6-(Bromomethyl)-2-(2-quinolyl)pyridine | 149775-34-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(Bromomethyl)-2-(2-quinolyl)pyridine
• 英文别名: 2-[6-(Bromomethyl)pyridin-2-yl]quinoline
• CAS: 149775-34-8
• 化学式: C₁₅H₁₁BrN₂
• 分子量: 299.17
• InChiKey: GLBKVHXDSNPWSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二氮杂18-冠醚-6 、 6-(Bromomethyl)-2-(2-quinolyl)pyridine 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 以63%的产率得到N,N'-Bis((6-(2'-quinoyl)-2-pyridyl)methyl)diaza-18-crown-6
  参考文献：
  名称：

  Side arm effects on cation binding, extraction, and transport functions of oligopyridine-functionalized aza-crown ethers

  摘要：

  A new series of lariat ethers and double-armed crown ethers was prepared in which oligopyridine-functionalized side arms were attached as secondary donor sites. A novel preparative method of oligopyridine derivatives was successfully applied to the synthesis of these crown ethers. Introduction of an oligopyridine-functionalized side arm into the crown ether system, if of the proper chain length and geometrical arrangement, significantly offered three-dimensional complexation with various metal cations suitable for extraction and transport. Liquid-liquid extraction, C-13-NMR binding, and liquid membrane transport experiments revealed that the present type of double-armed crown ethers exhibited cation-binding abilities superior to corresponding lariat ethers.

  DOI：

  10.1021/jo00068a038
• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 二异丁基氢化铝 、 过氧化苯甲酰 作用下， 反应 0.08h， 生成 6-(Bromomethyl)-2-(2-quinolyl)pyridine
  参考文献：
  名称：

  Synthesis of ι-(bromomethyl)bipyridines and related ι-(bromomethyl)pyridinoheteroaromatics: useful functional tools for ligands in host molecules

  摘要：

  Pyridines and 2,2'-bipyridines have been employed as useful ligands in molecular recognition chemistries. Halomethyl-substituted bipyridine or oligopyridine derivatives were required for the assembly of bipyridine or oligopyridine units with a supporting mother functional part in artificial biofunctional molecules. A series of omega-(bromomethyl)bipyridines and related omega-(bromomethyl)pyridinoheteroaromatic compounds (types I-III) were synthesized in this paper. Preparation of oligopyridines and pyridinoheteroaromatic compounds have been carried out by either intermolecular ligand coupling of alkyl heteroaryl sulfoxide with pyridyllithium or intramolecular ligand coupling of pyridyl heteroaryl sulfoxide with methylmagnesium bromide for the type I compounds. The type II and III compounds were synthesized by addition of pyridyllithium to pyridinecarboxaldehyde. The omega-bromo group was introduced by radical bromination reaction of methylpyridyl group using NBS and BPO (dibenzoyl peroxide) or bromination of omega-(hydroxymethyl)pyridine using a combination of CBr4 and Ph3P.

  DOI：

  10.1021/jo00068a037

文献信息

• Synthesis of ι-(bromomethyl)bipyridines and related ι-(bromomethyl)pyridinoheteroaromatics: useful functional tools for ligands in host molecules
  作者：Junichi Uenishi、Takakazu Tanaka、Kenji Nishiwaki、Shoji Wakabayashi、Shigeru Oae、Hiroshi Tsukube

  DOI：10.1021/jo00068a037

  日期：1993.7

  Pyridines and 2,2'-bipyridines have been employed as useful ligands in molecular recognition chemistries. Halomethyl-substituted bipyridine or oligopyridine derivatives were required for the assembly of bipyridine or oligopyridine units with a supporting mother functional part in artificial biofunctional molecules. A series of omega-(bromomethyl)bipyridines and related omega-(bromomethyl)pyridinoheteroaromatic compounds (types I-III) were synthesized in this paper. Preparation of oligopyridines and pyridinoheteroaromatic compounds have been carried out by either intermolecular ligand coupling of alkyl heteroaryl sulfoxide with pyridyllithium or intramolecular ligand coupling of pyridyl heteroaryl sulfoxide with methylmagnesium bromide for the type I compounds. The type II and III compounds were synthesized by addition of pyridyllithium to pyridinecarboxaldehyde. The omega-bromo group was introduced by radical bromination reaction of methylpyridyl group using NBS and BPO (dibenzoyl peroxide) or bromination of omega-(hydroxymethyl)pyridine using a combination of CBr4 and Ph3P.
• Side arm effects on cation binding, extraction, and transport functions of oligopyridine-functionalized aza-crown ethers
  作者：Hiroshi Tsukube、Junichi Uenishi、Hiromi Higaki、Kenichi Kikkawa、Takakazu Tanaka、Shoji Wakabayashi、Shigeru Oae

  DOI：10.1021/jo00068a038

  日期：1993.7

  A new series of lariat ethers and double-armed crown ethers was prepared in which oligopyridine-functionalized side arms were attached as secondary donor sites. A novel preparative method of oligopyridine derivatives was successfully applied to the synthesis of these crown ethers. Introduction of an oligopyridine-functionalized side arm into the crown ether system, if of the proper chain length and geometrical arrangement, significantly offered three-dimensional complexation with various metal cations suitable for extraction and transport. Liquid-liquid extraction, C-13-NMR binding, and liquid membrane transport experiments revealed that the present type of double-armed crown ethers exhibited cation-binding abilities superior to corresponding lariat ethers.