6-(Hydroxymethyl)-2,2':6',2''-terpyridine | 149775-43-9

• 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-(Hydroxymethyl)-2,2':6',2''-terpyridine
• 英文别名: 6-hydroxymethyl-2,2';6',2''-terpyridine；[6-(6-pyridin-2-ylpyridin-2-yl)pyridin-2-yl]methanol
• CAS: 149775-43-9
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: SALLAPAUDNREEE-UHFFFAOYSA-N

物化性质

• 沸点：
  455.3±40.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.9
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(Hydroxymethyl)-2,2':6',2''-terpyridine 在 四溴化碳 、 三苯基膦 作用下， 生成 6-(Bromomethyl)-2,2':6':2''-terpyridine
  参考文献：
  名称：

  2-烷基亚磺酰基吡啶被2-吡啶基锂的异丙基取代；寡吡啶及其溴甲基衍生物的新制备方法

  摘要：

  已经制备了不对称和对称的2,2'-联吡啶5和6。所应用的方法是新方法，可提供高级寡吡啶及其溴代甲基衍生物的有效合成方法。

  DOI：

  10.1016/s0040-4039(00)97692-5
• 作为产物：
  描述：

  6-溴-2,2':6',2''-三联吡啶 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 6-(Hydroxymethyl)-2,2':6',2''-terpyridine
  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

• Controlling allostery using redox chemistryElectronic supplementary information (ESI) available: Experimental and X-ray structure determination and crystal data for [Cu(1)][PF6]. See http://www.rsc.org/suppdata/cc/b1/b109051h/
  作者：Mohammad H. Al-Sayah、Neil R. Branda

  DOI：10.1039/b109051h

  日期：2002.1.18

  The binding of a hydrogen-bonding receptor to its substrate is reversibly regulated by varying the oxidation state of a copper allosteric cofactor.

  氢键受体与其底物的结合通过改变铜的别构辅因子的氧化状态可逆地调节。