1,6-dihydroxy-phenanthro<1,10,9,8-o,p,q,r,a>perylene-7,14-dione | 141600-17-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,6-dihydroxy-phenanthro<1,10,9,8-o,p,q,r,a>perylene-7,14-dione
• 英文别名: 1,6-dihydroxy-phenanthro[1,10,9,8-opqra]perylene-7,14-dione；1,6-Dihydroxy-phenanthro[1,10,9,8-opqra]perylen-7,14-dion；7,22-dihydroxyoctacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
• CAS: 141600-17-1
• 化学式: C₂₈H₁₂O₄
• 分子量: 412.401
• InChiKey: MBIGJGQBVHVXPK-UHFFFAOYSA-N

物化性质

• 沸点：
  819.4±60.0 °C(Predicted)
• 密度：
  1.739±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  32.0
• 可旋转键数：
  0.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1,6-dihydroxydibenzoperylene-7,16-dione 在 4-二甲氨基吡啶 吡啶 、 sodium hydroxide 作用下， 反应 11.0h， 生成 1,6-dihydroxy-phenanthro<1,10,9,8-o,p,q,r,a>perylene-7,14-dione
  参考文献：
  名称：

  Deprotonation and protonation of hydroxyphenanthroperylenes

  摘要：

  Ground and excited state deprotonation and protonation pK(a) values of hydroxyanthraquinones, hydroxyanthrones, hydroxyphenanthroperylenes, and the natural pigments hypericin and pseudohypericin were determined by means of spectrophotometric titrations and Forster cycle calculations. It was concluded that there is a strong intramolecular excited state proton transfer in the hydroxyanthraquinones and hydroxyanthrones due to a reversion of acidity and basicity of the hydroxyl and carbonyl groups in the excited state. However, in the hydroxyphenanthroperylene and the natural pigment excited states the order of basicity and acidity of these two functional groups remain unchanged. The site of deprotonation in hypericin and pseudohypericin was deduced by comparison between the pK(a) values of suited model compounds and these pigments to be the hydroxyl group in position 3 or 4, respectively.

  DOI：

  10.1007/bf00810476

文献信息

• XXII.—Reduction products of the hydroxyanthraquinones. Part XII
  作者：Gordon Frederick Attree、Arthur George Perkin

  DOI：10.1039/jr9310000144

  日期：——
• Deprotonation and protonation of hydroxyphenanthroperylenes
  作者：Heinz Falk、Joachim Meyer、Manfred Oberreiter

  DOI：10.1007/bf00810476

  日期：1992.3

  Ground and excited state deprotonation and protonation pK(a) values of hydroxyanthraquinones, hydroxyanthrones, hydroxyphenanthroperylenes, and the natural pigments hypericin and pseudohypericin were determined by means of spectrophotometric titrations and Forster cycle calculations. It was concluded that there is a strong intramolecular excited state proton transfer in the hydroxyanthraquinones and hydroxyanthrones due to a reversion of acidity and basicity of the hydroxyl and carbonyl groups in the excited state. However, in the hydroxyphenanthroperylene and the natural pigment excited states the order of basicity and acidity of these two functional groups remain unchanged. The site of deprotonation in hypericin and pseudohypericin was deduced by comparison between the pK(a) values of suited model compounds and these pigments to be the hydroxyl group in position 3 or 4, respectively.