4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane | 257863-40-4

• 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-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
• 英文别名: 2,2,3,3,8,8,9,9-Octafluoro-5-iodotricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene
• CAS: 257863-40-4
• 化学式: C₁₆H₇F₈I
• 分子量: 478.123
• InChiKey: IAHUQHGHBREPFX-UHFFFAOYSA-N

物化性质

• 熔点：
  109-111 °C
• 沸点：
  324.9±42.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 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-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 在 苯基溴化镁 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以98%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：

  钯催化4-卤代-1,1,2,2,9,9,10,10-八氟[2.2]对环环烷与各种有机金属试剂的交叉和均偶联反应

  摘要：

  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。

  DOI：

  10.1016/j.jfluchem.2015.02.016
• 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 platinum(IV) oxide 盐酸 、 nitronium tetrafluoborate 、 硫酸 、 氢气 、 铁粉 、 sodium nitrite 作用下， 以 环丁砜 、 乙醇 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 47.0h， 生成 4-iodo-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

• 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。
• Remarkable Efficiency of the Aryne Chemistry of (Dehydro)octafluoro[2.2]paracyclophane When Using the Cadogan Method
  作者：William R. Dolbier,、Yi-An Zhai、Will Wheelus、Merle A. Battiste、Ion Ghiviriga、Michael D. Bartberger

  DOI：10.1021/jo0620009

  日期：2007.1.1

  [GRAPHIC]Generation of the aryne, (dehydro)octafluoro[2.2]paracyclophane, from its acetamide derivative utilizing the Cadogan method led to remarkable results with respect to Diels-Alder and ene reactivity. A comparison was made between this new and virtually unused method and our earlier reported results using Cram methodology (reaction of aryl iodide with potassium tert-butoxide). Surprisingly, no ene reactivity was observed with the Cram methodology. This mechanistic conundrum was examined extensively with no unambiguous explanation for the difference in reactivity being found.
• 4,5-Dehydro- and 4,5,15,16-Bis(dehydro)octafluoro[2.2]paracyclophanes:  Facile Generation and Extraordinary Diels−Alder Reactivity
  作者：Merle A. Battiste、Jian-Xin Duan、Yi-An Zhai、Ion Ghiviriga、Khalil A. Abboud、William R. Dolbier

  DOI：10.1021/jo0268815

  日期：2003.4.1

  Dehydroiodination of 4-iodo- and 4,15-diiodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane by treatment with (KOBu)-Bu-t in the presence of benzene, naphthalene, anthracene, and [2.2]paracyclophane affords each of the corresponding Diels-Alder mono- and bis-cycloadducts derived from the presumed aryne intermediates in high yield. Monoadducts of t-butylbenzene and furan are also obtained in excellent yield. All of the products were characterized by their NMR spectra, with four of them also being confirmed by X-ray crystallography. The extraordinary selectivity/reactivity of the aryne intermediate is discussed.
• 4,5-Dehydrooctafluoro[2.2]paracyclophane: facile generation and extraordinary Diels–Alder reactivity
  作者：Merle A. Battiste、Jian-Xin Duan、Yi-An Zhai、Ion Ghiviriga、Khalil A. Abboud、Adrian Roitberg、G.Robert Shelton、William R. Dolbier

  DOI：10.1016/s0040-4039(02)01554-x

  日期：2002.9

  Dehydroiodination of 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane by treatment with KO'Bu in the presence of benzene, naphthalene, anthracene, or t-butylbenzene affords each of the corresponding Diels-Alder cycloadducts of the presumed aryne intermediate in high yield. The products were characterized by their NMR spectra, with one of them also being confirmed by X-ray crystallography. The extraordinary selectivity/reactivity of the aryne intermediate is discussed. (C) 2002 Published by Elsevier Science Ltd.
• The SRN1 chemistry of 4-iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
  作者：Kai Wu、William R. Dolbier、Merle A. Battiste、Yian Zhai

  DOI：10.1070/mc2006v016n03abeh002311

  日期：2006.1

  4-Iodo-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane undergoes high-yield nucleophilic substitution by arene thiolates and the malonate anion via the S(RN)1 mechanism.