5,12-dihydro-5,12-dioxo-N-(2'-hydroxyethyl)-2-naphthacenecarboxamide | 793716-66-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 5,12-dihydro-5,12-dioxo-N-(2'-hydroxyethyl)-2-naphthacenecarboxamide
• 英文别名: N-(2-hydroxyethyl)-5,12-dioxotetracene-2-carboxamide
• CAS: 793716-66-2
• 化学式: C₂₁H₁₅NO₄
• 分子量: 345.354
• InChiKey: IGAPWLQIJBYQSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氰乙基N,N-二异丙基氯亚磷酰胺 、 5,12-dihydro-5,12-dioxo-N-(2'-hydroxyethyl)-2-naphthacenecarboxamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到N-[2-[2-cyanoethoxy-[di(propan-2-yl)amino]phosphanyl]oxyethyl]-5,12-dioxotetracene-2-carboxamide
  参考文献：
  名称：

  Synthesis and Study of Naphthacenedione (TQ) as a Photosensitizer for One-Electron Oxidation of DNA

  摘要：

  (GRAPHICS)Photosensitizers; are useful for the study of one-electron oxidation of DNA. Most such photosensitizers; absorb light in the UV spectral region. We report the synthesis and investigation of a 5,12-naphthacenedione (TO) derivative as a DNA photosensitizer. Irradiation of a TQ-linked duplex with visible light results in reaction of the DNA that is characteristic of one-electron oxidation. The results from TO sensitization are identical, within experimental error, with that of a well-studied anthraquinone derivative.

  DOI：

  10.1021/ol048407m
• 作为产物：
  描述：

  5,12-naphthacenequinone-2-carboxaldehyde 在 水 chromium(VI) oxide 、 氯化亚砜 、 硫酸 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 10.0h， 生成 5,12-dihydro-5,12-dioxo-N-(2'-hydroxyethyl)-2-naphthacenecarboxamide
  参考文献：
  名称：

  Synthesis and Study of Naphthacenedione (TQ) as a Photosensitizer for One-Electron Oxidation of DNA

  摘要：

  (GRAPHICS)Photosensitizers; are useful for the study of one-electron oxidation of DNA. Most such photosensitizers; absorb light in the UV spectral region. We report the synthesis and investigation of a 5,12-naphthacenedione (TO) derivative as a DNA photosensitizer. Irradiation of a TQ-linked duplex with visible light results in reaction of the DNA that is characteristic of one-electron oxidation. The results from TO sensitization are identical, within experimental error, with that of a well-studied anthraquinone derivative.

  DOI：

  10.1021/ol048407m