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CAS No. : | 132-54-7 | MDL No. : | MFCD00014310 |
Formula : | C17H12O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QHDYIMWKSCJTIM-UHFFFAOYSA-N |
M.W : | 264.28 | Pubchem ID : | 67236 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 77.37 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.52 cm/s |
Log Po/w (iLOGP) : | 2.78 |
Log Po/w (XLOGP3) : | 4.78 |
Log Po/w (WLOGP) : | 3.76 |
Log Po/w (MLOGP) : | 3.63 |
Log Po/w (SILICOS-IT) : | 3.48 |
Consensus Log Po/w : | 3.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.88 |
Solubility : | 0.00345 mg/ml ; 0.0000131 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.49 |
Solubility : | 0.000858 mg/ml ; 0.00000325 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.71 |
Solubility : | 0.00052 mg/ml ; 0.00000197 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.95 |
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 |
---|---|---|
31.5 g (59.7%) | With hydrogenchloride;aluminium trichloride; In water; toluene; | EXAMPLE 1 To a 500-mL, three-neck, nitrogen-purged flask were added 28.8 g (0.20 mole) of 1-naphthol and 90 mL of toluene. To this stirred slurry was added 26.6 g (0.20 mole) of anhydrous aluminum chloride in portions over five minutes. The temperature of the mixture rose to 40-50 C. during this addition. The orange slurry was heated to reflux, then 32.0 g (0.204 mole) of phenyl chloroformate was added over a period of 30 minutes. After this addition, the mixture was refluxed for 30 minutes then cooled to 30-40 C. To the red reaction mixture was added 100 mL of water while holding the temperature at 35-50 C. This addition is very exothermic initially, and ice bath cooling is used. During addition of the remaining water, the bath is lowered or removed in order to avoid cooling below 35 C. After this addition, 20 mL of 32% hydrochloric acid was added quickly at 35 -50 C. The mixture was stirred for 15 minutes, then the layers are allowed to separate. The lower (aqueous) layer was discarded. The top layer was washed (at 40-50 C.) successively with: two 100-mL portions of 10% hydrochloric acid and two 100-mL portions of 40-50 C. water. The solvent was then stripped off under vacuum (150-200 mm) to a pot temperature of 90 C. To the resulting amber liquid was added 120 mL of isopropyl alcohol at 70 C. The solution was cooled slowly to 0-5 C. After stirring at 0-5 C. for one hour, the slurry was filtered and the solids washed with three 25-mL portions of 0-5 C. isopropyl alcohol. The yellow solids were air dried at 40 C. to give 31.5 g (59.7%) of phenyl 1-hydroxy-2-naphthoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | at 200℃; for 1.5h; | The compound was prepared by the above reaction without any solvent. Yield 84%; M.p 175 0C (DSC, onset). It was further purified by colum chromatography ( silica gel-CH2CI2). Elemental analysis: table. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | at 200℃; for 2.0h; | The compound was prepared by the above reaction without any solvent, isolated as a light greenish yellow solid after column chromatography over silica gel (dichloromethane- petroleum ether 40-60 0C 3:2). Yield 37%. M. p 181 0C (DSC, onset). Elemental analysis: table. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In tetrahydrofuran; for 24.0h;Reflux; | To a stirred solution of <strong>[132-54-7]phenyl 1-hydroxy-2-naphthoate</strong> (0.53 g, 2.0 mmol) in THF (25 mL) was added 4-picolylamine(0.22 g, 2.0 mmol). The mixture was stirred at reflux for 24 hand then evaporated. The crude product was purified by columnchromatography (eluent: CH2Cl2 then CH2Cl2/MeOH 7:3) givingcompound 19 (0.42 g, 75%) as an orange solid, mp 132-134 C.HRMS (NSI) for C17H14N2O2. Calculated mass of molecular ion279.1128 [M+H]+. Measured mass: 279.1132; IR mmax cm1 3244;3044; 1622, 1597; 1548, 1401, 1332, 1272, 999, 790, 764; 1HNMR (400 MHz; d6-DMSO) dH 9.82 (1H, s, br, NH), 8.56 (2H,d, J = 6.0 Hz, Ar-H), 8.32 (1H, d, J = 8.2 Hz, Ar-H), 8.01 (1H, d,J = 8.7 Hz, Ar-H), 7.90 (1H, d, J = 7.8 Hz, Ar-H), 7.66 (1H, t,J = 7.6 Hz, Ar-H), 7.57 (1H, t, J = 7.1 Hz, Ar-H), 7.46-7.36 (3H, m,Ar-H), 4.64 (2H, d, J = 5.0 Hz, CH2NH); 13C NMR (101 MHz;d6-DMSO) dC 171.3 (CO), 160.6 (Ar-C), 150.2 (2 Ar-C), 148.4(Ar-C), 136.5 (Ar-C), 129.4 (Ar-C), 128.0 (Ar-C), 126.23 (Ar-C),125.5 (Ar-C), 123.7 (Ar-C), 123.3 (Ar-C), 122.7 (2 Ar-C), 118.0(Ar-C), 107.5 (Ar-C), 42.1 (CH2). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With sodium hydrogencarbonate; In tetrahydrofuran; N,N-dimethyl-formamide; for 72.0h;Reflux; | A mixtureof compound 33 (1.00 g, 3.46 mmol), phenyl-1-hydroxy-2-naphthoate(0.92 g, 3.46 mmol) and NaHCO3 (0.29 g, 3.46 mmol) inTHF/DMF (50 mL, 2:1) was heated at reflux for 72 h. The solventswere evaporated and the residue was recrystallized from ethanol/methanol (40 mL, 50:50) giving compound 34 (1.40 g, 96%) asa yellow powder, mp 232 C. HRMS (NSI) for C22H21N3O6. Calculatedmass of molecular ion 446.1323 [M+Na]+. Measured mass:446.1321; IR mmax cm1 3368, 3300-2500, 1640, 1581, 1538,1333, 1276, 1285, 1253, 756; 1H NMR (400 MHz; d6-DMSO) dH9.22 (1H, m, NH), 8.30-8.22 (2H, m, NH, Ar-H), 8.01-7.90 (3H, m,Ar-H), 7.87 (1H, d, J = 8.2 Hz, Ar-H), 7.66-7.60 (1H, m, Ar-H),7.57-7.52 (1H, m, Ar-H), 7.37 (1H, d, J = 8.7 Hz, Ar-H), 7.04 (1H,d, J = 9.2 Hz, Ar-H), 3.40 (2H, q, J = 6.4 Hz, CH2NH), 3.30 (2H, q,J = 6.0 Hz, CH2NH), 2.84 (2H, t, J = 7.8 Hz, CH2), 2.43 (2H, t,J = 7.8 Hz, CH2); 13C NMR (101 MHz; d6-DMSO) dC 172.3 (CO),171.1 (CO), 163.3 (Ar-C), 160.2 (Ar-C), 139.3 (Ar-C), 136.3(Ar-C), 129.2 (2 Ar-C), 128.0 (Ar-C), 126.2 (Ar-C), 126.0 (Ar-C),125.3 (Ar-C), 124.4 (Ar-C), 123.5 (Ar-C), 123.4 (Ar-C), 117.9 (Ar-C), 115.6 (Ar-C), 107.6 (Ar-C), 39.6 (CH2NH, signal obscured by d6-DMSOsignal, re-appears by DEPT), 38.6 (CH2), 35.1 (CH2), 26.0 (CH2). |