4-氨基-AF4 | 257863-37-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 中文名称: 4-氨基-AF4
• 英文名称: 4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
• 英文别名: 4-amino-AF4；2,2,3,3,8,8,9,9-Octafluorotricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaen-5-amine
• CAS: 257863-37-9
• 化学式: C₁₆H₉F₈N
• 分子量: 367.241
• InChiKey: WQGBQDGMXLBTEW-UHFFFAOYSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  310.9±42.0 °C(Predicted)
• 密度：
  1.52±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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：
  26
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-氨基-AF4 在 palladium dichloride 硫酸 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 19.0h， 生成 1,1,2,2,9,9,10,10-八氟[2.2]二聚对二甲苯
  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
• 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 、 氢气 、 铁粉 作用下， 以 环丁砜 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 44.0h， 生成 4-氨基-AF4
  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

• 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。
• 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.
• 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.