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CAS No. : | 81474-46-6 | MDL No. : | MFCD00792457 |
Formula : | C10H9BrO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LBTTXOWOLNELBG-UHFFFAOYSA-N |
M.W : | 289.08 | Pubchem ID : | 11449108 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 3 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 57.98 |
TPSA : | 53.99 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) : | -6.47 cm/s |
Log Po/w (iLOGP) : | 2.69 |
Log Po/w (XLOGP3) : | 2.25 |
Log Po/w (WLOGP) : | 1.97 |
Log Po/w (MLOGP) : | 1.51 |
Log Po/w (SILICOS-IT) : | 2.41 |
Consensus Log Po/w : | 2.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.13 |
Solubility : | 0.215 mg/ml ; 0.000743 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.02 |
Solubility : | 0.276 mg/ml ; 0.000955 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.2 |
Solubility : | 0.182 mg/ml ; 0.00063 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.6 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P270-P301+P312-P330 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
51% | With bromine; In acetic acid; | REFERENTIAL EXAMPLE 3 In 35 ml of acetic acid was dissolved 10.5 g of methyl 5-methoxy-3,4-methylenedioxybenzoate, and a solution of bromine (formed by diluting 8 g of bromine with 25 ml of acetic acid) was dropped into the solution over a period of 1 hour. The mixture was stirred at room temperature for 10 hours and the reaction liquid was poured into ice water, and the formed precipitate was recovered by filtration and recrystallized from ethanol to obtain methyl 2-bromo-5-methoxy-3,4-methylenedioxybenzoate (the yield was 51%). Melting point: 103 to 105 C. Infrared absorption spectrum EQU3 cm-1 2944, 1726, 1626, 1488, 1462, 1434, 1404, 1326, 1248, 1194, 1176, 1108, 1040, 936 Proton nuclear magnetic resonance spectrum (delta ppm in CDCl3) 3.90 (s, 3H), 3.92 (s, 3H), 6.11 (s, 2H), 7.27 (s, 1H) Mass spectrum: m/z (%) 290 (89, M+), 288 (91, M+), 259 (100), 257 (100) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.6% | With potassium carbonate; In N,N-dimethyl-formamide; at 95℃; for 3.0h; | 15g (54.2mmol) of bromide, 150ml of DMF, 18g (130mmol) of potassium carbonate,Diiodomethane 17.4g (64.9mmol) was added to the reaction flask, warmed to 95 for 3 hours,After recovering most of the DMF under negative pressure, add 100ml of water and stir to cool to 12 .Filtration and drying yielded 15.2g of the target compound with a yield of 95.6% and HPLC> 99.3%. |
93.7% | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; for 3.0h; | The bromide 15g (54.2mmol), DMF 150ml, potassium carbonate 18g (130mmol),Diiodomethane 17.4g (64.9mmol) was added to the reaction flask, and the temperature was raised to 90 for 3 hours,After recovering most of the DMF under negative pressure, add 100ml of water, stir and cool to 10, filter,After drying, the target compound was 14.9g, the yield was 93.7%, and the HPLC>99.2%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | To a solution of 8 (14.4 g, 50.0 mmol) in THF (100.0 mL) at 0 C was added dropwise DIBALH (1.0 mol/L in hexane, 150.0 mL, 150.0 mmol). This mixture was stirred at 0 C for 30 min, then quenched by aq Rochelle salt (1 mol/L, 200 mL). It was evaporated in vacuo to remove the organic solvents, and water (100 mL) and CH2Cl2 (100 mL) was added to the residue. The organic layer was separated, and the water layer was extracted with CH2Cl2 (100 mL×2). The combined organic layer was washed with brine (150 mL×2), dried over anhydrous Na2SO4, filtered through a short silica gel pad and concentrated in vacuo to give 9 (13.0 g) as a white solid. Yield: 99%; mp 139-141 C; 1H NMR (300 MHz, CDCl3): delta 6.71 (s, 1H), 6.06 (s, 2H), 4.68 (d, 2H, J=6.24 Hz), 3.91 (s, 3H), 1.88 (t, 1H, J=6.24 Hz); 13C NMR (75 MHz, CDCl3): delta 147.0, 142.9, 135.0, 133.5, 108.4, 102.0, 93.3, 64.5, 56.7; IR (KBr) 3213, 2904, 1628, 1446, 1342, 1161, 1106, 1036, 699 cm-1; HRMS (ESI): calcd for C9H9BrO4Na [M+Na]+ 282.9576, found 282.9571. |
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