1-Butyl-3-hydroxy-1H-pyridin-2-one | 116407-52-4

• 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: 1-Butyl-3-hydroxy-1H-pyridin-2-one
• 英文别名: 2(1H)-Pyridinone, 1-butyl-3-hydroxy-；1-butyl-3-hydroxypyridin-2-one
• CAS: 116407-52-4
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: LQQCVHOXXXWSIC-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  333.7±42.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-甲氧基-2(1H)-吡啶酮 在 氢氧化钾 、 三溴化硼 作用下， 以 丙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-Butyl-3-hydroxy-1H-pyridin-2-one
  参考文献：
  名称：

  羟基吡喃酮和羟基吡啶酮的合成，理化性质和生物学评估：用于细胞标记的新型双齿配体。

  摘要：

  描述了一系列可能与铟（III）螯合的羟基吡喃酮和羟基吡啶酮。给出了两种铟配合物的晶体结构。报告了配体和相应的铁（III），镓（III）和铟（III）配合物的分布系数。在铁和镓配合物与铁和铟配合物的分布系数之间获得了良好的线性关系。相反，在游离配体的分布系数与三组配合物的分布系数之间获得了非线性关系。后一种关系用于鉴定具有最佳细胞标记特性的化合物。已经将两种这样的化合物（6-（烷氧基甲基）-3-羟基-4H-吡喃-4-酮）与托酚酮比较了它们用111 In标记人白细胞的能力。所选配体的白细胞标记效率更高，体外血浆稳定性与111In-对羟基苯甲酸类似。这些结果表明，新的双齿配体可能比目前用于细胞标记的配体具有优势。

  DOI：

  10.1021/jm960220g

文献信息

• Novel 3-hydroxy-2(1H)-pyridinones. Synthesis, iron(III)-chelating properties and biological activity
  作者：Michael Streater、Paul D. Taylor、Robert C. Hider、John Porter

  DOI：10.1021/jm00168a033

  日期：1990.6

  The synthesis of a range of novel bidentate and hexadentate ligands containing the chelating moiety 3-hydroxy-2(1H)-pyridinone is described. The pKa values of the ligands and the stability constants of their iron(III) complexes have been determined. The stability constant of the iron(III) complex of one of the hexadentate ligands is comparable to that of desferrioxamine B. The distribution coefficients

  描述了一系列包含螯合部分3-羟基-2（1H）-吡啶酮的新颖的二齿和六齿配体的合成。已经确定了配体的pKa值及其铁（III）配合物的稳定性常数。六齿配体之一的铁（III）配合物的稳定性常数与去铁胺B相当。配体及其铁（III）配合物的分布系数也被确定。新型六齿化合物之一已显示出可显着增强肝细胞和铁超载小鼠的铁（III）排泄。
• VICINAL PRIMARY DIAMINES ASSOCIATED WITH METAL AND/OR FREE RADICAL CHELATION MOTIFS, AND ACTIVE AGAINST CARBONYL AND OXIDATIVE STRESS, AND USE THEREOF
  申请人：UNIVERSITE AMIENS PICARDIE JULES VERNE

  公开号：US20180201602A1

  公开（公告）日：2018-07-19

  The invention relates to compounds of Formula I: or the salts thereof, as well as the use thereof in the pharmaceutical, cosmetic or agrofood industry.

  该发明涉及公式I的化合物：或其盐，以及在制药、化妆品或农业食品工业中的使用。
• Pharmaceutical compositions
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0145228A1

  公开（公告）日：1985-06-19

  Zinc (11) complexes in which at least one ligand is provided by a compound being: (1) 3-hydroxy-4-pyrone or a 3-hydroxy-4-pyrone in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by an aliphatic hydrocarbon group of 1 to 6 carbon atoms; or (2) a 3-hydroxypyrid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is replaced by an aliphatic acyl group, by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphatic hydrocarbon group substituted by one or, except in the case of ionisable groups, more than one substituent selected from aliphatic acyl, alkoxy, aliphatic amine, aliphatic amide, carboxy, aliphatic ester, halogen, hydroxy and sulpho groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group; are of value in medicine, particularly in the systemic treatment of zinc depletion. Mixtures of these zinc complexes with the metal-free compound(s) providing the ligands contained therein and with iron (III) complexes containing ligands of types (1) and (2) are also of value.

  锌(11)配合物，其中至少一种配体由以下化合物提供： (1) 3-羟基-4-吡喃酮或 3-羟基-4-吡喃酮，其中与环碳原子相连的一个或多个氢原子被 1 至 6 个碳原子的脂肪族烃基取代；或 (2) 3-羟基吡啶-2-酮或 3-羟基吡啶-4-酮，其中与氮原子相连的氢原子被脂族酰基、1 至 6 个碳原子的脂族烃基取代，或被选自脂族酰基、烷氧基、脂族胺、脂族酰胺、羧基的一个或一个以上取代基取代（可电离基团除外）的脂族烃基取代、脂肪族酰胺、羧基、脂肪族酯、卤素、羟基和砜基，可选地，其中一个或多个与环碳原子相连的氢原子被上述取代基之一、1 至 6 个碳原子的脂肪族烃基或被烷氧基、脂肪族酯、卤素或羟基取代的脂肪族烃基所取代；具有医药价值，特别是在系统治疗锌缺乏症方面。这些锌络合物与提供其中所含配体的无金属化合物的混合物，以及与含有(1)和(2)型配体的铁(III)络合物的混合物也很有价值。
• Iron 3-hydroxypyrone or 3-hydroxypyridone complexes and pharmaceutical compositions containing them
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：EP0159194A2

  公开（公告）日：1985-10-23

  Iron complexes comprising a ferric cation in combination with at least two different ligands, at least one of which is provided by a compound being: (1) 3-hydroxy-4-pyrone or a 3-hydroxy-4-pyrone in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by an aliphatic hydrocarbon group of 1 to 6 carbon atoms; or (2) a 3-hydroxyprid-2-one or 3-hydroxypyrid-4-one in which the hydrogen atom attached to the nitrogen atom is . replaced by an aliphtic acyl group, by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphtic hydrocarbon group substituted by one or more substituents selected from aliphatic acyl, alkoxy, aliphatic amide, aliphatic ester, halogen and hydroxy groups and, optionally, in which one or more of the hydrogen atoms attached to ring carbon atoms are replaced by one of said substituents, by an aliphatic hydrocarbon group of 1 to 6 carbon atoms, or by an aliphatic hydrocarbon group substituted by an alkoxy, aliphatic ester, halogen or hydroxy group; the charge on the ferric cation being neutralised by the charge on the ligands covalently bound thereto; are of value in medicine, particularly in the treatment of iron deficiency anaemia.

  铁络合物，包括一个铁阳离子与至少两个不同配体的组合，其中至少一个配体由以下化合物提供： (1) 3-羟基-4-吡喃酮或 3-羟基-4-吡喃酮，其中与环碳原子相连的一个或多个氢原子被 1 至 6 个碳原子的脂族烃基取代；或 (2) 3-羟基-2-吡啶酮或 3-羟基-4-吡啶酮，其中与氮原子相连的氢原子被.被脂族酰基、1 至 6 个碳原子的脂族烃基或 1 至 6 个碳原子的脂族烃基取代，或被一个或多个选自脂族酰基、烷氧基、脂族酰胺、脂族酯的取代基取代的脂族烃基取代、卤素和羟基基团取代的脂族烃基，或由 1 至 6 个碳原子的脂族烃基取代的脂族烃基，或由烷氧基、脂族酯、卤素或羟基基团取代的脂族烃基；铁阳离子上的电荷被与其共价结合的配体上的电荷所中和；这些物质在医学上，特别是在治疗缺铁性贫血症方面具有重要价值。
• Vicinal primary diamines associated with metal and/or free radical chelation motifs, and active against carbonyl and oxidative stress, and use thereof
  申请人：UNIVERSITE AMIENS PICARDIE JULES VERNE

  公开号：US10464920B2

  公开（公告）日：2019-11-05

  The invention relates to compounds of Formula I: or the salts thereof, as well as the use thereof in the pharmaceutical, cosmetic or agrofood industry.

  本发明涉及式 I 的化合物： 或其盐类，以及它们在制药、化妆品或农产食品工业中的用途。