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CAS No. : | 26153-38-8 | MDL No. : | MFCD00016611 |
Formula : | C7H6O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HAQLHRYUDBKTJG-UHFFFAOYSA-N |
M.W : | 138.12 | Pubchem ID : | 94365 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 35.88 |
TPSA : | 57.53 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 : | Yes |
Log Kp (skin permeation) : | -6.11 cm/s |
Log Po/w (iLOGP) : | 0.76 |
Log Po/w (XLOGP3) : | 1.45 |
Log Po/w (WLOGP) : | 0.91 |
Log Po/w (MLOGP) : | 0.18 |
Log Po/w (SILICOS-IT) : | 1.02 |
Consensus Log Po/w : | 0.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.99 |
Solubility : | 1.42 mg/ml ; 0.0103 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.26 |
Solubility : | 0.752 mg/ml ; 0.00545 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -1.17 |
Solubility : | 9.4 mg/ml ; 0.0681 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
39% | With potassium carbonate In N,N-dimethyl-formamide at -10℃; Inert atmosphere | To a stirredsuspension of 3,5-dihydroxybenzaldehyde, 12 (2.76 g,20.0 mmol) and K2CO3 (2.76 g, 20.0 mmol) in DMF(50 mL) was added methyl iodide (1.25 mL, 20.0 mmol)dropwise at −10 C under nitrogen atmosphere. The mixturewas stirred for 3 h at this temperature. After completion of thereaction, water (70 mL) was added. The mixture was thenextracted with ether (2 × 80 mL), the combined organic layerwas washed with brine (2 × 80 mL), dried over anhydrousNa2SO4, filtered and the filtrate was concentrated in vacuo.The crude residue was purified by column chromatography(EtOAc/hexane = 1/4) to yield the compound 17 (1.19 g,39percent) as white solid. Rf = 0.23 (EtOAc/hexane = 1/4); mp128–130 C; 1H NMR (300 MHz, CDCl3) δ 9.86 (1H, s),6.98 (1H, dd, J = 2.4, 1.5 Hz), 6.95 (1H, dd, J = 2.4,1.5 Hz), 6.67 (1H, t, J = 2.4 Hz), 5.79 (1H, s), 3.84 (3H, s);13C NMR (75 MHz, CDCl3) δ 191.8, 161.3, 157.2, 138.4,109.0, 108.1, 107.0, 55.7. |
39% | With potassium carbonate In N,N-dimethyl-formamide at -10℃; for 3 h; Inert atmosphere | To a suspension of 3,5-dihydroxybenzaldehyde (3,5-dihydroxybenzaldehyde, compound 12) (2.76 g, 20.0 mmol) and K2CO3 (2.76 g, 20.0 mmol) in DMF (50 mL) was added methyl iodide (1.25 mL, 20.0 mmol) in a nitrogen atmosphere, - 10°C. The reaction mixture was stirred at this temperature for three hours. After the reaction was completed, 70 ml of water was added. The reaction mixture was then extracted with ether (2 x 80 mL) and the combined organic layers were washed with brine (2 x 80 mL), dried over anhydrous Na2SO4,The filtrate was concentrated in vacuo. The crude compound was purified by column chromatography (EtOAc / hexane = 1/4) to obtain a white solid compound 17 (1.19 g, 39percent). |
29% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h; Stage #2: at 20℃; for 16 h; |
3-Hydroxy-5-methoxybenzaldehyde (240)A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at O0C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent). |
29% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h; Stage #2: for 16 h; |
3-Hydroxy-5-methoxybenzaldehyde (240)A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) was treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction was treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It was then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase was washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound was obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent). |
29% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h; Stage #2: for 16 h; |
3-Hydroxy-5-methoxybenzaldehyde (240); A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent).. |
29% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5 h; Stage #2: for 16 h; |
Synthesis of Compound 394; 3-Hydroxy-5-methoxybenzaldehyde (240); A stirred solution of 3,5-dihydroxybenzaldehyde (1.0 g, 7.24 mmol) in DMF (20 mL) is treated with sodium hydride (319 mg, 8.0 mmol, 60percent dispersion in mineral EPO <DP n="361"/>oil) at 0°C. After warming to RT and stirring 0.5 h, the reaction is treated with iodomethane (0.50 mL, 8.0 mmol) via syringe and stirred 16 h. It is then diluted with 1 M HCl (100 mL) and extracted into EtOAc (50 mL). The EtOAc phase is washed with 1 M HCl (50 mL), water (2 x 50 mL) and brine (50 mL), dried over Na2SO4 then the EtOAc removed in vacuo. The title compound is obtained after chromatography (gradient elution - 0-50percent EtOAc in heptane). Yield: 315 mg (29percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; for 0.5 h; | a) 3 Hydroxy-5-methoxybenzaldehyde Diethyl azodicarboxylate (1.5 mL, 9.53 mmol) was added to a solution of 1.14 g (8.26 mmol) of 3,5-dihydroxybenzaldehyde, 2.39 g (9.12 mmol) of triphenylphosphine, and 380 μL (9.4 mmol) of methanol in anhydrous tetrahydrofuran (20 mL) at 0 °C. The reaction mixture was stirred at ambient temperature for 30 min and quenched with 10percent aqueous citric acid. The reaction mixture was extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane / petroleum ether (2: 1 then 100: 0)) to give the title compound (309 mg, 25percent) as a gum. 1H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1 H), 6.98 - 6.99 (m, 2 H), 6.94 - 6.96 (m, 1 H), 3.80 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25% | With triphenylphosphine In tetrahydrofuran; methanol; Petroleum ether | a 3-Hydroxy-5-methoxybenzaldehyde Diethyl azodicarboxylate (1.5 mL, 9.53 mmol) was added to a solution of 1.14 g (8.26 mmol) of 3,5-dihydroxybenzaldehyde, 2.39 g (9.12 mmol) of triphenylphosphine, and 380 μL (9.4 mmol) of methanol in anhydrous tetrahydrofuran (20 mL) at 0° C. The reaction mixture was stirred at ambient temperature for 30 min and quenched with 10percent aqueous citric acid. The reaction mixture was extracted into diethyl ether, dried (MgSO4), and purified by flash chromatography (dichloromethane/petroleum ether (2:1 then 100:0)) to give the title compound (309 mg, 25percent) as a gum. 1 H-NMR (300 MHz, CDCl3) δ 9.82 (s, 1 H), 6.98-6.99 (m, 2 H), 6.94-6.96 (m, 1 H), 3.80 (s, 3 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With potassium carbonate In acetone at 0 - 40℃; for 12 h; Inert atmosphere | General procedure: To the stirred solution of phenolic aldehyde (2.00 mmol) in anhydrous acetone (10 mL) was added K2CO3 (3.00 mmol, 1.5 eq.) In a nitrogen atmosphere0 And cooled.Benzyl bromide (2.4 mmol, 1.2 eq.) Was slowly added,The mixture temperature was raised to 40 ,Stir for 12 hours.After completion of the reaction, the reaction mixture was cooled to room temperature,Filter through a Celite pad and concentrate in vacuo.The crude compound was purified by column chromatography (EtOAc / Hexane = 1/3) to give the pure aromatic aldehyde in which the benzyl group was protected [note: two equivalents of K2CO3 were used in the synthesis of compound 18, 2.4 equivalents of benzyl bromide and 4.0 equivalents of K2CO3 was used for the synthesis of Compound 19). |
82% | With potassium carbonate; potassium iodide In acetone at 20℃; for 4 h; Inert atmosphere | A stirred suspension of 3,5-dihydroxybenzaldehyde (690mg, 5mmol), potassium carbonate (3.46g, 25mmol) and potassium iodide (166.0mg, 1mmol) in acetone (15mL) was treated dropwise with benzyl bromide (1.18mL, 10mmol) and stirring continued for 4h at room temperature. The resulting suspension was concentrated under reduced pressure and the crude mass subjected to flash column chromatography (silica, 4:1 v/v hexane/ethyl acetate) and concentration of the relevant fractions (Rf=0.58 in 4:1 v/v hexane/ethyl acetate) afforded the title compound as a white powder (1.3g, 82percent) m.p. 80–81°C. (0031) 1H NMR (DMSO-d6, 500MHz): δ 9.91 (s, 1H), 7.48–7.44 (m, 4H), 7.43–7.38 (m, 4H), 7.37–7.32 (m, 2H), 7.17 (d, J=2.3Hz, 2H), 7.01 (t, J=2.3Hz, 1H), 5.17 (s, 4H) ppm. 13C NMR (DMSO-d6, 126MHz): δ 192.6, 159.9, 138.3, 136.6, 128.4, 127.9, 127.7, 108.2, 108.1, 69.6ppm. IR (diamond cell, neat) νmax: 1686, 1591, 1447, 1381, 1349, 1296, 1170, 1048, 829, 739, 719, 694, 675, 629cm−1. LRMS (+ESI) m/z: 319 [(M+H)+, 100percent] |
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