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CAS No. : | 13047-06-8 | MDL No. : | MFCD00032462 |
Formula : | C13H9BrO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | ABEVIHIQUUXDMS-UHFFFAOYSA-N |
M.W : | 261.11 | Pubchem ID : | 2735534 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 64.02 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.04 cm/s |
Log Po/w (iLOGP) : | 2.41 |
Log Po/w (XLOGP3) : | 4.02 |
Log Po/w (WLOGP) : | 3.68 |
Log Po/w (MLOGP) : | 3.66 |
Log Po/w (SILICOS-IT) : | 4.08 |
Consensus Log Po/w : | 3.57 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.45 |
Solubility : | 0.00923 mg/ml ; 0.0000354 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.08 |
Solubility : | 0.0217 mg/ml ; 0.0000829 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.72 |
Solubility : | 0.0005 mg/ml ; 0.00000191 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.77 |
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 |
---|---|---|
91% | With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique | General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1,10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With dichloro bis(acetonitrile) palladium(II); cesium fluoride In 1-methyl-pyrrolidin-2-one at 80℃; for 6 h; | General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 molpercent), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 2C60H80NaO12(2+)*Cl6Pd2(2-); potassium carbonate; triphenylphosphine In toluene at 70℃; for 12 h; | General procedure: A 5 mL flask charged with benzoyl chloride (1.0 mmol), arylboronic acid (0.5 mmol),K2CO3 (1.0 mmol), complex 1 (0.5 molpercent, 3.1 mg), PPh3 (0.01 mmol, 1.3 mg) and toluene (2.0mL) was put into a preheated 70 oC oil bath for an appropriate period of time under air. After thereaction was finished, the reaction mixture was cooled to room temperature, filtered through ashort silica column and washed with ethyl acetate. Then the combined filtrates were concentratedin vacuo and the residue was purified by flash chromatography (eluent: ethylacetate/petroleumether). All the products were known compounds and characterized by comparing mp, 1H NMRand 13C NMR spectra with literature. |
85% | With [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; potassium carbonate In toluene at 60℃; for 12 h; Inert atmosphere | General procedure: A reaction vessel was charged with a mixture of phenylboronic acid (0.5 mmol), K2CO3 (1.0 mmol), catalyst 2 (0.5 mol percent) in toluene (2.0 mL), and stirred for about 20 min under nitrogen atmosphere. Then benzoic anhydride or benzoyl chloride was then added. The mixture was heated to 60 °C and incubated in an oil bath at 60 °C for 12 h under nitrogen atmosphere. After the completion of the reaction, the mixture was quenched by 5 mL water and then extracted with ethyl acetate (3.x.10 mL). The combined organic layer was dried over MgSO4. After removal of the solvent in vacuo, the product was obtained by purifying on preparative TLC, eluting with ethyl acetate/petroleum ether and the yield was calculated based on the phenylboronic acid (the purified products were identified by NMR spectra and comparison of the melting points with the literature data). In the recycle experiment, the residue was subjected to a second run of the acylation reaction by charging with the same substrates (benzoic anhydride or benzoyl chloride, phenylboronic acid, dioxane, and K2CO3) without further addition of cyclopalladated catalyst 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21.22g | Stage #1: With aluminum (III) chloride In chloroform at 20℃; for 0.25 h; Stage #2: at 20℃; for 4 h; |
2-Bromo-benzoic acid (21g, 100mmol) was dissolved in thionyl chloride was heated at reflux for 1h, the spin off the excess thionyl chloride, to give 2-bromobenzoyl chloride; followed by 2-bromo-benzoyl chloride 50ml chloroform was added and after drying anhydrous aluminum (16g, 120mmol), stirred for 15min at room temperature was added dropwise benzene (9.4g, 11ml, 120mmol) in dry chloroform solution, stirred at room temperature 4h, poured slowly into ice-hydrochloric acid aqueous solution, CH2Cl2Extraction, drying over anhydrous MgSO4. After filtration spin dry, PE: EA = 20: 1 by column to give a pale yellow solid (21.22g, yield 77.8percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With copper(l) iodide; silver carbonate In N,N-dimethyl-formamide at 120℃; for 24 h; | General procedure: Thiolester (0.25 mmol), arylboronic acids (0.375 mmol), CuI (20 molpercent, 10 mg), Ag2CO3 (5 molpercent, 4 mg) and DMF (3 ml) were taken in a 25 ml round bottomed flask. The reaction mixture was heated at 120 C for 8–24 h. The reaction monitored using TLC. Upon completion, the reaction mixture was diluted with water and extracted with DCM (3x10 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting ketone was purified was purified using silica gel column chromatography (EtOAc and petroleum ether 60–80 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With N-Bromosuccinimide; water In chloroform for 3 h; Reflux | General procedure: In around-bottom flask, diarylmethanes (1.0 mmol), NBS (889.9 mg, 5.0 mmol) andwater (0 or 5.0 mmol) were dissolved in CHCl3 (4.0 mL). After refluxing for 3 h in the air, the reaction mixture was quenched withNa2S2O3·5H2O, cooled to roomtemperature, washed with 5mL CH2Cl2, dried with MgSO4,and filtered to get clear organic solution. The solvent was removed reduced pressure by a rotary evaporator, and the resulting residue was subjected to column chromatography on silica gel using co-solvent(ethyl acetate / petroleum ether, v/v) as eluent to give the corresponding diaryllketones. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | at 0℃; for 15 h; Inert atmosphere | General procedure: Under a nitrogen atmosphere 2-bromo-Nmethoxy-N-methylbenzamide (10) (about 1 mmol) was dissolved in anhydrous THF (3 mL). The solution was cooled to 0 °C and the appropriate Grignard reagent (3.0 equiv) was added. The mixture was stirred for 15 h, then 2M hydrochloric acid (10 mL) was added and extracted with ethyl acetate (3*15 mL). The combined organic layers were dried over MgSO4 and the solvents were evaporated under reduced pressure. Purification was accomplished by FCC. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | Stage #1: With TurboGrignard In tetrahydrofuran at -15℃; for 1.5 h; Stage #2: With CuCN*2LiCl In tetrahydrofuran at -15℃; for 0.166667 h; Stage #3: at -15℃; for 1 h; |
Preparation of (2-bromophenyl)(phenyl)methanone 2ka:; A dry and argon flushed 10 mL flask, equipped with a magnetic stirrer and a septum, was charged with i-PrMgCl*LiCl (1 mL, 1.05 M in THF, 1.05 mmole), the reaction mixture was cooled to -15°C and 1,2-dibromobenzene (235.9 mg, 1 mmole) was then added dropwise. The Br/Mg-exchange was complete after 1.5 h (checked by GC analysis of reaction aliquots, conversion more than 98percent) and solution of CuCN*2LiCl (0.1 mL, 1.0 M in THF, 0.1 mmole) was added. After stirring for 10 min at -15°C benzoyl chloride (140.6 mg, 1 mmole) was added. The reaction mixture was stirred for 1 h at -15°C and was then quenched with sat. NH4Cl solution (2 mL) and also 5 drops of concentrated NH3 was added. The aqueous phase was extracted with ether (3 x 4 mL) and the organic fractions were washed with brine (5 mL), dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography (dichloromethane) yielding the ketone (2ka) as a white cristals (219.3 mg, 84 percent). 1H-NMR (CDCl3, 200 MHz):δ = 7.86-7.78 (m, 2 H); 7.68 - 7.56 (m, 2 H); 7.52 - 7.30 (m, 5 H). |
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