(E)-9,10-dihydro-6-(2-(4-dimethylaminophenyl)ethenyl)-1,3,8-trihydroxyanthracen-9-one | 428854-18-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-9,10-dihydro-6-(2-(4-dimethylaminophenyl)ethenyl)-1,3,8-trihydroxyanthracen-9-one
• 英文别名: (e)-9,10-Dihydro-6-(2-(4-dimethylaminophenyl)-ethenyl)-1,3,8-trihydroxy-anthracene-9-one；3-[(E)-2-[4-(dimethylamino)phenyl]ethenyl]-1,6,8-trihydroxy-10H-anthracen-9-one
• CAS: 428854-18-6
• 化学式: C₂₄H₂₁NO₄
• 分子量: 387.435
• InChiKey: SPPIZZKJDNFLDQ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  81
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  大黄素蒽酮 、 (E)-9,10-dihydro-6-(2-(4-dimethylaminophenyl)ethenyl)-1,3,8-trihydroxyanthracen-9-one 在 哌啶 、 吡啶-N-氧化物 、 iron(II) sulfate 作用下， 以 吡啶 为溶剂， 反应 1.0h， 生成 protohypericin 、 (E)-10-(4-(dimethylamino)styryl)-1,3,4,6,8,15-hexahydroxy-13-methyldibenzo[a,o]perylene-7,16-dione 、
  参考文献：
  名称：

  Concerning the Absorption and Photochemical Properties of an ω-4-Dimethylaminobenzal Hypericin Derivative

  摘要：

  A hypericin derivative containing omega,omega'-4-dimethylaminobenzal residues was shown to undergo an intramolecular [2 + 2] cycloaddition upon irradiation leading to a cyclobutane derivative whose main absorption band is hardly shifted as compared to hypericin. The corresponding omega-substituted derivative displayed a 34 nm bathochromic shift and a strongly reduced fluorescence quantum yield rendering it a nice candidate for a photodynamic therapy agent. Unfortunately, however, it produced virtually no photosensitized active oxygen species, making it thus unsuited for this purpose.

  DOI：

  10.1007/s007060170009
• 作为产物：
  描述：

  (E)-6-(2-(4-dimethylaminophenyl)ethenyl)-1,3,8-trimethoxyanthraquinone 在 氢溴酸 、 tin(ll) chloride 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以97%的产率得到(E)-9,10-dihydro-6-(2-(4-dimethylaminophenyl)ethenyl)-1,3,8-trihydroxyanthracen-9-one
  参考文献：
  名称：

  Concerning the Absorption and Photochemical Properties of an ω-4-Dimethylaminobenzal Hypericin Derivative

  摘要：

  A hypericin derivative containing omega,omega'-4-dimethylaminobenzal residues was shown to undergo an intramolecular [2 + 2] cycloaddition upon irradiation leading to a cyclobutane derivative whose main absorption band is hardly shifted as compared to hypericin. The corresponding omega-substituted derivative displayed a 34 nm bathochromic shift and a strongly reduced fluorescence quantum yield rendering it a nice candidate for a photodynamic therapy agent. Unfortunately, however, it produced virtually no photosensitized active oxygen species, making it thus unsuited for this purpose.

  DOI：

  10.1007/s007060170009