4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane | 257863-41-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
• 英文别名: 5-Bromo-2,2,3,3,8,8,9,9-octafluorotricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene
• CAS: 257863-41-5
• 化学式: C₁₆H₇BrF₈
• 分子量: 431.123
• InChiKey: XITZMQTWIRABIN-UHFFFAOYSA-N

物化性质

• 沸点：
  307.0±42.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以96%的产率得到1,1,2,2,9,9,10,10-八氟[2.2]二聚对二甲苯
  参考文献：
  名称：

  di [2.2]对环环糊精的两种非对映异构体的首次合成和表征：4,4'-bis（1,1,2,2,9,9,10,10-八氟[2.2]对环环糊精）。

  摘要：

  描述了由两个通过单一4,4'键连接的[2.2]对环环烷单元组成的系统的两种非对映异构体的合成和表征。4，4′-双（八氟[2.2]对环环烷）的内消旋和d，l非对映异构体均通过铜催化钯催化的还原均偶联反应制备，生成的内消旋和d，l非对映异构体比例为3：2。伪-邻-碘三氟甲基八氟[2.2]对环环烷的类似还原均偶联仅给出类似的内消旋非对映异构体。对于所有的双对环烷产物都获得了单晶X射线结构。

  DOI：

  10.1021/jo0157775
• 作为产物：
  描述：

  1,1,2,2,9,9,10,10-八氟[2.2]二聚对二甲苯 在 盐酸 、 nitronium tetrafluoborate 、 硫酸 、 铁粉 、 sodium nitrite 作用下， 以 环丁砜 、 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 23.0h， 生成 4-bromo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
  参考文献：
  名称：

  Electrophilic Substitution of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane

  摘要：

  Nitration of octafluoro[2.2]paracyclophane (OFP) provides an entry into the synthesis of a series of II monosubstituted OFPs, including the nitro, amino, chloro, bromo, iodo, hydroxy, and trifluoromethyl compounds. The NMR, mass spectrometric, and UV spectral properties of all of these derivatives are presented and discussed, and they are compared with those of its hydrocarbon analogue, [2.2]paracyclophane.

  DOI：

  10.1021/jo9910536

文献信息

• Palladium catalyzed cross- and homo-coupling reactions of 4-Halo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanes with various organometallic reagents
  作者：Alex J. Roche

  DOI：10.1016/j.jfluchem.2015.02.016

  日期：2015.7

  type reactions between various Grignard reagents and mono-substituted octafluoroparacyclophane derivatives revealed that by varying the reaction temperature, and mode of addition of the Grignard reagent, it was possible to influence whether the major product was the cross-coupled, or the homo-coupled (reductive dimer) paracyclophane product. This provides an improved methodology to prepare aryl substituted

  对钯在各种Grignard试剂与单取代的八氟对环环糊精衍生物之间催化的Kumada型反应的研究表明，通过改变反应温度和Grignard试剂的添加方式，可以影响主要产物是否为交叉偶联，或均耦合的（还原性二聚体）对环烷产物。这提供了一种制备芳基取代的对环环烷的改进方法，并提供了另一种通往不寻常且稀有的双环烷骨架的方法。还探索了与烷基锂试剂的类似反应，从而产生了一些以前未报道的八氟对环环烷产物。
• Multiple Electrophilic Substitution of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane
  作者：Alex J. Roche、William R. Dolbier

  DOI：10.1021/jo000436x

  日期：2000.8.1

  Synthetic methods for introduction of two substituents into the rings of octafluoroparacyclophane are presented. Nitration gives three isomers with nitro substituents on different rings: pseudoortho, pseudo-mete, and pseudo-para, in equal amounts. These dinitro compounds are shown to be precursors of a variety of other disubstituted OFF derivatives. Methods of characterization of isomeric disubstituted OFPs are extensively discussed, and the H-1 and F-19 NMR spectra of these derivatives are analyzed explicitly.
• Electrophilic Substitution of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane
  作者：Alex J. Roche、William R. Dolbier

  DOI：10.1021/jo9910536

  日期：1999.12.1

  Nitration of octafluoro[2.2]paracyclophane (OFP) provides an entry into the synthesis of a series of II monosubstituted OFPs, including the nitro, amino, chloro, bromo, iodo, hydroxy, and trifluoromethyl compounds. The NMR, mass spectrometric, and UV spectral properties of all of these derivatives are presented and discussed, and they are compared with those of its hydrocarbon analogue, [2.2]paracyclophane.
• The First Synthesis and Characterization of Both Diastereomers of a Di[2.2]paracyclophane:  4,4‘-Bis(1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane)
  作者：A. J. Roche、J.-X. Duan、W. R. Dolbier,、K. A. Abboud

  DOI：10.1021/jo0157775

  日期：2001.10.1

  of two [2.2]paracyclophane units linked through a single 4,4' bond are described. Both the meso and d,l diastereomers of 4,4'-bis(octafluoro[2.2]paracyclophane) have been prepared via a palladium-catalyzed reductive homocoupling reaction by copper, producing a 3:2 ratio of meso and d,l diastereomers. A similar reductive homocoupling of pseudo-o-iodotrifluoromethyloctafluoro[2.2]paracyclophane gave only

  描述了由两个通过单一4,4'键连接的[2.2]对环环烷单元组成的系统的两种非对映异构体的合成和表征。4，4′-双（八氟[2.2]对环环烷）的内消旋和d，l非对映异构体均通过铜催化钯催化的还原均偶联反应制备，生成的内消旋和d，l非对映异构体比例为3：2。伪-邻-碘三氟甲基八氟[2.2]对环环烷的类似还原均偶联仅给出类似的内消旋非对映异构体。对于所有的双对环烷产物都获得了单晶X射线结构。