喹啉-2-羧酸乙酯 | 4491-33-2

• 物质功能分类: 有机原料 - 无机酸酯
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 喹啉-2-羧酸乙酯
• 中文别名: 2-喹啉甲酸乙酯
• 英文名称: ethyl quinoline-2-carboxylate
• 英文别名: ethyl 2-quinolinecarboxylate
• CAS: 4491-33-2
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD02149441
• 分子量: 201.225
• InChiKey: PWOYTBYNBYNZCO-UHFFFAOYSA-N

物化性质

• 熔点：
  30-33 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  180 °C(Press: 14 Torr)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温和干燥环境中使用。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Ethyl quinoline-2-carboxylate
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 quinoline-2-carboxylate
CAS number: 4491-33-2

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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, refrigerated.
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: C12H11NO2
Molecular weight: 201.2

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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

制备方法与用途

概述

喹啉-2-羧酸乙酯是合成喹啉-2-羧酸的重要中间体。作为关键的有机合成原料之一，喹啉-2-甲酸广泛应用于有机合成、医药和农药等领域。

在合成化学领域，喹啉-2-甲酸主要用于制备喹啉-2-甲腈及喹啉-2-甲酸甲酯，而喹啉-2-甲腈则是合成喹啉基嘧啶、喹啉基噻唑和喹啉基三氮唑等杂环化合物的关键中间体。此外，喹啉-2-甲酸甲酯也是生产精细化工品的重要原料。

在医药研究方面，罗稳等人通过合成一系列喹啉多胺衍生物，在保护肾上腺嗜铬细胞瘤方面取得了显著成效，并且部分化合物的活性甚至超过了尼莫地平。而在农药合成领域，喹啉-2-甲酸常作为有机锡羧酸酯的重要前体，这类化合物具有良好的杀虫和杀菌效果。

由于喹啉-2-甲酸的应用范围广泛，其合成方法也成为了研究的热点。

反应信息

• 作为反应物：
  描述：

  喹啉-2-羧酸乙酯 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 3-[(3-Chloroanilino)methyl]-5-quinolin-2-yl-1,3,4-oxadiazole-2-thione
  参考文献：
  名称：

  Synthesis, molecular modeling and biological evaluation of 2-aminomethyl-5-(quinolin-2-yl)-1,3,4-oxadiazole-2(3H)-thione quinolone derivatives as novel anticancer agent

  摘要：

  A series of quinoline derivatives (4a-4o) have been synthesized and their biological activities were also evaluated as potential telomerase inhibitors. Bioassay tests demonstrated that most of the compounds exhibited substantial broad-spectrum antitumor activity against the three cancer cell lines (HepG2, SGC-7901 and MCF-7). Moreover, all the title compounds were assayed for telomerase inhibition using the TRAP-PCR-ELISA assay. Compounds 4d and 4i displayed the most potent anticancer activities, which were comparable to the positive control. Docking simulation was performed to position compounds 4d and 4i into the telomerase structure active site to determine the probable binding model. Compounds 4d and 4i with potent inhibitory activity in tumor growth inhibition may be potential anticancer agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.11.039
• 作为产物：
  描述：

  1,2,3,4-四氢喹啉-2-羧酸乙酯 生成 喹啉-2-羧酸乙酯
  参考文献：
  名称：

  Highly enantioselective hydrogenation of new 2-functionalized quinoline derivatives

  摘要：

  The asymmetric hydrogenation of a new series of 2-functionalized quinolines has been developed in the presence of in situ generated catalysts obtained from [Ir(cod)Cl](2)/(R)-bisphosphine/I-2 combinations. The enantioselectivity levels were as high as 84-94% ee for the synthesis of 1,2,3,4-tetrahydroquinolines. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.114

文献信息

• A new air-stable Si,S-chelating ligand for Ir-catalyzed directed <i>ortho</i> C–H borylation
  作者：Jiao Jiao、Wenzheng Nie、Peidong Song、Pengfei Li

  DOI：10.1039/d0ob02335c

  日期：——

  reaction with a broad substrate scope. This study provides the first example of using a sulfur-containing ligand in the catalytic C–H borylation process. It provides a rapid, efficient, and economical method for the preparation of organoboron compounds.

  已开发出一种新型的空气稳定的Si，S螯合配体，并用于具有广泛底物范围的铱催化的邻位C-H硼酸酯化反应中。这项研究提供了在催化C–H硼化过程中使用含硫配体的第一个例子。它提供了一种快速，有效和经济的有机硼化合物的制备方法。
• ANTAGONISTS OF THE TRPV1 RECEPTOR AND USES THEREOF
  申请人：Bayburt Erol K.

  公开号：US20080153871A1

  公开（公告）日：2008-06-26

  The present application is directed to compounds that are TRPV1 antagonists and have formula (I) wherein variables Ar 1 , L 1 , R 1 , R 2 , R 3 , R 4 , R 5 , Y 1 , Y 2 , and Y 3 , are as defined in the description, which are useful for treating disorders caused by or exacerbated by vanilloid receptor activity.

  本申请涉及的化合物是TRPV1拮抗剂，其化学式为（I），其中变量Ar1，L1，R1，R2，R3，R4，R5，Y1，Y2和Y3如描述中所定义，对于治疗由辣椒素受体活性引起或加剧的疾病是有用的。
• 4-Alkyl-1,2,4-triazole-3-thione analogues as metallo-β-lactamase inhibitors
  作者：Laurent Gavara、Alice Legru、Federica Verdirosa、Laurent Sevaille、Lionel Nauton、Giuseppina Corsica、Paola Sandra Mercuri、Filomena Sannio、Georges Feller、Rémi Coulon、Filomena De Luca、Giulia Cerboni、Silvia Tanfoni、Giulia Chelini、Moreno Galleni、Jean-Denis Docquier、Jean-François Hernandez

  DOI：10.1016/j.bioorg.2021.105024

  日期：2021.8

  (BLs), including the highly worrying carbapenemases. Whereas inhibitors of these enzymes were recently marketed, they only target serine-carbapenemases (e.g. KPC-type), and no clinically useful inhibitor is available yet to neutralize the class of metallo-β-lactamases (MBLs). We are developing compounds based on the 1,2,4-triazole-3-thione scaffold, which binds to the di-zinc catalytic site of MBLs

  在革兰氏阴性菌中，对 β-内酰胺类抗生素产生耐药性的主要机制是产生一种或多种 β-内酰胺酶 (BLs)，包括令人担忧的碳青霉烯酶。尽管这些酶的抑制剂最近上市，但它们仅针对丝氨酸-碳青霉烯酶（例如 KPC 型），尚无临床上有用的抑制剂来中和金属-β-内酰胺酶 (MBL) 类。我们正在开发基于 1,2,4-三唑-3-硫酮支架的化合物，该支架以原始方式与 MBL 的二锌催化位点结合，我们之前报道了其产生广谱抑制剂的潜力。然而，到目前为止，在微生物测定中只能观察到适度的抗生素增强作用，需要进一步探索以改善外膜渗透。这里，我们合成并表征了一系列在杂环的 4 位具有不同官能化烷基链的化合物。我们发现在烷基链末端存在羧基会产生有效的 VIM 型酶抑制剂K i值在 μM 到亚 μM 范围内，并且该烷基链必须更长或等于丙基链。该结果证实了羧基官能团对 1,2,4-三唑-3-硫酮杂环的 4-取代基的重要性。如
• Synthesis, anti-tuberculosis activity and 3D-QSAR study of amino acid conjugates of 4-(adamantan-1-yl) group containing quinolines
  作者：Amit Nayyar、Sanjay R. Patel、Mushtaque Shaikh、Evans Coutinho、Rahul Jain

  DOI：10.1016/j.ejmech.2008.10.004

  日期：2009.5

  The synthesis, antimycobacterial activity and 3D-QSAR study of two series of 4-(adamantan-1-yl) group containing quinolines conjugated to amino acids are described. The most potent analogs displayed in vitro antimycobacterial activity ranging between 1.00 and 3.125 μg/mL. To understand the relationship between structure and activity, a 3D-QSAR analysis has been carried out by Comparative Molecular

  描述了两个系列的4-（金刚烷-1-基）基团与氨基酸缀合的喹啉的合成，抗分枝杆菌活性和3D-QSAR研究。最有效的类似物在1.00和3.125μg/ mL之间显示出体外抗分枝杆菌活性。为了了解结构和活性之间的关系，已通过比较分子场分析（CoMFA）进行了3D-QSAR分析。通过场对准生成的CoMFA模型很好地预测了测试集中分子的活性。使用原子拟合比对可获得最佳模型。基于分子领域，结构和活性之间的关系很容易理顺。
• Simple and Mild Method for Preparation of .ALPHA.-Pyridinecarboxylates and .ALPHA.-Pyridyl Ketones via Trimethylstannyl Derivatives.
  作者：Yutaka YAMAMOTO、Hidekazu OUCHI、Takuo TANAKA

  DOI：10.1248/cpb.43.1028

  日期：——

  Alkoxycarbonylation and acylation at the α-position of pyridine, quinoline, and isoquinoline via the respective trimethylstannyl derivatives were satisfactorily performed by employing ethyl chloroglyoxylate and acylformyl chloride under mild conditions.

  通过相应的三甲基锡衍生物，在温和条件下使用乙基氯代甘油酸酯和酰基甲酰氯，能够成功地进行吡啶、喹啉和异喹啉的α位上的烷氧羰基化和酰基化反应。