8-(3-Phenylprop-2-enoyl)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 8-(3-Phenylprop-2-enoyl)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione
• 化学式: C₂₁H₁₂O₄
• 分子量: 328.324
• InChiKey: LAFJLBVIUYXSFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(3-Phenylprop-2-enoyl)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione 、 C.I.酸性橙108 以77%的产率得到
  参考文献：
  名称：

  Effect of linker length on the spectroscopic properties of bacteriochlorin – 1,8-naphthalimide conjugates for fluorescence-guided photodynamic therapy

  摘要：

  Conjugation of 4-pyrazolinyl-1,8-naphthalimide and propargyl-15(2),17(3)-dimethoxy-13(1)-amide of bacteriochlorin e by the oligo(ethylene glycol) linker resulted in the dual function system comprising the modalities of a photosensitizer and a fluorescence imaging agent. In comparison with the conjugate of the same structure but containing the shorter linker, the system demonstrated the higher emission intensity originating from the naphthalimide unit, which could be explained by the decrease in resonance energy transfer efficiency between the chromophores. It has been shown that the ability of bacteriochlorin to generate singlet oxygen remains at the same level when this fragment is introduced in the conjugate structure. 4-Pyrazolinyl-1,8-naphthalimide group in the studied compounds was found to easily undergo photooxidation yielding highly emissive 4-pyrazolyl-1,8-naphthalimide derivatives.

  DOI：

  10.1016/j.jphotochem.2019.112338
• 作为产物：
  描述：

  4-乙酰基-1,8-萘二甲酸酐 、 苯甲醛 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以58%的产率得到8-(3-Phenylprop-2-enoyl)-3-oxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene-2,4-dione
  参考文献：
  名称：

  Effect of linker length on the spectroscopic properties of bacteriochlorin – 1,8-naphthalimide conjugates for fluorescence-guided photodynamic therapy

  摘要：

  Conjugation of 4-pyrazolinyl-1,8-naphthalimide and propargyl-15(2),17(3)-dimethoxy-13(1)-amide of bacteriochlorin e by the oligo(ethylene glycol) linker resulted in the dual function system comprising the modalities of a photosensitizer and a fluorescence imaging agent. In comparison with the conjugate of the same structure but containing the shorter linker, the system demonstrated the higher emission intensity originating from the naphthalimide unit, which could be explained by the decrease in resonance energy transfer efficiency between the chromophores. It has been shown that the ability of bacteriochlorin to generate singlet oxygen remains at the same level when this fragment is introduced in the conjugate structure. 4-Pyrazolinyl-1,8-naphthalimide group in the studied compounds was found to easily undergo photooxidation yielding highly emissive 4-pyrazolyl-1,8-naphthalimide derivatives.

  DOI：

  10.1016/j.jphotochem.2019.112338