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CAS No. : | 20151-46-6 | MDL No. : | MFCD13179101 |
Formula : | C10H11NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SNPPISFHRFQHLP-UHFFFAOYSA-N |
M.W : | 161.20 | Pubchem ID : | 10702124 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.51 |
TPSA : | 29.1 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.27 cm/s |
Log Po/w (iLOGP) : | 1.78 |
Log Po/w (XLOGP3) : | 1.43 |
Log Po/w (WLOGP) : | 1.31 |
Log Po/w (MLOGP) : | 1.76 |
Log Po/w (SILICOS-IT) : | 2.57 |
Consensus Log Po/w : | 1.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.11 |
Solubility : | 1.25 mg/ml ; 0.00776 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.65 |
Solubility : | 3.64 mg/ml ; 0.0226 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.54 |
Solubility : | 0.0461 mg/ml ; 0.000286 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.56 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P270-P271-P272-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P321-P330-P333+P313-P337+P313-P362-P403+P233-P405-P501 | UN#: | N/A |
Hazard Statements: | H302-H315-H317-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminium trichloride at 100℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | In toluene at 200℃; for 36h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
N-o-Tolyl-3-chlor-propionylchlorid, AlCl3, 100grad, neben 3,4-Dihydro-8-methyl-carbostyril; | ||
5-Methyl-carbostyril, H2, Pd/C, in A.; | ||
5-Methyl-chinolin 1. NaNH2, in Dimethylanilin, Δ 2. H2O; |
(yield)geringe Menge; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With palladium on activated charcoal; ethanol Hydrogenation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Schmelzen; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6% | With hydrogenchloride; NaH In N,N-dimethyl-formamide | 1-(3-Chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one and 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one 1-(3-Chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one and 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one Neat 2-chloro-N-m-tolylacetamide (92LH85) (1.7 g, 8.5 mmol) was heated to 135° C. and AlCl3 (3.4 mg, 26 mmol) was added under an Argon atmosphere, in small portions, during 30 min. The reaction was allowed cool to 60° C. and then HCl (10 mL, 4 M) was added. The mixture was extracted with EtOAc (2*30 mL) and the combined organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2; CH2Cl2/MeOH 9:1) to yield The compound 7-Methyl-3,4-dihydro-1H-quinolin-2-one and 5-Methyl-3,4-dihydro-1H-quinolin-2-one (1.1 g). This mixture was dissolved in dry DMF(8 mL) and NaH (60% in oil, 310 mg, 7.7 mmol) was added and the solution was stirred under a N2 atmosphere at rt for 45 min. Thereafter, 1-bromo-3-chloropropan was added and the reaction was stirred overnight at rt. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (10 mL). The organic phase was dried over Na2SO4 filtered, concentrated under reduced pressure and the residue was purified by prep RP-HPLC to yield 1-(3-chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one (0.057 g, 3%) and 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one (0.12 g, 6%). 1-(3-Chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one, (107LH27-11.7). Retention time=11.7 min. 1H NMR (CD3OD) δ7.12 (vbrt, 7.7 Hz, 1H), 6.98 (d, J=8.0 Hz, 1H), 6.90 (d, J=7.2 Hz, 1H), 4.09-4.02 (m, 2H), 3.59 (t, J=6.4 Hz, 2H), 2.85-2.78 (m, 2H), 2.58-2.50 (m, 2H), 2.27 (s, 3H), 2.10-2.01 (m, 2H); 13C NMR (CD3OD) δ171.5 135.9, 126.9, 125.4, 125.3, 113.1, 42.2, 40.1, 31.1, 30.3, 21.2, 18.5. 1-(3-Chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one, (107LH27-13.1). Retention time =13.1 min. 1H NMR (CD3OD) δ7.02 (brd, J=7.6 Hz, 1H), 6.94 (brs, 1H), 6.81 (brd, J=7.6 Hz, 1H), 4.03 (brt, J=7.2 Hz, 2H), 3.58 (t, J=6.2 Hz, 2H), 2.78 (t, J=7.4 Hz, 2H), 2.51 (t, J=7.4 Hz), 2.30 (s, 3H), 2.09-2.00 (m, 2H); 13C NMR (CD3OD) δ171.6, 139.0, 137.4, 127.8, 123.9, 115.7, 42.3, 39.8, 31.7, 30.3, 24.6, 20.4. |
6% | With hydrogenchloride; NaH In N,N-dimethyl-formamide | 1 1-(3-Chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one and 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one 1-(3-Chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one and 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one Neat 2-chloro-N-m-tolylacetamide (92LH85) (1.7 g, 8.5 mmol) was heated to 135° C. and AlCl3 (3.4 mg, 26 mmol) was added under an Argon atmosphere, in small portions, during 30 min. The reaction was allowed cool to 60° C. and then HCl (10 mL, 4 M) was added. The mixture was extracted with EtOAc (2*30 mL) and the combined organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2; CH2Cl2/MeOH 9:1) to yield The compound 7-Methyl-3,4-dihydro-1H-quinolin-2-one and 5-Methyl-3,4-dihydro-1H-quinolin-2-one (1.1 g). This mixture was dissolved in dry DMF(8 mL) and NaH (60% in oil, 310 mg, 7.7 mmol) was added and the solution was stirred under a N2 atmosphere at rt for 45 min. Thereafter, 1-bromo-3-chloropropan was added and the reaction was stirred overnight at rt. The reaction mixture was diluted with EtOAc (50 mL) and washed with water (10 mL). The organic phase was dried over Na2SO4 filtered, concentrated under reduced pressure and the residue was purified by prep RP-HPLC to yield 1-(3-chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one (0.057 g, 3%) and 1-(3-chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one (0.12 g, 6%). 1-(3-Chloropropyl)-5-methyl-3,4-dihydro-1H-quinolin-2-one, (107LH27-11.7). Retention time=11.7 min. 1H NMR (CD3OD) δ 7.12 (vbrt, 7.7 Hz, 1H), 6.98 (d, J=8.0 Hz, 1H), 6.90 (d, J=7.2 Hz, 1H), 4.09-4.02 (m, 2H), 3.59 (t, J=6.4 Hz, 2H), 2.85-2.78 (m, 2H), 2.58-2.50 (m, 2H), 2.27 (s, 3H), 2.10-2.01 (m, 2H); 13C NMR (CD3OD) δ 171.5, 139.2, 135.9, 126.9, 125.4, 125.3, 113.1, 42.2, 40.1, 31.1, 30.3, 21.2, 18.5. 1-(3-Chloropropyl)-7-methyl-3,4-dihydro-1H-quinolin-2-one, (107LH27-13.1). Retention time=13.1 min. 1H NMR (CD3OD) δ 7.02 (brd, J=7.6 Hz, 1H), 6.94 (brs, 1H), 6.81 (brd, J=7.6 Hz, 1H), 4.03 (brt, J=7.2 Hz, 2H), 3.58 (t, J=6.2 Hz, 2H), 2.78 (t, J=7.4 Hz, 2H), 2.51 (t, J=7.4 Hz), 2.30 (s, 3H), 2.09-2.00 (m, 2H); 13C NMR (CD3OD) δ 171.6, 139.0, 137.4, 127.8, 123.9, 115.7, 42.3, 39.8, 31.7, 30.3, 24.6, 20.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dodecacarbonyl-triangulo-triruthenium; tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide; toluene at 20 - 120℃; for 6.08h; Sealed tube; Overall yield = 90 %; regioselective reaction; | ||
With dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl acetamide; chlorobenzene at 20 - 120℃; Sealed tube; Overall yield = 95 %; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate / tetrahydrofuran; water / 16 h / Reflux 2: dodecacarbonyl-triangulo-triruthenium / chlorobenzene; N,N-dimethyl acetamide / 20 - 120 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: aluminum (III) chloride / 6 h / 140 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With aluminum (III) chloride at 140℃; for 6h; | Step B: 5-methyl-3.4-dihydroiuinolin-2(1H)-one Step B: 5-methyl-3.4-dihydroiuinolin-2(1H)-oneTo a solution of 3-chloro-N-(m-tolyl)propanamide (6.00 g, 30.5 mmol) in chlorobenzene (60 mL)was added AlCl3 (16.08 g, 122 mmol) in several portions. The temperature was slowly raised to140 °C and the solution was stirred at this temperature for 6 hours. The mixture was cooled, diluted with 100 mL of toluene, quenched with 200 mL water and then extracted with DCM. The organic layer was concentrated to afford the title compound and 7-methyl-3,4- dihydroquinolin-2(1I])-one (1:1 mixture). LC/MS [M+1] =162. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With palladium(II) trifluoroacetate; toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 20h; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C19H19Cl3IrNO; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate at 60℃; for 12h; Sealed tube; Overall yield = 71 %; Overall yield = 11 mg; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane / 0.5 h / 25 °C 2: C19H19Cl3IrNO; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate / 12 h / 60 °C / Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dimethylsulfide borane complex In tetrahydrofuran at 0 - 45℃; for 3h; Inert atmosphere; | Step 1 General procedure: To a solution of prepared lactam (1 eq) in THF, borane-dimethyl sulfide complex 2.0mol/l in THF (3 eq) was slowly added at 0°C. The reaction mixture was stirred under N2 at 45°C for 3h. The reaction mixture was cooled to room temperature and poured slowly into methanol. After stirring at reflux for 30min, solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel to afford the secondary amine intermediate 10. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere 4: tin(II) chloride dihdyrate; hydrogenchloride / ethanol; water / 6 h / 95 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere 4: tin(II) chloride dihdyrate; hydrogenchloride / ethanol; water / 6 h / 95 °C 5: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / dichloromethane / 20 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 0 - 45 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 1% Pd on activated carbon; ammonium formate In ethanol; water for 2h; Reflux; | 1.1.1. 5-Methyl-3,4-dihydroquinolin-2(1H)-one(10-6) 8-Chloro-5-methyl-3,4-dihydroquinoline-2(1H)-one(100 mg, 0.5 mmol), ammonium formate (160 mg, 2.5 mmol) and 1% palladium oncarbon were added into mixture of 1 mL water and 1 mL ethanol. The mixture wasstirred reflux for 2 h and then cooled to room temperature. The mixture wasfiltrated by celite. The filtrate was poured into water, and extracted by ethylacetate three times. The combined organic layers were washed with a saturatedsodium chloride solution, dried over anhydrous sodium sulfate, and concentratedunder vacuo to give a pale green solid: 5- methyl-3,4-dihydroquinoline-2(1H)-one 80 mg, yield 98%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: water; acetone / 6 h / Reflux 2: aluminum (III) chloride / 5 h / 150 °C 3: ammonium formate; 1% Pd on activated carbon / ethanol; water / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aluminum (III) chloride / 5 h / 150 °C 2: ammonium formate; 1% Pd on activated carbon / ethanol; water / 2 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 8-quinolinol; sodium tetrafluoroborate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver carbonate at 20℃; for 3h; Inert atmosphere; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 1 h / 20 °C 1.2: 20 °C 2.1: dichloromethane / 20 °C 3.1: carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; 8-quinolinol; sodium tetrafluoroborate; silver carbonate / 3 h / 20 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: dichloromethane / 20 °C 2: carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; 8-quinolinol; sodium tetrafluoroborate; silver carbonate / 3 h / 20 °C / Inert atmosphere; Sealed tube |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 22% 2: 12% | With Ir(CF3ppy)<SUB>3</SUB> In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ferric(III) chloride In 1,4-dioxane at 60℃; for 4h; Sealed tube; Inert atmosphere; Irradiation; Overall yield = 75 percent; | 2.1. General procedure for the synthesis of products 2 General procedure: 3-Phenyl-N-(pivaloyloxy)propanamide 1 (0.2 mmol), FeCl3 (20mmol%) and 1,4-dioxane (2.0 mL) were added to a sealed tube. Then themixture was stirred at 60 C, under the irradiation of 3 W blue LEDs(455 nm) for 4 h. After the disappearance of substrate as indicated byTLC,the mixture was concentrated in vacuo and the product was purifiedby column chromatography (PE: EA=5:1) to afford the products 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ferric(III) chloride In 1,4-dioxane at 60℃; for 4h; Sealed tube; Inert atmosphere; Irradiation; Overall yield = 90 percent; | 2.1. General procedure for the synthesis of products 2 General procedure: 3-Phenyl-N-(pivaloyloxy)propanamide 1 (0.2 mmol), FeCl3 (20mmol%) and 1,4-dioxane (2.0 mL) were added to a sealed tube. Then themixture was stirred at 60 C, under the irradiation of 3 W blue LEDs(455 nm) for 4 h. After the disappearance of substrate as indicated byTLC,the mixture was concentrated in vacuo and the product was purifiedby column chromatography (PE: EA=5:1) to afford the products 2. |
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