7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸 | 68077-26-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 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: 7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸
• 中文别名: 7-氯-1-乙基-6-氟-1,4-二氢-4-羰基喹啉-3-羧酸；7-氯-1-乙基-6-氟-4-氧代-1,4-二氢-3-喹啉羧酸；1-乙基-7-氯-6-氟-1,4-二氢-4-氧代喹啉-3-羧酸；7-氯-1,4-二氢-1-乙基-6-氟-4-氧代-3-喹啉羧酸
• 英文名称: 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；7-chloro-6-fluoro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid；7-chloro-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 68077-26-9
• 化学式: C₁₂H₉ClFNO₃
• mdl: MFCD00792459
• 分子量: 269.66
• InChiKey: WNNSMMJBBOPPOT-UHFFFAOYSA-N

物化性质

• 熔点：
  245°C
• 沸点：
  437.9±45.0 °C(Predicted)
• 密度：
  1.3905 (estimate)
• 溶解度：
  可溶于DMSO（略微加热）、甲醇（略微加热）
• 稳定性/保质期：
  远离氧化物。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S61
• 危险类别码：
  R52/53
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放在密封容器中，并置于阴凉、干燥处。请确保存储地点远离氧化剂。

SDS

Name:	7-Chloro-1-Ethyl-6-Fluoro-4-Oxohydroquinoline-3-Carboxylic Acid 98% Material Safety Data Sheet
Synonym:	None Known
CAS:	68077-26-9

Section 1 - Chemical Product MSDS Name:7-Chloro-1-Ethyl-6-Fluoro-4-Oxohydroquinoline-3-Carboxylic Acid 98% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
68077-26-9	7-Chloro-1-Ethyl-6-Fluoro-4-Oxohydroqu	98%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 68077-26-9: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C12H9ClFNO3
Molecular Weight: 269.66

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 68077-26-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
7-Chloro-1-Ethyl-6-Fluoro-4-Oxohydroquinoline-3-Carboxylic Acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 68077-26-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 68077-26-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 68077-26-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

应用范围：7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸是一种羧酸类衍生物，可用作医药中间体。

化学性质
该化合物为结晶固体。

用途
主要用于合成氟哌酸。

反应信息

• 作为反应物：
  描述：

  7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 培氟沙星
  参考文献：
  名称：

  抗菌的6,7-和7,8-二取代的1-烷基-1,4-二氢-4-氧代喹啉-3-羧酸的结构活性关系。

  摘要：

  先前在抗菌单取代的1-乙基-1,4-二氢-4-氧代喹啉3-羧酸中进行的定量和定性结构活性研究促使我们合成了6,7,8-多取代的化合物。在本文中，描述了6,7-和7,8-二取代化合物及其衍生物的制备和抗菌活性。在这些化合物中，1-乙基-6-氟-1,4-二氢-4-氧代-7-（1-哌嗪基）喹啉-3-羧酸（34）具有许多显着的活性，并且比草酸（ 84）对抗革兰氏阳性和革兰氏阴性细菌。讨论了构效关系。

  DOI：

  10.1021/jm00186a014
• 作为产物：
  描述：

  2,4-二氯-5-氟苯酰氯 在 盐酸 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.33h， 生成 7-氯-1-乙基-6-氟-4-氧氢喹啉-3-羧酸
  参考文献：
  名称：

  诺氟沙星化工合成方法

  摘要：

  本发明公开了一种诺氟沙星化工合成方法，如下步骤：（1）、化合物喹啉酸乙酯的合成：将3‑乙胺基‑2‑（2,4‑二氯‑5‑氟苯甲酰基）丙烯酸乙酯溶解在DMF中，加入碳酸钾，之后加热到50‑80℃，反应过夜，冷却，倒入冰水中，将产生的固体过滤，固体用大量的水洗涤，得到产物喹啉酸乙酯；（2）、化合物喹啉酸的合成：将喹啉酸乙酯溶解在甲醇中，加入1:1盐酸，回流2小时，有白色的固体析出，过滤，用水洗涤，真空烘箱烘干2小时，得到产物喹啉酸。本发明设计合理，选择一种新的合成诺氟沙星的方法，具有很好的市场应用价值。

  公开号：

  CN107445892A

文献信息

• Synthesis of antimicrobial agents. 1. Syntheses and antibacterial activities of 7-(azole substituted)quinolones
  作者：Toshio Uno、Masanori Takamatsu、Yoshimasa Inoue、Yoshihiro Kawahata、Koji Iuchi、Goro Tsukamoto

  DOI：10.1021/jm00395a001

  日期：1987.12

  Structure-activity relationship studies indicated that the antibacterial potency was better when the 6,8-substituents were fluorine atoms and the 7-substituent was either 1-imidazolyl, 20, or 4-methyl-1-imidazolyl, 25. From the results of studies on pharmacokinetic profile and toxicity, 20 and 25 were found to possess excellent antibacterial activities and to show high blood levels after oral administration

  制备了一系列6-氟-和6,8-二氟-7-（唑取代的）-1,4-二氢-4-氧代-3-喹啉羧酸。结构活性关系研究表明，当6,8-取代基是氟原子，而7-取代基是1-咪唑基20或4-甲基-1-咪唑基25时，抗菌效果更好。在药代动力学和毒性研究中，发现20和25具有出色的抗菌活性，并且对低毒性小鼠口服后显示出较高的血药浓度。
• [EN] QUINOLIN-4-ONE AND 4(1H)-CINNOLINONE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE QUINOLIN-4-ONE ET DE 4(1H)-CINNOLINONE ET PROCÉDÉS D'UTILISATION ASSOCIÉS
  申请人：FREQUENCY THERAPEUTICS INC

  公开号：WO2020163816A1

  公开（公告）日：2020-08-13

  The present disclosure relates to quinolin-4-one and 4(1H)-cinnolinone compounds and methods of using them to induce self-renewal of stem/progenitor supporting cells, including inducing the stem/progenitor cells to proliferate while maintaining, in the daughter cells, the capacity to differentiate into tissue cells.

  本公开涉及喹啉-4-酮和4(1H)-喹啉酮化合物，以及使用它们诱导干/祖细胞支持细胞自我更新的方法，包括诱导干/祖细胞增殖，同时在子细胞中保持分化为组织细胞的能力。
• Selective Inhibition of DNA Polymerase β by a Covalent Inhibitor
  作者：Shelby C. Yuhas、Daniel J. Laverty、Huijin Lee、Ananya Majumdar、Marc M. Greenberg

  DOI：10.1021/jacs.1c02453

  日期：2021.6.2

  has been closely linked to cancer. Selective inhibitors of this enzyme are lacking. Inspired by DNA lesions produced by antitumor agents that inactivate Pol β, we have undertaken the development of covalent small-molecule inhibitors of this enzyme. Using a two-stage process involving chemically synthesized libraries, we identified a potent irreversible inhibitor (14) of Pol β (KI = 1.8 ± 0.45 μM, kinact

  DNA 聚合酶 β (Pol β) 在 DNA 修复中起着至关重要的作用，并且与癌症密切相关。缺乏这种酶的选择性抑制剂。受使 Pol β 失活的抗肿瘤剂产生的 DNA 损伤的启发，我们着手开发这种酶的共价小分子抑制剂。使用涉及化学合成文库的两阶段过程，我们确定了Pol β的有效不可逆抑制剂 ( 14 ) ( K I = 1.8 ± 0.45 μM, k inact = (7.0 ± 1.0) × 10 –3 s –1 )。抑制剂14比其他 DNA 聚合酶选择性地灭活 Pol β。用14处理的 Pol β 胰蛋白酶消化物的 LC-MS/MS 分析鉴定了聚合酶结合位点内共价修饰的两个赖氨酸，其中一个先前被确定在DNA结合中起作用。荧光各向异性实验表明，用14预处理 Pol β可防止 DNA 结合。在野生型小鼠胚胎成纤维细胞 (MEF) 中使用前抑制剂 ( pro - 14 ) 的实验表明，抑制剂
• 7-(substituted)piperaziny
  申请人：American Cyanamid Company

  公开号：US04940710A1

  公开（公告）日：1990-07-10

  7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.

  7-(取代)哌嗪基-1-乙基-6-氟-4-氧代-3-喹啉羧酸，其药理上可接受的盐，含有它们的组合物，生产它们的过程和中间体，以及使用它们治疗温血动物细菌感染的方法。
• Process for preparing piperazinyl quinolone derivatives
  申请人：Korea Institute of Science and Technology

  公开号：US05051505A1

  公开（公告）日：1991-09-24

  A novel process for preparing piperazinyl quinolone derivatives of the formula (I) is disclosed. The process comprises reacting dihaloquinolones with piperazine derivatives and tetraalkyl ammonium halides in the presence of a polar solvent such as acetonitrile, dimethylformamide, pyridine, sulfolane and dimethyl sulfoxide. ##STR1##

  揭示了一种制备式(I)的哌嗪喹诺酮衍生物的新工艺。该工艺包括在极性溶剂（如乙腈、二甲基甲酰胺、吡啶、磺醚烷和二甲基亚砜）的存在下，将二卤喹诺酮与哌嗪衍生物和四烷基铵卤化物反应。

表征谱图