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CAS No. : | 4265-16-1 | MDL No. : | MFCD00015463 |
Formula : | C9H6O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ADDZHRRCUWNSCS-UHFFFAOYSA-N |
M.W : | 146.14 | Pubchem ID : | 61341 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 41.6 |
TPSA : | 30.21 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.52 cm/s |
Log Po/w (iLOGP) : | 1.49 |
Log Po/w (XLOGP3) : | 2.35 |
Log Po/w (WLOGP) : | 2.25 |
Log Po/w (MLOGP) : | 0.88 |
Log Po/w (SILICOS-IT) : | 2.56 |
Consensus Log Po/w : | 1.91 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.77 |
Solubility : | 0.25 mg/ml ; 0.00171 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.62 |
Solubility : | 0.347 mg/ml ; 0.00238 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.21 |
Solubility : | 0.0895 mg/ml ; 0.000612 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.09 |
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 |
---|---|---|
90% | at 80℃; | POCl3 (4.73 mL, 50.79 mmol) was slowly added to a solution of DMF (6.56 mL, 84.75 mmol) while the temperature was maintained below 40 °C. Then, benzofuran 1 (2.00 g,16.93 mol) was added dropwise to this reaction mixture below 40 °C, over a period of 15 min. The mixture was heated at 80 °C for 24 h. The reaction mixture was then poured into ice-water and carefully quenched with a solution of sodium hydroxide. The organic material was separated, and the aqueous layer was extracted with ethyl acetate. It was washed with brine and dried over anhydrous magnesium sulfate. The filtrate was concentrated, and was purified on silica gel column (petroleum ether: EtOAc = 10:1) to give product 2 (2.27 g, 90percent) as brown oil. 1H NMR (400 MHz,CDCl3): δ 9.83 (1H, s, COH), 7.75-7.70 (1H, m, H-4), 7.56-7.54 (2H, m, H-6,7), 7.46 (1H, s, H-3), 7.32-7.28 (1H, m, H-5). 13C NMR (100 MHz, CDCl3): δ 179.63 (COH), 156.03 (C-7a), 152.52 (C-2), 129.07 (C-3a), 126.51 (C-6), 124.05 (C-5), 123.58 (C-4), 117.93 (C-3), 112.44 (C-7). |
80% | Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: at 20℃; |
1. To a solution of benzofuran (1.5 g, 12.69 mmol) in 60 mL of THF, was added 5.08 mL(12.69 mmol) of n-BuLi solution in hexanes (2.5 M) at -78 °C. After 1 hr at -78 °C, the reaction mixture was added DMF (3.43 mL). After overnight at RT, the reaction was quenched with saturated ammonium chloride, and extracted with EtOAc (x3). The combined organic extracts were dried (MgS04), filtered, and concentrated. Flash chromatography (10 percentEtOAc/Hexanes) gave benzofuran-2-carbaldehyde (1.48 g, 80percent). *H NMR (400 MHz, CDC13) δ ppm: 9.88 (s, IH), 7.76 (d, J=8.4 Hz, IH), 7.62 (d, J=8.4 Hz, IH), 7.57 (s, IH), 7.52 (td, J=7.2, 1.2 Hz IH), 7.35 (td, J=7.2, 1.2 Hz, IH). |
61% | Stage #1: With n-butyllithium; ammonium chloride In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere Stage #2: at -78℃; for 1 h; |
Step 1: benzofuran-2-carbaldehyde To a solution of benzofuran (10 g, 84.7 mmol) in dry THF was added n-BuLi (2.5 M solution in hexane, 33.9 mL, 84.7 mmol) dropwise at -78° C. under nitrogen, the mixture was stirred at -78° C. for 0.5 h, and then added DMF (19.6 mL, 254 mmol). The resulted mixture was kept at -78° C. and stirred for 1 h. The reaction was quenched by addition of saturated NH4Cl aqueous solution (20 mL), and then added ethyl acetate (300 mL) and H2O (100 mL), the aqueous layer was extracted with ethyl acetate (50 mL). The combined organic layer was washed with water and brine, dried over sodium sulfate and concentrated under vacuum, the residue was purified by column chromatography on silica gel (ethyl acetate:petroleum ether=10:1) to afford benzofuran-2-carbaldehyde (7.5 g, yield: 61percent) as yellow oil. 1H NMR (400 MHz, CDCl3): δ 9.90 (s, 1H), 7.78 (d, J=8.8 Hz, 1H), 7.63 (d, J=8.2 Hz, 1H), 7.59 (s, 1H), 7.53-7.57 (m, 1H), 7.35-7.39 (m, 1H). |
40% | at 80℃; | Preparation of 2,3-Benzofuran-5-carboxaldehyde 39[0201] To a DMF (0.580 mL) solution of 2,3-benzofuran 38 (0.331 mL, 3.0 mmol) was added phosphorous oxychloride (0.302 mL, 3.3 mmol). The reaction mixture was stirred overnight at 80 °C, then the excess solvent was removed in vacuo. The residue was diluted with ethyl acetate (100 mL), then washed with water (2 X 20 mL). The organic layer was dried with brine and MgSC>4, then concentrated in vacuo. Flash column chromatography on silica gel (n-hexanes : ethyl acetate = 50:1) of the residue afforded the desired product 39 in 40percent yield (172 mg, yellow oil). LH NMR (400 MHz, CDC13): 9.88 (s, 1H), 7.76 (d, J= 7.2 Hz, 2H), 7.62 (dd, J= 8.4, 0.8 Hz, 1H), 7.54 (d, J= 0.8 Hz, 1H), 7.53 (td, J= 12, 1.2 Hz, 1H), 7.35 (td, J= 7.2, 0.8 Hz, 1H). |
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