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8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one

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Name

8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one

EINECS 1308068-626-2
CAS No. 173140-90-4 Density 1.298
PSA 54.62000 LogP 3.17840
Solubility N/A Melting Point N/A
Formula C18H15NO3 Boiling Point 556.0±50.0 °C(Predicted)
Molecular Weight 293.322 Flash Point N/A
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 173140-90-4 (2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)-) Hazard Symbols N/A
Synonyms

5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone;

Article Data 4

8-benzoxy-5-(R)-oxiranyl-1H-quinolin-2-one Synthetic route

8-(phenylmethoxy)-5-((R)-2-chloro-1-hydroxy-ethyl)-(1H)-quinolin-2-one

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
With potassium carbonate In water; acetone for 5 - 10h; Heating / reflux;
With potassium carbonate In water; acetone for 5 - 10h; Heating / reflux;
With potassium carbonate In water; butanone Product distribution / selectivity; Heating / reflux;
With potassium carbonate In water; acetone Product distribution / selectivity; Heating / reflux;
530084-79-8

8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
With potassium carbonate In water; acetone for 2.5h; Product distribution / selectivity; Heating / reflux;
100331-89-3

8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Stage #1: 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one With dimethylsulfide borane complex; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole In tetrahydrofuran; toluene at 0 - 2℃; for 1.75h;
Stage #2: With piperidine; water In tetrahydrofuran; toluene at 0 - 2℃; for 1h; Product distribution / selectivity;
Multi-step reaction with 2 steps
1.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
1.2: 0.25 - 0.33 h
2.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
148-24-3

8-quinolinol

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 1,2-dichloro-ethane / 2.25 - 2.33 h / 30 °C
1.2: 15.25 - 16.33 h / 25 - 70 °C
1.3: 0.25 - 0.33 h / 0 - 30 °C
2.1: hydrogenchloride; water / 0.25 - 0.33 h
3.1: potassium carbonate / acetone / 14 h / Heating / reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
5.1: acetic anhydride / 2 h / 25 - 40 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
6.2: 4.5 h / Heating / reflux
6.3: 30 °C / pH 8 - 9
7.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
7.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 8 steps
1.1: 1,2-dichloro-ethane / 2.25 - 2.33 h / 30 °C
1.2: 15.25 - 16.33 h / 25 - 70 °C
1.3: 0.25 - 0.33 h / 0 - 30 °C
2.1: hydrogenchloride; water / 0.25 - 0.33 h
3.1: potassium carbonate / acetone / 14 h / Heating / reflux
4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
5.1: acetic anhydride / 2 h / 25 - 40 °C
6.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
6.2: 4.5 h / Heating / reflux
6.3: 30 °C / pH 8 - 9
7.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
7.2: 0.25 - 0.33 h
8.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
2598-31-4

5-acetyl-8-hydroxyquinoline

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
5.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
5.2: 0.25 - 0.33 h
6.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
26872-48-0

1-(8-benzyloxyquinolin-5-yl)ethanone

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
2.1: acetic anhydride / 2 h / 25 - 40 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
3.2: 4.5 h / Heating / reflux
3.3: 30 °C / pH 8 - 9
4.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
4.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 5 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
2.1: acetic anhydride / 2 h / 25 - 40 °C
3.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
3.2: 4.5 h / Heating / reflux
3.3: 30 °C / pH 8 - 9
4.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
4.2: 0.25 - 0.33 h
5.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
100331-93-9

5-Acetyl-8-benzyloxyquinoline-N-oxide

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic anhydride / 2 h / 25 - 40 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
2.2: 4.5 h / Heating / reflux
2.3: 30 °C / pH 8 - 9
3.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
3.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 4 steps
1.1: acetic anhydride / 2 h / 25 - 40 °C
2.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
2.2: 4.5 h / Heating / reflux
2.3: 30 °C / pH 8 - 9
3.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
3.2: 0.25 - 0.33 h
4.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
57434-96-5

5-acetyl-8-hydroxyquinoline hydrochloride

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogenchloride; water / 0.25 - 0.33 h
2.1: potassium carbonate / acetone / 14 h / Heating / reflux
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
4.1: acetic anhydride / 2 h / 25 - 40 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
5.2: 4.5 h / Heating / reflux
5.3: 30 °C / pH 8 - 9
6.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
6.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 7 steps
1.1: hydrogenchloride; water / 0.25 - 0.33 h
2.1: potassium carbonate / acetone / 14 h / Heating / reflux
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
4.1: acetic anhydride / 2 h / 25 - 40 °C
5.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
5.2: 4.5 h / Heating / reflux
5.3: 30 °C / pH 8 - 9
6.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
6.2: 0.25 - 0.33 h
7.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
100-39-0

benzyl bromide

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
5.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 6 steps
1.1: potassium carbonate / acetone / 14 h / Heating / reflux
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 3.5 h / 20 - 30 °C
3.1: acetic anhydride / 2 h / 25 - 40 °C
4.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
4.2: 4.5 h / Heating / reflux
4.3: 30 °C / pH 8 - 9
5.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
5.2: 0.25 - 0.33 h
6.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
93609-84-8

5-acetyl-8-benzyloxy-1H-quinolin-2-one

173140-90-4

(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
1.2: 4.5 h / Heating / reflux
1.3: 30 °C / pH 8 - 9
2.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.75 h / 0 - 2 °C
2.2: 1 h / 0 - 2 °C
View Scheme
Multi-step reaction with 3 steps
1.1: boron trifluoride diethyl etherate / dichloromethane / Heating / reflux
1.2: 4.5 h / Heating / reflux
1.3: 30 °C / pH 8 - 9
2.1: dimethylsulfide borane complex / (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 3.25 - 3.33 h / 0 - 2 °C
2.2: 0.25 - 0.33 h
3.1: potassium carbonate / water; acetone / 2.5 h / Heating / reflux
View Scheme
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