10-(4-Ethoxycarbonylmethylphenyl)-3-methylflavin | 253868-78-9

• 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-(4-Ethoxycarbonylmethylphenyl)-3-methylflavin
• 英文别名: Ethyl 2-[4-(3-methyl-2,4-dioxobenzo[g]pteridin-10-yl)phenyl]acetate；ethyl 2-[4-(3-methyl-2,4-dioxobenzo[g]pteridin-10-yl)phenyl]acetate
• CAS: 253868-78-9
• 化学式: C₂₁H₁₈N₄O₄
• 分子量: 390.398
• InChiKey: YBBVOOMJVBKOEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  10-(4-Ethoxycarbonylmethylphenyl)-3-methylflavin 在 盐酸 、 水 作用下， 反应 16.0h， 以72%的产率得到10-(4-Carboxylmethylphenyl)-3-methylflavin
  参考文献：
  名称：

  Synthesis, Spectroscopy, and Semiempirical Study of a Novel Porphyrin-Flavin Dyad

  摘要：

  A new synthetic methodology for the preparation of donor-bridge-acceptor compounds incorporating a porphyrin donor and an all-aromatic oligo(diazaphenylene) bridge is introduced. This approach allows the controlled preparation of photosynthetic model compounds with well-defined spacer structure and properties. The synthesis of the porphyrin - flavin dyads 1a-c is described to exemplify the strategy. This type of structure has a number of interesting spectroscopic and photophysical properties. The aromatic bridge results in a well-defined donor-acceptor distance; it can favor conjugation and at the same time be nonabsorbing in the visible and near-UV range. The choice of a flavin as the acceptor unit opens the way to a spectroscopic study by excitation of the acceptor in addition to the usual porphyrin donor excitation. Based on these premises, a spectroscopic, photophysical and semiempirical study of the dyad la has been performed in three solvents of varying polarity. The results demonstrate energy transfer from flavin to porphyrin with unit efficiency at high solvent polarity. In solvents of medium polarity an additional internal conversion pathway is opened Following excitation of the flavin moiety. Spectroscopic, cyclovoltammetric, and semiempirical results all suggest that this pathway involves the intermediate population of a short-lived charge-separated state.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3208::aid-chem3208>3.0.co;2-o
• 作为产物：
  描述：

  6-氯-3-甲基尿嘧啶 在 乙酸酐 、 溶剂黄146 、 N,N-二甲基苯胺 作用下， 反应 0.92h， 生成 10-(4-Ethoxycarbonylmethylphenyl)-3-methylflavin
  参考文献：
  名称：

  Synthesis, Spectroscopy, and Semiempirical Study of a Novel Porphyrin-Flavin Dyad

  摘要：

  A new synthetic methodology for the preparation of donor-bridge-acceptor compounds incorporating a porphyrin donor and an all-aromatic oligo(diazaphenylene) bridge is introduced. This approach allows the controlled preparation of photosynthetic model compounds with well-defined spacer structure and properties. The synthesis of the porphyrin - flavin dyads 1a-c is described to exemplify the strategy. This type of structure has a number of interesting spectroscopic and photophysical properties. The aromatic bridge results in a well-defined donor-acceptor distance; it can favor conjugation and at the same time be nonabsorbing in the visible and near-UV range. The choice of a flavin as the acceptor unit opens the way to a spectroscopic study by excitation of the acceptor in addition to the usual porphyrin donor excitation. Based on these premises, a spectroscopic, photophysical and semiempirical study of the dyad la has been performed in three solvents of varying polarity. The results demonstrate energy transfer from flavin to porphyrin with unit efficiency at high solvent polarity. In solvents of medium polarity an additional internal conversion pathway is opened Following excitation of the flavin moiety. Spectroscopic, cyclovoltammetric, and semiempirical results all suggest that this pathway involves the intermediate population of a short-lived charge-separated state.

  DOI：

  10.1002/(sici)1521-3765(19991105)5:11<3208::aid-chem3208>3.0.co;2-o

文献信息

• Synthesis, Spectroscopy, and Semiempirical Study of a Novel Porphyrin-Flavin Dyad
  作者：Dominik T. Hermann、Anne Christina Schindler、Kurt Polborn、Rudolf Gompper、Susanne Stark、Andreas B. J. Parusel、Gottfried Grabner、Gottfried Köhler

  DOI：10.1002/(sici)1521-3765(19991105)5:11<3208::aid-chem3208>3.0.co;2-o

  日期：1999.11.5

  A new synthetic methodology for the preparation of donor-bridge-acceptor compounds incorporating a porphyrin donor and an all-aromatic oligo(diazaphenylene) bridge is introduced. This approach allows the controlled preparation of photosynthetic model compounds with well-defined spacer structure and properties. The synthesis of the porphyrin - flavin dyads 1a-c is described to exemplify the strategy. This type of structure has a number of interesting spectroscopic and photophysical properties. The aromatic bridge results in a well-defined donor-acceptor distance; it can favor conjugation and at the same time be nonabsorbing in the visible and near-UV range. The choice of a flavin as the acceptor unit opens the way to a spectroscopic study by excitation of the acceptor in addition to the usual porphyrin donor excitation. Based on these premises, a spectroscopic, photophysical and semiempirical study of the dyad la has been performed in three solvents of varying polarity. The results demonstrate energy transfer from flavin to porphyrin with unit efficiency at high solvent polarity. In solvents of medium polarity an additional internal conversion pathway is opened Following excitation of the flavin moiety. Spectroscopic, cyclovoltammetric, and semiempirical results all suggest that this pathway involves the intermediate population of a short-lived charge-separated state.