Structure of 4079-54-3
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CAS No. : | 4079-54-3 |
Formula : | C9H10O2 |
M.W : | 150.17 |
SMILES Code : | O=C(C1=CC=C(C)C=C1)CO |
MDL No. : | MFCD07778990 |
InChI Key : | BFOWHGYYZRTDOV-UHFFFAOYSA-N |
Pubchem ID : | 317549 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 |
* 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 |
---|---|---|
6 g | With hydrogenchloride; water; In ethanol;Reflux; | General procedure: α-bromo-3’-chloroacetophenone (6a, 17.5 g, 75 mM) in ethanol (100 mL) was refluxed for 10 h with anhydrous sodium acetate (6.2 g, 76 mM). The mixture was diluted with water and the solid which separated was collected and recrystallized from ethyl acetate. Then the solid (2-(3-chlorophenyl)-2-oxoethyl acetate, 10.4 g, 49 mM, 65%) in ethanol (50 mL) and hydrochloric acid (50 mL of 1 M) was refluxed for 6 h. The mixture was diluted with water and was then extracted with ethyl acetate. The extract was dried (sodium sulfate) and concentrated to give 2a (6.8 g, 40 mM, 53%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To a stirred solutionof the corresponding α-aryl ketones (32 mmol, 1.0 equiv.) and powderedpotassium hydroxide (176 mmol, 5.5 equiv.) in 80 mL methanol was added iodobenzenediacetate (35 mmol, 1.1 equiv) slowly at 0 C. The reaction mixturewas kept at room temperature until TLC indicated the total consumption of the α-arylketones. Then the whole reaction mixture was concentrated. The residue wasshaken with water and ethyl acetate. The combined organic layer was evaporatedunder reduced pressure. The residue was dissolved in a mixture of 20 mL methanoland 20 mL 2 M aqueous hydrochloric acid and then stirred overnight at roomtemperature, and then filtered. The solid was washed with hexanes, and the obtained1-aryl-2-hydroxypropan-1-one 1 wasused directly for the next step without further purifications.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With N-Bromosuccinimide; In methanol; water; at 20℃; for 5.5h;Green chemistry; | General procedure: Aromatic alcohol (1-2 mmol) was dissolved in methanol (or acetone in somecases, 2-4 mL) at room temperature, followed by addition of the aqueous solutionof N-bromosuccinimide (1.5 eq.=alcohol) with continuous stirring. GMP-b-CD (3,100mg=mmol of alcohol) were added in the reaction mixture and stirring was continued.Progress of the reaction was monitored by TLC until the reaction was completed(4-6 h). GMP was separated by filtration after completion of the reaction. Thereaction mixture was extracted with ethyl acetate (45 mL), combined organiclayers were dried over Na2SO4, and solvent was removed under reduced pressure.The product was further purified by flash column chromatography and analyzedby NMR spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With anhydrous sodium formate; In methanol; for 12h;Reflux; | A mixture of 10d (3.0 mmol) and sodium formate (8.0equiv.) in 9 mL MeOH was heated to reflux for 12 h. After the reaction was completed, the mixturewas cool to room temperature, and ethanol was removed in vacuum, diluted with water (10 mL),aqueous layer was extracted with ethyl acetate (3 × 20 mL), and the combined organic phases weredried over Na2SO4, filtered and concentrated. After evaporation, the crude residue was purified bysilica gel column chromatography (200-300 mesh) using petroleum ether and ethyl acetate (15:1, v/v)as eluent to give target compound 15d: Light yellow solid, yield 53%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86.7%Chromat. | With D-(+)-glucose; NADPH; at 20℃; for 6h;pH 6.5;aq. phosphate buffer; | General procedure: In order to exclude the catalysis of heteroprotein and prove that the reactions were catalyzed by the recombinant protein, we conducted the reduction of ketones by using cell-free extract of E. coli BL21(DE3)/pET-21c and purified enzyme. The reaction mixture in 2 mL comprised 1 mL potassium phosphate buffer (pH 6.5, 0.1 M), 1 mL cell-free extract of E. coli BL21(DE3)/pET-21c (or 5 mg purified enzyme), 10 g/L glucose, NADPH and substrate. The mixture was shaken for 6 h at 20oC. After reaction, mixture was extracted with five volumes of ethyl acetate by vigorous mixing. The organic layer was analyzed by HPLC or GC. The results indicated that the reactions were catalyzed by the purified enzyme and the heteroprotein had no effect on the reactions. (Table 1) |
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; f-amphol; hydrogen; sodium hydroxide; In isopropyl alcohol; at 20℃; under 15201.0 Torr; for 12h; | Under argon atmosphere within the glove box, ligand L24 (Ar=3,5-(tBu)2C6H3) (12.9 mg, 0.0168mmol) and [Ir(COD)Cl]2 (5.4 mg, 0.008mmol) are added into a 2.5 ml vial. After dissolving in iPrOH (1.6 ml), at room temperature complexation for 1h to get the catalyst solution. The catalyst solution (10uL, 0.0001mmol) was added in the 5 ml of hydrogenation vial. Then sequentially add isopropanol solution of NaOH (0.05mmol/mL, 20uL, 0.001mmol), <strong>[4079-54-3]p-methyl-α-hydroxyacetophenone</strong> substrate (0.1mmol), 1 ml isopropanol solvent. Place the hydrogenation vial into the hydrogenation reactor. After replacing with hydrogen three time, place 20atm H2. At room temperature, react for 12h. After completion of reaction the release of hydrogen, the reaction mixture over a short silica gel column. NMR fixed conversion (> 99%), using high performance liquid chromatography (HPLC) assay reaction enantioselectivity ee value (> 99%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With triethylamine; In dichloromethane; benzene; | (2) A mixture of <strong>[4079-54-3]2-hydroxy-1-p-tolyl-ethanone</strong> (5.6 g, 37 mmol), prepared in the previous step, isopropyl isocyanate (5.5 ml, 56 mmol) and triethylamine (5.16 ml, 37 mmol) in 100 ml of benzene was refluxed under nitrogen for approximately 23 hours. The solvent was removed under reduced pressure. The residue was dissolved in CH2 Cl2 and extracted with 1N HCl. The organic layer was dried (MgSO4) and the solvent removed under reduced pressure to give 8.295 g of an oil. Crystallization of the oil from isopropyl alcohol gave isopropyl-carbamic acid 2-oxo-2-p-tolyl-ethyl ester (2.5267 g, 29%) as a light yellow solid, mp 130-133 C. Elemental Analysis for C13 H17 NO3, Calc'd: C, 66.36; H, 7.28; N, 5.95, Found: C, 66.02; H, 7.39; N, 5.93 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With gallium(III) perchlorate; In ethanol; at 25℃; | General procedure: Representative experimental procedure for the synthesis of 2-phenylquinoxaline (3a) (Table 2, entry 1): A mixture of o-phenylenediamine (1a, 0.0541 g, 0.5 mmol), 2-hydroxyaceto-phenone (2a, 0.0681 g, 0.5 mmol) and Ga(ClO4)3 (0.018g, 0.05 mmol) in EtOH (3 mL) was stirred at room temperature. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was directly purified by silica gel column chromatography (petroleum ether/ethyl acetate, 10:1) to afford the product 3a. The structures of all products were confirmed by IR, 1H NMR spectroscopy and melting points, which were consistent with literature data. |
70% | With triphenylantimony; In toluene; at 20℃; for 3h; | General procedure: Triphenylstibane(35.5 mg, 0.1 mmol, 10 mol%) and diamine 2 (1.2 mmol) were added to a solution of -hydroxy ketone 1(1 mmol) in toluene (6 mL) under air. The solution was stirred at room temperature and monitored byTLC. The reaction mixture was concentrated under reduced pressure and the residue was purified bycolumn chromatography (CH2Cl2) on silica gel. The products were confirmed by comparison of mp,NMR data, and MS spectra with that in the literature. 822: |
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