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CAS No. : | 18085-37-5 | MDL No. : | MFCD06657098 |
Formula : | C12H15NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CTFFWKWHYDAMKP-UHFFFAOYSA-N |
M.W : | 205.25 | Pubchem ID : | 4385248 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.42 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 61.43 |
TPSA : | 29.54 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.25 cm/s |
Log Po/w (iLOGP) : | 2.44 |
Log Po/w (XLOGP3) : | 1.84 |
Log Po/w (WLOGP) : | 0.9 |
Log Po/w (MLOGP) : | 1.59 |
Log Po/w (SILICOS-IT) : | 1.85 |
Consensus Log Po/w : | 1.72 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.3 |
Solubility : | 1.02 mg/ml ; 0.00497 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.08 |
Solubility : | 1.7 mg/ml ; 0.0083 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.82 |
Solubility : | 0.311 mg/ml ; 0.00151 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.91 |
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 |
---|---|---|
67% | With triethylamine In acetonitrile for 4 h; Reflux | To a solution of methyl 1,3-dibromopropionate (7.8 mL, 55.2 mmol, 1 equiv) in CH3CN (120 mL), were added NEt3 (23 mL, 166 mmol, 3 equiv) and benzylamine (6 mL, 55.2 mmol, 1 equiv). The solution was heated to reflux and stirred for 4 h. After cooling, water (70 mL) was added and the product was extracted with Et2O (3.x.40 mL). The combined organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (AcOEt/petroleum ether, 1:7 to 2:1) to afford azetidine 4 (7.58 g, 67percent) as an orange oil. TLC Rf 0.21 (silica gel, AcOEt/petroleum ether, 1:3); 1H NMR (300 MHz, CDCl3) δ 7.33-7.17 (m, 5H, Ph), 3.78 (d, 1H, J=12.6 Hz, CH2Ph), 3.71 (t, 1H, J=8.4 Hz, H-1), 3.60 (s, 3H, CO2Me), 3.56 (d, 1H, J=12.6 Hz, CH2Ph), 3.29 (m, 1H, H-4a), 2.91 (m, 1H, H-4b), 2.34 (m, 1H, H-3a), 2.18 (m, 1H, H-3b). Spectroscopic data are in accordance with literature data.26 |
26% | Stage #1: With triethylamine In methanol at 0℃; for 0.166667 h; Stage #2: at 20℃; |
A solution of methyl 2,4-dibromobutanoate 20 (10.01 g, 38.49 mmol, 1.0 eq.) in methanol (15 ml) was added drop-wise to a stirred solution of triethylamine (11.68 g, 16.01 ml, 115.5 mmol, 3.0 eq.) in methanol (40 ml) at 0 °C. The solution was stirred for 15 min after which time benzylamine (4.33 g, 4.41 ml, 40.4 mmol, 1.05 eq.) in methanol (25 ml) was added in a drop-wise manner and stirring was continued for a further 30 min after which time the solutionwas left to warm to rt and finally left to stir overnight. The reaction mixture was concentrated in vacuo and then diluted with diethylether (100 ml). The resulting solids were removed by filtration. The organic phase was washed with water (200 ml) and the aqueous phase was extracted with diethyl ether (3 50 ml). The combinedorganic phases were dried (Na2SO4), filtered and evaporated invacuo. The crude material was purified by column chromatography(25percent ethyl acetate: hexane) to afford methyl 1-benzylazetidine-2-carboxylate 21 as an orange oil (2.02 g, 26percent). Rf 0.35 (1:3 ethylacetate: hexane); νmax (neat)/cm-1 2953, 2837, 1737, 1442, 1201,1172; 1H NMR (300 MHz, CDCl3); δ 7.35e7.17 (m, 5H, ArH's),3.84e3.70 (m, 2H, CH2Ph), 3.62 (s, 3H, OCH3), 3.58 (d, 1H,J 12.5 Hz, COCH), 3.35e3.27 (m, 1H, NCH2a), 2.98e2.88 (m, 1H,NCH2b), 2.36 (dt, 1H, J 8.7 & 17.6 Hz, CHCH2a), 2.25e2.13 (m, 1H,CHCH2b); 13C NMR (75 MHz, CDCl3); δ 173.10, 137.08, 129.17, 128.36,127.32, 64.40, 62.45, 51.83, 50.85, 21.72; HRMS m/z (ESI) 206.1198([M + H]+ requires 206.1175). |
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