7-(9-phenyl-9-fluorenyl)-1,3,5-cycloheptatriene | 135256-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 7-(9-phenyl-9-fluorenyl)-1,3,5-cycloheptatriene
• 英文别名: 9-cyclohepta-2,4,6-trien-1-yl-9-phenylfluorene
• CAS: 135256-53-0
• 化学式: C₂₆H₂₀
• 分子量: 332.445
• InChiKey: VOWMZNIYNYOKQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  430.2±40.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  tropylium tetrafluoroborate 、 lithium,9-phenylfluoren-9-ide 以 四氢呋喃 为溶剂， 反应 0.25h， 以49%的产率得到7-(9-phenyl-9-fluorenyl)-1,3,5-cycloheptatriene
  参考文献：
  名称：

  Self-Initiated Autoxidation of a Sterically Crowded Cycloheptatriene Derivative via Norcaradienyloxyl Radicals

  摘要：

  An extremely crowded cycloheptatriene derivative, 1,3,5-tri-tert-butyl-7-(9-phenyl-9-fluorenyl)-1,3,5-cycloheptatriene (1), underwent autoxidation at 25 degrees C in cyclohexane to give 4-tert-butyl-2-pivaloylphenol (3) (33%), 5-tert-butyl-2-pivaloylphenol (4) (11%), 1,3,5-tri-tert-butylbenzene (5) (5%), tert-butyl 9-phenyl-9-fluorenyl peroxide (6) (44%), bis(9-phenyl-9-fluorenyl) peroxide (7) (7%), 1,1',3,3',5,5'-hexa-tert-butyl-7,7'-bicycloheptatriene (8) (2%), and carbon monoxide (4%). ESR studies showed that 1 dissociates into 1,3,5-tri-tert-butyltropyl radical (II) and 9-phenylfluorenyl radical (12) at 25-85 degrees C. The enthalpy and entropy of dissociation were determined to be 23.3 kcal/mol and 22.0 cal/mol . K, respectively. The formation of 3-5 can be explained by a mechanism involving attack of molecular oxygen to 11 and subsequent valence tautomerism of cycloheptatrienyloxyl radicals to norcaradienyloxyl radicals.

  DOI：

  10.1021/jo961321p

文献信息

• Self-Initiated Autoxidation of a Sterically Crowded Cycloheptatriene Derivative via Norcaradienyloxyl Radicals
  作者：Toshikazu Kitagawa、Atsushi Miyabo、Hideki Fujii、Takao Okazaki、Tetsuya Mori、Masaki Matsudou、Takeshi Sugie、Ken'ichi Takeuchi

  DOI：10.1021/jo961321p

  日期：1997.2.1

  An extremely crowded cycloheptatriene derivative, 1,3,5-tri-tert-butyl-7-(9-phenyl-9-fluorenyl)-1,3,5-cycloheptatriene (1), underwent autoxidation at 25 degrees C in cyclohexane to give 4-tert-butyl-2-pivaloylphenol (3) (33%), 5-tert-butyl-2-pivaloylphenol (4) (11%), 1,3,5-tri-tert-butylbenzene (5) (5%), tert-butyl 9-phenyl-9-fluorenyl peroxide (6) (44%), bis(9-phenyl-9-fluorenyl) peroxide (7) (7%), 1,1',3,3',5,5'-hexa-tert-butyl-7,7'-bicycloheptatriene (8) (2%), and carbon monoxide (4%). ESR studies showed that 1 dissociates into 1,3,5-tri-tert-butyltropyl radical (II) and 9-phenylfluorenyl radical (12) at 25-85 degrees C. The enthalpy and entropy of dissociation were determined to be 23.3 kcal/mol and 22.0 cal/mol . K, respectively. The formation of 3-5 can be explained by a mechanism involving attack of molecular oxygen to 11 and subsequent valence tautomerism of cycloheptatrienyloxyl radicals to norcaradienyloxyl radicals.