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CAS No. : | 209984-30-5 | MDL No. : | MFCD11977772 |
Formula : | C15H13NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VLYOZVMUFWIJIQ-UHFFFAOYSA-N |
M.W : | 223.27 | Pubchem ID : | 46856420 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.13 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 72.07 |
TPSA : | 20.31 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.83 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 2.58 |
Log Po/w (WLOGP) : | 2.49 |
Log Po/w (MLOGP) : | 2.87 |
Log Po/w (SILICOS-IT) : | 3.09 |
Consensus Log Po/w : | 2.69 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.37 |
Solubility : | 0.0948 mg/ml ; 0.000425 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.65 |
Solubility : | 0.494 mg/ml ; 0.00221 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.08 |
Solubility : | 0.00184 mg/ml ; 0.00000822 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.61 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319 | 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 |
---|---|---|
63% | Stage #1: With sodium hydride In N,N-dimethyl-formamide at 60℃; for 1 h; Stage #2: for 17 h; |
Step A - Synthesis of 7-Methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one A round bottom flask was charged with sodium hydride (0.295 g, 7.46 mmol) in 9.0 ml of DMF and treated with 5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.3 g, 6.22 mmol) (CAS # 20011-90-9, prepared as described in) and references cited therein). After stirring at 60°C for 1 h, the solution was treated with methyl iodide (1.16 ml, 18.6 mmol) and stirring continued for 17 h with the exclusion of light. After cooling, the reaction was diluted with CH2Cl2/H2O, washed with NaHSO4 solution, H2O, and dried over Na2SO4. Evaporation and flash chromatography (SiO2, CHCl3) gave 0.885 g (63percent) of the title compound as a colorless solid. NMR data was as follows: 1H-nmr (CDCl3): δ = 7.62 (d, 2H), 7.26-7.47 (m, 6H), 3.51 (m, 2H), 3.32 (s, 3H). C15H13NO(MW = 223.27); mass spectroscopy (MH+) 223. Anal. Calcd for C15H13NO; C, 80.69 H, 5.87 N, 6.27. Found: C, 80.11 H, 5.95 N, 6.23. |
63% | Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 60℃; for 1 h; Stage #2: for 17 h; |
A round bottom flask was charged with sodium hydride (0.295 g, 7.46 mmol) in 9.0 mL of DMF and treated with 5,7-dihydro-6H-dibenz[b,d]azepin-6-one (1.3 g, 6.22 mmol) (CAS No. 20011-90-9, prepared as described in R. F. C. Brown, et. al., Tetrahedron Letters 1971, 8, 667-6709 and references cited therein). After stirring at 60° C. for 1 h, the solution was treated with methyl iodide (1.16 mL, 18.6 mmol) and stirring continued for 17 h with the exclusion of light. After cooling, the reaction was diluted with CH2Cl2/H2O, washed with NaHSO4 solution, H2O, and dried over Na2SO4. Evaporation and flash chromatography (SiO2, CHCl3) gave 0.885 g (63percent) of the title compound as a colorless solid.Physical data were as follows:1H-NMR (CDCl3): δ=7.62 (d, 2H), 7.26-7.47 (m, 6H), 3.51 (m, 2H), 3.32 (s, 3H).C15H13NO (MW=223.27); mass spectroscopy (MH+) 223.Anal. Calcd for C15H13NO; C, 80.69 H, 5.87 N, 6.27. Found: C, 80.11 H, 5.95 N, 6.23. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | at 100 - 170℃; for 1 h; Inert atmosphere | In a perfectly dried three-necked flask, aluminum chloride (4 eq.) was added portion wise to 23 under a nitrogen stream. The mixture was vigorously stirred and heated at 100 °C for 1 h and then the temperature was raised to 170 °C until gas evolution ceased. After removing the oil bath, ice was added and the mixture was vigorously stirred foradditional 30 min, then HCl 2N was added. The aqueous layer was extracted exhaustively withchloroform. The combined organic phases were washed with brine, dried over Na2SO4 and evaporated.The crude product was recrystallized from EtOH; Rf: 0.55 (n-hexane/EtOAc 98:2); yield: 59percent. |
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