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Basic Information
CAS No.: 123447-62-1
Name: Prulifloxacin
Article Data: 9
Molecular Structure:
Molecular Structure of 123447-62-1 (Prulifloxacin)
Formula: C21H20FN3O6S
Molecular Weight: 461.471
Synonyms: 1H,4H-[1,3]Thiazeto[3,2-a]quinoline-3-carboxylic acid,6-fluoro-1-methyl-7-[4-[(5-methyl- 2-oxo-1,3-dioxol-4-yl)methyl]-1- piperazinyl]-4-oxo-;PUFX;(+-)-7-(4-((Z)-2,3-Dihydroxy-2-butenyl)-1-piperazinyl)-6-fluoro-1-methyl-4-oxo-1H,4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic acid, cyclic carbonate;Sword;Sword (TN);
EINECS: 819-932-1
Density: 1.62 g/cm3
Melting Point: 211-214°C
Boiling Point: 633.2 °C at 760 mmHg
Flash Point: 336.8 °C
Solubility: Slightly soluble in dimethyl formamide, 0.1M NaOH or glacial acetic acid; insoluble in water or methanol
Appearance: Yellow or slightly yellow power
PSA: 134.43000
LogP: 2.64270
Related products
Synthetic route
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

112984-60-8

ulifloxacin

123447-62-1

prulifloxacin

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 5h; Large scale;95.4%
With potassium hydrogencarbonate In N,N-dimethyl-formamide for 5h; Ambient temperature;62%
Stage #1: ulifloxacin With potassium hydrogencarbonate In acetonitrile at 25 - 30℃;
Stage #2: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one at 15 - 30℃; for 27 - 28.25h;
Stage #1: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one; ulifloxacin With potassium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 28℃; for 3 - 4h;
Stage #2: With hydrogenchloride In chloroform; water for 0.25h; pH=0.8 - 1.0;
Stage #1: ulifloxacin With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 0.166667h;
Stage #2: 4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one In acetonitrile at 10 - 30℃; for 21h; Product distribution / selectivity;
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

112984-60-8

ulifloxacin

A

123447-62-1

prulifloxacin

B

156834-57-0

6-fluoro-1-methyl-4-oxo-7-<4-<(2-oxo-1-methylenepropyl)oxycarbonyl>-1-piperazinyl>-4H-<1,3>thiazeto<3,2-a>quinoline-3-carboxylic acid

C

7-<4-<1-<4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinolin-7-yl)>-1-piperazinylmethyl>-2-oxopropoxycarbonyl>-1-piperazinyl>-6-fluoro-1-methyl-4-oxo-4H-<1,3>thazeto<3,2-a>quinoline-3-carboxylic acid

D

1,1-bis<(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl>-4-(3-carboxy-6-fluoro-1-methyl-4-oxo-4H-<1,3>thiazeto<3,2-a>quinoline-7-yl)-1-piperazinium bromide

Conditions
ConditionsYield
With potassium hydrogencarbonate In N,N-dimethyl-formamide at 30℃; for 2h; Product distribution; Rate constant; various periods of time (3 h); activation energy 29.1 kJ mol-1;A 93.6 % Spectr.
B 2.0 % Spectr.
C 0.5 % Spectr.
D 1.1 % Spectr.
...Expand
80715-22-6

4-bromomethyl-1,3-dioxa-5-methylcyclopentene-2-one

112984-60-8

ulifloxacin

A

123447-62-1

prulifloxacin

B

6-Fluoro-1-methyl-7-[4-(5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl)-piperazin-1-yl]-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid 5-methyl-2-oxo-[1,3]dioxol-4-ylmethyl ester

Conditions
ConditionsYield
With potassium hydrogencarbonate for 3h; Product distribution; also in presence of DIPEA, car. concn. of substrates;
...Expand
80841-78-7

4-chloromethyl-5-methyl-1,3-dioxol-2-one

112984-60-8

ulifloxacin

123447-62-1

prulifloxacin

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; sodium bromide 1.) DMF, 303 K, 2 h, 2.) DMF, 304 K, 1 h; Yield given. Multistep reaction;
113028-75-4

3,4-difluorophenyl isothiocyanate

123447-62-1

prulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h
2: 2.22 g / K2CO3 / dimethylformamide / 1 h / 70 °C
3: 0.350 g / PPE / 1.5 h / 80 °C
4: 84 percent / dimethylformamide / Ambient temperature
5: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
6: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h
2: dimethylformamide / 1.) 0 deg C, 1.5 h, 2.) RT, 2 h
3: 58 percent / diphenyl ether / 5 h / 240 °C
4: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature
5: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C
6: 84 percent / dimethylformamide / Ambient temperature
7: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
8: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
84339-06-0

ethyl 7,6-difluoro-4-hydroxy-2-mercaptoquinoline-3-carboxylate

123447-62-1

prulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C
2: 84 percent / dimethylformamide / Ambient temperature
3: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
4: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
144514-15-8

3,4-difluorophenyl dithiocarbamic acid triethylammonium

123447-62-1

prulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: ethyl chloroformate, triethylamine / CHCl3 / 3.5 h / Ambient temperature
2: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h
3: 2.22 g / K2CO3 / dimethylformamide / 1 h / 70 °C
4: 0.350 g / PPE / 1.5 h / 80 °C
5: 84 percent / dimethylformamide / Ambient temperature
6: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
7: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
Multi-step reaction with 9 steps
1: ethyl chloroformate, triethylamine / CHCl3 / 3.5 h / Ambient temperature
2: 1.) KOH / 1.) dioxane, RT, 30 min., 2.) 4 deg C, 15 h
3: dimethylformamide / 1.) 0 deg C, 1.5 h, 2.) RT, 2 h
4: 58 percent / diphenyl ether / 5 h / 240 °C
5: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature
6: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C
7: 84 percent / dimethylformamide / Ambient temperature
8: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
9: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
113046-72-3

ethyl 6,7-difluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate

123447-62-1

prulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / dimethylformamide / Ambient temperature
2: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
3: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
113028-77-6

ethyl 6,7-difluoro-4-hydroxy-2-<(methoxymethyl)thio>-quinoline-3-carboxylate

123447-62-1

prulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / 35percent HCl / ethanol / 2 h / Ambient temperature
2: 47 percent / K2CO3, KI / dimethylformamide / 0.5 h / 105 - 110 °C
3: 84 percent / dimethylformamide / Ambient temperature
4: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
5: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
144514-35-2

3-(3,4-difluorophenyl)-4-methyl<1,3>thiazetidin-2-ylidenemalonate

123447-62-1

prulifloxacin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 0.350 g / PPE / 1.5 h / 80 °C
2: 84 percent / dimethylformamide / Ambient temperature
3: 88 percent / KOH / 2-methyl-propan-2-ol; H2O / 1 h / 50 - 60 °C
4: 62 percent / KHCO3 / dimethylformamide / 5 h / Ambient temperature
View Scheme
Raw Materials
80715-22-6
3863-11-4
113028-75-4
80841-78-7
112984-60-8
113046-72-3
113028-17-4
113028-77-6
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  • Prulifloxacin CAS:123447-62-1

  • Casno:

    123447-62-1

    Prulifloxacin CAS:123447-62-1

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Chemistry

Molecular Structure of Prulifloxacin (CAS NO.123447-62-1):

IUPAC Name: (1R)-6-fluoro-1-methyl-7-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]piperazin-1-yl]-4-oxo-1H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid 
CAS Registry Number 123447-62-1
Molecular Formula:C21H20FN3O6S
Molecular Weight:461.46
H bond acceptors: 9
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 113.92 Å2
Molar Volume: 283.5 cm3
Surface Tension: 82 dyne/cm
Index of Refraction: 1.72
Surface Tension: 82 dyne/cm
Density: 1.62 g/cm3
Flash Point: 336.8 °C
Enthalpy of Vaporization:  98.39 kJ/mol
Boiling Point:  633.2 °C at 760 mmHg
Vapour Pressure:  6.62E-17 mmHg at 25°C
Product Categories: API
Solubility: Slightly soluble in dimethyl formamide, 0.1M NaOH or glacial acetic acid; insoluble in water or methanol
Appearance: Yellow or slightly yellow power
InChI
InChI=1/C21H20FN3O6S/c1-10-16(31-21(29)30-10)9-23-3-5-24(6-4-23)15-8-14-12(7-13(15)22)18(26)17(20(27)28)19-25(14)11(2)32-19/h7-8,11H,3-6,9H2,1-2H3,(H,27,28)
Smiles
o1c(oc(CN2CCN(CC2)c2c(cc3c(c2)n2c(c(c3=O)C(O)=O)S[C@@H]2C)F)c1C)=O

Specification

 Prulifloxacin , its cas register number is 123447-62-1. It also can be called (+/-)-7-{4-[(Z)-2,3-Dihydroxy-2-butenyl]-1-piperazinyl}-6-fluoro-1-methyl-4-oxo-1H,4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid cyclic carbonate ; 6-Fluoro-1-methyl-7-(4-(5-methyl-2-oxo-1,3-dioxelen-4-yl)methyl-1-piperazinyl)-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic acid , it can be used as gatifloxacin for the whole synthetic antibacterial drugs.