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CAS No. : | 4049-39-2 | MDL No. : | MFCD03840812 |
Formula : | C14H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HUNGEAFDVLSPAM-UHFFFAOYSA-N |
M.W : | 228.24 | Pubchem ID : | 561369 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.07 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 64.83 |
TPSA : | 46.53 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) : | -5.95 cm/s |
Log Po/w (iLOGP) : | 2.12 |
Log Po/w (XLOGP3) : | 2.46 |
Log Po/w (WLOGP) : | 2.63 |
Log Po/w (MLOGP) : | 1.99 |
Log Po/w (SILICOS-IT) : | 3.08 |
Consensus Log Po/w : | 2.46 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.06 |
Solubility : | 0.197 mg/ml ; 0.000864 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.08 |
Solubility : | 0.189 mg/ml ; 0.00083 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.44 |
Solubility : | 0.00827 mg/ml ; 0.0000362 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.73 |
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 |
---|---|---|
80.6% | With sodium hydrogencarbonate; potassium iodide In acetonitrile at 60 - 80℃; | Example 9 N-(2-cvano- 1 -( 1 -hvdroxy-7-isopropoxy- 1.3-dihvdrobenzo [c] [ 1.2"|oxaborol-6-yloxy) propan-2-yl)-4-(trifluoromethoxy)benzamide Into a round-bottom flask equipped with a stir bar are placed 3,4-dihydroxybenzaldehyde (10.0 g, 72.5mmol), sodium bicarbonate (7.91 g, 94.2mmol), KI (2.07 g, 14.5mmol) and MeCN (200mL). The flask is fitted with a refluxing condenser and slowly heated to 60°C. At this time, benzyl bromide (8.5mL, 72.5mmol) is added and the mixture heated to 80°C. After refluxing overnight, the mixture is then cooled to rt and concentrated by rotary evaporation. The residue is quenched with 10percent aq. HCl (50mL) and extracted with EtOAc (3 x lOOmL). The combined organic extracts are washed with brine (lOOmL), dried with Na2S04, filtered, and concentrated. The resulting oil is purified by flash chromatography (Si02, 100percent hexane until removal of benzyl bromide, then PE: EA=6:1) to afford an amorphous yellow solid (13.3 g, yield 80.6percent). |
63% | With potassium carbonate In acetone for 4 h; Reflux | To a solution of 3,4-dihydroxybenzaldehyde (2.03g, 14.7mmol) in acetone (150mL) was added K2CO3 (3.05g, 22.1mmol) and benzyl bromide (1.74mL, 14.7mmol). After stirring at reflux for 4h, the reaction mixture was filtered through Celite®535RVS and concentrated in vacuo. The residue was purified by column chromatography eluted with toluene/EtOAc (13:1) to give 4-(benzyloxy)-3-hydroxybenzaldehyde (2.12g, 63percent) as a colorless prism. 1H NMR (300MHz, CDCl3) δ 5.21 (2H, s), 5.77 (1H, s), 7.05 (1H, d, J=8.2Hz), 7.37–7.43 (7H, m), 9.86 (1H, s); 13C NMR (75MHz) δ 71.2, 111.5 114.4, 124.4, 127.9, 128.8, 128.9, 130.8, 135.2, 146.3, 150.9, 191.0; IR (ATR) 3201, 1671, 1604, 1577, 1511, 1454, 1389, 1343, 1283, 1165, 1151, 1015, 962, 874, 811, 786, 738, 698, 678cm−1; EIMS m/z (relative intensity) 228 [M]+ (40), 91 (100); HR-EIMS m/z: [M]+ calcd for C14H12O3 228.0786; found 228.0789; mp 120.0–122.0°C. |
62% | With potassium carbonate; potassium iodide In acetone for 5 h; Reflux | To a solution of 3,4-dihydroxybenzaldehyde (10.0 g, 72.4 mmol) and benzyl bromide (12.4 mmol, 72.4 mmol, 1.0 eq.) in acetone (400 mL) was added K2C03 (15.0 g, 109 mmol) and KI (1.2 g, 7.14 mmol) and the mixture was heated at reflux for 5 h. The solid was removed by filtration and washed with EtOAc. The filtrate was concentrated in vacuo and the residue was purified by column chromatography (DCM/Pet. Ether, 0-100percent, v/v) to give the product (9.2 g, 62percent) as a white solid. TLC: Rf = 0.65 (silica gel, Pet.ether/EtOAc=4/l,v/v); MR: (400 MHz, CDC13) δ ppm 9.83 (s, 1H), 7.42 (m, 7H), 7.03 (d, J= 8.3 Hz, 1H), 6.00 (s, 1H), 5.20 (s, 2H). |
60% | With sodium hydrogencarbonate In acetonitrile at 60 - 80℃; | 3,4-Dihydroxybenzaldehyde (10 g, 72.5 mmol) was dissolved in acetonitrile (150 mL).Add sodium bicarbonate (8 g, 94.3 mmol), warm to 60 ° C, add benzyl bromide (12.4 g, 72.5 mmol),Then the temperature was raised to 80 ° C and stirred overnight. The acetonitrile was removed by concentration, and 10percent aqueous hydrochloric acid (200 mL) was added to the residue.Extract with ethyl acetate (150 mL * 3), combine and dry.Filtration, concentration, and residue were purified by column chromatography to yield 10 g (yield: 60percent). |
51% | With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide | 0187] Benzyl bromide (9 mL, 0.073 mol, 1.05 eq) was added to a stirred solution of 3,4-dihydroxybenzaldehyde (10 g, 0.07 mol, 1 eq), tetra-n-butylammonium iodide (29.4 g, 0.077 mol, 1.1 eq) and cesium carbonate (24.8 g, 0.073 mol, 1.05 eq) in N,N-dimethylformamide (200 mL). The reaction mixture was stirred overnight, and then concentrated in vacuo. The residual solution was diluted with ethyl acetate (200 mL) and washed with water (2.x.200 mL). The organic solution was then extracted with 0.5M aqueous sodium hydroxide (5.x.200 mL), and the basic extracts combined and washed with ethyl acetate (400 mL), then acidified to pH 1 with concentrated HCl and back extracted with ethyl acetate (2.x.300 mL). The organic extracts were combined, washed with brine (200 mL), dried over sodium sulfate and evaporated in vacuo. This gave a gummy solid, which was recrystallized from ethyl acetate and petroleum ether to give the product as a brown powder (8.4 g, 51percent). 1H NMR (CDCl3) δ 9.84 (s, 1H, OC-H), 5.84 (s, 1H, OH), 5.21 (s, 2H, CH2Ph). |
50% | With potassium carbonate In acetone at 20℃; for 15 h; Inert atmosphere | A mixture of 3,4-dihydroxybenzaldehyde (1.38 g, 10 mmol), benzyl bromide (1.71 g, 10 mmol), and K2CO3 (1.24 g, 9 mmol) in 20 mL acetone was <n="111"/>stirred at rt for 15 h under Ar atmosphere. Solid was filtered off and the filtrated was diluted with EtOAc (100 mL) and washed with NaH2PO4 (sat. 100 mL), and dried over MgSO4 and concentrated. The residue was chromatographed (hexane/EtOAc) to afford 4-(benzyloxy)-3-hydroxybenzaldehyde as a white solid(1.15 g, 50percent). 1H NMR (400 MHz, CDC13) δ 9.84 (s, 1 H), 7.46 (d, J = 2.0 Hz, 1 H), 7.44-7.40 (m, 6 H), 7.04 (d, J = 8.0 Hz, 1 H), 5.80 (s, 1 H), 5.21 (s, 2 H); MS(ESI) m/z 229 (M+H+). |
49% | Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5 h; Inert atmosphere; Cooling with ice Stage #2: at 20℃; for 18 h; Inert atmosphere; Cooling with ice |
An ice cooled, stirred suspension of 60percent sodium hydride/oil (1.76 g, 44 mmol) in anhydrous DMF (40 mL) under nitrogen was treated dropwise with a solution of 3,4-di-hydroxybenzaldehyde (5.525 g, 40 mmol) in anhydrous DMF (40 mL) and the mixture was stirred at room temperature for 30 min and recooled on an ice bath. Benzyl bromide (5.25 mL, 44 mmol) was then added via syringe and the mixture allowed to reach room temperature and stirred overnight (18 h). The mixture was combined with 1percent aqueous sodium hydroxide (300 mL) and the cloudy solution was extracted with ether (2 × 75 mL) and acidified with concentrated hydrochloric acid. A precipitate soon formed, and the resulting suspension was stirred for a few minutes and filtered. The solid was rinsed with water, partially air dried, dissolved in dichloromethane (100 mL), and dried (Na2SO4). The solution was added directly to a column of silica gel and eluted with dichloromethane to yield a solid, which was triturated from petroleum ethers to afford 4-benzyloxy-3-hydroxybenzaldehyde (4.46 g, 49percent) as a white solid: mp 122–123 °C (lit.38 121–122 °C); LC/MS m/z 229 [M+H]; 1H NMR (CDCl3, 400 MHz) δ 5.20 (s, 2H), 5.92 (s, 1H), 7.03 (d, J = 8.3, 1H), 7.35–7.44 (m, 6H), 7.46 (d, J = 1.9, 1H), 9.82 (s, 1H); 13C NMR (CDCl3, 100 MHz) δ 71.5, 111.7, 114.6, 124.4, 128.0, 128.9, 129.0, 131.0, 135.4, 146.5, 151.1, 191.1. Anal. Calcd for C14H12O3: C, 73.67; H, 5.30. Found: C, 73.91; H, 5.19. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 40℃; for 5 h; | To the solution of 3,4-dihydroxybenzaldehyde (27, 285 mg, 2.00 mmol) in DMF (10 mL), NaHCO3 (252 mg, 3.00 mmol), NaI (90 mg, 0.600 mmol), and benzyl chloride (460 μL, 4.00 mmol) were added. The mixture was stirred at 40 °C overnight, acidified with 10percent HCl (20 mL) and the product extracted with ethyl acetate (3 .x. 15 mL). The combined organic phases were washed with brine (2 .x. 10 mL), dried over Na2SO4, filtered and the solvent evaporated under reduced pressure. The crude product was purified with flash column chromatography using ethyl acetate/petroleum ether as an eluent. Yield, 60percent (276 mg); white crystals; mp 105-108 °C (lit. [11] 118-120 °C); IR (KBr) ν = 3200, 2931, 2870, 1672, 1605, 1578, 1512, 1454, 1389, 1344, 1284, 1223, 1166, 1116, 1017, 1008, 963, 874, 812, 786, 739, 699, 647 cm-1. 1H NMR (CDCl3) δ 5.23 (s, 2H, CH2), 5.81 (s, 1H, OH), 7.06 (d, 1H, 3J = 8.1 Hz, Ar-H-5), 7.42-7.49 (m, 7H, Ar-H), 9.87 (s, 1H, CHO). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5 h; Inert atmosphere Stage #2: at 0℃; for 12 h; |
To a solution of 3,4-dihydroxybenzaldehyde (5.0 g, 36.2 mmol) in DMF (100 mL) at 0°C under N2 was added NaH (60percent dispersion in mineral oil, 2.90 g, 72.4 mmol) and the mixture was stirred at 0°C for 0.5 h. Benzyl chloride (4.12 g, 32.6 mmol) was then added dropwise and stirring was continued at 0°C for 12 h. The mixture was diluted with water (200 mL), extracted with EtOAc and the organic extracts were dried over Na2SC>4, filtered and concentrated in vacuo. The residue was purified by column chromatography (EtO Ac/Pet. Ether, 0-25percent, v/v) followed by rinsing with a 25percent EtO Ac/Pet. ether solution to give the product, which contained a small amount of the undesired 4-benzyloxy isomer (G2-a). Further purification by column chromatography (DCM Pet. Ether, 0-100percent, v/v) then enabled separation and gave the desired product G-a (4.5 g, 60percent) and the minor isomer G2-a (0.3 g, 4percent) as white solids. TLC: Rf = 0.70( silica gel, Pet.ether/EtOAc=4/l,v/v); LCMS: m/z 229 1 [M+H]+, 251.0 [M+Naf; 1HNMR: (400 MHz, CDC13) δ ppm 9.77 (s, 1H), 7.50 (d, J= 1.6 Hz, 1H), 7.41 (m, 6H), 7.06 (d, J= 8.0 Hz, 1H), 6.54 (s, 1H), 5.15 (s, 2H). |
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