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CAS No. : | 1313279-48-9 | MDL No. : | MFCD30146461 |
Formula : | C8H15ClN2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PVCCBMZCSWIUCI-UHFFFAOYSA-N |
M.W : | 174.67 | Pubchem ID : | 67123709 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.88 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.88 |
TPSA : | 49.81 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) : | -6.44 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.3 |
Log Po/w (WLOGP) : | 2.22 |
Log Po/w (MLOGP) : | 1.07 |
Log Po/w (SILICOS-IT) : | 1.1 |
Consensus Log Po/w : | 1.14 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.68 |
Solubility : | 3.68 mg/ml ; 0.0211 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.95 |
Solubility : | 1.98 mg/ml ; 0.0113 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.19 |
Solubility : | 11.3 mg/ml ; 0.0647 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.53 |
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 |
---|---|---|
96% | With hydrogenchloride In 1,4-dioxane at 10 - 25℃; | To a 1 0-L round-bottom flask was placed tert-butyl N-[(lr,4r)-4-(cyanomethyl)cyclohexyl]carbamate (620 g, 2.60mol, 1.00 equiv.), and 1,4-dioxane (2 L). This was followed by the addition of a solution of HC1 in 1,4-dioxane (5 L, 4 M) dropwise with stirring at 10°C. The resulting solution was stirred overnight at 25 °C. This reaction was performed for 4 times and the reaction mixtures were combined. The solids were collected by filtration. The solids were washed with 1,4-dioxane (3 x3 L), ethyl acetate (3 x 3 L) and hexane (3 x 3 L). This resulted in 2-[(lr,4r)-4- aminocyclohexyl]acetonitrile hydrochloride (1753 g, 96percent) as a white solid. MS (ESI): mass calcd. for C8H14N2, 138.12; m/z found 139.25, [M+H] ‘HNIVIR: (300 IVIFIz, DMSO-d6): 8.14 (s, 3H), 2.96-2.84 (m, 1H), 2.46 (d, J= 6.3 Hz, 2H), 1.98 (d, J 11.1 Hz, 2H), 1.79 (d, J 12.0 Hz, 2H), 1.64-1.49 (m, 1H), 1.42-1.29 (m, 2H), 1.18-1.04 (m, 2H) |
89% | With hydrogenchloride In 1,4-dioxane at 20℃; | Tert -butyl (1r,4r)-4-(cyanomethyl)cyclohexylcarbamate (Preparation 47a, 0.348 g, 1.46 mmol) was added to a 4M hydrogen chloride solution in dioxane (3.65 mL) and the resulting solution was stirred overnight at room temperature. The solvent was evaporated in vacuo and the residue was treated with diethyl ether. The resultant suspension was filtered to give the title compound (0.226 g, 89percent) as a white solid.LRMS (m/z): 139 (M+H)+.1H-NMR δ (DMSO-d6): 1.14 (ddd, 2H), 1.37 (ddd, 2H), 1.60 (m, 1 H), 1.83 (d, 2H), 1.99 (d, 2H), 2.50 (d, 2H), 2.94 (m, 1 H), 8.08 (br s, 2H). |
89% | With hydrogenchloride In 1,4-dioxane at 20℃; | d) 2-((1r,4r)-4-Aminocyclohexyl)acetonitrile hydrochloride A solution of tert-butyl (1r,4r)-4-(cyanomethyl)cyclohexylcarbamate (Preparation 50c, 0.348 g, 1.46 mmol) in 4M hydrogen chloride in dioxane (3.65 mL) was stirred overnight at room temperature. The mixture was evaporated in vacuo and treated with diethyl ether and the resultant suspension was filtered to give the hydrochloride salt of the title compound (0.226 g, 89percent) as a white solid. LRMS (m/z): 139 (M+H)+.1H NMR (300 MHz, DMSO-d6) δ ppm 1.14 (ddd, 2H), 1.37 (ddd, 2H), 1.60 (m, 1H), 1.83 (d, 2H), 1.99 (d, 2H), 2.50 (d, 2H), 2.94 (m, 1H), 8.08 (br s, 2H). |
89% | With hydrogenchloride In 1,4-dioxane at 20℃; | d) 2-((1r,4r)-4-Aminocyclohexyl)acetonitrile hydrochloride A solution of tert-butyl (1r,4r)-4-(cyanomethyl)cyclohexylcarbamate (Preparation 50c, 0.348 g, 1.46 mmol) in 4M hydrogen chloride in dioxane (3.65 mL) was stirred overnight at room temperature. The mixture was evaporated in vacuo and treated with diethyl ether and the resultant suspension was filtered to give the hydrochloride salt of the title compound (0.226 g, 89percent) as a white solid. LRMS (m/z): 139 (M+H)+.1H NMR (300 MHz, DMSO-d6) δ ppm 1.14 (ddd, 2H), 1.37 (ddd, 2H), 1.60 (m, 1H), 1.83 (d, 2H), 1.99 (d, 2H), 2.50 (d, 2H), 2.94 (m, 1H), 8.08 (br s, 2H). |
89% | With hydrogenchloride In 1,4-dioxane at 20℃; | d) 2-((1r,4r)-4-Aminocyclohexyl)acetonitrile hydrochloride A mixture of tert-butyl (1r,4r)-4-(cyanomethyl)cyclohexylcarbamate (Preparation 14c, 0.348 g, 1.46 mmol) and 4M hydrogen chloride solution in dioxane (3.65 mL) was stirred overnight at ambient temperature. The mixture was evaporated in vacuo and treated with diethyl ether and the resultant suspension was filtered to give the hydrochloride salt of the title compound (0.226 g, 89percent) as a white solid. LRMS (m/z): 139 (M+H)+. 1H NMR δ (300 MHz, DMSO-d6): 1.14 (ddd, 2H), 1.37 (ddd, 2H), 1.60 (m, 1H), 1.83 (d, 2H), 1.99 (d, 2H), 2.50 (d, 2H), 2.94 (m, 1H), 8.08 (br s, 2H). |