3-羟基-6-(羟甲基)-2-(哌啶-1-基甲基)吡喃-4-酮 | 82647-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 3-羟基-6-(羟甲基)-2-(哌啶-1-基甲基)吡喃-4-酮
• 英文名称: 3-hydroxy-6-hydroxymethyl-2-[(piperidin-1-yl)methyl]-pyran-4(1H)-one
• 英文别名: 3-hydroxy-6-hydroxymethyl-2-piperidinomethylpyran-4(1H)-one；3-hydroxy-6-hydroxymethyl-2-piperidin-1-ylmethyl-pyran-4-one；5-Hydroxy-2-hydroxymethyl-6-piperidinomethyl-γ-pyron；6-Piperidinomethyl-kojisaeure；6-(Hydroxymethyl)-4-oxo-2-(piperidin-1-ium-1-ylmethyl)pyran-3-olate
• CAS: 82647-26-5
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: VRGCYEBOWZEYAK-UHFFFAOYSA-N

物化性质

• 熔点：
  167 °C
• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-羟基-6-(羟甲基)-2-(哌啶-1-基甲基)吡喃-4-酮 、 溴甲苯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Basic 3-hydroxypyridin-4-ones: Potential antimalarial agents

  摘要：

  3-Hydroxypyridin-4-ones selectively bind iron under biological conditions and one such compound has found application in the treatment of thalassaemia-linked iron overload. Related molecules have also been demonstrated to possess an antimalarial effect at levels which are non-toxic to mammalian cells. In an attempt to improve the efficiency of such molecules we have investigated the effect of introducing basic nitrogen centres into 3-hydroxypyridin-4-ones in an attempt to achieve targeting to lysosomes and other intracellular acidic vacuoles. Several of the compounds reported in this communication possess enhanced antimalarial activity over that of the simple hydroxypyridinone class. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.07.011
• 作为产物：
  描述：

  哌啶 、 曲酸 、 聚合甲醛 以 甲醇 为溶剂， 以94%的产率得到3-羟基-6-(羟甲基)-2-(哌啶-1-基甲基)吡喃-4-酮
  参考文献：
  名称：

  曲酸和N-杂环曼尼希产物及其Ru（II）-芳烃配合物的合成，表征和稳定性

  摘要：

  的Ru（II） - η 6 - p -cymene化合物轴承吡喃酮衍生的配体，其通过用哌啶和相关类似物曼尼希反应而得到，已被合成。通过NMR光谱，质谱，热重分析和在2-（2,6-二甲基吗啉-4-基甲基）-3-羟基-6-羟基甲基-吡喃-4-酮X-的情况下对化合物进行表征。射线衍射分析。氯离子络合物在水溶液中易于水合，导致形成二聚体。如1 H NMR光谱所证明的，二聚体的形成可以通过用咪唑原位取代氯代配体来抑制，从而产生在水中明显更稳定的化合物。

  DOI：

  10.1016/j.jorganchem.2010.01.007

文献信息

• Basic 3-hydroxypyridin-4-ones: Potential antimalarial agents
  作者：Lotfollah S. Dehkordi、Zu D. Liu、Robert C. Hider

  DOI：10.1016/j.ejmech.2007.07.011

  日期：2008.5

  3-Hydroxypyridin-4-ones selectively bind iron under biological conditions and one such compound has found application in the treatment of thalassaemia-linked iron overload. Related molecules have also been demonstrated to possess an antimalarial effect at levels which are non-toxic to mammalian cells. In an attempt to improve the efficiency of such molecules we have investigated the effect of introducing basic nitrogen centres into 3-hydroxypyridin-4-ones in an attempt to achieve targeting to lysosomes and other intracellular acidic vacuoles. Several of the compounds reported in this communication possess enhanced antimalarial activity over that of the simple hydroxypyridinone class. (C) 2007 Elsevier Masson SAS. All rights reserved.
• Mannich products of kojic acid and N-heterocycles and their Ru(II)–arene complexes: Synthesis, characterization and stability
  作者：Johanna H. Kasser、Wolfgang Kandioller、Christian G. Hartinger、Alexey A. Nazarov、Vladimir B. Arion、Paul J. Dyson、Bernhard K. Keppler

  DOI：10.1016/j.jorganchem.2010.01.007

  日期：2010.3

  Ru(II)–η6-p-cymene compounds bearing pyrone-derived ligands, which were obtained by Mannich reaction with piperidine and related analogues, have been synthesized. The compounds were characterized by NMR spectroscopy, mass spectrometry, thermogravimetric analysis and in the case of 2-(2,6-dimethyl-morpholin-4-ylmethyl)-3-hydroxy-6-hydroxymethyl-pyran-4-one by X-ray diffraction analysis. The chlorido

  的Ru（II） - η 6 - p -cymene化合物轴承吡喃酮衍生的配体，其通过用哌啶和相关类似物曼尼希反应而得到，已被合成。通过NMR光谱，质谱，热重分析和在2-（2,6-二甲基吗啉-4-基甲基）-3-羟基-6-羟基甲基-吡喃-4-酮X-的情况下对化合物进行表征。射线衍射分析。氯离子络合物在水溶液中易于水合，导致形成二聚体。如1 H NMR光谱所证明的，二聚体的形成可以通过用咪唑原位取代氯代配体来抑制，从而产生在水中明显更稳定的化合物。