6-(二溴甲基)-2,2'-联吡啶 | 83478-64-2

• 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
• 中文名称: 6-(二溴甲基)-2,2'-联吡啶
• 英文名称: 6-(dibromomethyl)-2,2'-bipyridine
• 英文别名: 2-(Dibromomethyl)-6-pyridin-2-ylpyridine
• CAS: 83478-64-2
• 化学式: C₁₁H₈Br₂N₂
• 分子量: 328.006
• InChiKey: JVFOIRZROLMVEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 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 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 0.08h， 生成 6-(二溴甲基)-2,2'-联吡啶
  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 and Metal-Binding Properties of Polybipyridine Ligands Derived from Acyclic and Macrocyclic Polyamines
  作者：Raymond Ziessel、Jean-Marie Lehn

  DOI：10.1002/hlca.19900730502

  日期：1990.8.8

  been developed for the preparation of ligands bearing two to six pendent, unsubstituted or substituted 2, 2′-bipyridine groups attached to acyclic (tripode, tetrapode) and macrocyclic (triazanonade-cane, cyclam, hexacyclen, bis(bipyrido)hexaazamacrocycle) polyamines. Ligands 1-5 have been obtained in high yield by condensation of 6-(bromomethyl)-2, 2′-bipyridine (9b) with the corresponding amines in

  已经开发出用于制备配体的合成程序，所述配体带有两个至六个悬垂，未取代或取代的2、2'-联吡啶基团，这些基团连接于无环（三叠，四足）和大环（三嗪酮-甘蔗，Cyclam，六环，双（双吡啶）六氮杂大环） ）多胺。通过在NaOH，H 2 O和MeOH的存在下使6-（溴甲基）-2、2'-联吡啶（9b）与相应的胺缩合，以高收率获得了配体1-5。通过在Na 2存在下分别缩合9b或二或四取代的单（溴甲基）联吡啶10b或11b与相应的胺，可以高收率制备配体6-8。CO 3和MeCN。配体1与Ru II，Fe I，Cr II和Cr III阳离子形成半笼式络合物，与[RuCl 2（bpy）2 ]和[ReCl（CO）5 ]形成三核络合物。四足动物2和六足动物4通过与Fe11盐反应分别得到四核和双核复合物。这些络合物具有各种有趣的物理和化学性质。
• ZIESSEL, RAYMOND;LEHN, JEAN-MARIE, HELV. CHIM. ACTA , 73,(1990) N, C. 1149-1162
  作者：ZIESSEL, RAYMOND、LEHN, JEAN-MARIE

  DOI：——

  日期：——
• LIGANDS D'OLIGOBIPYRIDINES, PROCEDES D'OBTENTION ET APPLICATION A TITRE D'AGENTS COMPLEXANTS
  申请人：CIS BIO INTERNATIONAL

  公开号：EP0360820B1

  公开（公告）日：1992-08-19
• 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.