pseudo-o-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane | 300700-89-4

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: pseudo-o-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
• 英文别名: pseudo-p-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane；4,12-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane；4,16-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane；pseudo-ortho-diamino-AF4；pseudo ortho-diamino-1,1,2,2,9,9,10,10-octafluoro[2,2]paracyclophane；2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-1(12),4,6,10,13,15-hexaene-5,11-diamine
• CAS: 300700-89-4；300766-01-2
• 化学式: C₁₆H₁₀F₈N₂
• 分子量: 382.256
• InChiKey: VVBYNXMVOZPNQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 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：
  52
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  pseudo-o-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 在 tetrafluoroboric acid 、 sodium nitrite 作用下， 以 水 为溶剂， 生成 pseudo-ortho-difluoro-AF4
  参考文献：
  名称：

  单氟和二氟1,1,2,2,9,9,10,10-八氟[2.2]对环磷烯（AF4s）-A（1）H和（19）F NMR研究。

  摘要：

  4-氟-AF4（1）中（1）H和（19）F化学位移的完全分配是基于在（19）F-（1）H HOESY光谱中看到的nOes。这可以鉴定特征，这些特征可以进一步应用于取代的全氟对环环烷（PCP）和AF4的区域化学的分配：（i）芳族氟与最接近的桥中与之同位的两个氟偶合，常数为约。20赫兹; （ii）在相同的对亚苯基部分中，芳族氟与桥氟偶合了五个键，该氟与它反键，其常数为约3。3.5赫兹; （iii）桥氟的邻位氟为246 Hz，如果不含邻氟，则为238 Hz；（iv）桥氟与相同的对亚苯基部分中的芳族质子偶合，它们相隔四个或五个键且反。这些特征已被用于分配假邻位，假元和假对二氟AF4 2-4的区域化学。还已经证明，用于桥氟的SCS也可以用于该分配。

  DOI：

  10.1002/mrc.2392
• 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 、 铁粉 作用下， 以 环丁砜 、 乙醇 为溶剂， 反应 20.0h， 生成 pseudo-o-diamino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
  参考文献：
  名称：

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

  摘要：

  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.

  DOI：

  10.1021/jo000436x

文献信息

• Process for the preparation of derivatives of octafluoro-[2,2] paracylophane
  申请人：Specialty Coating Systems, Inc.

  公开号：US06392097B1

  公开（公告）日：2002-05-21

  Processes for the preparation of parylene dimers, and more particularly to processes for the preparation of derivatives of octafluoro-[2,2]paracylophane, otherwise known as AF4.

  用于制备对聚对二甲苯二聚物的方法，更具体地说是用于制备八氟[2,2]对环烷衍生物的方法，也称为AF4。
• A Highly Pyramidalized Cage Alkene Formed via the Double Diels−Alder Cycloaddition of <i>syn</i>-4,5,13,14-Bis(dehydro)octafluoroparacyclophane to Anthracene
  作者：William R. Dolbier,、Yi-An Zhai、Merle A. Battiste、Khalil A. Abboud、Ion Ghiviriga

  DOI：10.1021/jo051488v

  日期：2005.12.1

  A double Diels−Alder reaction of the formal syn-bis(dehydro)octafluoroparacyclophane with anthracene leads to formation of a novel cage compound that contains a highly pyramidal double bond. The measures of pyramidality of this double bond constitute what appear to be the highest combined values of ψ and φ (34.3° and 33.5°, respectively) yet reported to have been determined by X-ray crystallography

  正规的双Diels-Alder反应顺式双（脱氢）octafluoroparacyclophane与蒽导致形成包含高度锥体双键的新颖笼化合物。该双键的锥体度测量值似乎是ψ和φ的最高组合值（分别为34.3°和33.5°），但据报道已通过X射线晶体学测定。该笼状化合物尽管在空气中作为结晶化合物无限期地稳定，但在溶液中与三重态和单重态O 2均显示出高反应性，这是这种高度金字塔形的π系统的特征。
• 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.
• 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.
• Mono- and difluorinated 1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophanes (AF4s)-A¹H and¹⁹F NMR study
  作者：Ion Ghiviriga、Florian Dulong、William R. Dolbier

  DOI：10.1002/mrc.2392

  日期：2009.4

  Complete assignment of the (1)H and (19)F chemical shifts in 4-fluoro-AF4 (1) were based on the nOes seen in its (19)F-(1)H HOESY spectrum. This allowed for identification of features which can further be applied to the assignment of the regiochemistry of substituted perfluoroparacyclophanes (PCPs) and AF4s: (i) an aromatic fluorine couples with the two fluorines in the closest bridge that are syn

  4-氟-AF4（1）中（1）H和（19）F化学位移的完全分配是基于在（19）F-（1）H HOESY光谱中看到的nOes。这可以鉴定特征，这些特征可以进一步应用于取代的全氟对环环烷（PCP）和AF4的区域化学的分配：（i）芳族氟与最接近的桥中与之同位的两个氟偶合，常数为约。20赫兹; （ii）在相同的对亚苯基部分中，芳族氟与桥氟偶合了五个键，该氟与它反键，其常数为约3。3.5赫兹; （iii）桥氟的邻位氟为246 Hz，如果不含邻氟，则为238 Hz；（iv）桥氟与相同的对亚苯基部分中的芳族质子偶合，它们相隔四个或五个键且反。这些特征已被用于分配假邻位，假元和假对二氟AF4 2-4的区域化学。还已经证明，用于桥氟的SCS也可以用于该分配。