3,4-dibenzyloxypyridine-2-carboxy-N-(2-hydroxyethyl)amide | 718596-13-5

• 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: 3,4-dibenzyloxypyridine-2-carboxy-N-(2-hydroxyethyl)amide
• 英文别名: N-(2-hydroxyethyl)-3,4-bis(phenylmethoxy)pyridine-2-carboxamide
• CAS: 718596-13-5
• 化学式: C₂₂H₂₂N₂O₄
• 分子量: 378.428
• InChiKey: PBEZKOHPHQVAMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dibenzyloxypyridine-2-carboxy-N-(2-hydroxyethyl)amide 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以87%的产率得到3-hydroxypyridin-4(1H)-one-2-carboxy-(N-hydroxyethyl)-amide hydrochloride
  参考文献：
  名称：

  Design and characterisation of novel hexadentate 3-hydroxypyridin-4-one ligands

  摘要：

  Two novel hexadentate 3-hydroxypyridin-4-one ligands have been designed and synthesised. The physico-chemical properties of one of the hexadentate ligands have been determined and the results indicate that the hexadentate ligand possesses high affinity for iron(III). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.115
• 作为产物：
  描述：

  3-苄氧基-2-甲基-4(1H)-吡啶酮 在 sodium chlorite 、 氨基磺酸 、 三氧化硫吡啶 、 乙酸酐 、 焦磷酸硫胺素 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3,4-dibenzyloxypyridine-2-carboxy-N-(2-hydroxyethyl)amide
  参考文献：
  名称：

  Design and characterisation of novel hexadentate 3-hydroxypyridin-4-one ligands

  摘要：

  Two novel hexadentate 3-hydroxypyridin-4-one ligands have been designed and synthesised. The physico-chemical properties of one of the hexadentate ligands have been determined and the results indicate that the hexadentate ligand possesses high affinity for iron(III). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.115

文献信息

• Amido-3-hydroxypyridin-4-ones as Iron(III) Ligands
  作者：Sirivipa Piyamongkol、Yong M. Ma、Xiao L. Kong、Zu D. Liu、Mutlu D. Aytemir、Dick van der Helm、Robert C. Hider

  DOI：10.1002/chem.200902455

  日期：——

  AbstractThe synthesis and physicochemical properties of a range of 2‐ and 6‐amido‐3‐hydroxypyridin‐4‐ones are described. All the amido‐substituted 3‐hydroxypyridin‐4‐ones have lower pKa values than 1,2‐dimethyl‐3‐hydroxypyridin‐4‐one (deferiprone). This is due to the inductive effect of the amido group. Furthermore, the pKa values of the 3‐hydroxy group in 1‐nonsubstituted pyridinones are dramatically lower than those of the corresponding 1‐alkyl analogues, indicating that a strong hydrogen bond exists between the 2‐amido function and the 3‐oxygen anion, which stabilises the anion. As a result of the decreased competition with protons, the pFe3+ values of this group of molecules are higher than that of deferiprone. The distribution coefficients of these molecules are also increased despite the lack of a hydrophobic 1‐alkyl substituent and this is ascribed to the intramolecular hydrogen bond. X‐ray diffraction studies confirm the existence of the intramolecular hydrogen bond.