2,3-Dehydro Ofloxacin

Base Information

• Chemical Name: 2,3-Dehydro Ofloxacin
• CAS No.: 115841-55-9
• Molecular Formula: C18H18FN3O4
• Molecular Weight: 359.3516232
• DSSTox Substance ID: DTXSID80554319
• Nikkaji Number: J340.586I
• Mol file: 115841-55-9.mol

Synonyms:2,3-Dehydro Ofloxacin;115841-55-9;7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-2,5(13),6,8,11-pentaene-11-carboxylic acid;9-Fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylic Acid;dehydroofloxacin;SCHEMBL9461276;DTXSID80554319;9-Fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid

Chemical Property of 2,3-Dehydro Ofloxacin

Chemical Property:

• PSA: 78.40000
• LogP: 1.94610
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 359.12813423
• Heavy Atom Count: 26
• Complexity: 686

Purity/Quality:

95% ^*data from raw suppliers

2,3-Dehydro ofloxacin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=COC2=C3N1C=C(C(=O)C3=CC(=C2N4CCN(CC4)C)F)C(=O)O
• Uses: 2,3-Dehydro analog of antibacterial agent Ofloxacin, showing diminished antimicrobial activity to its parent compound.

Technology Process of 2,3-Dehydro Ofloxacin

There total 7 articles about 2,3-Dehydro Ofloxacin 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: 79.0%

1-methyl-piperazine (109-01-3) + 9,10-difluoro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid (115841-54-8) → 2,3-dehydroofloxacin (115841-55-9)

Guidance literature:

In dimethyl sulfoxide; at 70 ℃; for 16h;

DOI:10.1002/jhet.5570270561

Reference yield:

ethyl 2-(ethoxymethylene)-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (94714-58-6) → 2,3-dehydroofloxacin (115841-55-9)

Guidance literature:

Multi-step reaction with 6 steps

1: aq. ethanol / 2 h / 0 °C

2: 95 percent / NaH / 1,2-dimethoxy-ethane / 1 h / 0 °C

3: 1.) O₃ 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 1h 2.) -78 deg C --> RT

4: NaH / dimethylformamide / 30 °C

5: 80 percent / 2N aq. HCl / tetrahydrofuran / 5 h / Heating

6: 79 percent / dimethylsulfoxide / 16 h / 70 °C

With hydrogenchloride; dimethylsulfide; sodium hydride; ozone; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570270561

Reference yield:

ethyl 9,10-difluoro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate (130713-36-9) → 2,3-dehydroofloxacin (115841-55-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / 2N aq. HCl / tetrahydrofuran / 5 h / Heating

2: 79 percent / dimethylsulfoxide / 16 h / 70 °C

With hydrogenchloride; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1002/jhet.5570270561

upstream raw materials:

1-methyl-piperazine

9,10-difluoro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylic acid

ethyl 2-(ethoxymethylene)-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate

ethyl 9,10-difluoro-3-methyl-7-oxo-7H-pyrido<1,2,3-de><1,4>benzoxazine-6-carboxylate