110548-06-6

Basic information

• Product Name: ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate
• Synonyms: ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate;Levofloxacin Impurity 3
• CAS NO: 110548-06-6
• Molecular Formula: C15H13F2NO4
• Molecular Weight: 309.2648264
• Mol File: 110548-06-6.mol

Chemical Properties

• Melting Point: 254-255 °C(Solv: ethanol (64-17-5))
• Boiling Point: 442.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.43±0.1 g/cm3(Predicted)
• PKA: -3.62±0.60(Predicted)
• CAS DataBase Reference: ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate(110548-06-6)
• EPA Substance Registry System: ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate(110548-06-6)

Safety Data

• Hazardous Substances Data: 110548-06-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate is used as a potential pharmaceutical agent for [specific medical application, if known] due to its unique chemical structure and pharmacological properties. Its fluorine substitution and quinoline backbone may contribute to its interaction with biological targets, offering therapeutic benefits in treating certain diseases or conditions.
Used in Chemical Research:
In the field of chemical research, ethyl (R)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate serves as a valuable compound for studying the effects of structural modifications on the properties and activities of organic esters. Its synthesis and modification can provide insights into the development of new drugs and materials with improved efficacy and selectivity.

Upstream product

• 106939-33-7 (+)-ethyl 9,10-difluoro-2,3-dihydro-3-iodomethyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate 
• 110548-04-4 (-)-ethyl 2-<<<(R)-1-hydroxyprop-2-yl>amino>methylene>-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate 
• 103995-33-1 3-(2,3,4,5-tetrafluorophenyl)-3-oxo-2-(ethoxymethylene)-propanoic acid ethyl ester 
• 91040-39-0 (+/-)-9,10-difluoro-3-hydroxymethyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid ethyl ester 
• 106939-32-6 (+)-ethyl 9,10-difluoro-2,3-dihydro-3-hydroxymethyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate 
• 87-13-8 diethyl 2-ethoxymethylenemalonate 
• 112136-69-3 (R)-(+)-7,8-difluoro-3,4-dihydro-3-methyl-2H-[1,4]benzoxazine 
• 126872-13-7 (R)-diethyl (7,8-difluoro-2,3-dihydro-3-methyl-4H-[1,4]benzoxazin-4-yl)methylenemalonate 
• 100993-11-1 (R)-3-(3,5-Dinitro-benzoyloxymethyl)-8,9-difluoro-6-oxo-2,3-dihydro-6H-1-oxa-3a-aza-phenalene-5-carboxylic acid ethyl ester 
• 100986-91-2 (+/-)-ethyl 9,10-difluoro-2,3-dihydro-3-(3,5-dinitrobenzoyloxy)methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate 
• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 

Downstream Products

• 110548-07-7 (+)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid 
• 100986-86-5 (R)-ofloxacin 

Relevant articles and documents

Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation

A highly enantioselective organocatalytic transfer hydrogenation enabling the synthesis of both 6-fluoro-2-methyltetrahydroquinoline and 7,8-difluoro-3-methyl-benzoxazine has been developed. These key building blocks can for the first time be synthesized using the same methodology allowing fast and efficient, metal-free access to the antibiotic fluoroquinolones flumequine and levofloxacine.

Optically active benzoxazines and bezothiazines and a process for their stereospecific preparation

Optically active 7,8-difluoro-3,4-dihydro-3--methyl-2H-[1,4]benzoxazines and 7,8-difluoro-3,4-dihydro-2--methyl-2H-[1,4]benzoxazines and the corresponding benzothiazines of formula III, where, one of the substituents R1, R2, R3 and R4 is CH2OH or -CH2Z, the remaining being hydrogen, X denotes fluoro, chloro, methyl or hydrogen, Y is oxygen or sulfur and Z is hydrogen, fluoro or protected hydroxyl are obtained as the stereochemically pure products of a stereospecific synthesis using a 3,4-difluoronitrobenzene substituted with a stereochemically pure 2-(1-hydroxyisopropoxy), 2-(2--hydroxypropoxy), 2-(1-hydroxyisopropylthio) or 2-(2--hydroxypropylthio) substituent. The obtained compounds are suited for the production of optically active pyridobenzoxazines and pyridobenzothiazines, among which are useful antibacterial optically active quinolones, particularly (S)-(-)-ofloxacin.

Chiral DNA gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-py ido[1,2,3,-de]-1,4-benzoxazine-6-carboxylic acid (ofloxacin)

A short and efficient synthesis, starting with (R)- and (S)-alaninol, of the two optical antipodes of the quinolone antimicrobial agent ofloxacin has been devised. Testing in vitro of the products against a range of bacteria and in an assay system incorporating purified DNA gyrase from different bacterial species demonstrates that the S-(-) enantiomer is substantially the more active.