3-甲氧基-2(1H)-吡啶酮 | 20928-63-6

• 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 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 3-甲氧基-2(1H)-吡啶酮
• 中文别名: 2-羟基-3-甲氧基吡啶；3-甲氧基-2(1H)-羟基吡啶；3-甲氧基-2-羟基吡啶
• 英文名称: 3-methoxy-1H-pyridin-2-one
• 英文别名: 3-methoxypyridin-2(1H)-one；3-methoxy-2-pyridone；3-methoxy-2(1H)-pyridone；3-methoxy-2(1H)-pyridinone；3-methoxypyridin-2-one；3-methoxy-1,2-dihydro-pyridin-2(1H)-one
• CAS: 20928-63-6
• 化学式: C₆H₇NO₂
• mdl: MFCD00006015
• 分子量: 125.127
• InChiKey: LKIMDXQLHFCXQF-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117 °C(lit.)
• 沸点：
  354.2±42.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解，请避免接触氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 安全说明：
  S26
• 危险类别码：
  R22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2933399090
• 危险标志：
  GHS07
• 危险性描述：
  H302,H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338
• 储存条件：
  将贮藏器密封后，放入一个紧密的容器中，并存放在阴凉、干燥的地方。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Hydroxy-3-methoxypyridine
Synonyms: 3-Methoxypyridin-2-ol

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Hydroxy-3-methoxypyridine
CAS number: 20928-63-6

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H7NO2
Molecular weight: 125.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3-甲氧基-2(1H)-吡啶酮 在 正丁基锂 、 2,6-二叔丁基-4-甲基苯酚 、 甲基锂 作用下， 以 二氯甲烷 为溶剂， 反应 82.33h， 生成 dimethyl 1β-methoxy-4α-<(4'-methylbenzenesulfonyl)amino>cyclohex-5-ene-1,2-dicarboxylate
  参考文献：
  名称：

  Diels-Alder cycloadditions using nucleophilic 2-pyridones. Regiocontrolled and stereocontrolled synthesis of unsaturated, bridged, bicyclic lactams

  摘要：

  Captodative 3-oxy-and 3-(tolylthio)-1-tosyl-2-pyridones 1a-1d are shown to be reactive as nucleophilic dienes undergoing 2 + 4-cycloadditions with various electrophilic alkenes under sufficiently mild thermal conditions (90-100-degrees-C) that the initial bicylic lactam adducts can be isolated on gram scale in fair to very good yields (23-83%) without loss of an isocyanate from the heteroatom bridge. These bicyclic adducts are formed with complete regiocontrol and stereocontrol. For pyridone sulfide 1d, these Diels-Alder cycloadditions are the first examples of a captodative unsaturated sulfide acting as an enophile. NMR data (C-13) are presented correlating the electron density in the pyridone diene systems with their Diels-Alder reactivity, and some transformations of the bicyclic lactam adducts are shown to illustrate the value and versatility of these richly functionalized synthetic intermediates.

  DOI：

  10.1021/jo00041a010
• 作为产物：
  描述：

  2-溴-3-甲氧基吡啶 在 copper(l) iodide 、 C₁₄H₁₄N₂O₃ 、 potassium hydroxide 作用下， 以 环丁砜 、 水 为溶剂， 以95 %的产率得到3-甲氧基-2(1H)-吡啶酮
  参考文献：
  名称：

  使用羟基吡啶甲酰胺配体的铜催化芳基卤化物的羟基化

  摘要：

  卤代芳烃的羟基化是有机合成化学中的一个基本转变。羟基吡啶甲酰胺配体能够实现杂芳基卤化物的有效铜催化羟基化，并具有广泛的官能团耐受性。 Cu-MPBS 系统最初设计用于 C-N 偶联，可实现铜催化芳基溴的羟基化。相关衍生物 Cu-HMPS 为芳基溴、芳基碘和活化芳基氯的羟基化提供了出色的反应性和纯度。邻位活化底物对铜催化的羟基化表现出极高的反应活性和选择性。更困难的芳基氯化物，需要更高活化温度（120°C）的底物，可以通过具有优异的内在配体稳定性的Cu-DMPS系统进行羟基化。可以通过配体、溶剂和碱基的选择来调整反应条件以适应目标底物。采用 KOH、K 2 CO 3 或 K 3 PO 4 水溶液（溶于环丁砜或环丁砜）设计了安全可靠的加工条件和酒精混合物。

  DOI：

  10.1021/acs.oprd.4c00108

文献信息

• Substituted Heteroaromatic Pyrazole-Containing Carboxamide and Urea Compounds as Vanilloid Receptor Ligands
  申请人：FRANK Robert

  公开号：US20130029962A1

  公开（公告）日：2013-01-31

  Substituted heteroaromatic pyrazole-containing carboxamide and urea compounds as vanilloid receptor ligands, pharmaceutical compositions containing these compounds and also to a method of using these compounds for treating and/or inhibiting pain and further diseases and/or disorders.

  含有杂环吡唑基的羧酰胺和脲化合物作为辣椒素受体配体，含有这些化合物的药物组合物，以及使用这些化合物治疗和/或抑制疼痛以及进一步疾病和/或疾病的方法。
• PYRROLO AND PYRAZOLOPYRIMIDINES AS UBIQUITIN-SPECIFIC PROTEASE 7 INHIBITORS
  申请人：Forma Therapeutics, Inc.

  公开号：US20160185785A1

  公开（公告）日：2016-06-30

  The invention relates to inhibitors of USP7 inhibitors useful in the treatment of cancers, neurodegenerative diseases, immunological disorders, inflammatory disorders, cardiovascular diseases, ischemic diseases, viral infections and diseases, and bacterial infections and diseases, having the Formula: where m, n, X 1 , X 2 , R 1 -R 5 , R 5′ and R 6 are described herein.

  这项发明涉及USP7抑制剂，用于治疗癌症、神经退行性疾病、免疫紊乱、炎症性疾病、心血管疾病、缺血性疾病、病毒感染和疾病、细菌感染和疾病，具有以下结构式： 其中m、n、X1、X2、R1-R5、R5'和R6如本文所述。
• Synthesis and iron chelating properties of hydroxypyridinone and hydroxypyranone hexadentate ligands
  作者：Tao Zhou、Xiao-Le Kong、Robert C Hider

  DOI：10.1039/c8dt05014g

  日期：——

  chelators, four hexadentate ligands were synthesized by conjugating the corresponding bidentate ligands (3-hydroxypyridin-4-one (3,4-HOPO), 3-hydroxypyridin-2-one (3,2-HOPO), 1-hydroxypyridin-2-one (1,2-HOPO), and 3-hydroxypyran-4-one) each with a free amino group to a tripodal acid. Their pKa values and affinities for iron(III) were investigated. The pFe3+ values of the hexadentate pyridinones 1 (3

  螯合疗法已成为治疗某些疾病的重要方法。为了确定临床上有用的螯合剂，通过缀合相应的二齿配体（3-羟基吡啶-4-酮（3,4-HOPO），3-羟基吡啶-2-酮（3,2-HOPO）， 1-羟基吡啶-2-酮（1,2-HOPO）和3-羟基吡喃-4-酮）各自具有与三脚架酸形成的游离氨基。研究了它们对铁（III）的p K a值和亲和力。该PFE 3+的六齿吡啶酮的值1（3,4- HOPO），3（3,2-HOPO）和4（1,2- HOPO）和吡喃酮2被发现跟随序列1 >4 » 3 > 2，这是对PFE不同3+的相应的二齿形式（3,4- HOPO»3,2-HOPO> 1,2- HOPO> 3- hydroxypyranone）值序列。六齿的3,4-HOPO和1,2-HOPO具有最大的除铁剂潜力。
• DIARYLMETHYLAMIDE DERIVATIVE HAVING ANTAGONISTIC ACTIVITY ON MELANIN-CONCENTRATING HORMONE RECEPTOR
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：EP2272841A1

  公开（公告）日：2011-01-12

  [Problem] To provide a melanin-concentrating hormone receptor antagonist useful as a pharmaceutical agent for central diseases, circulatory diseases, and metabolic diseases. [Means for Resolution] Provided is a diarylmethylamide derivative represented by formula (I): Wherein R1a, R1b, R2a, R2b, R3a, and R3b independently represent a hydrogen atom or the like, R4 represents a hydrogen atom, C1-6 alkyl, or the like, R5 represents a hydrogen atom or the like, Z represents C1-6 alkyl or the like, or R4 and Z together form a 4- to 6-membered nitrogen-containing hetero ring, Y1 represents H or the like, Y2 represents H, or Y1 and Y2 together form - O-CH2-, W represents C, SO, or the like, Ar1 represents 6-membered aryl or the like, Ar2 represents 6-membered aryl or the like, and ring A represents a benzene ring, a pyridine ring, or the like.

  [问题] 提供一种对黑色素浓缩激素受体拮抗剂，用作中枢疾病、循环疾病和代谢疾病的药用制剂。 [解决方法] 提供一种由式(I)表示的二芳基甲酰胺衍生物： 其中R1a、R1b、R2a、R2b、R3a和R3b独立地表示氢原子或类似物，R4表示氢原子、C1-6烷基或类似物，R5表示氢原子或类似物，Z表示C1-6烷基或类似物，或者R4和Z一起形成一个含氮杂环的4-至6-成员环，Y1表示H或类似物，Y2表示H，或者Y1和Y2一起形成-O-CH2-，W表示C、SO或类似物，Ar1表示6-成员芳基或类似物，Ar2表示6-成员芳基或类似物，环A表示苯环、吡啶环或类似物。
• Regioselective N‐Functionalization of Tautomerizable Heterocycles through Methyl Trifluoromethanesulfonate‐Catalyzed Substitution of Alcohols and Alkyl Group Migrations
  作者：Surajit Duari、Subrata Biswas、Arnab Roy、Srabani Maity、Abhishek Kumar Mishra、Aguinaldo R. Souza、Asma M. Elsharif、Nelson H. Morgon、Srijit Biswas

  DOI：10.1002/adsc.202101196

  日期：2022.2.15

  (MeOTf) was found to catalyze the reaction, which revealed the catalytic property of MeOTf. A mechanism was established through experiments as well as DFT calculations wherein the −OH group of alcohols were converted to the corresponding −OMe groups and in situ generated TfOH. The −OMe groups produced underwent TfOH catalyzed −X alkylation (X=O, S) of the heterocycles followed by −X- to −N-alkyl group

  已经开发了一种催化合成策略，结合了两种方案，例如醇的直接亲核取代，然后是X - 到N - 烷基迁移 ( X = O , S ) 以获得N - 官能化苯并恶唑酮、苯并噻唑硫酮、吲哚啉酮、苯并咪唑硫酮和吡啶酮衍生物。发现三氟甲磺酸甲酯 (MeOTf) 可催化该反应，这揭示了 MeOTf 的催化性能。通过实验和 DFT 计算建立了一种机制，其中醇的 -OH 基团原位转化为相应的 -OMe 基团生成 TfOH。产生的 -OMe 基团经历了 TfOH 催化的杂环的 - X烷基化（X = O，S），然后在一个步骤中进行 - X-到 - N-烷基迁移。

表征谱图