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CAS No. : | 138500-85-3 | MDL No. : | MFCD02179493 |
Formula : | C13H18BBrO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CBUOGMOTDGNEAW-UHFFFAOYSA-N |
M.W : | 297.00 | Pubchem ID : | 3734506 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.54 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 75.75 |
TPSA : | 18.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -5.65 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 3.47 |
Log Po/w (WLOGP) : | 2.73 |
Log Po/w (MLOGP) : | 2.41 |
Log Po/w (SILICOS-IT) : | 2.87 |
Consensus Log Po/w : | 2.3 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.0 |
Solubility : | 0.0299 mg/ml ; 0.000101 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.54 |
Solubility : | 0.0857 mg/ml ; 0.000289 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -5.24 |
Solubility : | 0.00169 mg/ml ; 0.0000057 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.03 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P301+P312-P302+P352-P304+P340-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 |
---|---|---|
92% | With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 4 h; Cooling with ice | 4-hydroxymethylphenylboronic acid, pinacol ester (1.08 g, 4.61 mmol) was dissolved in THF (20 ml) together with triphenylphosphine (2.42 g, 9.23mmol). The reaction mixture was cooled in an ice-water bath, and carbon tetrabromide (3.06 g, 9.23 mmol) was added portion wise. After stirring for 4 hours at room temperature, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was combined and dried by sodium sulfate. After filtration, the solvent was evaporated, and the residue was purified by flash chromatography to give the product as a white solid (1.72 g, 92percent). 1H NMR (300 MHz, CD2C12, δ): 7.62 (d, J = 6.0 Hz, 2H), 7.32 (d, J = 6.0 Hz, 2H), 4.58 (d, 2H), 1.34 (s, 9H); MS (ESI) m/z 297.0. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 12 h; Reflux | Scheme 1. Synthesis of 4-(4,4,5,5-tetrarnethyl- 1,3,2 -dioxaboratophenyl)-methyl triphenylphosphonium bromide 4. [00120] Compound 6 (8) was prepared starting from 4,4,5,5-tetramethyl-2-p-tolyl- 1 ,2>,2- dioxaborolane 7, NBS and A1BN in carbon tetrachloride were refluxed for 12 hours. In an initial attempt 4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaboratophenyl)-methyl triphenylphosphonium bromide 4 was isolated as a white solid in 92percent yield. The minor excess of PPh3 was removed from the product by trituration with ether 2-3 times and the product was found to be stable under normal atmospheric conditions. Subsequently, the Wittig reaction of the ylide derived from this salt using benzaldehyde (Scheme 2) was optimized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76.1% | With 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 14 h; Reflux | P-toluene boronic acid pinacol ester (10.91 g, 50.0 mmol),Bromosuccinimide (NBS, 9.91 g, 55.0 mmol),Azobisisobutyronitrile (AIBN, 0.44 g, 2.0 mmol) was dissolved in dry carbon tetrachloride (CCl4, 200 mL).It was stirred at reflux for 14 hours, filtered, the solvent was removed by rotary evaporation, and the ethyl acetate (200 mL) was dissolved.After washing once with distilled water (100 mL) and saturated aqueous sodium chloride solution (100 mL), it was dried over anhydrous sodium sulfate.Spin-steaming, finally using petroleum ether as eluent to cross the column,4-Bromomethylphenylboronic acid pinacol ester (11.30 g, yield 76.1percent) was isolated. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | at 20℃; | 2-(4-Bromomethyl-phenyl)-4,4,5,5-tetramethyl-[ 1,3,2]dioxaborolane (200mg, 0.673mmol) was dissolved in THF (5mL) and morpholine (0.088mL, 1.01 mmol) was added. The mixture stirred overnight at room temperature and was then filtered and concentrated to afford the title compound (223mg, 100percent). lH NMR (300 MHz, CDCI3): 8 7.79 (d, 2H), 7.36 (d, 2H), 3.73 (t, 4H), 3.55 (s, 2H), 2.47 (t, 4H). |
72.6% | With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4 h; | 4-bromomethylphenylboronic acid pinacol ester (5.00 g, 1.68 mmol),Morpholine (1.74 g, 2.00 mmol),Potassium carbonate (2.80g, 2.OOmmol) was added to the reaction flask,Add 50 mL of N,N-dimethylformamide,The reaction was stirred at 80° C. for 4 hours.Cool to room temperature,Pour the reaction solution into 250mL ice water,Stir for 30 minutes,The title product was filtered by suction to give 3.7 g of a white solid. The yield was 72.6percent. |
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