1,5-dihydro-3-methyllumiflavin | 23542-57-6

• 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: 1,5-dihydro-3-methyllumiflavin
• 英文别名: 3-Methyllumiflavin；3,7,8,10-Tetramethyl-1,5-dihydrobenzo[g]pteridine-2,4-dione；3,7,8,10-tetramethyl-1,5-dihydrobenzo[g]pteridine-2,4-dione
• CAS: 23542-57-6
• 化学式: C₁₄H₁₆N₄O₂
• 分子量: 272.307
• InChiKey: XGTDWQJYHMXZHA-UHFFFAOYSA-N

物化性质

• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,7,8,10-四甲基-苯并[g]蝶啶-2,4(3H,10H)-二酮 在 3,4-dimethyl-2-(α-hydroxybenzyl)-5-(2-hydroxyethyl)thiazolium iodide 作用下， 以 水 、 乙腈 为溶剂， 生成 1,5-dihydro-3-methyllumiflavin
  参考文献：
  名称：

  Mechanism of Base Catalyzed Oxidation of 2-(1-Hydroxyalkyl)thiazolium Ion with 3-Methyllumiflavin

  摘要：

  在缓冲水溶液中对 2-(α-羟基苄基)-和 2-(1-羟乙基)噻唑鎓离子与 3-甲基亮黄素的氧化进行了动力学研究。结果表明，速率决定步骤是碳负离子形成，然后是快速氧化。碳负离子的形成受到一般碱催化作用。

  DOI：

  10.1246/bcsj.53.2340

文献信息

• Photochemistry of flavins with sulfur-activated carboxylic acids: identification and reactions of the photoproducts
  作者：Gert A. Eberlein、Michael F. Powell

  DOI：10.1021/ja00323a041

  日期：1984.5

  Photoreduction de methyl-3 lumiflavine par divers diacides carboxyliques α-sulfures ou α-disulfures (par exemple les acides thio-2,2' bis-acetique et dithio-2,2 bis-acetique) conduisant a des derives alkylthioxymethyl en 4a de l'isoalloxazine

  光还原甲基-3 光黄素二酸二酸羧基α-硫或α-二硫（例如硫代-2,2' 双乙酸和二硫-2,2 双乙酸）的载体 a des 衍生烷基硫氧甲基 en 4a de l '异咯嗪
• Amine-flavin electron transfer photochemistry. Potential models for monoamine oxidase catalysis and inhibition
  作者：Jong Man Kim、In Seop Cho、Patrick S. Mariano

  DOI：10.1021/jo00016a026

  日期：1991.8

  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.
• Photochemical and photophysical studies of amines with excited flavins. Relevance to the mechanism of action of the flavin-dependent monoamine oxidase
  作者：J. T. Simpson、A. Krantz、F. D. Lewis、B. Kokel

  DOI：10.1021/ja00389a044

  日期：1982.12
• The mechanism of flavin 4a substitution which accompanies photolytic decarboxylation of .alpha.-substituted acetic acids. Carbanion vs. radical intermediates
  作者：Michael Novak、Audrey Miller、Thomas C. Bruice、Gordon Tollin

  DOI：10.1021/ja00524a063

  日期：1980.2
• Mechanism of Base Catalyzed Oxidation of 2-(1-Hydroxyalkyl)thiazolium Ion with 3-Methyllumiflavin
  作者：Yumihiko Yano、Yoshiharu Tamura、Yutaka Hoshino、Waichiro Tagaki

  DOI：10.1246/bcsj.53.2340

  日期：1980.8

  The oxidation of 2-(α-hydroxybenzyl)- and 2-(1-hydroxyethyl)thiazolium ions with 3-methyllumiflavin was studied kinetically in an aqueous buffer solution. The results indicate that the rate-determining step is carbanion formation followed by rapid oxidation. The carbanion formation was subjected to general base catalysis.

  在缓冲水溶液中对 2-(α-羟基苄基)-和 2-(1-羟乙基)噻唑鎓离子与 3-甲基亮黄素的氧化进行了动力学研究。结果表明，速率决定步骤是碳负离子形成，然后是快速氧化。碳负离子的形成受到一般碱催化作用。