7-methyl-8-chloro-N(10)-isobutylisoalloxazine | 649763-45-1

• 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: 7-methyl-8-chloro-N(10)-isobutylisoalloxazine
• 英文别名: 8-chloro-7-methyl-10-isobutylflavin；8-Chloro-7-methyl-10-(2-methylpropyl)benzo[g]pteridine-2,4-dione
• CAS: 649763-45-1
• 化学式: C₁₅H₁₅ClN₄O₂
• 分子量: 318.763
• InChiKey: HSAZFMQVMMCUAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  74.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  二甲胺 、 7-methyl-8-chloro-N(10)-isobutylisoalloxazine 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以97%的产率得到7-methyl-8-dimethylamino-N(10)-isobutylisoalloxazine
  参考文献：
  名称：

  Model Systems for Flavoenzyme Activity:  Relationships between Cofactor Structure, Binding and Redox Properties

  摘要：

  A series of flavins were synthesized bearing electron-withdrawing and -donating substituents. The electrochemical properties of these flavins in a nonpolar solvent were determined. The recognition of these flavins by a diamidopyridine (DAP) receptor and the effect this receptor has on flavin redox potential was also quantified. It was found that the DAP-flavin binding affinity and the reduction potentials (E-1/2) for both the DAP-bound and unbound flavins correlated well with functions derived from linear free energy relationships (LFERs). These results provide insight and predictive capability for the interplay of electronics and redox state-specific interactions for both abiotic and enzymatic systems.

  DOI：

  10.1021/ja036940b
• 作为产物：
  描述：

  1,5-二氯-2-甲基-4-硝基苯 在 boron trioxide 、 ammonium hydroxide 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.0h， 生成 7-methyl-8-chloro-N(10)-isobutylisoalloxazine
  参考文献：
  名称：

  Model Systems for Flavoenzyme Activity:  Relationships between Cofactor Structure, Binding and Redox Properties

  摘要：

  A series of flavins were synthesized bearing electron-withdrawing and -donating substituents. The electrochemical properties of these flavins in a nonpolar solvent were determined. The recognition of these flavins by a diamidopyridine (DAP) receptor and the effect this receptor has on flavin redox potential was also quantified. It was found that the DAP-flavin binding affinity and the reduction potentials (E-1/2) for both the DAP-bound and unbound flavins correlated well with functions derived from linear free energy relationships (LFERs). These results provide insight and predictive capability for the interplay of electronics and redox state-specific interactions for both abiotic and enzymatic systems.

  DOI：

  10.1021/ja036940b

文献信息

• Model systems for flavoenzyme activity: an electrochemically tuneable model of roseoflavinElectronic supplementary information (ESI) available: synthesis of 2, CV and spectral data. See http://www.rsc.org/suppdata/cc/b4/b401470g/
  作者：Graeme Cooke、Yves-Marie Legrand、Vincent M. Rotello

  DOI：10.1039/b401470g

  日期：——

  The electrochemically tuneable hydrogen bonding interactions between roseoflavin analogue 2 and apoenzyme mimic 3 are described.

  本文描述了类黄酮2和酶模拟物3之间的电化学可调节氢键相互作用。