2,2,3,3,8,8,9,9-Octafluoropentacyclo[8.6.2.24,7.212,15.011,16]docosa-1(16),4,6,10,13,17,19,21-octaene | 498556-71-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2,3,3,8,8,9,9-Octafluoropentacyclo[8.6.2.24,7.212,15.011,16]docosa-1(16),4,6,10,13,17,19,21-octaene
• CAS: 498556-71-1
• 化学式: C₂₂H₁₂F₈
• 分子量: 428.325
• InChiKey: CSVNULUIRYIFRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,2,3,3,8,8,9,9-Octafluoropentacyclo[8.6.2.24,7.212,15.011,16]docosa-1(16),4,6,10,13,17,19,21-octaene 在 3,6-bis(2-pyridyl)-tetrazine 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以89%的产率得到1,1,2,2,11,11,12,12-octafluoro[2.2]-(1,4)naphthalenoparacyclophane
  参考文献：
  名称：

  新型萘-和蒽-八氟[2.2]对环烷的高效合成

  摘要：

  四种新型桥氟化 [2.2] 对环芳烃含有萘和蒽稠合的多环芳族亚基，由 AF4 的单芳烃或双芳烃与苯和萘的 Diels-Alder 反应得到的加合物采用高效的一步法制备。提供了它们的 NMR 和 UV 光谱的详细信息。

  DOI：

  10.1055/s-2004-831260
• 作为产物：
  描述：

  4-acetamido-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 、 苯 在 p-chlorobenzoyl nitrite 作用下， 以 二丁醚 为溶剂， 以90%的产率得到2,2,3,3,8,8,9,9-Octafluoropentacyclo[8.6.2.24,7.212,15.011,16]docosa-1(16),4,6,10,13,17,19,21-octaene
  参考文献：
  名称：

  Remarkable Efficiency of the Aryne Chemistry of (Dehydro)octafluoro[2.2]paracyclophane When Using the Cadogan Method

  摘要：

  [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.

  DOI：

  10.1021/jo0620009

文献信息

• 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.
• 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.
• Efficient Syntheses of Novel Naphthaleno- and Anthraceno-Octafluoro[2.2]paracyclophanes
  作者：William R. Dolbier、Yian Zhai、Ion Ghiviriga、Merle A. Battiste

  DOI：10.1055/s-2004-831260

  日期：——

  Four novel bridge fluorinated [2.2]paracyclophanes containing naphthalene and anthracene condensed polycyclic aromatic subunits have been prepared in efficient one-step procedures from adducts obtained from the Diels-Alder reactions of mono- or bis-arynes of AF4 with benzene and naphthalene. Details of their NMR and UV spectra are provided.

  四种新型桥氟化 [2.2] 对环芳烃含有萘和蒽稠合的多环芳族亚基，由 AF4 的单芳烃或双芳烃与苯和萘的 Diels-Alder 反应得到的加合物采用高效的一步法制备。提供了它们的 NMR 和 UV 光谱的详细信息。