5-乙酰氨基烟酸 | 82817-65-0

• 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 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-乙酰氨基烟酸
• 英文名称: 3-carboxy-5-acetylaminopyridine
• 英文别名: 5-(acetamido)nicotinic acid；5-acetamido nicotinic acid；5-acetamidonicotinic acid；5-acetamidopyridine-3-carboxylic acid
• CAS: 82817-65-0
• 化学式: C₈H₈N₂O₃
• 分子量: 180.163
• InChiKey: KMRQIJRSLWWZAM-UHFFFAOYSA-N

物化性质

• 熔点：
  292-294

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Acetamidonicotinic acid
Synonyms: 5-Acetamido-3-pyridinecarboxylic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 5-Acetamidonicotinic acid
CAS number: 82817-65-0

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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.
Store in closed vessels.
Storage:

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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
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C8H8N2O3
Molecular weight: 180.2

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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：

  5-乙酰氨基烟酸 在 rhodium on alumina ammonium hydroxide 、 氢气 作用下， 以 水 为溶剂， 反应 72.0h， 以44%的产率得到(3RS,5SR)-5-acetamidopiperidine-3-carboxylic acid
  参考文献：
  名称：

  Hydroxy- and amino-substituted piperidinecarboxylic acids as .gamma.-aminobutyric acid agonists and uptake inhibitors

  摘要：

  The syntheses of (3RS,4RS)-4-hydroxypiperidine-3-carboxylic acid (4), (3RS,5SR)-5-hydroxypiperidine-3-carboxylic acid (20), (3RS,4SR)-4-acetamidopiperidine-3-carboxylic acid (10), and (3RS,5SR)-5-acetamidopiperidine-3-carboxylic acid (18), related to the specific gamma-aminobutyric acid (GABA) uptake inhibitors (RS)-piperidine-3-carboxylic acid (nipecotic acid) and (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (21), are described. Furthermore, (3RS,4SR)-3-hydroxypiperidine-4-carboxylic acid (14), related to the specific GABA agonist piperidine-4-carboxylic acid (isonipecotic acid), has been synthesized. The structures of 4, 10, 14, 18, and 20 have been established by 270-MHz 1H NMR spectroscopic analyses. The affinity of the compounds for the GABA receptors and for the neuronal (synaptosomal) GABA uptake system in vitro has been measured. Compound 14 interacts selectively with the GABA receptors but less effectively than isonipecotic acid and the cis-isomer 22. Compounds 4, 18, and 20 are inhibitors of the GABA uptake system, although much weaker than nipecotic acid and (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (21). Compound 10 is inactive in both test systems.

  DOI：

  10.1021/jm00352a012
• 作为产物：
  描述：

  5-氨基烟酸 、 sodium acetate 以 乙酸酐 为溶剂， 反应 1.0h， 以4.2 g的产率得到5-乙酰氨基烟酸
  参考文献：
  名称：

  研究吡啶和吡啶N-氧化物环中的电子效应。第4部分。重氮二苯基甲烷与取代的羧基吡啶和2-羧基吡啶N-氧化物在二甲基甲酰胺中的反应动力学和机理

  摘要：

  通过已知的分光光度法，在30°C下测定15个取代的羧基吡啶和四个取代的2-羧基吡啶N-氧化物与重氮二苯基甲烷（DDM）在二甲基甲酰胺（DMF）中的反应的速率常数。为了比较，在相同条件下确定12种取代的苯甲酸反应的速率常数。所获得的动力学和热力学参数，连同产物分析，基本上验证了先前提出的在该溶剂中的反应机理。对结果进行了经验性的Hammett处理，结果表明，散布的总体图（ρ= 1.019，log k o = –2.98，r = 0.91，s = 0.22，n从吡啶氮杂基团和N-氧化物基团的相应σ值以及取代基的Hammettσ常数中，通过加法σ常数获得= = 31）。从取代的苯甲酸（ρ= 1.213，log k o = –2.91，r = 0.985，s = 0.12，n = 12），卤素和硝基取代酸（ρ= 1.07， log k o = –2.99，r = 0.998，s = 0.02，n =

  DOI：

  10.1039/p29840001975

文献信息

• NEW COMPOUNDS
  申请人：HAUEL Norbert

  公开号：US20100240669A1

  公开（公告）日：2010-09-23

  The present invention relates to the compounds of general formula I wherein n, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and X are defined as described hereinafter, the enantiomers, the diastereomers, the mixtures and the salts thereof, particularly the physiologically acceptable salts thereof with organic or inorganic acids or bases, which have valuable properties, the preparation thereof, the medicaments containing the pharmacologically effective compounds, the preparation thereof and the use thereof.

  本发明涉及一般式I的化合物，其中n、R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和X的定义如下所述，其对映体、非对映体、混合物及其盐，特别是其与有机或无机酸或碱形成的生理上可接受的盐，具有有价值的性质，其制备方法，含有药理学有效化合物的药物，其制备方法和用途。
• Rh(III)-Catalyzed C–H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones
  作者：John R. Huckins、Eric A. Bercot、Oliver R. Thiel、Tsang-Lin Hwang、Matthew M. Bio

  DOI：10.1021/ja405140f

  日期：2013.10.2

  general Rh(III)-catalyzed synthesis of naphthyridinone derivatives is described. It relies on a double-activation and directing approach leveraging nicotinamide N-oxides as substrates. In general, high yields and selectivities can be achieved using low catalyst loadings and mild conditions (room temperature) in the couplings with alkynes, while alkenes require slightly more elevated temperatures.

  描述了一般的 Rh(III) 催化合成萘啶酮衍生物。它依赖于利用烟酰胺 N 氧化物作为底物的双重激活和导向方法。通常，在与炔烃的偶联中使用低催化剂负载量和温和条件（室温）可以实现高产率和选择性，而烯烃需要稍微升高的温度。
• Piperidine Derivatives
  申请人：ROTH Gerald Juergen

  公开号：US20130165444A1

  公开（公告）日：2013-06-27

  Piperidine derivatives of which the following is exemplary and their use in the treatment of obesity, diabetes or dyslipidemia.

  哌啶衍生物及其在肥胖、糖尿病或血脂异常治疗中的用途。
• [EN] NEW AZETIDINE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS D'AZÉTIDINE, COMPOSITIONS PHARMACEUTIQUES CORRESPONDANTES ET LEURS UTILISATIONS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2013098373A1

  公开（公告）日：2013-07-04

  The invention relates to new azetidine derivatives of the formula (I) to their use as medicaments, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  这项发明涉及到新的式(I)的氮杂环丁烷衍生物，以及它们作为药物的用途，用于它们的治疗用途的方法，以及含有它们的药物组合物。
• Azetidine Derivatives
  申请人：NOSSE Bernd

  公开号：US20130172312A1

  公开（公告）日：2013-07-04

  Azetidine derivatives of which the following is exemplary and their use in the treatment of obesity, diabetes or dyslipidemia.

  以下是示例性的氮杂环丙烷衍生物及其在肥胖、糖尿病或血脂异常治疗中的用途。