| 1005139-86-5

• 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
• CAS: 1005139-86-5
• 化学式: C₂₈H₄₂N₅O₇P
• 分子量: 591.645
• InChiKey: OUBYBGVTUNFXDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  41.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  154.5
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 碘 、 三乙胺 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以46%的产率得到(6-([flavin-pentyloxy]-phosphoryloxy)hexyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and Redox Behavior of Flavin Mononucleotide-Functionalized Single-Walled Carbon Nanotubes

  摘要：

  In this contribution, we describe the synthesis and covalent attachment of an analogue of the flavin mononucleotide (FMN) cofactor onto carboxylic functionalities of single-walled carbon nanotubes (SWNTs). The synthesis of FMN derivative (12) was possible by coupling flavin H-phosphonate (9) with an aliphatic alcohol, using a previously unreported N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride coupling. We found that the flavin moiety of 12-SWNT shows a strong pi-pi interaction with the nanotube side-walls. This leads to a collapsed FMN configuration that quenches flavin photoluminescence (PL). The treatment of 12-SWNT with sodium dodecyl sulfate (SDS) overcomes this strong nanotube/ isoalloxazine interaction and restores the FMN into extended conformation that recovers its luminescence. In addition, redox cycling as well as extended sonication were proven capable to temporally restore PL as well. Cyclic voltammetry of FMN onto SWNT forests indicated profound differences for the extended and collapsed FMN configurations in relation to oxygenated nanotube functionalities that act as mediators. These findings provide a fundamental understanding for flavin-related SWNT nanostructures that could ultimately find a number of usages in nanotube-mediated biosensing devices.

  DOI：

  10.1021/ja076598t
• 作为产物：
  描述：

  、 N-(6-羟基己基)氨基甲酸叔丁酯 在 吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 反应 24.0h， 以78%的产率得到
  参考文献：
  名称：

  Synthesis and Redox Behavior of Flavin Mononucleotide-Functionalized Single-Walled Carbon Nanotubes

  摘要：

  In this contribution, we describe the synthesis and covalent attachment of an analogue of the flavin mononucleotide (FMN) cofactor onto carboxylic functionalities of single-walled carbon nanotubes (SWNTs). The synthesis of FMN derivative (12) was possible by coupling flavin H-phosphonate (9) with an aliphatic alcohol, using a previously unreported N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride coupling. We found that the flavin moiety of 12-SWNT shows a strong pi-pi interaction with the nanotube side-walls. This leads to a collapsed FMN configuration that quenches flavin photoluminescence (PL). The treatment of 12-SWNT with sodium dodecyl sulfate (SDS) overcomes this strong nanotube/ isoalloxazine interaction and restores the FMN into extended conformation that recovers its luminescence. In addition, redox cycling as well as extended sonication were proven capable to temporally restore PL as well. Cyclic voltammetry of FMN onto SWNT forests indicated profound differences for the extended and collapsed FMN configurations in relation to oxygenated nanotube functionalities that act as mediators. These findings provide a fundamental understanding for flavin-related SWNT nanostructures that could ultimately find a number of usages in nanotube-mediated biosensing devices.

  DOI：

  10.1021/ja076598t