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CAS No. : | 949892-14-2 | MDL No. : | MFCD18732769 |
Formula : | C14H18BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NMESVFJGKMPJPM-UHFFFAOYSA-N |
M.W : | 259.11 | Pubchem ID : | 68929100 |
Synonyms : |
|
Num. heavy atoms : | 19 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 74.12 |
TPSA : | 51.48 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.03 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 2.6 |
Log Po/w (WLOGP) : | 1.87 |
Log Po/w (MLOGP) : | 0.73 |
Log Po/w (SILICOS-IT) : | 1.88 |
Consensus Log Po/w : | 1.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.19 |
Solubility : | 0.169 mg/ml ; 0.000651 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.33 |
Solubility : | 0.121 mg/ml ; 0.000467 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.21 |
Solubility : | 0.0158 mg/ml ; 0.0000611 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.01 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 | UN#: | |
Hazard Statements: | H315-H319 | Packing Group: | |
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 |
---|---|---|
100% | With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,4-dioxane; at 90℃; for 3h;Inert atmosphere; | A mixture of <strong>[120315-65-3]4-bromo-3-methoxybenzonitrile</strong>(lg, 4.72 mmol), 4,4,4',4',5,5,5',5'- octamethyl-2,2'-bi(l,3,2-dioxaborolane) (1.796 g, 7.07 mmol), K3P04 (1.157 g, 11.79 mmol) and PdCl2(dppf) CH2C12 adduct (0.207 g, 0.283 mmol) in dioxane (12 mL) was degassed and then heated at 90 °C for 3 h. The reaction was cooled to rt and was filtered through a pad of CELITE®. The solvent was removed. Normal phase chromatography afforded X-lb as brown oil (1.7 g, 5.76 mmol, 100percent). LC-MS (ESI) of the boronic acid m/z: 178.0 [M+H]+. |
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 19h;Inert atmosphere; | Intermediate S: 3-Methoxy-4-(4,4,5,5-tetramethyl-ri ,3,21dioxaborolan-2ylbenzonitrile 4-Bromo-3-methoxy-benzonitrile (300 mg, 1.4 mmol) was dissolved in dioxane (2.5 mL) and the solution was flushed with argon. Bis-pinacolatodiboron (719 mg, 2.8mmol), Pd(dppf)CI2 (58 mg, 0.07 mmol) and KOAc (417 mg, 4.2 mmol) were added and the reaction mixture was heated to 100 °C and stirred at this temperature for 19 h. It was then allowed to cool to rt and diluted with EtOAc. The organic phase was washed with brine, dried (Na2S04) and concentrated. The residual crude product was purified by flash chromatography (25g silica gel cartridge, hexanes/EtOAc, 100:0? 60:40) to give the title compound as a white solid; H-NMR (DMSO-c 6, 400 MHz) delta ppm 7.68 (d, 1 H), 7.42 (s, 1 H), 7.39 (d, 1 H), 3.82 (s, 3H), 1.32 (s, 12H). |