2,2':6',2''-terpyridin-4'(1'H)-one acetic acid adduct | 474745-38-5

• 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: 2,2':6',2''-terpyridin-4'(1'H)-one acetic acid adduct
• 英文别名: 2,6-dipyridin-2-yl-1H-pyridin-1-ium-4-one;acetate
• CAS: 474745-38-5
• 化学式: C₂H₄O₂*C₁₅H₁₁N₃O
• 分子量: 309.324
• InChiKey: LPRFYNISVHBUGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.94
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2,2':6',2''-terpyridin-4'(1'H)-one acetic acid adduct 在 五氯化磷 、 三氯氧磷 作用下， 反应 18.0h， 以68%的产率得到4'-氯-2,2':6',2''-三联吡啶
  参考文献：
  名称：

  Synthesis of substituted terpyridine ligands for use in protein purification

  摘要：

  A number of 4,4 ''-disubstituted terpyridines bearing a 4'-thioethanamine linker, and regioisomers thereof, have been synthesised from 4-substituted picolinates. The substituted terpyridines were immobilised onto epoxy-activated Sepharose (TM) FF gel, creating functionalised solid supports for the fractionation of proteins-including antibodies-by mixed mode affinity chromatography. The metal chelating properties of the immobilised ligand render the stationary phase also amenable for use in immobilised metal-ion affinity chromatography (IMAC), and have been demonstrated with the purification of suitably tagged green fluorescent protein (GFP). (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.09.074
• 作为产物：
  描述：

  2-吡啶甲酸乙酯 在 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙醇 、 mineral oil 为溶剂， 反应 20.0h， 生成 2,2':6',2''-terpyridin-4'(1'H)-one acetic acid adduct
  参考文献：
  名称：

  Synthesis of substituted terpyridine ligands for use in protein purification

  摘要：

  A number of 4,4 ''-disubstituted terpyridines bearing a 4'-thioethanamine linker, and regioisomers thereof, have been synthesised from 4-substituted picolinates. The substituted terpyridines were immobilised onto epoxy-activated Sepharose (TM) FF gel, creating functionalised solid supports for the fractionation of proteins-including antibodies-by mixed mode affinity chromatography. The metal chelating properties of the immobilised ligand render the stationary phase also amenable for use in immobilised metal-ion affinity chromatography (IMAC), and have been demonstrated with the purification of suitably tagged green fluorescent protein (GFP). (C) 2014 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2014.09.074

文献信息

• Isolation and Structure of a Hydrogen-bonded 2,2′:6′,2′′-Terpyridin-4′-one Acetic Acid Adduct
  作者：Pas Florio、Campbell J. Coghlan、Chih-Pei Lin、Kei Saito、Eva M. Campi、W. Roy Jackson、Milton T. W. Hearn

  DOI：10.1071/ch13571

  日期：——

  crystal structure of a key intermediate in the synthesis of 4′-substituted-terpyridines. Our findings confirm that the terpyridin-4′-one intermediate as generated from the condensation reaction of the corresponding triketone precursor with ammonium acetate is isolated as a hydrogen-bonded adduct with acetic acid, and not, as previously reported, as the acetate salt of a protonated pyridine nitrogen. This

  在此，我们报道了合成4'-取代的吡啶的关键中间体的晶体结构。我们的发现证实，由相应的三酮前体与乙酸铵的缩合反应生成的三联吡啶-4'-中间体是作为氢键加成的乙酸与乙酸分离的，而不是以前报道的那样，作为乙酸的乙酸盐分离。质子化的吡啶氮 这一发现为固态和溶液中取代的吡啶并4'-酮和吡啶酮的行为和结构提供了理论依据。