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CAS No. : | 93465-26-0 | MDL No. : | MFCD03424639 |
Formula : | C14H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZYNNXRUYVVQLOW-UHFFFAOYSA-N |
M.W : | 212.24 | Pubchem ID : | 602528 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.07 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 63.76 |
TPSA : | 26.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.48 cm/s |
Log Po/w (iLOGP) : | 2.35 |
Log Po/w (XLOGP3) : | 2.98 |
Log Po/w (WLOGP) : | 3.17 |
Log Po/w (MLOGP) : | 2.6 |
Log Po/w (SILICOS-IT) : | 3.7 |
Consensus Log Po/w : | 2.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.39 |
Solubility : | 0.0864 mg/ml ; 0.000407 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.2 |
Solubility : | 0.135 mg/ml ; 0.000637 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.0 |
Solubility : | 0.00214 mg/ml ; 0.0000101 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.87 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H317-H319 | 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 |
---|---|---|
61% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In N,N-dimethyl-formamide; for 6h;Inert atmosphere; Reflux; | General procedure: To a solution of 2-bromobenzaldehyde (315 mul, 2.70 mmol) in DMF (20 ml) was added phenyl boronic acid (395 mg, 3.24 mmol), tetrakis-(triphenylphosphine)-palladium (31 mg, 0.027 mmol) and Na2CO3 (430 mg, 4.05 mmol). The result solution was stirred and refluxed for 6 h. After the reaction completed, the solution was cooled to room temperature, then partitioned between satd NaHCO3 and EtOAc, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/diethyl ether = 8:1) to afford the product (369 mg, 2.03 mmol, 75% yield). |
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate; In water; acetonitrile; at 60℃;Inert atmosphere; Sealed vessel; | Typical preparative procedures were performed on 10.0 mmol scale using a Mettler-Toledo FlexiWeigh 30 automated solid handling unit to pre-weigh the aryl halide (10.0 mmol, 1.0 equiv), aryl boronic acid (12.0 mmol, 1.2 equiv) and Pd-118 (65.2 mg, 0.1 mmol, 1.0 mol %). Acetonitrile (10.0 mL) was added, followed by K2CO3 added as a stock aqueous solution (10.0 mL water containing 2.07 g, 15.0 mmol, 1.5 equiv). NB. No internal standard was added for preparative reactions. Reaction mixtures were sealed under a N2 atmosphere and heated to 60 C with magnetic stirring. HPLC analysis showed that reactions using aryl bromides were complete within 1 h but that aryl chlorides typically required 24 h.After reaction mixtures had cooled to room temperature, stirring was stopped and the phases were allowed to separate. The lower aqueous phase was removed and discarded (cutting away any interfacial catalyst residues if present) and the acetonitrile phase concentrated to dryness to give typically a light to dark brown solid or dark-coloured gum. Solids were triturated with methanol (20 mL) for 1-2 h, then isolated by filtration, washed once or twice with methanol (4 mL each wash) and dried under vacuum. Oils were purified by flash silica gel chromatography as noted below. All isolated compounds gave 1H NMR data in agreement with published values. Literature data is given for mp values for comparison. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 2h;Inert atmosphere; | 2'-Methoxybiphenyl-2-carbaldehyde 40b (3.20 g, 15.09 mmol) was dissolved in 140 mL of freshly distilled dry THF under inert conditions. LiAlH4 (1.71 g, 45.28 mmol) was added to the mixture carefully at 0 C. The reaction was warmed up to room temperature and allowed to stir at rt under inert conditions for 2 h. When completed, the reaction was cooled down to 0 C and a 2% aq. NaOH(50 mL) solution was added dropwise to quench the unreacted LiAlH4 and then the mixture diluted with ice-cold water (100 mL). The organic material was then extracted into EtOAc (100 mL * 3) and combined organic phases were washed with brine (100 mL), dried over anhydrous MgSO4, filtered and the solvent was removed under reduced pressure. The crude product was then subjected to column chromatography (20% EtOAc/Hexane) to obtain the product 41b as a clear oil (2.97 g, 13.87 mmol, 92%); 1H NMR (500 MHz, CDCl3) d 7.49 (1H, dd, J = 7.4, 1.6 Hz, ArH), 7.35-7.27 (3H, m, ArH), 7.16 (1H, dd, J = 7.4, 1.6 Hz, ArH), 7.11 (1H, dd, J = 7.4, 1.8 Hz, ArH), 6.98 (1H, td, J = 7.5, 1.1 Hz, ArH), 6.92 (1H, dd, J = 8.4, 1.0 Hz, ArH), 4.40-4.27 (2H, bm, CH2OH), 3.64 (3H, s, OMe), 2.66 (1H, s, OH); 13C NMR (126 MHz, CDCl3) d 156.3, 139.3, 137.3, 131.2, 130.2, 129.0, 128.0, 127.8, 127.4, 126.8, 120.9, 111.0, 63.3, 55.6. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | General procedure: To a solution of 1-phenylpiperazine (266 mg, 1.64 mmol) in methanol (10 ml) was added [1,1?-biphenyl]-2-carbaldehyde (150 mg, 0.82 mmol). The reaction mixture was stirred at room temperature for 2 h, and NaBH(OAc)3 (529 mg, 2.46 mmol) was added. The resulting mixture was stirred for 8 h. After termination of the reaction, the solution was partitioned between sat. NaHCO3 and CH2Cl2, and the mixture was extracted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane/diethyl ether = 8:1) to afford the product (50 mg, 0.15 mmol, 18% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water; for 18h;Inert atmosphere; Reflux; | To a deoxygenated solution of 2-bromoanisole (4.00 g, 21.34 mmol) and 2-formylphenylboronic acid (4.80 g, 32.09 mmol) in DME (160 mL) was added Pd(PPh3)4 (2.46 g, 2.13 mmol) under argon atmosphere with stirring. To this mixture was added a deoxygenated aq. Na2CO3 (2M, 42.7 mL, 85.36 mmol). The mixture was then heated at reflux for 18 h. After this time, the mixture was cooled to rt and reaction quenched with H2O (100 mL). The organic material was extracted into EtOAc (3 * 100 mL), the combined extract dried with MgSO4, and the solvent removed in vacuo. The crude product was purified by column chromatography on silica gel (5-10% EtOAc/hexane) to afford product 40b as an off-white solid (3.95 g, 18.63 mmol, 87%). 1H NMR (500 MHz, CDCl3) d 9.78 (1H, d, J = 0.9 Hz, CHO), 7.98 (1H, dd, J = 7.8, 1.5 Hz, ArH), 7.60 (1H, td, J = 7.5, 1.5 Hz, ArH), 7.44 (1H, t, J = 7.6 Hz, ArH), 7.39 (1H, td, J = 7.5, 1.8 Hz, ArH), 7.33 (1H, dd, J = 7.7, 1.2 Hz, ArH), 7.26 (1H, dd, J = 7.5, 1.8 Hz, ArH), 7.06 (1H, td, J = 7.5, 1.1 Hz, ArH), 6.95 (1H, dd, J = 8.3, 1.0 Hz, ArH), 3.70 (3H, s, OMe); 13C NMR (126 MHz, CDCl3) d 192.5, 156.5, 41.8, 134.0, 133.6, 131.4, 131.2, 130.0, 127.7, 126.8, 126.5, 121.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; for 5h;Inert atmosphere; Reflux; | General procedure: Ethanol (500 mE), boronic acid Ar2-B(OH)2 (92.7 mmol, 1.2 eq) and bromoarylaldehyde or bromoheteroarylaldehyde Br-Ar,--CHO (77.3 mmol) are introduced in succession into a 1 E flask under argon and at ambient temperature. The solution is degassed with argon for 15 minutes. Pd(PPh3)4 (1.78 g, 1.55 mmol) and Na2CO3 (92.7 mE of a 2M solution in H20, 185 mmol, 2.4 eq) are then introduced in a single portion. Afier the addition, the reaction mixture is heated at reflux for 5 hours. The mixture is then evaporated to dryness. The residue is taken up in DCM (1 E) and H20 (200 mE). After decantation, the aqueous phase is extracted with DCM (200 mE). The organic phases are combined and then washed with a saturated NaC1 solution (400 mE), dried over Mg504 and concentrated under reduced pressure. The residue is then purified by flash chromatography on silica gel. The expected product is obtained with yields of from 59 to 94%. |
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