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CAS No. : | 76240-27-2 | MDL No. : | MFCD08669475 |
Formula : | C9H8O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XJWBVGDAFGVJEG-UHFFFAOYSA-N |
M.W : | 164.16 | Pubchem ID : | 10855817 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.04 |
TPSA : | 46.53 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) : | -6.58 cm/s |
Log Po/w (iLOGP) : | 1.46 |
Log Po/w (XLOGP3) : | 1.02 |
Log Po/w (WLOGP) : | 1.36 |
Log Po/w (MLOGP) : | 0.43 |
Log Po/w (SILICOS-IT) : | 1.93 |
Consensus Log Po/w : | 1.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.87 |
Solubility : | 2.21 mg/ml ; 0.0135 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.59 |
Solubility : | 4.25 mg/ml ; 0.0259 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.27 |
Solubility : | 0.878 mg/ml ; 0.00535 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.98 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
100% | With potassium carbonate In acetone at 60℃; for 3 h; | 7-Methoxychroman-4-one[00154] 7-Hydroxychroman-4-one (3.86 g, 23.5 mmol) was mixed with potassiumcarbonate (649 g, 47.0 mmol) in acetone (80 mL) under 60°C oil bath. lodomethane (9.3 g,66 mmol) was added slowly. The reaction mixture was stirred for 3 hours and then filtered. The filtrate was concentrated under vacuum and the residue was dissolved in dichioromethane and washed with water and brine. The organic layer was dried with magnesium sulfate and concentrated in vacuum give 7-methoxychroman-4-one (4.19 g,100percent yield) as sticky solid. |
97% | With potassium carbonate In acetone for 4 h; Heating / reflux | C. 7-methoxychroman-4-one7-hydroxychroman-4-one (1.0 g, 6.1 mmol) was dissolved in 20 ml acetone in a 250 ml round-bottomed flask. Potassium carbonate (1.68 g, 12.2 mmol, Aldrich) and iodomethane (2.4 g, 17.1 mmol, Aldrich) were added successively. The solution was refluxed for 4 h, cooled to room temperature, and diluted with dichloromethane. The solid was removed by filtration. The filtrate was concentrated in vacuum to yield <n="33"/>yellowish clear oil. The oil was dissolved in dichloromethane (100 ml) and extracted with H2O (2 x 50 ml). The organic was dried over magnesium sulfate and concentrated in vacuum to give 7-methoxychroman-4-one as a white waxy solid (1.05 g, 97percent), which was of great purity indicated by NMR. 1U NMR (CDCl3, 500 MHz): δ 7.84 (d, J= 8.8 Hz, IH), 6.58 (dd, Ji = 8.8 Hz, J2 = 2.4 Hz, IH), 6.40 (d, J = 2.4 Hz, IH), 4.52 (t, J= 6.5 Hz, 2H), 3.84 (s, 3H), 2.76 (t, J= 6.5 Hz, 2H). |
89% | With potassium carbonate In acetone at 20℃; for 4 h; Inert atmosphere | Step3: 7-Methoxy-2,3-dihydro-4H-chromen-4-one [00185] To a stirred solution of 7-Hydroxy-2,3-dihydro-4H-chromen-4-one (27 g, 0.16 mol) in acetone (700 mL) was added dry K2CO3 (45.6 g, 0.32 mol) in lots at RT under nitrogen. The reaction mixture was stirred at RT for 10 min and then methyl iodide (65.4 g, 0.46 mol) was added drop wise at RT. The reaction mixture was stirred at RT for 4 h. The reaction mixture was filtered and filtrate was concentrated under vacuum. The crude product was dissolved in DCM (200 mL), washed with water (100 mL), brine (50 mL), dried over sodium sulphate and concentrated under vacuum to afford the desired compound (15 g, 89 percent) as light yellow solid. 1H NMR (400 MHz, CDC13) δ 7.85-7.83 (d, / = 8.0 Hz, 1H), 6.60-6.57 (dd, / = 4.0, 12.0 Hz, 1H), 6.41-6.41 (d, / = 4.0 Hz, 1H), 4.52 (t, / = 8.0 Hz, 2H), 3.77 (s, 3H), 2.76 (t, / = 4.0 Hz, 2H). |
72.1% | With potassium carbonate In tetrahydrofuran at 70℃; for 5 h; | 7-Hydroxy-2,3-dihydrochromen-4-one (4.47 g, 27.2 mmol) was diluted with tetrahydrofuran (40 mL) followed by the addition Of K2CO3 (5.64 g, 40.8 mmol) and MeI (2.55 mL, 40.8 mmol). The reaction was heated at 70 0C for 5 hours. The reaction was allowed to cool and loaded onto a Biotage 4OM cartridge running a gradient 5percent ethyl acetate/hexanes to 75percent to yield the title compound (3.5 g, 72.1percent yield). |
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