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CAS No. : | 56427-63-5 | MDL No. : | MFCD18642371 |
Formula : | C11H13BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | NTRWNKUDEDMRBR-UHFFFAOYSA-N |
M.W : | 273.12 | Pubchem ID : | 10333471 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 61.86 |
TPSA : | 35.53 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) : | -6.07 cm/s |
Log Po/w (iLOGP) : | 2.77 |
Log Po/w (XLOGP3) : | 2.67 |
Log Po/w (WLOGP) : | 2.61 |
Log Po/w (MLOGP) : | 2.65 |
Log Po/w (SILICOS-IT) : | 3.12 |
Consensus Log Po/w : | 2.77 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.18 |
Solubility : | 0.18 mg/ml ; 0.000658 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.07 |
Solubility : | 0.234 mg/ml ; 0.000855 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.26 |
Solubility : | 0.0149 mg/ml ; 0.0000546 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.18 |
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 |
---|---|---|
52% | With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 78℃; | Step B: Synthesis of ethyl 2-(bromomethyl)-4-methoxybenzoate as an intermediate <n="71"/>; [0175] A mixture of ethyl 4-methoxy-2-methylbenzoate (2.24 g, 11.5 mmol) in carbon tetrachloride (20 mL) was heated to 78 0C in an oil bath then a mixture of N- bromosuccinimide (2.26 g, 12.6 mmol) and benzoyl peroxide (0.28 g, 1.15 mmol) was added portionwise over 4 h. The mixture was stirred overnight at 78 °C. After this time, the reaction mixture was cooled to room temperature and the solids removed by filtration. The filtrate was concentrated under reduced pressure and purification by flash chromatography (silica, 1 :50 ethyl acetate/hexanes) afforded ethyl 2-(bromomethyl)-4-methoxybenzoate (1.60 g, 52percent) as a clear oil: 1H NMR (300 MHz, CDCl3) δ 7.99 (d, J= 8.7 Hz, IH), 6.96 (s, IH), 6.86 (dd, J= 8.7, 2.6, IH), 4.96 (s, 2H), 4.37 (q, J= 7.1, 2H), 3.86 (s, 3H), 1.41 (t, J= 7.1 Hz, 3H); ESI MS m/z 273 [M+ H]+. |
48% | With N-Bromosuccinimide In tetrachloromethane for 6 h; Heating / reflux | Ethyl 2-nnethyl-4-methoxybenzoate (583 mg, 3 mmol) andN-bromosuccinimide (1335 mg, 7.5 mmol) were added to carbon tetrachloride (8 mL), and the resultant was refluxed for six hours. After the reaction was completed, N-bromosuccinimide was filtered out and carbon tetrachloride was distilled under a reduced pressure. The resultant was purified by a column <n="28"/>chromatography on silica gel (hexane/ethyl acetate=40:1 ) to obtain 340 mg of the desired compound(yield 48percent).1H NMR (400 MHz, CDCI3) δ 7.99 (d, J=2.6 Hz, 1 H), 6.96 (d, J=2.6 Hz, 1 H), 6.85 (dd, J=8.8, 2.6 Hz, 1 H), 4.96 (s, 2H), 4.37 (q, J=7.1 Hz, 2H), 3.86 (s, 3H), 1.40 (t, J=7.1 Hz, 3H).13C NMR (100 MHz, CDCI3) δ 166.15, 162.46, 141.56, 133.63, 121 .33, 117.03, 113.56, 60.93, 55.50, 31.91 , 14.29. |
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