precedents established in other alicyclic systems. The dependence of (1)J(CF) upon electronegativity has been interpreted as evidence for the occurrence of sigma-induction over four bonds, the longest reported to date. Significantly, resonance parameters are found to be very important in describing the effect of substituents on both the fluorine chemical shifts and the magnitude of the one-bond and four-bond C-13-F-19 coupling constants. This represents one of the rare occasions that resonance effects have been observed in a fully saturated system in the ground state. A possible mechanism by which these resonance effects may be transmitted is presented.

  DOI：

  10.1021/jo00121a059