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CAS No. : | 5060-82-2 | MDL No. : | MFCD00075494 |
Formula : | C11H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | UNFNRIIETORURP-UHFFFAOYSA-N |
M.W : | 174.20 | Pubchem ID : | 853173 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.09 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 52.46 |
TPSA : | 29.46 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) : | -5.78 cm/s |
Log Po/w (iLOGP) : | 1.92 |
Log Po/w (XLOGP3) : | 2.23 |
Log Po/w (WLOGP) : | 2.55 |
Log Po/w (MLOGP) : | 2.17 |
Log Po/w (SILICOS-IT) : | 2.48 |
Consensus Log Po/w : | 2.27 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.83 |
Solubility : | 0.259 mg/ml ; 0.00149 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.48 |
Solubility : | 0.572 mg/ml ; 0.00328 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.62 |
Solubility : | 0.0416 mg/ml ; 0.000239 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 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 |
---|---|---|
63.4% | With potassium carbonate In acetonitrile for 1 h; Reflux | General procedure: A mixture of 2-hydroxy-1-nitronaphthalene (500 mg,2.64 mmol), dimethyl sulfate (0.5 ml, 5.3 mmol), and K2CO3 (73.1 mg, 5.3 mmol) inacetonitrile (10 ml) was refluxed for 1hrs. The solvent was evaporated and the residue waspoured into water and extracted with ethyl acetate. The organic layer was washed with waterand brine and dried over anhydrous MgSO4 and concentrated in vacuo. The residue waspurified by column chromatography on silica gel with nhexane/ethyl acetate (15:1) as theeluent to obtain the product |
30% | With sodium hydroxide In dichloromethane; water at 20℃; for 2 h; | Step A: Sodium hydroxide (20 ml, 1M) and dimethyl sulfate (15.0 ml, 158 mmol) were added dropwise to a solution of 2,7-dihydroxynaphthalene (6.6 g, 40 mmol) in dichloromethane (100 ml) and water (60 ml). Additional sodium hydroxide (20 ml, 1M) and dimethyl sulfate (15.0 ml, 158 mmol) were added and the resulting mixture was stirred at room temperature for 2 hours. The two phases were separated and the aqueous layer was extracted with dichloromethane twice. The combined organic extracts were washed with 1 M HCl, dried over magnesium sulfate and concentrated under vacuum. The crude material was purified by column chromatography (5:1 heptane/ethyl acetate) to give 2-hydroxy-7-methoxynaphthalene (2.1 g, 30percent, 100percent AUC HPLC): 1H NMR (300 MHz, CDCl3) δ 7.66-7.70 (m, 2H), 6.94-7.08 (m, 4H), 4.90 (s, 1H), 3.92 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With potassium carbonate In acetone at 0 - 20℃; | [0709] To a mixture of naphthalene-2,7-diol (25 g, 156.08 mmol) and K2CO3 (32.3 g, 232.02 mmol) in acetone (300 ml) was added iodomethane (22.2 g, 156.41 mmol) dropwise with stirring at 0° C. The resulting solution was stirred overnight at room temperature. The solids were filtered off and the filtrate was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography using 1percent-10percent ethyl acetate in petroleum ether to afford 7-methoxynaphthalen-2-ol as a light yellow solid (10 g, 37percent). (ES, m/z): [M+H]+ 175.1; 1H NMR (400 MHz, DMSO-d6): δ 9.65 (s, 1H), 7.65 (d, J=8.8 Hz, 2H), 6.79 (dd, J=13.6, 1.6 Hz, 2H), 6.92-6.89 (m, 2H), 3.84 (s, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
19% | Stage #1: With bromine; triphenylphosphine In acetonitrile for 2 h; Reflux Stage #2: at 250℃; Sealed tube |
Triphenylphosphine (500 mg, 2.9 mmol) was dissolved in MeCN (5 mL), and bromine (0.15 mL, 2.9 mmol) was added at 0 °C whilst stirring. The solution was allowed to warm up to rt, and 7-methoxy-naphthalen-2-ol, 44 (490 mg, 2.8 mmol) was added portionwise. The solution was refluxed for 2 h, and the solvent removed in vacuo. The residue was heated to 250 °C in a sealed tube overnight. After cooling to rt, the residue was purified by chromatography using a stepped gradient of 10–20percent EtOAc in heptane to yield 45 as a beige solid. Yield: 120 mg (19percent). 1H NMR (CDCl3), δ: 5.17 (br, 1H, OH), 7.06 (d, J = 2.5, 1H, ArH), 7.11 (dd, J = 8.7, 2.4, 1H, ArH), 7.40 (dd, J = 8.7, 2.0, 1H, ArH), 7.63 (d, J = 8.9, 1H, ArH), 7.72 (d, J = 8.9, 1H, ArH), 7.84 (s, 1H, ArH). LC–MS: Rf = 2.01 min; m/z 221/223 ([M+H]+, 100). |
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