(R)-Flumequine

Base Information

• Chemical Name: (R)-Flumequine
• CAS No.: 215178-95-3
• Molecular Formula: C₁₄H₁₂FNO₃
• Molecular Weight: 261.253
• UNII: RQ67033LRC
• Nikkaji Number: J1.113.735K
• Wikidata: Q27158449
• ChEMBL ID: CHEMBL1572972
• Mol file: 215178-95-3.mol

Synonyms:(R)-Flumequine;Flumequine, (R)-;215178-95-3;RQ67033LRC;UNII-RQ67033LRC;CHEBI:85273;1H,5H-Benzo(ij)quinolizine-2-carboxylic acid, 9-fluoro-6,7-dihydro-5-methyl-1-oxo-, (5R)-;(12~{R})-7-fluoranyl-12-methyl-4-oxidanylidene-1-azatricyclo[7.3.1.0^{5,13}]trideca-2,5(13),6,8-tetraene-3-carboxylic acid;(12R)-7-fluoro-12-methyl-4-oxo-1-azatricyclo[7.3.1.05,13]trideca-2,5,7,9(13)-tetraene-3-carboxylic acid;CAS-42835-25-6;CHEMBL1572972;NCGC00016852-01;NCGC00018211-01;NCGC00018211-07;Q27158449;(5R)-9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid;7X9

Chemical Property of (R)-Flumequine

Chemical Property:

• Melting Point: 249-252 °C(Solv: N,N-dimethylformamide (68-12-2))
• Boiling Point: 439.7±45.0 °C(Predicted)
• PKA: 5.70±0.40(Predicted)
• Density: 1.45±0.1 g/cm3(Predicted)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 261.08012141
• Heavy Atom Count: 19
• Complexity: 462

Purity/Quality:

90%+ ^*data from raw suppliers

(R)-Flumequine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC2=C3N1C=C(C(=O)C3=CC(=C2)F)C(=O)O
• Isomeric SMILES: C[C@@H]1CCC2=C3N1C=C(C(=O)C3=CC(=C2)F)C(=O)O
• Uses: (R)-Flumequine, an isomer of Flumequine (F445000), a fluorinated quinolone antibacterial.

Technology Process of (R)-Flumequine

There total 6 articles about (R)-Flumequine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.4%

9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester (233765-85-0) → R-(+)-flumequine (215178-95-3,202349-45-9)

Guidance literature:

With water; at 100 ℃; for 3h;

DOI:10.1016/S0957-4166(99)00071-3

Reference yield:

(R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (199186-69-1) → R-(+)-flumequine (215178-95-3,202349-45-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.1 percent / 2.5 h / 125 °C

2: 80.5 percent / polyphosphoric acid / toluene / 6 h / 110 °C

3: 75.4 percent / H₂O / 3 h / 100 °C

With PPA; water; In toluene;

DOI:10.1016/S0957-4166(99)00071-3

Reference yield:

flumequine (42835-25-6,202349-45-9) → R-(+)-flumequine (215178-95-3,202349-45-9) + S-(-)-flumequine (202349-45-9)

Guidance literature:

With Chiralpak OD-H; In ethanol; hexane; Resolution of racemate;

DOI:10.1002/chir.22625

upstream raw materials:

9-fluoro-5-methyl-1-oxo-6,7-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-2-carboxylic acid ethyl ester

6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline

(R)-6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline

2-(6-fluoro-2-methyl-3,4-dihydro-2H-quinolin-1-ylmethylene)-malonic acid diethyl ester

Refernces

• 1、 Ali, Imran,Suhail, Mohd,Asnin, Leonid. "Chiral separation and modeling of quinolones on teicoplanin macrocyclic glycopeptide antibiotics CSP". . p. 1304 - 1311. Retrieved 2018/10/24.
• 2、 Rueping, Magnus,Stoeckel, Mirjam,Sugiono, Erli,Theissmann, Thomas. "Asymmetric metal-free synthesis of fluoroquinolones by organocatalytic hydrogenation". experimental part. p. 6565 - 6568. Retrieved 2010/10/19.