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[ CAS No. 20151-46-6 ] {[proInfo.proName]}

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Chemical Structure| 20151-46-6
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Product Details of [ 20151-46-6 ]

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 :

Calculated chemistry of [ 20151-46-6 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 20151-46-6 ]

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:

Application In Synthesis of [ 20151-46-6 ]

* 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.

  • Downstream synthetic route of [ 20151-46-6 ]

[ 20151-46-6 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 19422-76-5 ]
  • [ 20151-46-6 ]
  • [ 20151-47-7 ]
YieldReaction ConditionsOperation in experiment
With aluminium trichloride at 100℃;
  • 2
  • [ 19342-88-2 ]
  • [ 20151-46-6 ]
  • [ 20150-83-8 ]
  • [ 19352-59-1 ]
  • [ 20151-47-7 ]
  • 3
  • [ 226710-94-7 ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation in experiment
89% In toluene at 200℃; for 36h;
YieldReaction ConditionsOperation 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;

YieldReaction ConditionsOperation in experiment
With palladium on activated charcoal; ethanol Hydrogenation;
  • 6
  • [ 7446-70-0 ]
  • [ 19352-22-8 ]
  • [ 20151-46-6 ]
  • [ 19352-59-1 ]
YieldReaction ConditionsOperation in experiment
Schmelzen;
  • 7
  • [ 20151-46-6 ]
  • [ 19352-59-1 ]
  • 2-chloro-N-m-tolylacetamide (92LH85) [ No CAS ]
  • [ 109-70-6 ]
  • [ 145969-91-1 ]
  • [ 560083-03-6 ]
YieldReaction ConditionsOperation 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.
  • 8
  • [ 1536478-31-5 ]
  • [ 20151-46-6 ]
  • 3,4-dimethylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 9
  • [ 1529018-51-6 ]
  • [ 20151-46-6 ]
  • 3,4-dimethylindolin-2-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 10
  • [ 108-44-1 ]
  • [ 20151-46-6 ]
  • [ 19352-59-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 16 h / 20 °C 2: aluminum (III) chloride / 6 h / 140 °C
  • 11
  • [ 19352-22-8 ]
  • [ 20151-46-6 ]
  • [ 19352-59-1 ]
YieldReaction ConditionsOperation 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.
  • 12
  • [ 201230-82-2 ]
  • [ 146667-90-5 ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation in experiment
73% With palladium(II) trifluoroacetate; toluene-4-sulfonic acid In tetrahydrofuran at 80℃; for 20h; regioselective reaction;
  • 13
  • 3-(2-methylphenethyl)-1,4,2-dioxazol-5-one [ No CAS ]
  • [ 20151-46-6 ]
  • [ 20151-47-7 ]
YieldReaction ConditionsOperation 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;
  • 15
  • C10H13NO2 [ No CAS ]
  • [ 20151-46-6 ]
  • [ 20151-47-7 ]
YieldReaction ConditionsOperation 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
  • 16
  • [ 20151-46-6 ]
  • C18H18N2O3 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 17
  • [ 20151-46-6 ]
  • [ 58960-02-4 ]
YieldReaction ConditionsOperation 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.
  • 18
  • [ 20151-46-6 ]
  • C18H22N2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 19
  • [ 20151-46-6 ]
  • 2-(4-(ethylsulfonyl)phenyl)-N-(4-(2-(5-methyl-3,4-dihydroquinolin-1(2H)-yl)ethyl)phenyl) acetamide [ No CAS ]
YieldReaction ConditionsOperation 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
  • 20
  • [ 20151-46-6 ]
  • C18H20N2O2 [ No CAS ]
YieldReaction ConditionsOperation 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
  • 21
  • 8-chloro-5-methyl-3,4-dihydroquinolin-2(1H)-one [ No CAS ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation 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%.
  • 22
  • [ 95-81-8 ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation 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
  • 23
  • C10H11Cl2NO [ No CAS ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation 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
  • 24
  • 3-(2-methylphenethyl)-1,4,2-dioxazol-5-one [ No CAS ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation in experiment
65% With 8-quinolinol; sodium tetrafluoroborate; carbonyl(pentamethylcyclopentadienyl)cobalt diiodide; silver carbonate at 20℃; for 3h; Inert atmosphere; Sealed tube;
  • 25
  • [ 22084-89-5 ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation 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
  • 26
  • C10H13NO2 [ No CAS ]
  • [ 20151-46-6 ]
YieldReaction ConditionsOperation 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
  • 27
  • C19H15F6NO3 [ No CAS ]
  • [ 20151-46-6 ]
  • [ 20151-47-7 ]
YieldReaction ConditionsOperation in experiment
1: 22% 2: 12% With Ir(CF3ppy)<SUB>3</SUB> In acetonitrile at 25℃; for 12h; Inert atmosphere; Irradiation;
  • 28
  • C15H21NO3 [ No CAS ]
  • [ 20151-46-6 ]
  • [ 19352-59-1 ]
YieldReaction ConditionsOperation 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.
  • 29
  • C15H21NO3 [ No CAS ]
  • [ 20151-46-6 ]
  • [ 20151-47-7 ]
YieldReaction ConditionsOperation 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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