1-环丙基-6,7-二氟-1,4-二氢-4-氧喹啉-3-羧酸 | 93107-30-3

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: 1-环丙基-6,7-二氟-1,4-二氢-4-氧喹啉-3-羧酸
• 中文别名: Q酸；1-环丙基-6,7-二氟-4-氧-1,4-二氢喹啉-3-羧酸；1-环丙基-6,7-二氟-1,4-二氢-4-氧代喹啉-3-甲酸；1-环丙基-6,7-二氟-1,4-二氢-4-氧代-3-喹啉甲酸；BES-1
• 英文名称: 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid；1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 93107-30-3
• 化学式: C₁₃H₉F₂NO₃
• 分子量: 265.216
• InChiKey: KNEXGVPHPGXAGF-UHFFFAOYSA-N

物化性质

• 熔点：
  289°C(lit.)
• 沸点：
  434.2±45.0 °C(Predicted)
• 密度：
  1.630±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R62,R52/53
• 海关编码：
  2933499090
• 安全说明：
  S22,S36/37,S61
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline- Revision number: 5
3-carboxylic Acid
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Reproductive toxicity Category 2
ENVIRONMENTAL HAZARDS
Acute aquatic hazard Category 3
Long-term aquatic hazard Category 3
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Suspected of damaging fertility or the unborn child
Hazard statements
Harmful to aquatic life
Harmful to aquatic life with long lasting effects
Precautionary statements:
Obtain special instructions before use.
[Prevention]
Do not handle until all safety precautions have been read and understood.
Avoid release to the environment.
Use personal protective equipment as required.
[Response] IF exposed or concerned: Get medical advice/attention.
[Storage] Store locked up.
[Disposal] Dispose of contents/container through a waste management company authorized by
the local government.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid
Components:
Percent: >98.0%(LC)(T)
93107-30-3
CAS Number:
Chemical Formula: C13H9F2NO3
1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-
oxoquinoline-3-carboxylic Acid

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention.
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Get medical advice/attention.
Ingestion: Get medical advice/attention.Rinse mouth.
Protection of first-aiders: A rescuer should wear personal protective equipment, such as rubber gloves and air-
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep
Personal precautions,
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Advice on safe handling: Avoid all contact!
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Hand protection: Impervious gloves.
Safety goggles. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.
1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-
oxoquinoline-3-carboxylic Acid

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
Form: Crystal- Powder
White - Almost white
Colour:
Odour: No data available
pH: No data available
Melting point/freezing point:289°C
No data available
Boiling point/range:
Flash point: No data available
Flammability or explosive
limits:
No data available
Lower:
Upper: No data available
Relative density: No data available
Solubility(ies):
No data available
[Water]
[Other solvents]
Hot dimethylformamide(DMF)
Soluble:

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Hydrogen fluoride
products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
No data available
IARC =
NTP = No data available
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
Crustacea: No data available
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
Log Pow: No data available
Soil adsorption (Koc): No data available
Henry's Law No data available
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.
1-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-
oxoquinoline-3-carboxylic Acid

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

该化合物**1-环丙基-6,7-二氟-1,4-二氢-4-氧代-3-喹啉甲酸**是一种羧酸类有机物，常被用作合成盐酸贝西沙星的中间体。

反应信息

• 作为反应物：
  描述：

  1-环丙基-6,7-二氟-1,4-二氢-4-氧喹啉-3-羧酸 以 水 为溶剂， 生成 环丙沙星
  参考文献：
  名称：

  Preparation of quinolinecarboxylic acids

  摘要：

  将##STR1##与胺##STR2##反应，得到化合物的结构式为##STR3##。由于起始物(I)的7-位上有F而不是Cl，因此反应在相对较低的温度下进行，最小化了副反应。

  公开号：

  US05155223A1
• 作为产物：
  描述：

  氧氟沙星 在 三乙醇胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 1-环丙基-6,7-二氟-1,4-二氢-4-氧喹啉-3-羧酸
  参考文献：
  名称：

  Process for making antimicrobial compounds

  摘要：

  本发明提供了一种制备具有如下式（I）的结构的化合物的方法##STR1##其中A.sup.1、A.sup.2和A.sup.3独立地为碳或氮，R.sup.1、R.sup.3、R.sup.4和R.sup.6为已知的喹诺酮取代基；其中R.sup.1、R.sup.3或R.sup.6中的一个可以是含有内酰胺的基团；或其保护形式、盐、药用可接受盐、生物水解酯或其溶剂合物；所述方法包括将一个或多个有机硅化合物与具有如下式（II）的结构的化合物反应##STR2##其中A.sup.1、A.sup.2和A.sup.3、R.sup.1、R.sup.3、R.sup.4和R.sup.6如上所述；其中R.sup.1、R.sup.3或R.sup.6中的一个可以是含有内酰胺的基团；X为脱离基团；或其保护形式、盐、生物水解酯或其溶剂合物。根据本发明的方法制备的化合物本身可用作抗微生物药物，或可用作制备其他含喹诺酮的抗微生物药物的中间体。

  公开号：

  US05703231A1

文献信息

• Structure−Activity Relationships of the Quinolone Antibacterials against Mycobacteria:  Effect of Structural Changes at N-1 and C-7
  作者：Thomas E. Renau、Joseph P. Sanchez、Jeffrey W. Gage、Julie A. Dever、Martin A. Shapiro、Stephen J. Gracheck、John M. Domagala

  DOI：10.1021/jm9507082

  日期：1996.1.1

  smegmatis as well as Gram-negative and Gram-positive bacteria. The activity of the compounds against M. fortuitum was used as a barometer of M. tuberculosis activity. The results demonstrate that (i) the activity against mycobacteria was related more to antibacterial activity than to changes in the lipophilicity of the compounds, (ii) the antimycobacterial activity imparted by the N-1 substituent was in the

  对常规药物治疗有抵抗力的结核感染的再次出现表明需要针对结核分枝杆菌的替代化学疗法。作为优化针对结核分枝杆菌的喹诺酮类抗菌药物研究的一部分，我们准备了一系列N-1-和C-7取代的喹诺酮类化合物，以研究这两个位置上喹诺酮类修饰物与活性之间的特定结构-活性关系。对抗分枝杆菌。通过文献方法合成的化合物被评估了对福分枝杆菌和耻垢分枝杆菌以及革兰氏阴性和革兰氏阳性细菌的活性。化合物对堡垒分枝杆菌的活性用作结核分枝杆菌活性的晴雨表。
• Drug efflux pump inhibitor
  申请人：DAIICHI PHARMACEUTICAL CO., LTD

  公开号：US20030092720A1

  公开（公告）日：2003-05-15

  A medicament for preventive and/or therapeutic treatment of a microbial infection which comprises as an active ingredient a compound represented by the following general formula (I): 1 wherein, R 1 and R 2 represent hydrogen atom, a halogen atom, hydroxyl group or the like, W 1 represents —CH═CH—, —CH 2 O—, —CH 2 CH 2 — or the like; R 3 represents hydrogen atom, a halogen atom, hydroxyl group or an amino group; R 4 represents hydrogen atom, a group of —OZ 0-4 R 5 (Z 0-4 represents an alkylene group, a fluorine-substituted alkylene group or a single bond, and R 5 represents a cyclic alkyl group, an aryl group or the like); W 2 represents a single bond or —C(R 8 )═C(R 9 )— (R 8 and R 9 represent hydrogen atom, a halogen atom, a lower alkyl group or the like, Q represents an acidic group, but W 2 and Q may together form vinylidenethiazolidinedione or an equivalent heterocyclic ring; m and n represent an integer of 0 to 2, and q represents an integer of 0 to 3.

  一种用于预防和/或治疗微生物感染的药物，其活性成分表示为以下一般式(I)的化合物： 其中，R1和R2代表氢原子、卤素原子、羟基或类似物，W1代表—CH═CH—、—CH2O—、—CH2CH2—或类似物；R3代表氢原子、卤素原子、羟基或氨基；R4代表氢原子、—OZ0-4R5（Z0-4代表烷基链、氟取代的烷基链或单键，R5代表环烷基、芳基或类似物）；W2代表单键或—C(R8)═C(R9)—（R8和R9代表氢原子、卤素原子、较低烷基或类似物，Q代表酸性基团，但W2和Q可以共同形成乙烯基噻唑二酮或等效的杂环环；m和n代表0到2的整数，q代表0到3的整数。
• Azabicyclo quinolone and naphthyridinone carboxylic acids
  申请人：Pfizer Inc

  公开号：US05164402A1

  公开（公告）日：1992-11-17

  Quinolone carboxylic acids 7-substituted by azabicyclo groups have antibacterial activity.

  喹诺酮羧酸7位被氮杂双环基团取代的化合物具有抗菌活性。
• Synthesis and structure-activity relationships of new 7-[3-(fluoromethyl)piperazinyl]- and -(fluorohomopiperazinyl)quinolone antibacterials
  作者：Carl B. Ziegler、P. Bitha、N. A. Kuck、T. J. Fenton、P. J. Petersen、Y. I. Lin

  DOI：10.1021/jm00163a024

  日期：1990.1

  6-fluoro-7-substituted-1,4-dihydro-4-oxoquinoline-3-carboxylic acids have been prepared. At the N-1 position "standard" substitution was employed with the ethyl, cyclopropyl, and p-fluorophenyl groups being used. At C-7 the introduction of some novel piperazines was made. Most notably, 2-(fluoromethyl)piperazine (10) and hexahydro-6-fluoro-1H-1,4-diazepine (16, fluorohomopiperazine) at the quinolone C-7 position

  已经制备了一些新颖的6-氟-7-取代的1，4-二氢-4-氧代喹啉-3-羧酸。在N-1位置，使用“标准”取代，使用乙基，环丙基和对氟苯基。在C-7中，引入了一些新颖的哌嗪。最值得注意的是，喹诺酮C-7位的2-（氟甲基）哌嗪（10）和六氢-6-氟-1H-1,4-二氮杂卓（16，氟高哌嗪）产生的产品具有与环丙沙星参考品相似的体外抗菌活性。1-环丙基-6-氟-7- [3-（氟甲基）哌嗪基] -1,4-二氢-4-氧喹啉-3-羧酸（20）的体内疗效优于环丙沙星（20） 2）。
• Process for preparing 2-chloro-4,5-difluorobenzoic acid
  申请人：American Cyanamid Company

  公开号：US04833270A1

  公开（公告）日：1989-05-23

  This disclosure describes a novel process for preparing 2-chloro-4,5-difluorobenzoic acid which is useful in the preparation of 7-(substituted)piperazinyl-1-substituted-6-fluoro-1,4-dihydro-4-oxo-3-quin oli necarboxylic acid antibacterial agents.

  这份披露描述了一种新颖的制备2-氯-4,5-二氟苯甲酸的过程，该过程在制备7-(取代)piperazinyl-1-取代-6-氟-1,4-二氢-4-氧-3-喹啉羧酸抗菌剂中很有用。