Benzo-4-oxo-2,5-cyclohexadienylidene | 3225-40-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Benzo-4-oxo-2,5-cyclohexadienylidene
• 英文别名: 4-ylo-naphthalen-1-yloxyl；4-oxo-4H-naphthalene-1,1-diyl；4H-naphthalen-4-ylium-1-olate
• CAS: 3225-40-9
• 化学式: C₁₀H₆O
• 分子量: 142.157
• InChiKey: GPNYUYMCVHLQDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Benzo-4-oxo-2,5-cyclohexadienylidene 以 various solvent(s) 为溶剂， 以91%的产率得到Cyclopropinden-6(6aH)-one
  参考文献：
  名称：

  Direct observation of the cyclopropene-vinylcarbene rearrangement. Matrix isolation of bicyclo[3.1.0]hexa-3,5-dien-2-ones

  摘要：

  4-Oxocyclohexa-2,5-dienylidenes 4b-g have been generated in argon matrices at 10 K by visible-light irradiation of the corresponding quinone diazides 5. Carbenes 4 have been characterized by IR and UV-vis spectroscopy and by their characteristic thermal reaction with molecular oxygen. On irradiation into the longest-wavelength absorption (420-700 nm), carbenes 4c-g rearrange to give the highly strained bicyclo[3.1.0]hexa-3,5-dien-2-ones 3c-g, while 4b is photostable under the same conditions. The photochemical 4 --> 3 rearrangement is completely reversible: infrared irradiation or visible light irradiation (lambda > 470 nm) of the cyclopropenes 3 lead back to triplet carbenes 4 quantitatively. In addition, several of the 1,3-bridged cyclopropenes 3 undergo a thermal rearrangement to give carbenes 4. This indicates that the highly strained cyclopropenes 3 are thermodynamically less stable than the corresponding carbenes 4 and kinetically only stabilized by a shallow energy barrier. Even under the conditions of matrix isolation at cryogenic temperatures, cyclopropenes 3 are metastable compounds.

  DOI：

  10.1021/jo00031a009
• 作为产物：
  描述：

  α-Diazo-2-ethynylacetophenone 以 solid matrix 为溶剂， 生成 Benzo-4-oxo-2,5-cyclohexadienylidene 、 (2-Ethynylphenyl)ketene
  参考文献：
  名称：

  Komnick, Peter; Sander, Wolfram, Liebigs Annalen, 1996, # 1, p. 7 - 9

  摘要：

  DOI：

文献信息

• Direct observation of the cyclopropene-vinylcarbene rearrangement. Matrix isolation of bicyclo[3.1.0]hexa-3,5-dien-2-ones
  作者：Goetz Bucher、Wolfram Sander

  DOI：10.1021/jo00031a009

  日期：1992.2

  4-Oxocyclohexa-2,5-dienylidenes 4b-g have been generated in argon matrices at 10 K by visible-light irradiation of the corresponding quinone diazides 5. Carbenes 4 have been characterized by IR and UV-vis spectroscopy and by their characteristic thermal reaction with molecular oxygen. On irradiation into the longest-wavelength absorption (420-700 nm), carbenes 4c-g rearrange to give the highly strained bicyclo[3.1.0]hexa-3,5-dien-2-ones 3c-g, while 4b is photostable under the same conditions. The photochemical 4 --> 3 rearrangement is completely reversible: infrared irradiation or visible light irradiation (lambda > 470 nm) of the cyclopropenes 3 lead back to triplet carbenes 4 quantitatively. In addition, several of the 1,3-bridged cyclopropenes 3 undergo a thermal rearrangement to give carbenes 4. This indicates that the highly strained cyclopropenes 3 are thermodynamically less stable than the corresponding carbenes 4 and kinetically only stabilized by a shallow energy barrier. Even under the conditions of matrix isolation at cryogenic temperatures, cyclopropenes 3 are metastable compounds.
• Komnick, Peter; Sander, Wolfram, Liebigs Annalen, 1996, # 1, p. 7 - 9
  作者：Komnick, Peter、Sander, Wolfram

  DOI：——

  日期：——