3-氰基-1,2-二氢-6-甲基-2-氧代-4-吡啶羧酸乙酯 | 18619-97-1

• 物质功能分类: 医药中间体 - 杂环化合物
• 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-氰基-1,2-二氢-6-甲基-2-氧代-4-吡啶羧酸乙酯
• 中文别名: 2-羟基-3-氰基-6-甲基异烟酸乙酯；3-氰基-2-羟基-6-甲基异烟酸乙酯
• 英文名称: ethyl 3-cyano-6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate
• 英文别名: 5-Cyano-2-methyl-pyrid-6-on-4-carbonsaeureethylester；Ethyl 3-cyano-2-hydroxy-6-methylisonicotinate；ethyl 3-cyano-6-methyl-2-oxo-1H-pyridine-4-carboxylate
• CAS: 18619-97-1
• 化学式: C₁₀H₁₀N₂O₃
• mdl: MFCD00052274
• 分子量: 206.201
• InChiKey: RJJRKBMJIICKDK-UHFFFAOYSA-N

物化性质

• 熔点：
  219 °C
• 沸点：
  371.6±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  室温和干燥环境下使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl 3-cyano-2-hydroxy-6-methylisonicotinate
Synonyms:

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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: Ethyl 3-cyano-2-hydroxy-6-methylisonicotinate
CAS number: 18619-97-1

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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: C10H10N2O3
Molecular weight: 206.2

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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：

  3-氰基-1,2-二氢-6-甲基-2-氧代-4-吡啶羧酸乙酯 在 盐酸 、 Pd-BaSO₄ 、 乙醇 、 五氯化磷 、 硝酸 、 乙酸酐 、 铁粉 、 尿素 、 三氯氧磷 作用下， 生成 5-Amino-6-methyl-cinchomeronsaeure
  参考文献：
  名称：

  Wuest et al., Recueil des Travaux Chimiques des Pays-Bas, 1959, vol. 78, p. 226,240

  摘要：

  DOI：
• 作为产物：
  描述：

  氰乙酰胺 生成 3-氰基-1,2-二氢-6-甲基-2-氧代-4-吡啶羧酸乙酯
  参考文献：
  名称：

  STOUT, D. M.;JAMAMOTO, D. M.;BARSELON-JANG, C.

  摘要：

  DOI：

文献信息

• [EN] ENHANCER OF ZESTE HOMOLOG 2 INHIBITORS<br/>[FR] ACTIVATEUR D'INHIBITEURS DE L'HOMOLOGUE 2 DE ZESTE
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2014195919A1

  公开（公告）日：2014-12-11

  This invention relates to novel compounds according to Formula (I) which are inhibitors of Enhancer of Zeste Homolog 2 (EZH2), to pharmaceutical compositions containing them, to processes for their preparation, and to their use in therapy for the treatment of cancers.

  这项发明涉及到按照式（I）的新化合物，这些化合物是增强子Zeste同源物2（EZH2）的抑制剂，以及含有它们的药物组合物，它们的制备方法，以及它们在治疗癌症方面的用途。
• Pyridone esters as inotropic agents
  申请人：E. I. Du Pont de Nemours & Co.

  公开号：US04657919A1

  公开（公告）日：1987-04-14

  Described are compounds of the formula ##STR1## wherein R is hydrogen, lower alkyl, halo, cyano, hydroxy, amino, lower alkylamino, --CH.sub.2 NH.sub.2, --CH.sub.2 OH or --COOR"; R' is hydrogen, lower cycloalkyl or lower alkyl; R' is lower alkenyl, lower alkynyl, lower cycloalkyl, --(W).sub.n Y wherein W is straight or branched chain lower alkyl or lower alkenyl, n is 0 to 5, and Y is Ar, lower cycloalkyl, lower alkenyl, lower alkynyl, --COOZ wherein Z is lower alkyl, ##STR2## or NAB wherein A and B are, independently, lower alkyl, benzyl or substituted benzyl, and Ar is 2, 3 or 4-pyridyl, pyridazinyl, pyrimidinyl, quinolyl, isoquinolyl, phthalazinyl, quinazolinyl, thiazolyl, phenyl, benzyl, furyl, tetrahydrofuryl or thienyl, unsubstituted or substituted with lower alkyl, lower alkoxy, halo, amino, or --CF.sub.3 ; R"' is --COOR", ##STR3## and X is oxygen or nitrogen; or a pharmaceutically acceptable salt thereof, and their use in the treatment of impaired ventricular myocardial contractility. The compounds exhibit cardiotonic activity.

  描述了公式##STR1##的化合物，其中R是氢、低级烷基、卤素、氰基、羟基、氨基、低级烷基亚胺、--CH.sub.2 NH.sub.2、--CH.sub.2 OH或--COOR"；R'是氢、低级环烷基或低级烷基；R'是低级烯基、低级炔基、低级环烷基、--(W).sub.n Y，其中W是直链或支链低级烷基或低级烯基，n是0到5，Y是Ar、低级环烷基、低级烯基、低级炔基、--COOZ，其中Z是低级烷基、##STR2##或NAB，其中A和B独立地是低级烷基、苄基或取代苄基，Ar是2、3或4-吡啶基、吡啶嗪基、嘧啶基、喹诺酮基、异喹诺酮基、酞嗪基、喹唑啉基、噻唑基、苯基、苄基、呋喃基、四氢呋喃基或噻吩基，未取代或取代有低级烷基、低级烷氧基、卤素、氨基或--CF.sub.3；R"'是--COOR"，##STR3##，X是氧或氮；或其药物可接受的盐，及其在治疗心室心肌收缩力受损中的应用。这些化合物具有强心作用。
• 6,6′-Dimethyl-2,2′-bipyridine-4-ester: A pivotal synthon for building tethered bipyridine ligands
  作者：Fabien Havas、Nadine Leygue、Mathieu Danel、Béatrice Mestre、Chantal Galaup、Claude Picard

  DOI：10.1016/j.tet.2009.06.111

  日期：2009.9

  describe an efficient and scalable synthesis of 4-carbomethoxy-6,6′-dimethyl-2,2′-bipyridine starting from easily available substituted 2-halopyridines and based on the application of modified Negishi cross-coupling conditions. This compound is a versatile starting material for the synthesis of 4-functionalized 2,2′-bipyridines bearing halide, alcohol, amine, and other functionalities, suitable for conjugation

  我们描述了从容易获得的取代的2-卤代吡啶开始，并基于改良的Negishi交叉偶联条件的应用，有效而可扩展地合成4-羰基甲氧基-6,6'-二甲基-2,2'-联吡啶。该化合物是通用的原料，可合成带有卤化物，醇，胺和其他官能团的4-官能化2,2'-联吡啶，适合与生物材料（2a - c，3a - g）结合。通过合成两种双功能镧系螯合剂进一步证明了该化合物在构建更复杂结构中的效用。基于一个2,2'-联吡啶单元的开链配体和基于三个2,2'-联吡啶单元的穴状配体[N 2（bpy）3 COOMe]。在发光生物标记的领域，报道了相应的Eu（III）隐窝的光物理性质。
• 3-Deoxy-3-fluoropyridoxamine 5‘-Phosphate:  Synthesis and Chemical and Biological Properties of a Coenzyme B₆ Analog
  作者：Patricia A. Pieper、Ding-yah Yang、Hui-qiang Zhou、Hung-wen Liu

  DOI：10.1021/ja9632668

  日期：1997.2.1

  The C-3 deoxygenation of CDP-6-deoxy-l-threo-d-glycero-4-hexulose is the key step in the biosynthesis of ascarylose which is a 3,6-dideoxy sugar found in the lipopolysaccharide of Yersinia pseudotuberculosis. This transformation, achieved by the catalysis of CDP-6-deoxy-l-threo-d-glycero-4-hexulose-3-dehydrase (E1) and CDP-6-deoxy-l-threo-d-glycero-4-hexulose-3-dehydrase reductase (E3), is initiated

  CDP-6-deoxy-l-threo-d-glycero-4-hexulose 的 C-3 脱氧是蛔虫糖生物合成的关键步骤，蛔虫糖是在假结核耶尔森氏菌的脂多糖中发现的 3,6-双脱氧糖。这种转化是通过 CDP-6-deoxy-l-threo-d-glycero-4-hexulose-3-dehydrase (E1) 和 CDP-6-deoxy-l-threo-d-glycero-4-hexulose 的催化实现的-3-脱水酶还原酶 (E3) 由可逆脱水启动，然后从 NADH 逐步电子转移以还原生成的葡萄糖 - PMP 加合物。在 E1-E3 催化过程中，EPR 检测到一种有机自由基中间体，其特征与苯氧基自由基一致。假设它的形成涉及葡萄糖-PMP 中间体的互变异构化为 PMP-醌甲基化物物种，然后在还原过程中充当电子受体。为了获得支持该机制的进一步实验证据，合成了标题化合物 (F-PMP)
• Synthesis and Physico-Chemical Properties of Homoleptic Copper(I) Complexes with Asymmetric Ligands as a DSSC Dye
  作者：Tomohiko Inomata、Mayuka Hatano、Yuya Kawai、Ayaka Matsunaga、Takuma Kitagawa、Yuko Wasada-Tsutsui、Tomohiro Ozawa、Hideki Masuda

  DOI：10.3390/molecules26226835

  日期：——

  develop low-cost and efficient dye-sensitized solar cells (DSSCs), we designed and prepared three homoleptic Cu(I) complexes with asymmetric ligands, M1, M2, and Y3, which have the advantages of heteroleptic-type complexes and compensate for their synthetic challenges. The three copper(I) complexes were characterized by elemental analysis, UV-vis absorption spectroscopy, and electrochemical measurements

  为了开发低成本、高效的染料敏化太阳能电池 (DSSC)，我们设计并制备了三种具有不对称配体M1、M2和Y3 的均配型 Cu(I) 配合物，它们具有杂配型配合物的优点并弥补了他们的综合挑战。通过元素分析、紫外-可见吸收光谱和电化学测量对三种铜 (I) 配合物进行了表征。评估了它们的吸收光谱和轨道能量，并在 TD-DFT 计算的背景下进行了讨论。复合物具有高V OC值（M1、M2和Y3为0.48、0.60和 0.66 V，分别）类似于先前报道的具有对称配体的铜（I）染料，尽管它们的能量转换效率相对较低（分别为 0.17、0.64 和 2.66%）。