4-Fluorocubane-1-carboxylic acid | 145193-69-7

• 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: 4-Fluorocubane-1-carboxylic acid
• 英文别名: 4-fluorocubanecarboxylic acid
• CAS: 145193-69-7
• 化学式: C₉H₇FO₂
• 分子量: 166.152
• InChiKey: FYGVUKWGPSBFGD-UHFFFAOYSA-N

物化性质

• 沸点：
  302.1±42.0 °C(Predicted)
• 密度：
  1.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  Methyl 4-fluoro-1-cubanecarboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到4-Fluorocubane-1-carboxylic acid
  参考文献：
  名称：

  古巴的均裂反应。cubyl 和 cubylcarbinyl 自由基的生成和表征

  摘要：

  通过从 1-bromo-4-取代的立方烷中提取溴原子，产生了一系列 4-取代的立方自由基。EPR 观察表明，cubyl 自由基从三乙基硅烷的乙基中提取二级氢原子，主要通过二级组合反应衰变。在-90 o C 时，叔丁氧基从立方烷中提取氢原子的速度至少比环丙烷快26 倍。立方烷上的吸电子取代基大大降低了这一速度。叔丁氧基自由基选择性地从甲基立方烷中提取笼氢而不是伯甲基氢

  DOI：

  10.1021/ja00053a008

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.
• Homolytic reactions of cubanes. Generation and characterization of cubyl and cubylcarbinyl radicals
  作者：Ernest W. Della、Nicholas J. Head、Philip Mallon、John C. Walton

  DOI：10.1021/ja00053a008

  日期：1992.12

  A series of 4-substituted cubyl radicals was generated by bromine atom abstraction from 1-bromo-4-substituted cubanes. EPR observations showed that the cubyl radicals abstracted secondary hydrogen atoms from the ethyl groups of triethylsilane and decayed mainly by second-order combination reactions. tert-Butoxyl radicals abstracted hydrogen atoms from cubane at least 26 times more rapidly than from

  通过从 1-bromo-4-取代的立方烷中提取溴原子，产生了一系列 4-取代的立方自由基。EPR 观察表明，cubyl 自由基从三乙基硅烷的乙基中提取二级氢原子，主要通过二级组合反应衰变。在-90 o C 时，叔丁氧基从立方烷中提取氢原子的速度至少比环丙烷快26 倍。立方烷上的吸电子取代基大大降低了这一速度。叔丁氧基自由基选择性地从甲基立方烷中提取笼氢而不是伯甲基氢