N-(6-aminohexyl)-N'-methyl-2,2'-biimidazole | 874116-35-5

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(6-aminohexyl)-N'-methyl-2,2'-biimidazole
• 英文别名: 6-(1'-Methyl-1H,1'H-[2,2'-biimidazol]-1-yl)hexan-1-amine；6-[2-(1-methylimidazol-2-yl)imidazol-1-yl]hexan-1-amine
• CAS: 874116-35-5
• 化学式: C₁₃H₂₁N₅
• 分子量: 247.343
• InChiKey: UETSKFWPRDLPLN-UHFFFAOYSA-N

物化性质

• 沸点：
  459.7±47.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  61.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1,1'-二甲基-1H,1'H-[2,2']联咪唑 、 diammonium hexachloroosmate(IV) 、 N-(6-aminohexyl)-N'-methyl-2,2'-biimidazole 以 乙二醇 为溶剂， 生成 [(N,N'-dimethyl-2,2'-biimidazole)2Os(N-(6-aminohexyl)-N'-methyl-2,2'-biimidazole)]Cl2
  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：

  2-(1H-咪唑-2-基)-1-甲基-咪唑 在 sodium hydride 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 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

文献信息

• 一种N-(6-氨己基)-N’-甲基-2,2’-联咪唑的合成方法
  申请人：华东数字医学工程研究院

  公开号：CN110734405A

  公开（公告）日：2020-01-31

  本发明提供了一种N‑(6‑氨己基)‑N’‑甲基‑2,2’‑联咪唑的合成方法，其特征在于，所述方法包括如下步骤：(1)N‑Boc‑6‑卤代己胺和1‑甲基‑1H,1’H‑[2,2’]联咪唑在碱的作用下，反应得到中间体N‑(6‑Boc‑氨己基)‑N’‑甲基‑2,2’‑联咪唑，所述的卤为氯、溴或碘；(2)N‑(6‑Boc‑氨己基)‑N’‑甲基‑2,2’‑联咪唑在酸的作用下反应得到产物N‑(6‑氨己基)‑N’‑甲基‑2,2’‑联咪唑；反应路线如下： 本发明的合成方法反应条件更温和，易操作，且不需用到易燃的氢化钠和易制爆的剧毒品水合肼，操作更加安全，反应路线更绿色环保，同时本发明的合成路线反应收率高，两步反应的收率均在80％以上。