2-Cyclopentadienyliden-1,3-benzodioxol | 53639-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-Cyclopentadienyliden-1,3-benzodioxol
• 英文别名: 1,4-Dioxa-2,3-benzofulvalen；Benzofulvalen；2-(Cyclopenta-2,4-dien-1-ylidene)-2H-1,3-benzodioxole；2-cyclopenta-2,4-dien-1-ylidene-1,3-benzodioxole
• CAS: 53639-64-8
• 化学式: C₁₂H₈O₂
• 分子量: 184.194
• InChiKey: IWQKFWZNKRIACS-UHFFFAOYSA-N

物化性质

• 沸点：
  313.9±22.0 °C(Predicted)
• 密度：
  1.326±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-Diazo-2,4-cyclohexadienon 以 异辛烷 为溶剂， 反应 0.03h， 生成 2-Cyclopentadienyliden-1,3-benzodioxol 、 2,4-环戊二烯-1-亚基甲酮
  参考文献：
  名称：

  Nitroxyl Radical Addition to Pentafulvenones Forming Cyclopentadienyl Radicals:  A Test for Cyclopentadienyl Radical Destabilization

  摘要：

  Photochemical Wolff rearrangements in alkane solvents of the 6-diazo-2,4-cyclohexadienones 4 and 13-15 give pentafulvenone (1), 2,3-benzopentafulvenone (2), dibenzopentafulvenone (3), and 2,4-di-tert-butylpentafulvenone (16), as identified by conventional UV and IR spectroscopy. Reactions of these fulvenyl ketenes with tetramethylpiperidinyloxyl (TEMPO) proceed by addition of TEMPO to the carbonyl carbon forming delocalized radicals for 1 and 2 which add one or more further TEMPO molecules, while the initial radical products formed from 3 and 16 dimerize. The rate constants of these reactions compared to hydration rate constants for the same compounds show the benzannulated derivatives 2 and 3 fit a previous correlation k(2)(TEMPO) vs k(H2O), whereas for 1 and 16 there is evidence for inhibition of reactions with radicals. The deviations are consistent with an absence of aromatic stabilization of the cyclopentadienyl radicals from 1 and 16 that is compensated in the benzannulated derivatives.

  DOI：

  10.1021/jo010601o

文献信息

• Nitroxyl Radical Addition to Pentafulvenones Forming Cyclopentadienyl Radicals:  A Test for Cyclopentadienyl Radical Destabilization
  作者：Annette D. Allen、Justin Porter、Daryoush Tahmassebi、Thomas T. Tidwell

  DOI：10.1021/jo010601o

  日期：2001.11.1

  Photochemical Wolff rearrangements in alkane solvents of the 6-diazo-2,4-cyclohexadienones 4 and 13-15 give pentafulvenone (1), 2,3-benzopentafulvenone (2), dibenzopentafulvenone (3), and 2,4-di-tert-butylpentafulvenone (16), as identified by conventional UV and IR spectroscopy. Reactions of these fulvenyl ketenes with tetramethylpiperidinyloxyl (TEMPO) proceed by addition of TEMPO to the carbonyl carbon forming delocalized radicals for 1 and 2 which add one or more further TEMPO molecules, while the initial radical products formed from 3 and 16 dimerize. The rate constants of these reactions compared to hydration rate constants for the same compounds show the benzannulated derivatives 2 and 3 fit a previous correlation k(2)(TEMPO) vs k(H2O), whereas for 1 and 16 there is evidence for inhibition of reactions with radicals. The deviations are consistent with an absence of aromatic stabilization of the cyclopentadienyl radicals from 1 and 16 that is compensated in the benzannulated derivatives.