1-Fluoro-4-methylcubane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 1-Fluoro-4-methylcubane
• 化学式: C₉H₉F
• 分子量: 136.169
• InChiKey: OQORGUCJKQBYTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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

• 作为产物：
  描述：

  1-Fluoro-4-iodocubane 、 三氟甲烷磺酸甲酯 在 叔丁基锂 作用下， 以 乙醚 、 正戊烷 为溶剂， 生成 六甲基乙烷 、 1-Fluoro-4-methylcubane
  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

文献信息

• Synthesis and 19F and 13C NMR Studies of a Series of 4-Substituted Fluorocubanes: Resonance Dependence of 19F Chemical Shifts in a Saturated System
  作者：Ernest W. Della、Nicholas J. Head

  DOI：10.1021/jo00121a059

  日期：1995.8

  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.