7,8-Difluoro-1,3-dimethyl-5-ethyl-5,10-dihydroalloxazine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 蝶啶及其衍生物
• 英文名称: 7,8-Difluoro-1,3-dimethyl-5-ethyl-5,10-dihydroalloxazine
• 英文别名: 5-ethyl-7,8-difluoro-1,3-dimethyl-10H-benzo[g]pteridine-2,4-dione
• 化学式: C₁₄H₁₄F₂N₄O₂
• 分子量: 308.288
• InChiKey: YFBGSGNYGMZFPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  55.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7,8-Difluoro-1,3-dimethyl-5-ethyl-5,10-dihydroalloxazine 在 air 作用下， 以75%的产率得到7,8-difluoro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine
  参考文献：
  名称：

  Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts

  摘要：

  Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.

  DOI：

  10.1021/ol3010326
• 作为产物：
  描述：

  乙醛 、 7,8-Difluoro-1,3-dimethylalloxazine 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 以10%的产率得到7,8-Difluoro-1,3-dimethyl-5-ethyl-5,10-dihydroalloxazine
  参考文献：
  名称：

  Mild and Efficient Flavin-Catalyzed H2O2 Oxidations

  摘要：

  Based on a previously discovered method for amine oxidations using flavins as catalysts and hydrogen peroxide as oxidant, a comparative kinetic study using NMR spectroscopy was undertaken with a series of flavins for amine and thioether oxidations. Included in this series is the newly prepared 7,8-difluoro-1,3dimethyl-5-ethyl-5,10-dihydroalIoxazine. This study shows that flavins, which bear electron-donating groups on the aromatic ring and/or the N-10 position, are less active and are deactivated during the course of the reaction, Moreover, flavins that are alkylated at the N-1 position instead of the N-10 position and having either no substituents or electron-withdrawing groups on the aromatic ring, remain the most active and stable.

  DOI：

  10.1002/1521-3765(20010105)7:1<297::aid-chem297>3.0.co;2-6

文献信息

• Mild and Efficient Flavin-Catalyzed H2O2 Oxidations
  作者：Alexander B. E. Minidis、Jan-E. Bäckvall

  DOI：10.1002/1521-3765(20010105)7:1<297::aid-chem297>3.0.co;2-6

  日期：2001.1.5

  Based on a previously discovered method for amine oxidations using flavins as catalysts and hydrogen peroxide as oxidant, a comparative kinetic study using NMR spectroscopy was undertaken with a series of flavins for amine and thioether oxidations. Included in this series is the newly prepared 7,8-difluoro-1,3dimethyl-5-ethyl-5,10-dihydroalIoxazine. This study shows that flavins, which bear electron-donating groups on the aromatic ring and/or the N-10 position, are less active and are deactivated during the course of the reaction, Moreover, flavins that are alkylated at the N-1 position instead of the N-10 position and having either no substituents or electron-withdrawing groups on the aromatic ring, remain the most active and stable.
• Organocatalytic Dakin Oxidation by Nucleophilic Flavin Catalysts
  作者：Shuai Chen、Mohammad S. Hossain、Frank W. Foss

  DOI：10.1021/ol3010326

  日期：2012.6.1

  Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.