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CAS No. : | 163439-82-5 | MDL No. : | MFCD01073894 |
Formula : | C11H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QJRIUWQPJVPYSO-GHMZBOCLSA-N |
M.W : | 193.24 | Pubchem ID : | 7021491 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.45 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 57.66 |
TPSA : | 43.7 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) : | -7.27 cm/s |
Log Po/w (iLOGP) : | 1.75 |
Log Po/w (XLOGP3) : | 0.3 |
Log Po/w (WLOGP) : | -0.31 |
Log Po/w (MLOGP) : | 0.58 |
Log Po/w (SILICOS-IT) : | 0.83 |
Consensus Log Po/w : | 0.63 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.41 |
Solubility : | 7.48 mg/ml ; 0.0387 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.78 |
Solubility : | 32.1 mg/ml ; 0.166 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.64 |
Solubility : | 4.43 mg/ml ; 0.0229 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.97 |
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 |
---|---|---|
88.5% | With borane-THF In tetrahydrofuran at 70℃; for 3 h; | Borane in THF (1.0 M) (17.19 mL, 180.99 mmol) was added drop-wise to a solution of 2a (10.0 g, 45.24 mmol) in THF (200 mL) at RT, after completion of addition, reaction mixture was slowly heated to 70 °C for 3 h. The reaction mixture was cooled to 0 °C, quenched with methanol (50 mL) by the drop-wise addition, slowly warmed to RT, stirred for 1 h. (Note: intensive gas evolution is occurred). The reaction mixture was concentrated in vacuo, crude was purified on a silica gel column using a linear gradient of ethyl acetate in Pet-ether yielding 7.73 g (88.5percent) of yellowish crystals of compound 3a. SOR (MeOH, 0.5percent): +22.800°; 1H NMR (400 MHz, DMSO-d6) δ 7.51-7.49 (2H, m), 7.39-7.37 (3H, m), 5.45 (1H, d, J = 4.4 Hz, OH), 5.20 (1H, d, J = 5.2 Hz, OH), 4.15-4.11 (1H, m), 4.04-3.94 (2H, m), 3.90-3.85 (1H, m), 3.48-3.43 (1H, m), 3.10-3.06 (1H, m), 2.97-2.93 (1H, m), 2.89-2.86 (1H, m); 13C NMR (100 MHz, DMSO-d6) δ 132.86, 128.97, 128.51, 127.73, 76.27, 65.47, 63.24; LC-MS (ESI) m/z Calcd. for C11H15NO2 [M+H]+: 193.11, Found 194.20 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With sodium bis(2-methoxyethoxy)aluminium dihydride In tetrahydrofuran; toluene at 0 - 20℃; for 2 h; | Step 2: (3R,4R)-1-Benzylpyrrolidine-3,4-diol To a mechanically stirred and cooled solution (0° C.) of the product from Step 1 (50 g, 0.23 mol) in dry THF (1.24 L) was added sodium aluminum hydride bis-(methoxyethoxide) (289 mL of a 65percent Red-A;.(R)./Toluene solution, 0.95 mol) under a nitrogen atmosphere at such a rate that the internal temperature did not exceed 20° C. The reaction mixture was allowed stir at room temperature for 2 h after the addition was complete. The reaction mixture was slowly poured into ice water (1.0 L) with stirring to quench the reaction. After warming to room temperature, 30percent ammonium hydroxide (100 mL) was added followed by EtOAc (1.5 L) and this mixture was stirred for 16 h. The suspension was filtered through diatomaceous earth and the solids were washed with EtOAc. The filtrate layers were separated and the organic phase was dried over sodium sulfate and concentrated to afford a syrup. Dissolution in dichloromethane and concentration affords a white solid that is collected and dried (43.7 g, 86percent). 1H NMR (400 MHz, CDCl3) δ 7.36-7.23 (5H, m), 6.23 (2H, m), 4.65 (1H, m), 4.15-4.00 (3H, m), 3.62-3.49 (1H, dd), 3.33 (1H, dd), 3.14 (1H, dd), 2.94 (1H dd). MS m/z 194 (MH+). Step 2: (3R,4R)-1-Benzylpyrrolidine-3,4-diolTo a mechanically stirred and cooled solution (0° C.) of the product from Step 1 (50 g, 0.23 mol) in dry THF (1.24 L) was added sodium aluminum hydride bis-(methoxyethoxide) (289 mL of a 65percent Red-Al.(R)./Toluene solution, 0.95 mol) under a nitrogen atmosphere at such a rate that the internal temperature did not exceed 20° C. The reaction mixture was allowed stir at room temperature for 2 h after the addition was complete. The reaction mixture was slowly poured into ice water (1.0 L) with stirring to quench the reaction. After warming to room temperature, 30percent ammonium hydroxide (100 mL) was added followed by EtOAc (1.5 L) and this mixture was stirred for 16 h. The suspension was filtered through diatomaceous earth and the solids were washed with EtOAc. The filtrate layers were separated and the organic phase was dried over sodium sulfate and concentrated to afford a syrup. Dissolution in methylene chloride and concentration affords a white solid that is collected and dried (43.7 g, 86percent). 1H NMR (300 MHz, CDCl3) δ 7.36-7.23 (5H, m), 6.23 (2H, m), 4.65 (1H, m), 4.15-4.00 (3H, m), 3.62-3.49 (1H, dd), 3.33 (1H, dd), 3.14 (1H, dd), 2.94 (1H dd). MS m/z 194 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | Stage #1: for 96 h; Heating / reflux Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; |
To a 1,4-dioxane (20 mL) solution of 1,4-di-O-tosyl-D-threitol (9.15 g, 21.25 mmol), benzylamine (9.29 mL, 85.0 mmol) was added, and the mixture was heated to reflux under a nitrogen stream for 4 days while stirring. The reaction liquor was returned to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (50 mL) was added. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by column chromatography using silica gel [NH(basic)-silica gel 100 g, ethyl acetate to chloroform/methanol (10/1)], to obtain the title compound (1.88 g, 46percent) as an oily matter. NMR(CDCl3)δ:2.49(2H,dd,J=10.4,3.3Hz),3.01(2H,dd,J=10.0,5.4Hz),3.68(2H,s),4.08-4.13(2H,m),7.35-7.27(5H,m). |
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