7,8-dichloro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine | 1377860-46-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 7,8-dichloro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine
• 英文别名: 7,8-Dichloro-5-ethyl-4a-hydroperoxy-1,3-dimethylbenzo[g]pteridine-2,4-dione
• CAS: 1377860-46-2
• 化学式: C₁₄H₁₄Cl₂N₄O₄
• 分子量: 373.196
• InChiKey: GFQYSZASOZYXOC-UHFFFAOYSA-N

物化性质

• 熔点：
  134-140 °C
• 沸点：
  555.5±60.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 氧气 作用下， 生成 7,8-dichloro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine
  参考文献：
  名称：

  Aerobic Organocatalytic Oxidation of Aryl Aldehydes: Flavin Catalyst Turnover by Hantzsch’s Ester

  摘要：

  The first Dakin oxidation fueled by molecular oxygen as the terminal oxidant is reported. Flavin and NAD(P)H coenzymes, from natural enzymatic redox systems, inspired the use of flavin organocatalysts and a Hantzsch ester to perform transition-metal-free, aerobic oxidations. Catechols and electron-rich phenols are achieved with as low as a 0.1 mol % catalyst loading, 1 equiv of Hantzsch ester, and O-2 or air as the stoichiometric oxidant source.

  DOI：

  10.1021/ol302479b
• 作为试剂：
  描述：

  2'-羟基苯乙酮 在 7,8-dichloro-1,3-dimethyl-5-ethyl-4a-hydroperoxyalloxazine 、 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 6.0h， 以79%的产率得到木榴油
  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