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CAS No. : | 131802-60-3 | MDL No. : | MFCD00870296 |
Formula : | C16H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SIDLHXXVIBTSJZ-UHFFFAOYSA-N |
M.W : | 235.28 | Pubchem ID : | 3035604 |
Synonyms : |
|
Num. heavy atoms : | 18 |
Num. arom. heavy atoms : | 16 |
Fraction Csp3 : | 0.06 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 72.72 |
TPSA : | 22.12 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -4.99 cm/s |
Log Po/w (iLOGP) : | 2.78 |
Log Po/w (XLOGP3) : | 3.86 |
Log Po/w (WLOGP) : | 3.66 |
Log Po/w (MLOGP) : | 2.87 |
Log Po/w (SILICOS-IT) : | 3.91 |
Consensus Log Po/w : | 3.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.19 |
Solubility : | 0.0152 mg/ml ; 0.0000645 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.02 |
Solubility : | 0.0224 mg/ml ; 0.0000952 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.37 |
Solubility : | 0.000101 mg/ml ; 0.000000428 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 1.67 |
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 |
---|---|---|
With pyridine; bromine In tetrachloromethane for 2h; Reflux; | General procedure: To a solution of 6-substituted or 7-substituted quinoline (14 mmol) in 20 mL of CCl4 was added Br2 (14 mmol) dropwise at room temperature. The mixture was heated to reflux and pyridine was added (14 mmol). The reaction solution was refluxed for another 2 h. The mixture was allowed to cool to room temperature, diluted with 50 mL of DCM, washed with 50 mL of water and brine, dried with Na2SO4, concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE: EA = 40: 1) to give 17-23, as an offwhite solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | With potassium carbonate In N,N-dimethyl-formamide | |
31% | In N,N-dimethyl-formamide at 80℃; Alkaline conditions; | 6 Intermediate 17 (I-17): 7-(Benzyloxy)quinoline A mixture of K2CO3 (3.81 g, 27.54 mmol) and 7-hydroxyquinoline (2.00 g, 13.77 mmol) in DMF (20 mL) was stirred at room temperature for 20 min. Benzyl bromide (3.53 g, 2.45 mL, 20.66 mmol) was added dropwise to the mixture and stirred at 80 οC for 12 h. The reaction was quenched with water, extracted with ethyl acetate three times, washed with brine, and dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by silica gel column chromatography to afford the desired product. White solid (1.00 g, 31%).1H NMR (400 MHz, Chloroform-d) δ 8.83 (dd, J = 4.4, 1.8 Hz, 1H), 8.12 (dt, J = 8.2, 1.1 Hz, 1H), 7.74 (d, J = 9.0 Hz, 1H), 7.57 (d, J = 2.5 Hz, 1H), 7.53 - 7.48 (m, 2H), 7.44 - 7.38 (m, 2H), 7.38 - 7.34 (m, 1H), 7.34 - 7.27 (m, 2H), 5.23 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; | 6 Intermediate 18 (I-18): 7-(Benzyloxy)quinoline 1-oxide To a solution of 7-(benzyloxy)quinoline (1.00 g, 4.25 mmol) in DCM (30 mL) at 0 οC was added m-CPBA (1.10 g, 6.38 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction was quenched with 1M NaOH until pH = 10. The aqueous layer was extracted with DCM three times and the combined organic extracts were dried over Na2SO4, filtered and concentrated under pressure. The crude product was used without further purification. White solid (1.00 g, 94%). 1H NMR (400 MHz, DMSO-d6) δ 8.58 - 8.53 (m, 1H), 8.06 - 7.99 (m, 2H), 7.89 (d, J = 8.3 Hz, 1H), 7.55 - 7.50 (m, 2H), 7.47 - 7.39 (m, 3H), 7.38 - 7.30 (m, 2H), 5.32 (s, 2H). |
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