6-hydroxy-2,7-dimethoxydibenzofuran-1,4-quinone | 43042-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6-hydroxy-2,7-dimethoxydibenzofuran-1,4-quinone
• 英文别名: 8-hydroxy-3,7-dimethoxybenzofuran-1,4-quinone；8-hydroxy-3,7-dimethoxydibenzofuran-1,4-dione；8-Hydroxy-3,7-dimethoxydibenzofuran-1,4-quinone；8-Hydroxy-3,7-dimethoxy-benzofuran-1,4-dion；8-Hydroxy-3,7-dimethoxy-dibenzofuran-1,4-chinon
• CAS: 43042-31-5
• 化学式: C₁₄H₁₀O₆
• 分子量: 274.23
• InChiKey: RPLSVIMEZUUUPL-UHFFFAOYSA-N

物化性质

• 熔点：
  250 °C
• 沸点：
  487.1±45.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-hydroxy-2,7-dimethoxydibenzofuran-1,4-quinone 生成 1,4,8-triacetoxy-3,7-dimethoxy-dibenzofuran
  参考文献：
  名称：

  Erdtman, Proceedings of the Royal Society of London, Series A: Mathematical, Physical and Engineering Sciences, 1934, vol. 143, p. 196,197

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二甲氧基[联-1,4-环己二烯-1-基]-3,3',6,6'-四酮 在 氧气 作用下， 以 乙二醇二甲醚 为溶剂， 生成 6-hydroxy-2,7-dimethoxydibenzofuran-1,4-quinone
  参考文献：
  名称：

  Forsskahl, Ingegerg; Gustafsson, Jean; Nybergh, Anna, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1981, vol. 35, # 6, p. 389 - 394

  摘要：

  DOI：

文献信息

• Diquinones II the formation of dibenzofuran derivatives by rearrangement of diquinones
  作者：A.J. Shand、R.H. Thomson

  DOI：10.1016/0040-4020(63)85007-3

  日期：1963.1

  Several diquinones (I, III, V) undergo photochemical and/or thermal rearrangement to dibenzofuranquinones (II, IV, VI). Structure IV has been established by synthesis and unambiguous structures have been assigned to several of its isomers.

  几个二醌（I，III，V）经历光化学和/或热重排，生成二苯并呋喃醌（II，IV，VI）。通过合成已经建立了结构IV，并且已经将明确的结构分配给了它的几种异构体。
• Erdtman, Svensk Kemisk Tidskrift, 1932, vol. 44, p. 135,143, 147
  作者：Erdtman

  DOI：——

  日期：——
• Hammam, A. S.; Youssef, M. S. K.; Abbady, M. A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 6, p. 565 - 570
  作者：Hammam, A. S.、Youssef, M. S. K.、Abbady, M. A.、Ibrahim, R. R.

  DOI：——

  日期：——
• Photophysics and Photochemistry of a Lignin-like Quinoid Dimer, 4,4‘-Dimethoxybiphenyl-2,5,2‘,5‘-bisquinone, in Relation to Color Alteration of Woody Materials Exposed to Daylight
  作者：Stéphane Béarnais-Barbry、Roland Bonneau、Alain Castellan

  DOI：10.1021/jp992534w

  日期：1999.12.1

  4,4'-Dimethoxybiphenyl-2,5,2',5'-bisquinone 1 is thought to be issued, in wood and lignin-rich pulps, from the photochemical coupling and oxidation of methoxy(hydro)quinone. Under irradiation in solution, 1 is transformed to a highly colored dibenzofuran derivative, 2, as unique photoproduct. The mechanism of the conversion 1 --> 2 has been studied by laser flash photolysis and by quantum yield measurements in several solvents at various temperatures. The reaction proceeds via the triplet state of 1 and a cyclized X transient species which rearranges to 2 by a sequence of deprotonation-protonation reactions, quite efficiently in polar or acidified solutions but with a low yield in nonpolar solvents. As temperature increases, the quantum yield increases in polar solutions but decreases in nonpolar solvents. This unusual temperature dependence is explained by activation energy barriers on the cyclization (3)1* --> X and reopening X --> 1 elementary reactions approximate to 35.5 and 58.5 kJ/mol respectively, and by a conversion X --> 2 much faster in polar solvents than in nonpolar ones. The zwitterionic or biradicaloid structure of X is discussed on the basis of semiempirical calculations'(AM1 or PM3) and of spectroscopic and kinetic measurements. Under laser flash photolysis conditions, a special mechanism involving a second-order rearrangement of X was found to be very efficient in any type of solvents.