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CAS No. : | 914299-79-9 | MDL No. : | MFCD11016232 |
Formula : | C10H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MHZXKVPCJBPNKI-SNVBAGLBSA-N |
M.W : | 163.22 | Pubchem ID : | 22860773 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 51.52 |
TPSA : | 21.26 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.62 cm/s |
Log Po/w (iLOGP) : | 2.0 |
Log Po/w (XLOGP3) : | 0.95 |
Log Po/w (WLOGP) : | 0.64 |
Log Po/w (MLOGP) : | 1.17 |
Log Po/w (SILICOS-IT) : | 2.19 |
Consensus Log Po/w : | 1.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.75 |
Solubility : | 2.87 mg/ml ; 0.0176 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.98 |
Solubility : | 17.0 mg/ml ; 0.104 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.06 |
Solubility : | 0.143 mg/ml ; 0.000875 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.93 |
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 |
---|---|---|
100% | With hydrogen bromide In acetic acid at 0 - 20℃; for 16 h; | Phenol (360mg, 3.82mmol) and 45percent HBr/ AcOH (1.6mL) were added to a solution of (3S)-3-phenyl-4-(para-toluenesulfonyl)morpholine (35mg, 0.11mmol) (prepared according to the procedures of Aggarwal21) at 0°C, before being warmed to room temperature and stirred for 16h. The reaction was cooled to 0°C and 20percent aqueous NaOH was cautiously added. The mixture was then diluted with Et2O, the organic layer was separated and extracted, dried (MgSO4), filtered and concentrated in vacuo. Purification by flash column chromatography (15percent MeOH/CH2Cl2) afforded the deprotected morpholine, (3S)-3-phenylmorpholine (19.4mg, quant.) as a colourless oil; Rf: (15percent MeOH/CH2Cl2) 0.35; [α]24D=+36.8[α]D24=+36.8 (c 0.87, CHCl3); νmax (ATR)/cm−1 3429, 2962, 2848, 2789, 1493, 1449, 1350, 1289, 1232, 1116, 1037, 984, 904, 880, 794, 756, 700, 650, 590; δH (400MHz, CDCl3) 7.42–7.26 (5H, m, 5×PhH), 3.94 (1H, dd, J 10.1 and 3.2), 3.88 (1H, dd, J 11.3 and 2.9), 3.84 (1H, dd, J 11.3 and 3.3), 3.69 (1H, td, J 11.3 and 2.7), 3.45 (1H, t, J 10.5), 3.12 (1H, td, J 11.6 and 3.3), 3.00 (1H, br dt, J 11.6); δC (100MHz, CDCl3) 139.8, 128.5, 127.9, 127.2, 73.2, 66.9, 60.4, 46.3; HRMS (ES+) M+ calculated for C10H14NO 164.1075, observed 164.1064. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
424 mg | With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 72℃; | Step 3. (S)-3-phenylmorpholine To a LiAlH4/THF slurry (0.47 g/2 mL) was added dropwise (S)-5-phenylmorpholin-3-one in THF solution (481 mg in 6 mL) at room temperature over 5 min. The resulting mixture was stirred at room temperature thereafter for 1 hour, then was heated with 72° C. oil bath overnight, then was cooled down to 0° C., quenched by sequential addition of H2O (0.47 mL), 3M aqueous solutionueous NaOH (0.47 mL) and H2O (1.4 mL), and the quenched residue was diluted with Et2O (30 mL), stirred for 10 min and the ethereal solution was separated by filtration. The filtrate was concentrated, further dried under vacuum and (S)-3-phenylmorpholine (424 mg, 96percent yield) was obtained as colorless solid. LCMS (m/z): 164.2 (MH+), 0.33 min. |
1.3 g | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 45℃; for 5 h; Inert atmosphere | To a stirred solution of (5)-5-phenylmorpholin-3-one (Step 2 intermediate) (3.0 g, 19.9 mmol) in anhydrous THF (40 mL) was added lithium aluminum hydride (2.57 g, 67.8 mmol) in small portions at 0 °C under nitrogen atmosphere. The mixture was warmed to 45 °C and stirred for 5 h at the same temperature. The mixture was quenched with saturated aqueous sodium sulfate solution. Ethyl acetate was added to the aqueous mixture and stirred for 10 min. The suspension was filtered through celite and the filtrate was dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was dried well to obtain 1.3 g of the desired product. NMR (300 MHz, CDCb) δ 3.00 (d, / = 1 1.7 Hz, 1H), 3.13 (t, = 8.7 Hz, 1H), 3.40 (t, = 10.8 Hz, 1H), 3.66 (t, = 10.5 Hz, 1H), 3.80-3.94 (m, 3H), 7.25-7.41 (m, 5H). |
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