N-methyl-N'-(6-phthalimidohexyl)-2,2'-biimidazole | 874116-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-methyl-N'-(6-phthalimidohexyl)-2,2'-biimidazole
• 英文别名: 2-(6-(1'-Methyl-1H,1'H-[2,2'-biimidazol]-1-yl)hexyl)isoindoline-1,3-dione；2-[6-[2-(1-methylimidazol-2-yl)imidazol-1-yl]hexyl]isoindole-1,3-dione
• CAS: 874116-34-4
• 化学式: C₂₁H₂₃N₅O₂
• 分子量: 377.446
• InChiKey: YBOAPMOAAAJXMW-UHFFFAOYSA-N

物化性质

• 沸点：
  605.1±57.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.14
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.02
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-methyl-N'-(6-phthalimidohexyl)-2,2'-biimidazole 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以50%的产率得到N-(6-aminohexyl)-N'-methyl-2,2'-biimidazole
  参考文献：
  名称：

  Long Tethers Binding Redox Centers to Polymer Backbones Enhance Electron Transport in Enzyme “Wiring” Hydrogels

  摘要：

  A redox hydrogel with an apparent electron diffusion coefficient (D-app) of (5.8 +/- 0.5) x 10(-6) cm(2) s(-1) is described. The order of magnitude increase in D-app relative to previously studied redox hydrogels results from the tethering of redox centers to the backbone of the cross-linked redox polymer backbone through 13 atom spacer arms. The long and flexible tethers allow the redox centers to sweep electrons from large-volume elements and to collect electrons of glucose oxidase efficiently. The spacer arms make the collection of electrons from glucose oxidase so efficient that glucose is electrooxidized already at -0.36 V versus Ag/AgCl, the reversible potential of the redox potential of the FAD/FADH(2) centers of the enzyme at pH 7.2. The limiting current density of 1.15 mA cm(-2) is reached at a potential as low as -0.1 V versus Ag/AgCl. The novel redox center of the polymer is a tris-dialkylated N,/\r-biimidazole Os2+/3+ complex. Its redox potential, -0.195 V versus Ag/AgCl, is 0.8 V reducing relative to that of Os(bpy)(2+/3+), its 2,2'-bipyridine analogue.

  DOI：

  10.1021/ja029510e
• 作为产物：
  描述：

  联咪唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-methyl-N'-(6-phthalimidohexyl)-2,2'-biimidazole
  参考文献：
  名称：

  Long Tethers Binding Redox Centers to Polymer Backbones Enhance Electron Transport in Enzyme “Wiring” Hydrogels

  摘要：

  A redox hydrogel with an apparent electron diffusion coefficient (D-app) of (5.8 +/- 0.5) x 10(-6) cm(2) s(-1) is described. The order of magnitude increase in D-app relative to previously studied redox hydrogels results from the tethering of redox centers to the backbone of the cross-linked redox polymer backbone through 13 atom spacer arms. The long and flexible tethers allow the redox centers to sweep electrons from large-volume elements and to collect electrons of glucose oxidase efficiently. The spacer arms make the collection of electrons from glucose oxidase so efficient that glucose is electrooxidized already at -0.36 V versus Ag/AgCl, the reversible potential of the redox potential of the FAD/FADH(2) centers of the enzyme at pH 7.2. The limiting current density of 1.15 mA cm(-2) is reached at a potential as low as -0.1 V versus Ag/AgCl. The novel redox center of the polymer is a tris-dialkylated N,/\r-biimidazole Os2+/3+ complex. Its redox potential, -0.195 V versus Ag/AgCl, is 0.8 V reducing relative to that of Os(bpy)(2+/3+), its 2,2'-bipyridine analogue.

  DOI：

  10.1021/ja029510e