N-(2-hydroxy-5-methylpyridin-3-yl)acetamide | 106837-93-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-hydroxy-5-methylpyridin-3-yl)acetamide
• 英文别名: N-(5-methyl-2-oxo-1H-pyridin-3-yl)acetamide
• CAS: 106837-93-8
• 化学式: C₈H₁₀N₂O₂
• 分子量: 166.18
• InChiKey: NBATYCCEAJREGB-UHFFFAOYSA-N

物化性质

• 熔点：
  253 °C
• 沸点：
  473.1±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-5-methylpyridin-3-yl)acetamide 在 硫酸 作用下， 生成 3-[(6-hydroxy-5-methyl-2-oxo-1H-pyridin-3-yl)imino]-5-methylpyridine-2,6-dione
  参考文献：
  名称：

  Azaquinones. I. Oxidation of Certain Hydroxy- and Aminopyridones¹

  摘要：

  DOI：

  10.1021/ja01570a066
• 作为产物：
  描述：

  2-羟基-5-甲基-3-硝基吡啶 在 铁粉 、 溶剂黄146 作用下， 生成 N-(2-hydroxy-5-methylpyridin-3-yl)acetamide
  参考文献：
  名称：

  Azaquinones. I. Oxidation of Certain Hydroxy- and Aminopyridones¹

  摘要：

  DOI：

  10.1021/ja01570a066

文献信息

• Ligand-Promoted <i>Meta</i>-C–H Arylation of Anilines, Phenols, and Heterocycles
  作者：Peng Wang、Marcus E. Farmer、Xing Huo、Pankaj Jain、Peng-Xiang Shen、Mette Ishoey、James E. Bradner、Steven R. Wisniewski、Martin D. Eastgate、Jin-Quan Yu

  DOI：10.1021/jacs.6b04966

  日期：2016.7.27

  Here we report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic

  在这里，我们报告了一种通用的 3-乙酰氨基-2-羟基吡啶类配体的开发，这些配体使用降冰片烯作为瞬态介质促进苯胺、杂环芳香胺、苯酚和 2-苄基杂环的间位 CH 芳基化。提供了 120 多个例子，证明了这种配体支架能够实现广泛的底物和偶联伙伴范围。使用该配体还首次实现了以杂环芳基碘化物作为偶联伙伴的间位 CH 芳基化。通过允许来那度胺衍生物的间位 CH 芳基化，展示了这种药物发现转化的效用。还展示了该反应的无银方案的第一步。
• [EN] A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS<br/>[FR] LIGAND POLYVALENT POUR DES FONCTIONNALISATIONS DE MÉTA-C-H CATALYSÉES PAR DU PALLADIUM
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2017184589A1

  公开（公告）日：2017-10-26

  A class of mono-protected 3-amino-2- hydroxypyridine (MPAHP) ligands that enable the meta- C-H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C-H functionalization processes is also illustrated by the development of a meta-C-H amination reaction and a meta-C-H alkynylation reaction.

  一种单保护的3-氨基-2-羟基吡啶（MPAHP）配体类别，能够利用去环戊烯作为瞬时介质，实现苯胺、酚、苯乙酸和生物相关杂环化合物的间位C-H芳基化。该间位芳基化方法在制药行业中的适用性通过对杂环底物和杂环碘化合物的示例进行说明，这一成就得益于使用MPAHP配体。MPAHP配体的启用性质还通过开发间位C-H氨化反应和间位C-H炔基化反应来展示其实现其他间位C-H官能化过程的能力。
• Versatile ligand for palladium-catalyzed meta-C—H functionalizations of aromatic substrates
  申请人：The Scripps Research Institute

  公开号：US10696635B2

  公开（公告）日：2020-06-30

  A class of mono-protected 3-amino-2-hydroxypyridine (MPAHP) ligands that enable the meta-C—H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed, such as in the formation of a reaction product of Formula IA: The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C—H functionalization processes is also illustrated by the development of a meta-C—H amination reaction and a meta-C—H alkynylation reaction.

  本发明公开了一类单保护 3-氨基-2-羟基吡啶（MPAHP）配体，该配体可以使用降冰片烯作为瞬时介质，对苯胺、苯酚、苯乙酸和生物相关杂环化合物进行元-C-H 芳基化反应，例如形成式 IA 的反应产物： 这种元芳基化方法在制药业中的适用性说明了杂芳基底物和杂芳基碘偶联剂的适用性，使用 MPAHP 配体使这一壮举成为可能。通过开发元-C-H 氨基化反应和元-C-H 炔化反应，还说明了 MPAHP 配体在实现其他元-C-H 功能化过程中的促进作用。
• A VERSATILE LIGAND FOR PALLADIUM-CATALYZED META-C-H FUNCTIONALIZATIONS
  申请人：The Scripps Research Institute

  公开号：US20190119212A1

  公开（公告）日：2019-04-25

  A class of mono-protected 3-amino-2-hydroxypyridine (MPAHP) ligands that enable the meta-C—H arylation of anilines, phenols, phenylacetic acids, and biologically relevant heterocyclic compounds using norbornene as a transient mediator is disclosed. The applicability of this meta-arylation methodology in the pharmaceutical industry is illustrated for heteroaryl substrates and heteroaryl iodide coupling partners, a feat made possible by using the MPAHP ligand. The enabling nature of MPAHP ligands to achieve other meta-C—H functionalization processes is also illustrated by the development of a meta-C—H amination reaction and a meta-C—H alkynylation reaction.