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CAS No. : | 133077-42-6 | MDL No. : | MFCD01931913 |
Formula : | C9H9FO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | TWGIQPNNPXKPLC-UHFFFAOYSA-N |
M.W : | 184.16 | Pubchem ID : | 15086015 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.22 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 44.28 |
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) : | -6.1 cm/s |
Log Po/w (iLOGP) : | 1.62 |
Log Po/w (XLOGP3) : | 1.86 |
Log Po/w (WLOGP) : | 2.1 |
Log Po/w (MLOGP) : | 1.79 |
Log Po/w (SILICOS-IT) : | 1.85 |
Consensus Log Po/w : | 1.84 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.23 |
Solubility : | 1.08 mg/ml ; 0.00587 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.46 |
Solubility : | 0.641 mg/ml ; 0.00348 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.6 |
Solubility : | 0.462 mg/ml ; 0.00251 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.71 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-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 |
---|---|---|
53% | Stage #1: With thionyl chloride In toluene for 1.5 h; Heating / reflux Stage #2: With trifluorormethanesulfonic acid In chloroform at -65 - 20℃; for 2 h; Stage #3: With sodium hydroxide In chloroform; water |
C. 7-Fluorochroman-4-one. To a solution of 3-(3-fluorophenoxy)propionic acid (2.2 g, 0.011 mol) in toluene (25 mL) was added thionyl chloride (4.0 mL, 0.054 mol). The solution was heated at reflux for 1.5 h and concentrated in vacuo. The residue was dissolved in CHCl3 (25 mL), cooled to -65° C. and treated dropwise with trifluoromethanesulfonic acid (1.5 mL, 0.017 mol). The mixture was allowed to warm to room temperature with stirring for 2 h. After the addition of H2O, the layers were separated, and the organic layers were washed with 1 N NaOH. The combined organic extracts were dried over MgSO4, filtered, concentrated, and purified by flash chromatography (hexanes/EtOAc) to provide the title compound (0.96 g, 53percent). HPLC (reverse phase): RT=8.22 min. 1H NMR (500 MHz, CDCl3): 7.92 (dd, J=8.8, 6.7 Hz, 1H), 6.75-6.72 (m, 1H), 6.66 (dd, J=9.9, 2.4 Hz, 1H), 4.55 (t, J=6.4 Hz, 2H), 2.80 (t, J=6.5 Hz, 2H). |
41% | at 90℃; for 1 h; | Step 2 7-Fluoro-chroman-4-one 3-(3-Fluoro-phenoxy)-propionic acid (3.37 g, 18.3 mmol), was dissolved in a mixture of 25 mL trifluoroacetic acid and 9 mL methanesulfonic acid. The reaction mixture was heated to 90 0C and was stirred at 90 0C for one hour. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over MgSψ4, and solvent was evaporated under reduced pressure. The residue was eluted through silica gel (15percentEtOAc in hexanes), and solvent was removed under reduced pressure to yield 1.24 g (7.5 mmol, 41percent) of 7-fluoro-chroman-4- one (MS: 167 (M+H)+. EPO <DP n="32"/>Step 3 7-Phenylsulfanyl-chroman-4-one |
41% | at 90℃; for 1 h; | 3-(3-Fluoro-phenoxy)-propionic acid (3.37 g, 18.3 mmol), was dissolved in a mixture of 25 mL trifluoroacetic acid and 9 mL methanesulfonic acid. The reaction mixture was hteated to 90 0C and was stirred at 900C for one hour. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, and solvent was evaporated under reduced pressure. The residue was eluted through silica gel (15percentEtOAc in hexanes), and solvent was removed under reduced pressure to yield 1.24 g (7.5 mmol, 41percent) of 7-fluoroo-chroman- 4-one (MS: 167 (M+H)+. |
26% | Stage #1: With oxalyl dichloride In dichloromethane at 20℃; for 0.5 h; Stage #2: With aluminum (III) chloride In dichloromethane for 1 h; Stage #3: With hydrogenchloride In dichloromethane; water |
7-Fluoro-chroman-4-one To a solution of 3- (3-fluorophenoxy)-propionic acid (4.94 g, 26. 8 mmol) in dichloromethane (135 mL) is added several drops of anhydrous dimethylformamide, followed by oxalyl chloride (4. 68 mL, 53.6 mmol). The reaction is stirred at room temperature until gas evolution ceases (No.30 min), then evaporated under reduced pressure and reconstituted in dichloromethane (135 mL). Following the addition of aluminum trichloride (4.28 g, 32.1 mmol), the reaction is stirred for 1 h, then 2 M aqueous hydrochloric acid (100 mL) and dichloromethane (100 mL) are added. The layers are separated, and the aqueous layer extracted with dichloromethane (2 x 100 mL). The combined organic layers are washed with brine (2 x 100 mL), dried over magnesium sulfate, filtered and evaporated under reduced pressure. The crude residue is recrystallized twice from 2-propanol to afford slightly impure title compound (1.79 g, 40percent), and the mother liquor subjected to flash chromatography (silica gel, 3: 1 pentane/Et20) to afford pure title compound (1.15 g, 26percent) : Rf 0.45 (1: 1 ethyl acetate/hexanes) ; mp 53-56 °C ; IH NMR (300 MHz, CDC13) 82. 75 (t, J = 6.4 Hz, 2H), 4.51 (t, J = 6.4 Hz, 2H), 6.61 (dd, J = 2.3, 9.9 Hz, 1H), 6.65-6.72 (m, 1H), 7.87 (dd, J = 6.7, 8.8 Hz, 1H); 19F NMR (282 MHz, CDCl3) No.-101.08; APCI MS m/z 167 [C9H7FO2+]+ |
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