fluorocubane | 72507-68-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: fluorocubane
• 英文别名: 1-Fluorocubane
• CAS: 72507-68-7
• 化学式: C₈H₇F
• 分子量: 122.142
• InChiKey: DIVWWCLPOLQNDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 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：

  fluorocubane 在 次氯酸叔丁酯 作用下， 以 四氯化碳 为溶剂， 反应 0.33h， 以37%的产率得到1-chloro-3-fluorocubane
  参考文献：
  名称：

  Pseudotetrahedral Polyhalocubanes:  Synthesis, Structures, and Parity Violating Energy Differences

  摘要：

  All possible pseudotetrahedral, stable polyhalocubanes were prepared, and their structures were proven by NMR spectroscopy and X-ray crystallography. Parity violating energy differences (DeltaEpv) and vibrational frequency shifts were computed. The DeltaEpv values are predicted to be one to two orders of magnitude smaller than those for the corresponding polyhalomethanes. However, the DeltaEpv energy ordering is the same as that for the methane analogues. For both substance classes, the (S) isomers are, with the exception of the bromochlorofluoroiodo derivatives, more stable than the (R) forms.

  DOI：

  10.1021/ja060781p
• 作为产物：
  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

文献信息

• Synthesis of bridgehead fluorides by fluorodeiodination
  作者：Ernest W. Della、Nicholas J. Head

  DOI：10.1021/jo00036a018

  日期：1992.5

  Fluorodeiodination is found to be an attractive procedure for the synthesis of bridgehead fluorides. Thus, treatment of the corresponding iodide with xenon difluoride in dichloromethane at ambient temperature generally leads to high yields of the fluoride. Evidence suggests the intermediacy of the bridgehead cation in this reaction, and accordingly the substrates which are unfavorably disposed to fluorodeiodination are the bicyclo[n.1.1]alkyl iodides. In this context the isolation of a small quantity of methyl 4-fluorobicyclo[2.1.1]hexane-1-carboxylate (46, R = COOMe) is significant because it represents the first occasion on which the elusive 1-bicyclo[2.1.1]hexyl cation has been trapped. We have also demonstrated that synthesis of the iodides themselves can be accomplished efficiently both by Barton halodecarboxylation and by treatment of the carboxylic acid with lead tetraacetate and iodine.
• Olah, George A.; Lee, Chang Soo; Prakash, G. K. Surya, Journal of the American Chemical Society, 1993, vol. 115, # 23, p. 10728 - 10732
  作者：Olah, George A.、Lee, Chang Soo、Prakash, G. K. Surya、Moriarty, Robert M.、Chander Rao, M. Suresh

  DOI：——

  日期：——