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CAS No. : | 51072-83-4 | MDL No. : | MFCD01475745 |
Formula : | C10H8N2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ZFFATLKERBHVHQ-UHFFFAOYSA-N |
M.W : | 156.18 | Pubchem ID : | 2752630 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 47.98 |
TPSA : | 39.58 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.71 cm/s |
Log Po/w (iLOGP) : | 1.71 |
Log Po/w (XLOGP3) : | 2.17 |
Log Po/w (WLOGP) : | 2.35 |
Log Po/w (MLOGP) : | 1.18 |
Log Po/w (SILICOS-IT) : | 2.95 |
Consensus Log Po/w : | 2.07 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.73 |
Solubility : | 0.291 mg/ml ; 0.00186 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.63 |
Solubility : | 0.363 mg/ml ; 0.00232 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.74 |
Solubility : | 0.0283 mg/ml ; 0.000181 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.55 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-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 |
---|---|---|
68% | With aluminum (III) chloride; sodium azide; In tetrahydrofuran; for 8h;Reflux; | General procedure: To a solution of AlCl3 (2.67 g, 20.0 mmol) in THF (100 mL), NaN3 (3.90 g, 60.0 mmol) and corresponding substituted 2-methylindole-3-carboxadehyde 7 (10.0 mmol) were added. The reaction mixture was heated at reflux for 8 hours. The solvent was then removed under reduced pressure, and the residue was diluted with 10% HCl (20 mL). This mixture was extracted with CH2Cl2 (2 X 60 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc/hexanes = 1:3) to obtain the corresponding carbonitrile. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With carbon monoxide; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 120℃; under 4560.31 Torr; for 72h;Autoclave; | General procedure: To an oven-dried ACE glass pressure tube was added 47 (155 mg, 0.67 mmol), Pd(OAc)2 (15.0 mg, 0.07 mmol), PPh3 (61 mg, 0.23 mmol), and DMF (5 mL). The tube was fitted with a pressure head and the solution was then saturated with CO (three cycles to 6 atm of CO). The reaction mixture was heated at 120 C under CO (6 atm, 72 h). The solvents were removed under reduced pressure and the crude product was purified by chromatography (hexanes/EtOAc, 8:2) affording 5 (107 mg, 0.53 mmol, 79%) as a pale yellow solid. Mp 145-150 C; 1H NMR delta 8.27 (s, 1H), 7.24 (d, J=9.0 Hz, 1H), 7.10 (d, J=2.4 Hz, 1H), 6.88 (dd, J=9.0, 2.4 Hz, 1H), 3.86 (s, 3H), 2.97 (q, J=7.2 Hz, 2H), 1.41 (t, J=7.2 Hz, 3H); 13C NMR delta 156.0, 150.5, 129.4, 128.8, 116.7, 113.8, 112.4, 100.8, 84.3, 56.0, 21.2, 13.4; IR (ATR) 3243, 2973, 2212, 1477, 1218 cm-1; HRMS (ESI) calcd for C12H13N2O (M+H+) 201.1028; found, 201.1023. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
37% | With copper(l) iodide; In N,N-dimethyl-formamide; at 100℃; for 34h; | General procedure: A mixture of CuI (0.6 mmol), indoles (0.5 mmol) and benzyl cyanide (0.6 mmol) in DMF (3.0 mL) was stirred under air at 100 C for 34 h and then cooled to room temperature. After the reaction mixture was quenched with 10 mL of water, it was extracted with DCM (3×10 mL). The combined organic layers were washed with the saturated aqueous solution of sodium chloride and dried over MgSO4. The solution was concentrated under reduced pressure and purified by column chromatography to afford 3-cyanoindoles. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With caesium carbonate; In N,N-dimethyl-formamide; at 140℃; for 5h;Inert atmosphere; | General procedure: To a suspension of 2-methylindole-3-carboxaldehyde (7a) (200 mg, 1.26 mmol) and Cs2CO3 (1.34 g, 3.80 mmol) in N,N-dimethylformamide (4 mL) was added 2-fluorobenzaldehyde (210 muL, 1.99 mmol) under a nitrogen atmosphere. The reaction mixture was heated at 140 C until the indole substrate was all consumed (monitored by TLC), and then allowed to cool down to room temperature. The resulting mixture was filtered and washed with ethyl acetate (80 mL). The filtrate was washed with water (3 X 80 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (EtOAc/hexanes = 1:3) to afford the desired indolo[1,2-a]quinoline. |
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