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CAS No. : | 21575-91-7 | MDL No. : | MFCD03424812 |
Formula : | C11H11BrO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JSVMCOQPWKQNGU-UHFFFAOYSA-N |
M.W : | 271.11 | Pubchem ID : | 179368 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.27 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 60.04 |
TPSA : | 43.37 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) : | -6.14 cm/s |
Log Po/w (iLOGP) : | 2.55 |
Log Po/w (XLOGP3) : | 2.56 |
Log Po/w (WLOGP) : | 2.59 |
Log Po/w (MLOGP) : | 2.3 |
Log Po/w (SILICOS-IT) : | 3.0 |
Consensus Log Po/w : | 2.6 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.1 |
Solubility : | 0.216 mg/ml ; 0.000795 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.12 |
Solubility : | 0.206 mg/ml ; 0.000761 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.08 |
Solubility : | 0.0223 mg/ml ; 0.0000824 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 1.86 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
76.9% | Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25 h; Inert atmosphere Stage #2: at -78℃; for 2 h; Inert atmosphere |
[00457] To a stirred solution of 1.3 M LHMDS (25 mL, 32.7 mmol) in THF (10 mL) was added EtOAc (1.9 g, 21.8 mmol) at -78 °C under inert atmosphere. After being stirred for 15 min, ethyl- 3-bromo benzoate (5 g, 21.8 mmol) was added and stirring was continued for 2 h; progress of the reaction was monitored by TLC. The reaction was quenched with aq. NH4C1 (10 mL) and extracted with EtOAc (3 x 20 mL). The combined organic extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain the crude product. The crude material was purified by silica gel column chromatography eluting with 4percent EtOAc/Hexane to afford compound G (4.5 g, 76.9percent) as a mixture with its enolic form as a brown oil. 1H NMR (500 MHz, CDCls): δ 8.07 (s, 1H), 7.86 (d, J= 7.5 Hz, 1H), 7.73-7.69 (m, 1H), 7.37 (t, J= 7.0 Hz, 1H), 4.28-4.26 (m, 2H), 3.92 (s, 2H), 1.24 (t, J= 6.2 Hz, 3H). MS (ESI): m/z 298.8 [M-l]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.583333 h; Stage #2: at 0 - 20℃; for 16 h; Stage #3: With hydrogenchloride; water In DMF (N,N-dimethyl-formamide) |
To a suspension of sodium hydride (0.361 g, 9 mmol) in DMF (9.4 ML) was added 3- bromoacetophenone (0.99 ML, 9.53 mmol) at 0°C and stirred at room temperature for 35 minutes. The reaction mixture was then cooled to 0°C and diethyloxalate (1.32 ML, 9.7 mmol) was added followed by stirring at room temperature for 16 hours. The reaction was then poured into ice-water and acidified with IN HC1. The solid precipitate formed was filtered, washed with cold water and dried under vacuum to give the titled product (2.1 g, 93 percent) as a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With magnesium chloride; triethylamine In acetonitrile | Example 2 Part A 3-(3-Bromophenyl)-3-oxopropanoic Acid Ethyl Ester To potassium ethyl malonate (3.25 g, 19.13 mmol) in acetonitrile (50 mL) was sequentially added triethyl amine (4.1 mL, 29.16 mmol) and magnesium chloride (2.16 g, 22.78 mmol) at room temperature. After stirring the reaction mixture at room temperature for 2 hours, 3-bromobenzoyl chloride (2.0 g, 9.11 mmol) was added and the mixture was heated at 60° C. for 18 hours, concentrated under reduced pressure and partitioned between ethyl acetate (100 mL) and 1N HCl (25 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated under reduced pressure to yield the title compound (2.45 g, 99percent). 1H NMR (CDCl3): δ 8.1 (s, 1H), 7.85 (d, 1H), 7.7 (d, 1H), 7.35 (t, 1H), 4.3 (m, 2H), 3.4 (s, 1H), 1.3 (m, 3H). |
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