6-(Hydroxymethyl)-2-(2-pyrazinyl)pyridine | 149775-46-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-(Hydroxymethyl)-2-(2-pyrazinyl)pyridine
• 英文别名: (6-Pyrazin-2-ylpyridin-2-yl)methanol
• CAS: 149775-46-2
• 化学式: C₁₀H₉N₃O
• 分子量: 187.201
• InChiKey: HKUCVGPKMIUKGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(Hydroxymethyl)-2-(2-pyrazinyl)pyridine 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到6-(Bromomethyl)-2-(2-pyrazinyl)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
• 作为产物：
  描述：

  2-巯基-6-甲基吡啶 在 锂硼氢 、 selenium(IV) oxide 、 magnesium bis(monoperoxyphthalate)hexahydrate 、 甲基溴化镁 、 sodium hydride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 乙醚 、 二氯甲烷 、 氯仿 为溶剂， 反应 45.08h， 生成 6-(Hydroxymethyl)-2-(2-pyrazinyl)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.