5,12-naphthacenequinone-2-carboxaldehyde | 144453-51-0

• 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-naphthacenequinone-2-carboxaldehyde
• 英文别名: 5,12-Dioxo-5,12-dihydrotetracene-2-carbaldehyde；5,12-dioxotetracene-2-carbaldehyde
• CAS: 144453-51-0
• 化学式: C₁₉H₁₀O₃
• 分子量: 286.287
• InChiKey: JPVHZLVXADGFRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  51.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,12-naphthacenequinone-2-carboxaldehyde 在 水 chromium(VI) oxide 、 氯化亚砜 、 硫酸 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 10.0h， 生成
  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：

  1,4-antraquinone 在 manganese(IV) oxide 作用下， 以 苯 为溶剂， 反应 2.0h， 生成 5,12-naphthacenequinone-2-carboxaldehyde
  参考文献：
  名称：

  A Diene Synthesis of Quinone Aldehydes

  摘要：

  Cycloaddition of 2-(hydroxymethyl)-l,3-butadiene with representative quinones occurs readily in refluxing toluene. Oxidative dehydrogenation of the resulting cycloadduct with activated manganese dioxide in refluxing benzene affords quinone aldehydes in good to excellent overall yield.

  DOI：

  10.1080/00397919208019067

文献信息

• A Diene Synthesis of Quinone Aldehydes
  作者：Russell A. Cormier、John S. Connolly、Libbie S. Pelter

  DOI：10.1080/00397919208019067

  日期：1992.8

  Cycloaddition of 2-(hydroxymethyl)-l,3-butadiene with representative quinones occurs readily in refluxing toluene. Oxidative dehydrogenation of the resulting cycloadduct with activated manganese dioxide in refluxing benzene affords quinone aldehydes in good to excellent overall yield.
• Synthesis and Study of Naphthacenedione (TQ) as a Photosensitizer for One-Electron Oxidation of DNA
  作者：Lezah W. Roberts、Gary B. Schuster

  DOI：10.1021/ol048407m

  日期：2004.10.1

  (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.