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CAS No. : | 5751-52-0 | MDL No. : | MFCD00218597 |
Formula : | C10H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZIPLCYUNFCYCCT-UHFFFAOYSA-N |
M.W : | 176.17 | Pubchem ID : | 600605 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 48.98 |
TPSA : | 39.44 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.12 cm/s |
Log Po/w (iLOGP) : | 2.07 |
Log Po/w (XLOGP3) : | 1.77 |
Log Po/w (WLOGP) : | 1.8 |
Log Po/w (MLOGP) : | 0.53 |
Log Po/w (SILICOS-IT) : | 2.44 |
Consensus Log Po/w : | 1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.55 |
Solubility : | 0.496 mg/ml ; 0.00281 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.22 |
Solubility : | 1.07 mg/ml ; 0.00608 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0324 mg/ml ; 0.000184 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.49 |
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 |
---|---|---|
70% | Stage #1: at 100℃; for 0.166667 h; Stage #2: With hydrogenchloride In dichloromethane; water at 40℃; for 0.5 h; |
Example 10A 7-methoxy-4H-1-benzopyran-4-one 1-(2-Hydroxy-4-methoxyphenyl)ethanone (47 g, 283 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (47 mL, 351 mmol), and the solution was heated to >100° C. in a sand bath for 10 minutes, at which point a solid mass had formed. The flask was cooled to ambient temperature, and 200 mL of heptanes were added. The solids were broken up with a spatula and collected by filtration with a frilled funnel. The solid material was crushed with a pestle and then washed with heptanes. The solid was then dried on the filter to give about 60 g of the crude intermediate. This intermediate was dissolved in dichloromethane (1 L) and stirred with 150 mL of concentrated HCl at 40° C. for 30 minutes. The flask was cooled to ambient temperature, and about 100 mL of water was added. The layers were separated, and the aqueous layer was extracted with dichloromethane (2*100 mL). The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate. The mixture was filtered, and the filtrate was concentrated in vacuo to give a solid. The solid was then precipitated from 500 mL of 1:1 cyclopentyl methyl ether:heptanes to give the title compound (35 g, 70percent yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=8.9 Hz, 1H), 7.77 (d, J=6.0 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.28 (d, J=6.0 Hz, 1H), 3.90 (s, 3H); MS(ESI+) m/z 176.9 (M+H)+. |
70% | Stage #1: at 100℃; for 0.166667 h; Stage #2: With hydrogenchloride In dichloromethane at 40℃; for 0.5 h; |
1-(2-Hydroxy-4-methoxyphenyl)ethanone (47 g, 283 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (47 mL, 351 mmol), and the solution was heated at >100° C. in a sand bath for 10 minutes, at which point a solid mass formed. The flask was cooled to ambient temperature, and 200 mL of heptanes were added. The solids were broken up with a spatula and collected by filtration with a fritted funnel. The solid material was crushed with a pestle and washed with heptanes. The solid was dried on the filter to give about 60 g of the crude intermediate. The intermediate was dissolved in dichloromethane (1 L) and stirred with 150 mL of concentrated HCl at 40° C. for 30 minutes. The flask was cooled to ambient temperature, and about 100 mL of water was added. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate. The mixture was filtered, and the filtrate was concentrated in vacuo to give a solid. The solid was taken into 500 mL of 1:1 cyclopentyl methyl ether:heptanes and the precipitate was collected to provide the title compound (35 g, 70percent yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=8.9 Hz, 1H), 7.77 (d, J=6.0 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.28 (d, J=6.0 Hz, 1H), 3.90 (s, 3H); MS(ESI+) m/z 176.9 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70.5% | With copper diacetate; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 6 h; Inert atmosphere; Green chemistry | To a solution of 3-iodo-7-methoxy-4H-chromen-4-one (1) (4 mmol) and methyl acrylate (2) (4.8 mmol) in solvent was added catalyst (5 mmol percent) and base (8 mmol). The reaction mixture was stirred via oil heating under nitrogen protection. Then the mixture was poured into 10percent HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compound 3 or 4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.854 g | With hydrogenchloride In dichloromethane; water for 1 h; Reflux | The enamine was dissolved in dichloromethane (40 mL) and treated with HCl (4 mL) at reflux for one hour. The aqueous layer was removed and extracted with 3 x 40mL of dichloromethane. The combined extracts were washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate, then filtered and the solvent removed under reduced pressure to give title compound (0.854 g, 4.85 mmol, 64.4 percent yield) as pale yellow crystals. 1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J = 6.0 Hz, 1H), 7.94 (d, J = 8.9 Hz, 1H), 7.13 (d, J = 2.4 Hz, 1H), 7.06 (dd, J = 8.9, 2.4 Hz, 1H), 6.27 (d, J = 6.0 Hz, 1H), 3.90 (s, 3H); MS (ESI+) m/z 177 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | at 60℃; for 2 h; | General procedure: The hydrazines (method 2) or hydrazine hydrochlorides (method 1) (2 mmol) were added in one portion to a stirred solution of the appropriate compound 11 (2 mmol) in acidified EtOH [10 mL containing 0.17 mL of HCl 37percent (method 2)] or EtOH [10 mL (method 1)]. The resulting solution was stirred for 2 h at 60 °C. |
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