4-acetamido-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-acetamido-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane
• 英文别名: N-(2,2,3,3,8,8,9,9-octafluoro-5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)acetamide
• 化学式: C₁₈H₁₁F₈NO
• 分子量: 409.279
• InChiKey: WMVMNXAMPMFOKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-acetamido-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane 、 萘 在 p-chlorobenzoyl nitrite 作用下， 以 二丁醚 为溶剂， 以93%的产率得到(3S,10R)-13,13,14,14,19,19,20,20-octafluorohexacyclo[10.8.2.23,10.215,18.02,11.04,9]hexacosa-1,4,6,8,11,15,17,21,23,25-decaene
  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

• 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.