4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane | 257863-35-7

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
• 英文别名: 4-nitro-AF4；2,2,3,3,8,8,9,9-Octafluoro-5-nitrotricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaene
• CAS: 257863-35-7
• 化学式: C₁₆H₇F₈NO₂
• 分子量: 397.224
• InChiKey: BMEVGIMHHXPZSK-UHFFFAOYSA-N

物化性质

• 熔点：
  119-119.5 °C
• 沸点：
  322.6±42.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 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：
  45.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 在 盐酸 、 硫酸 、 铁粉 、 sodium nitrite 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 7.0h， 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 硝酸 作用下， 以90%的产率得到4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
  参考文献：
  名称：

  4,5-Dehydro- and 4,5,15,16-Bis(dehydro)octafluoro[2.2]paracyclophanes:  Facile Generation and Extraordinary Diels−Alder Reactivity

  摘要：

  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.

  DOI：

  10.1021/jo0268815

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。
• 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.
• 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.
• Novel ring-cleaving reaction of 4-nitro-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane with nucleophiles
  作者：William R. Dolbier、Yian Zhai、Wei Xu、Will Wheelus、Florian Dulong、Efram Goldberg、Ion Ghiviriga、Merle A. Battiste

  DOI：10.1016/j.jfluchem.2008.08.003

  日期：2008.12

  When 4-vitro-AF4 is treated with nucleophiles such as alkoxides and cyanide, a novel ring opening, cyclophane destroying reaction is observed whereby, via an SNAr mechanism, the nucleophile attacks the bridgehead aryl carbon vicinal to the nitro group with subsequent aryl-CF2 bond cleavage. (c) 2008 Elsevier B.V. All rights reserved.
• 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.