(9ci)-3-甲氧基-4-羟基吡啶 | 62885-41-0

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (9ci)-3-甲氧基-4-羟基吡啶
• 英文名称: 4-hydroxy-3-methoxypyridine
• 英文别名: 3-methoxy-pyridin-4-ol；3-Methoxy-4-hydroxy-pyridin；3-Methoxypyridin-4-OL；3-methoxy-1H-pyridin-4-one
• CAS: 62885-41-0
• 化学式: C₆H₇NO₂
• mdl: MFCD16998801
• 分子量: 125.127
• InChiKey: XKECCYGTTKNLOC-UHFFFAOYSA-N

物化性质

• 熔点：
  180.5-181.5 °C
• 沸点：
  371.3±22.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9ci)-3-甲氧基-4-羟基吡啶 在 10 wt% Pd(OH)2 on carbon 、 三溴化硼 、 potassium carbonate 、 环己烯 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 204.25h， 生成 3-hydroxy-1,5-dimethyl-4(1H)-pyridone hydrobromide
  参考文献：
  名称：

  Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones – Attempted optimization of the orally active iron chelator, deferiprone

  摘要：

  A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe(3+) values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues.As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.014
• 作为产物：
  描述：

  2-(羟基甲基)-5-甲氧基-4H-吡喃-4-酮 在 Jones reagent 、 氨 作用下， 以 N-甲基吡咯烷酮 、 乙醇 、 水 、 丙酮 为溶剂， 反应 12.67h， 生成 (9ci)-3-甲氧基-4-羟基吡啶
  参考文献：
  名称：

  Systematic comparison of the mono-, dimethyl- and trimethyl 3-hydroxy-4(1H)-pyridones – Attempted optimization of the orally active iron chelator, deferiprone

  摘要：

  A range of close analogues of deferiprone have been synthesised. The group includes mono-, di- and trimethyl-3-hydroxy-4(1H)-pyridones. These compounds were found to possess similar pFe(3+) values to that of deferiprone, with the exception of the 2.5-dimethylated derivatives. Surprisingly the NH-containing hydroxy-4(1H)-pyridones were found to be marginally more lipophilic than the corresponding N-Me containing analogues. This same group are also metabolised less efficiently by Phase 1 hydroxylating enzymes than the corresponding N-Me analogues.As result of this study, three compounds have been identified for further investigation centred on neutropenia and agranulocytosis. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.014

文献信息

• A SYNTHESIS OF MIMOSINE
  作者：Ian D. Spenser、Albert D. Notation

  DOI：10.1139/v62-210

  日期：1962.7.1

  DL-Mimosine has been sinthesized by debenzylation and detosylation of the product obtained by condensation of 3-benzyloxy-4-pyrone with β-amino-α-tosylaminopropionic acid.A new method for the isolation of mimosine from Leucaena glauca Benth. is described.

  DL-Mimosine通过将3-苯甲氧基-4-吡喃酮与β-氨基-α-对甲苯磺酰氨基丙酸缩合后脱苯甲基和去甲基化合物制备而成。本文描述了从灰莉树中分离mimosine的一种新方法。
• Direct C–H Hydroxylation of <i>N</i>-Heteroarenes and Benzenes <i>via</i> Base-Catalyzed Halogen Transfer
  作者：Kendelyn I. Bone、Thomas R. Puleo、Jeffrey S. Bandar

  DOI：10.1021/jacs.3c14058

  日期：2024.4.10

  employs an alkoxide base to catalyze X-transfer from sacrificial 2-halothiophene oxidants to aryl substrates, forming SNAr-active intermediates that undergo nucleophilic hydroxylation. Key to this process is the use of 2-phenylethanol as an inexpensive hydroxide surrogate that, after aromatic substitution and rapid elimination, provides the hydroxylated arene and styrene byproduct. Use of simple 2-halothiophenes

  羟基化（杂）芳烃在许多行业中都受到重视，既是最终产品的关键成分，又是可多样化的合成结构单元。因此，开发补充和解决引入芳香族羟基的现有方法的局限性的反应是一个重要的目标。为此，我们应用碱催化的卤素转移（X-转移）来实现弱酸性N-杂芳烃和苯的直接C-H羟基化。该方案采用醇盐碱催化从牺牲的 2-卤代噻吩氧化剂到芳基底物的 X 转移，形成发生亲核羟基化的 S N Ar 活性中间体。该过程的关键是使用 2-苯基乙醇作为廉价的氢氧化物替代物，在芳族取代和快速消除后，提供羟基化芳烃和苯乙烯副产物。使用简单的2-卤代噻吩可以实现6元N-杂芳烃和1,3-唑衍生物的C-H羟基化，而合理设计的2-卤代苯并噻吩氧化剂则将范围扩展到缺电子苯底物。机理研究表明芳香族 X 转移是可逆的，这表明去质子化、卤化和取代步骤协同作用，表现出独特的选择性趋势，不一定依赖于酸性最强的芳基位置。通过简化的目标分子合成、与替代 C-H
• On the Structure of Leucaenine (Leucaenol) from Leucaena Glauca Bentham. IV
  作者：A. F. Bickel

  DOI：10.1021/ja01181a101

  日期：1948.1
• Peratoner; Tamburello, Chemisches Zentralblatt, 1905, p. II,681
  作者：Peratoner、Tamburello

  DOI：——

  日期：——
• On the Structure of Leucaenine (Leucaenol) from Leucaena glauca Bentham. II.
  作者：A. F. Bickel

  DOI：10.1021/ja01199a068

  日期：1947.7