N-(3-benzyloxypyran-4(1H)-one-6-carbonyl)-1,3-thiazolidine-2-thione | 669721-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: N-(3-benzyloxypyran-4(1H)-one-6-carbonyl)-1,3-thiazolidine-2-thione
• 英文别名: 5-Benzyloxy-2-(2-thioxothiazolidine-3-carbonyl)pyran-4-one；5-phenylmethoxy-2-(2-sulfanylidene-1,3-thiazolidine-3-carbonyl)pyran-4-one
• CAS: 669721-85-1
• 化学式: C₁₆H₁₃NO₄S₂
• 分子量: 347.416
• InChiKey: HIUVUVGRLDJBIN-UHFFFAOYSA-N

物化性质

• 沸点：
  570.1±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(3-benzyloxypyran-4(1H)-one-6-carbonyl)-1,3-thiazolidine-2-thione 、 甲胺 以 二氯甲烷 为溶剂， 反应 12.0h， 以54%的产率得到3-benzyloxypyran-4(1H)-one-6-carboxy-(N-methyl)amide
  参考文献：
  名称：

  Amido-3-hydroxypyridin-4-ones as Iron(III) Ligands

  摘要：

  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.

  DOI：

  10.1002/chem.200902455
• 作为产物：
  描述：

  2-巯基噻唑啉 、 5-苄氧基-4-氧代-4H-吡喃-2-羧酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 N-(3-benzyloxypyran-4(1H)-one-6-carbonyl)-1,3-thiazolidine-2-thione
  参考文献：
  名称：

  Amido-3-hydroxypyridin-4-ones as Iron(III) Ligands

  摘要：

  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.

  DOI：

  10.1002/chem.200902455

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.