2-(4-tolyl)-1-oxoheptafluoro-1,2-dihydronaphthalene | 152342-49-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-tolyl)-1-oxoheptafluoro-1,2-dihydronaphthalene
• 英文别名: 1-oxo-2-(p-tolyl)-2,3,4,5,6,7,8-heptafluoro-1,2-dihydronaphthalene
• CAS: 152342-49-9
• 化学式: C₁₇H₇F₇O
• 分子量: 360.231
• InChiKey: BSJQQKXDXXWDEW-UHFFFAOYSA-N

物化性质

• 沸点：
  415.1±45.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.22
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(4-tolyl)-1-oxoheptafluoro-1,2-dihydronaphthalene 在 sodium dithionite 作用下， 以 水 、 乙腈 为溶剂， 以82%的产率得到2-(p-tolyl)-3,4,5,6,7,8-hexafluoro-1-naphthol
  参考文献：
  名称：

  Selective ortho-arylation of polyfluorinated hydroxyaromatic compounds with lead aryl acetates

  摘要：

  Reactions of salts of pentafluorophenol and heptafluoronaphthols with lead aryl acetates have led to the formation of arylcyclohexadienones with an ortho-quinoid structure. The arylation of sodium pentafluorophenoxide and heptafluoro-2-naphthoxide is accompanied by nucleophilic substitution of fluorine at a double bond by pentafluorophenoxy and heptafluoro-2-naphthoxy groups, respectively. Reduction of the resulting arylcyclohexadienones gave polyfluorinated phenols and naphthols with aryl and hydroxy groups in the 1,2-position.

  DOI：

  10.1016/s0022-1139(00)80568-0
• 作为产物：
  描述：

  p-tolyllead triacetate 、 sodium heptafluoro-1-naphthoxide 以 四氯化碳 为溶剂， 反应 2.0h， 以42%的产率得到2-(4-tolyl)-1-oxoheptafluoro-1,2-dihydronaphthalene
  参考文献：
  名称：

  Selective ortho-arylation of polyfluorinated hydroxyaromatic compounds with lead aryl acetates

  摘要：

  Reactions of salts of pentafluorophenol and heptafluoronaphthols with lead aryl acetates have led to the formation of arylcyclohexadienones with an ortho-quinoid structure. The arylation of sodium pentafluorophenoxide and heptafluoro-2-naphthoxide is accompanied by nucleophilic substitution of fluorine at a double bond by pentafluorophenoxy and heptafluoro-2-naphthoxy groups, respectively. Reduction of the resulting arylcyclohexadienones gave polyfluorinated phenols and naphthols with aryl and hydroxy groups in the 1,2-position.

  DOI：

  10.1016/s0022-1139(00)80568-0

文献信息

• Photochemical cyclization of polyfluorinated aryloxo-1,2-dihydronaphthalenes and 6-phenyl-3-phenoxy-2,4-cyclohexadienone
  作者：V.N. Kovtonyuk、L.S. Kobrina

  DOI：10.1016/0022-1139(93)02947-d

  日期：1994.3

  On irradiation of solutions of polyfluorinated aryloxo-1,2-dihydronaphthalenes and 6-phenyl-3-phenoxy-2,4-cyclohexadienone, the main reaction pathway is cyclization leading to polyfluorinated benzonaphtho- and dibenzo-furans.