4a-<methyl>-4a,5-dihydro-3-methyllumiflavin | 135189-60-5

• 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: 4a-<methyl>-4a,5-dihydro-3-methyllumiflavin
• 英文别名: 4a-<2)-N-methylamino>methyl>-4a,5-dihydro-3-methyllumiflavin；4a-{[N-(benzyl-α,α-d₂)-N-methylamino]methyl}-4a,5-dihydro-3-methyllumiflavin
• CAS: 135189-60-5
• 化学式: C₂₃H₂₇N₅O₂
• 分子量: 407.484
• InChiKey: YFBCBGQDIDAFSU-KLTYLHELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  68.25
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苯甲腈 在 lithium aluminium tetrahydride 、 lithium aluminium deuteride 、 potassium carbonate 作用下， 以 乙醚 、 氘代乙腈 、 乙腈 为溶剂， 反应 105.67h， 生成 4a-<methyl>-4a,5-dihydro-3-methyllumiflavin
  参考文献：
  名称：

  Amine-flavin electron transfer photochemistry. Potential models for monoamine oxidase catalysis and inhibition

  摘要：

  The photoreactions of 3-methyllumiflavin (3MLF) and a variety of amines have been explored. These studies have demonstrated that 3MLF undergoes efficient photoreactions with alpha-silyl tertiary benzylamines to generate 4a-adducts by pathways involving sequential SET and desilylation followed by radical coupling. These adducts are unstable substances that react rapidly with nucleophiles (e.g., MeOH, H2O, and NaBH4) and oxygen. They are also photolabile, providing the corresponding 4a-benzyldihydroflavin upon irradiation. Non-silicon-containing primary and secondary amines also participate in SET-promoted photoreactions with 3MLF. The amine cation radicals formed in these processes undergo further transformations to produce radical intermediates by either alpha-CH or NH deprotonation pathways. The potential relevance of these findings to the area of monoamine oxidase chemistry is considered.

  DOI：

  10.1021/jo00016a026