10-Isobutyl-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione | 186766-02-9

• 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: 10-Isobutyl-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione
• CAS: 186766-02-9
• 化学式: C₁₆H₁₈N₄O₃
• 分子量: 314.344
• InChiKey: FXUGDZYLWINITN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  94.69
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  10-Isobutyl-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione 在 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 以82%的产率得到10-Isobutyl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Model Systems for Flavoenzyme Activity:  One- and Two-Electron Reduction of Flavins in Aprotic Hydrophobic Environments

  摘要：

  The processes occurring during the electrochemically irreversible reduction of flavins in aprotic organic medium have been the cause of considerable controversy. To provide insight into these events we have investigated the reduction of flavins alkylated at N(3). We have demonstrated that the reversible reduction of N(3)-methylated flavin can be converted to the irreversible reduction observed with unalkylated flavins through addition of the weak external proton donor phthalimide. Proton transfer to the flavin radical anion generated at the electrode leads to partial formation of the neutral flavin radical; which is instantaneously further reduced to the fully reduced flavin anion. This mirrors the reduction of unalkylated flavins, where the proton source is the imide proton at N(3) of fully oxidized flavin in bulk solution. Simultaneous electrochemistry and EPR experiments confirm the disappearance of electrogenerated flavin radical anion both methylated and non-methylated at N(3), upon addition of phthalimide. UV/vis spectroelectrochemistry likewise confirmed the generation of the radical anion in the absence of proton donors and fully reduced flavin in the presence of proton donors.

  DOI：

  10.1021/ja963704a
• 作为产物：
  描述：

  苯胺,3,4-二甲基-N-(2-甲基丙基)- 在 溶剂黄146 、 sodium nitrite 作用下， 反应 25.5h， 生成 10-Isobutyl-7,8-dimethyl-5-oxy-10H-benzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Model Systems for Flavoenzyme Activity:  One- and Two-Electron Reduction of Flavins in Aprotic Hydrophobic Environments

  摘要：

  The processes occurring during the electrochemically irreversible reduction of flavins in aprotic organic medium have been the cause of considerable controversy. To provide insight into these events we have investigated the reduction of flavins alkylated at N(3). We have demonstrated that the reversible reduction of N(3)-methylated flavin can be converted to the irreversible reduction observed with unalkylated flavins through addition of the weak external proton donor phthalimide. Proton transfer to the flavin radical anion generated at the electrode leads to partial formation of the neutral flavin radical; which is instantaneously further reduced to the fully reduced flavin anion. This mirrors the reduction of unalkylated flavins, where the proton source is the imide proton at N(3) of fully oxidized flavin in bulk solution. Simultaneous electrochemistry and EPR experiments confirm the disappearance of electrogenerated flavin radical anion both methylated and non-methylated at N(3), upon addition of phthalimide. UV/vis spectroelectrochemistry likewise confirmed the generation of the radical anion in the absence of proton donors and fully reduced flavin in the presence of proton donors.

  DOI：

  10.1021/ja963704a