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CAS No.: | 173140-90-4 |
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Name: | 2(1H)-Quinolinone, 5-(2R)-oxiranyl-8-(phenylmethoxy)- |
Article Data: | 4 |
Molecular Structure: | |
Formula: | C18H15NO3 |
Molecular Weight: | 293.322 |
Synonyms: | 5-(2R)-2-Oxiranyl-8-benzyloxy-2(1H)-quinolinone; |
EINECS: | 1308068-626-2 |
Density: | 1.298 |
Boiling Point: | 556.0±50.0 °C(Predicted) |
PSA: | 54.62000 |
LogP: | 3.17840 |
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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; |
8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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With potassium carbonate In water; acetone for 2.5h; Product distribution / selectivity; Heating / reflux; |
8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
8-quinolinol
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
5-acetyl-8-hydroxyquinoline
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
1-(8-benzyloxyquinolin-5-yl)ethanone
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
5-Acetyl-8-benzyloxyquinoline-N-oxide
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
5-acetyl-8-hydroxyquinoline hydrochloride
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
benzyl bromide
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |
5-acetyl-8-benzyloxy-1H-quinolin-2-one
(R)-5-(2-oxiranyl)-8-benzyloxy-2(1H)-quinolinone
Conditions | Yield |
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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 |