10-Isobutyl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione | 163657-00-9

• 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-10H-benzo[g]pteridine-2,4-dione
• 英文别名: 7,8-dimethyl-10-isobutyl flavin；N(10)-isobutyl flavin；N(10)-isopropylflavin；N(10)-isobutylflavin；7,8-Dimethyl-10-(2-methylpropyl)benzo[g]pteridine-2,4-dione
• CAS: 163657-00-9
• 化学式: C₁₆H₁₈N₄O₂
• 分子量: 298.345
• InChiKey: YYLMIQOQTVNYJD-UHFFFAOYSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  10-Isobutyl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione 在 四丁基高氯酸铵 作用下， 以 二氯甲烷 为溶剂， 生成 N⁽¹⁰⁾-isobutylflavin radical anion
  参考文献：
  名称：

  黄素酶活性的模型系统：辅因子氧化还原调节中氢键和芳族堆积的相互作用。

  摘要：

  [结构：见正文]已开发出一种模型系统来研究黄素衍生物结合中芳族堆积和氢键之间的协同作用。结果表明，氢键和pi堆积单元的同一性强烈决定了氧化阴离子和自由基阴离子形式中黄素的总体受体亲和力。

  DOI：

  10.1021/ol036279g
• 作为产物：
  描述：

  4，5-二甲-2-硝基苯胺 在 boron trioxide 、 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 氢气 、 ammonium formate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 10-Isobutyl-7,8-dimethyl-10H-benzo[g]pteridine-2,4-dione
  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

• Duplex strand formation using alternating copolymers
  作者：Hiroshi Nakade、M. Firat IlkerCurrent address: Department of、Brian J. Jordan、Oktay Uzun、Nicholas L. LaPointe、E. Bryan Coughlin、Vincent M. Rotello

  DOI：10.1039/b502929e

  日期：——

  The regular arrangement of complementary diaminopyridine-thymine (DAP-THY) on alternating copolymers permits cooperative binding events and the effective formation of well-controlled micrometre-scale aggregates.

  互补二氨基吡啶-胸腺嘧啶（DAP-THY）在交替共聚物上的规则排列可实现协作结合事件，并有效形成良好控制的微米级聚集体。
• Dendron-based model systems for flavoenzyme activity: towards a new class of synthetic flavoenzyme
  作者：Sarit S. Agasti、Stuart T. Caldwell、Graeme Cooke、Brian J. Jordan、Andrew Kennedy、Nadiya Kryvokhyzha、Gouher Rabani、Subinoy Rana、Amitav Sanyal、Vincent M. Rotello

  DOI：10.1039/b809568j

  日期：——

  Three generations of water-soluble flavin dendrons have been synthesized and the role dendrimer generation has on the physical and catalytic properties of these assemblies has been investigated.

  我们合成了三代水溶性黄素树枝状分子，并研究了树枝状分子的生成对这些组装体的物理和催化特性所起的作用。
• Flavin as a photo-active acceptor for efficient energy and charge transfer in a model donor–acceptor system
  作者：Xi Yu、Serkan Eymur、Vijay Singh、Boqian Yang、Murat Tonga、Amarnath Bheemaraju、Graeme Cooke、Chandramouleeswaran Subramani、Dhandapani Venkataraman、Robert J. Stanley、Vincent M. Rotello

  DOI：10.1039/c2cp40073a

  日期：——

  A donor–acceptor dyad model system using a flavin moiety as a photo-active acceptor has been synthesized for an energy and photo-induced electron transfer study. The photophysical investigations of the dyad revealed a multi-path energy and electron transfer process with a very high transfer efficiency. The photo-activity of flavin was believed to play an important role in the process, implying the potential application of flavin as a novel acceptor molecule for photovoltaics.

  为了研究能量和光诱导的电子转移，我们合成了一种以黄素部分作为光活性受体的供体-受体二元模型系统。对二元模型的光物理研究揭示了一种具有极高转移效率的多路径能量和电子转移过程。黄素的光活性被认为在这一过程中发挥了重要作用，这意味着黄素作为新型受体分子在光伏领域的潜在应用。
• Model Systems for Flavoenzyme Activity. Regulation of Flavin Recognition via Modulation of Receptor Hydrogen-Bond Donor−Acceptor Properties
  作者：Robert Deans、Graeme Cooke、Vincent M. Rotello

  DOI：10.1021/jo961877c

  日期：1997.2.1

  We have synthesized a new family of receptors for flavins based on 6-aryl-2,4-(acyldiamino)-s-triazines. In these synthetic hosts, systematic variation of the spatially remote substituents on the 6-aryl ring alters the hydrogen-bond-donating abilities of the amide functionality and the hydrogen-bond-accepting properties of the triazine N(3). This variation results in a strong modulation of the efficiency of flavin binding, with association constants for the receptor flavin complexes ranging over an 8-fold range.
• Model Systems for Flavoenzyme Activity. Molecular Recognition of Flavin at the Polymer−Liquid Interface
  作者：Robert Deans、Vincent M. Rotello

  DOI：10.1021/jo970415b

  日期：1997.6.1