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CAS No. : | 22766-68-3 | MDL No. : | MFCD19686937 |
Formula : | C10H17NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MMXIVBVOFFBDEB-UHFFFAOYSA-N |
M.W : | 183.25 | Pubchem ID : | 573424 |
Synonyms : |
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.9 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 53.79 |
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) : | -6.76 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 0.93 |
Log Po/w (WLOGP) : | 0.65 |
Log Po/w (MLOGP) : | 1.31 |
Log Po/w (SILICOS-IT) : | 1.58 |
Consensus Log Po/w : | 1.38 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.36 |
Solubility : | 7.93 mg/ml ; 0.0432 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.14 |
Solubility : | 13.4 mg/ml ; 0.073 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.62 |
Solubility : | 4.35 mg/ml ; 0.0237 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.99 |
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 |
---|---|---|
99.4% | With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -50 - 20℃; for 16.4167 h; Inert atmosphere | A solution of ethyl 1 -(2-chloroethyl)-4-piperidine-4-carboxylate (II) (5.0 g, 22.76 mmol) in tetrahydrofuran (THF, 147.0 mL) was cooled down to -50°C under nitrogen. LDA (2.0 in heptane THF/ethyl benzene, 17.0 mL, 34.0 mmol) was added to the solution at -50°C over 25 mins. The reaction mixture was allowed to warm up to room temperature over 16h. The reaction was quenched with saturated aqueous K2CO3 (122.0 mL) and extracted with diethyl ether (3 x 120.0 mL). The combined organic layers were dried with Mgs04, filtered and concentrated under vacuum. The resulting orange liquid was co-evaporated three times with dichloromethane to remove excess ethyl benzene, resulting in an orange oil (4.15g, 99.4percent). Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate (III): 1H-N R (300 MHz, CDC ) δ 4.10 (t, J = 5.23 Hz, 2H), 2.90 - 2.85 (m, 6H), 1 .71 - 1.66 (m, 6H), 1 .22 (t, J = 4.0 Hz, 3H). |
95.7% | With diisopropylamine In tetrahydrofuran; n-heptane; ethylbenzene at -50 - 20℃; for 16.4167 h; | Ethyl 1-azabicyclo[2.2.2]octane-4-carboxylate A solution of ethyl 1-(2-chloroethyl)-4-piperidinecarboxylate (20.42 g, 92.9 mmol) in THF (600 mL) was cooled to -50° C. under Ar. LDA (2.0 M in heptane/THF/ethyl benzene, 70 mL, 140 mmol) was slowly added to the solution at -50° C. over 25 min. The reaction was allowed to warm up to room temperature over 16 h. The reaction was quenched with K2CO3 (saturated aqueous) (500 mL) and extracted with Et2O (3*500 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated under vacuum. The resulting orange oil was co-evaporated three times with DCM to remove excess ethyl benzene, resulting in the title compound (16.29 g, 95.7percent). EI-MS m/z 184(M+H+) Rt (1.08 min). |
95.7% | Stage #1: With lithium diisopropyl amide In tetrahydrofuran; n-heptane; ethylbenzene at -50 - 20℃; Stage #2: With water; potassium carbonate In tetrahydrofuran; n-heptane; ethylbenzene |
Ethyll-azabicyclo[2.2.2 Joctane-4-carboxylate; A solution of ethyl 1-(2-chloroethyl)-4-piperidinecarboxylate (20.42 g, 92.9 mmol) in THF (600 mL) was cooled to-50 °C under Ar. LDA (2.0 M in heptane/THF/ethyl benzene, 70 mL, 140 mmol) was slowly added to the solution at -50 °C over 25 min. The reaction was allowed to warm up to room temperature overnight. The reaction was quenched with K2C03 (saturated aqueous) (500 mL) and extracted with Et20 (3 x 500 mL). The combined organic layers were dried over MgS04, filtered, and concentrated under vacuum. The resulting orange oil was co-evaporated three times with CH2C12 to remove excess ethyl benzene, resulting in the title compound (16.29 g, 95.7percent). EI-MS m/z 184 (M+H+) Rt (1.08 min). |
60.11% | With potassium hexamethylsilazane In tetrahydrofuran; toluene at 40℃; Inert atmosphere | In a 500 mL three-necked flask, potassium bis(trimethylsilyl)amide (150 mL, 1 M in tetrahydrofuran) Was added dropwise to a solution of compound 1-3 (21.55 g, 0 mol) in toluene (220 mL) at 40 ° C, Stir overnight at 40 ° C under nitrogen. The reaction was quenched with acetic acid (28 mL) and ethanol (14 mL) Stirred at 40 ° C for 20 min, adjusted to pH> 7 with aqueous potassium carbonate, extracted with ethyl acetate (500 mL) The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure to give 11g (yield 60.11percent) of a brown oil. |
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