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CAS No. : | 1427587-32-3 | MDL No. : | MFCD23106122 |
Formula : | C16H22BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KBKLZANEYMGZGD-UHFFFAOYSA-N |
M.W : | 287.16 | Pubchem ID : | 72208233 |
Synonyms : |
|
Num. heavy atoms : | 21 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.56 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 87.92 |
TPSA : | 38.77 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.46 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.24 |
Log Po/w (WLOGP) : | 1.51 |
Log Po/w (MLOGP) : | 1.64 |
Log Po/w (SILICOS-IT) : | 1.91 |
Consensus Log Po/w : | 1.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.18 |
Solubility : | 0.191 mg/ml ; 0.000665 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.69 |
Solubility : | 0.587 mg/ml ; 0.00204 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.43 |
Solubility : | 0.0106 mg/ml ; 0.0000369 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-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 |
---|---|---|
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | A flask was charged with 6-bromo-1-methyl-3,4-dihydro-1H-quinolin-2-one (3 g, 12.5 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1:1) [PdCl2(DPPF)-CH2Cl2 adduct] (457 mg, 0.625 mmol) was added and the resulting mixture was heated to 80° C. over night. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2×150 mL). The resulting filtrate was washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtOAc-heptane gradient to give the title compound (2.63 g, 73percent) as an off white solid. MS: 288.0 (M+H+) |
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane at 80℃; Inert atmosphere | [B] l-Methyl-6-(4,4,5.5-tetramethyl-[l,3,21dioxaborolan-2-yl -3.4-dihvdro-lH-quinolin-2- one A flask was charged with 6-bromo-l-methyl-3,4-dihydro-lH-quinolin-2-one (3 g, 12.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-?z'(l,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro [1,1 '-?z5(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1 : 1) [PdCl2(DPPF)-CH2Cl2 adduct] (457 mg, 0.625 mmol) was added and the resulting mixture was heated to 80 °C over night. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2 x 150 mL). The resulting filtrate was washed with brine, dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtO Ac- heptane gradient to give the title compound (2.63 g, 73 percent) as an off white solid. MS: 288.0 (M+H+). |
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | [B] l-Methyl-6-(4,4,5.5-tetramethyl-[l,3,21dioxaborolan-2-yl -3.4-dihvdro-lH-quinolin-2- oneA flask was charged with 6-bromo-l-methyl-3,4-dihydro-lH-quinolin-2-one (3 g, 12.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-¾z'(l,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro[l, -¾z5(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1 : 1) [PdCl2(DPPF)-CH2Cl2 adduct] (457 mg, 0.625 mmol) was added and the resulting mixture was heated to 80 °C over night. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2 x 150 mL). The resulting filtrate was washed with brine, dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtO Ac- heptane gradient to give the title compound (2.63 g, 73 percent) as an off white solid. MS: 288.0 (M+H+). |
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | A flask was charged with 6-bromo-l-methyl-3,4-dihydro-lH-quinolin-2-one (3 g, 12.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi'(l,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro[l,l'- bi5,(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1 : 1) [PdCl2(DPPF)- CH2C12 adduct] (457 mg, 0.625 mmol) was added and the resulting mixture was heated to 80 °C over night. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2 x 150 mL). The resulting filtrate was washed with brine, dried over Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtO Ac-heptane gradient to give the title compound (2.63 g, 73 percent) as an off white solid. MS: 288.0 (M+H+). |
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | ΓΒ1 l-Methyl-6-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,4-dihvdroquinolin-2-one A flask was charged with 6-bromo-l-methyl-3,4-dihydroquinolin-2-one (3 g, 12.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-b (l,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro[l, -b 5'(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1: 1) [PdCl2(DPPF) dichloromethane adduct] (457 mg, 0.560 mmol) was added and the resulting mixture was heated to 80 °C overnight. The reaction mixture was diluted with EtOAc, filtered through Celite and washed with EtOAc (2 x 150 mL). The resulting filtrate was washed with brine, dried over anhy. Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtO Ac- heptane gradient to give the title compound (2.63 g, 73 percent) as an off white solid. MS: 288.0 (M+H+). |
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | A flask was charged with 6-bromo-l-methyl-3,4-dihydroquinolin-2-one (3 g, 12.5 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-b (l,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro[l, -b 5'(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1: 1) [PdCl2(DPPF) dichloromethane adduct] (457 mg, 0.560 mmol) was added and the resulting mixture was heated to 80 °C overnight. The reaction mixture was diluted with EtOAc, filtered through Celite and washed with EtOAc (2 x 150 mL). The resulting filtrate was washed with brine, dried over anhy. Na2S04, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtOAc - heptane gradient to give the title compound (2.63 g, 73 percent) as an off white solid. MS: 288.0 (M+H+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere | [B] 1-Methyl-6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinolin-2-one[0342]6-bromo-1-methyl-3,4-dihydro-1H-quinolin-2-one (3 g, 12.5 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (3.81 g, 15.0 mmol), potassium acetate (3.68 g, 37.5 mmol) and dioxane (48 mL). The mixture was purged with Ar, then dichloro[1,1′-bis(diphenylphosphino)-ferrocene]palladium(II) dichloromethane complex (1:1) [PdCl2(DPPF)-CH2Cl2 adduct] (457 mg, 0.625 mmol) was added and the resulting mixture was heated to 80° C. over night. The reaction mixture was diluted with EtOAc, filtered through Dicalite and washed with EtOAc (2×150 mL). The resulting filtrate was washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40percent EtOAc-heptane gradient to give the title compound (2.63 g, 73percent) as an off white solid. MS: 288.0 (M+H+). |
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