A kind of 2,3-dimethylallyl chalcone compound and its preparation and application
A technology of dimethylallylchalcones and compounds, applied in the field of 2,3-dimethylallylchalcones and their preparation and application, capable of solving failure, retention, and no PTP1B inhibitors Issues such as listing and sales
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Embodiment 1
[0028] Example 1 Synthesis of 4-(3-methyl-2-butenyloxy)benzaldehyde (2)
[0029] Dissolve 1.0g (8.18mmol) of 4-hydroxybenzaldehyde (1) and 2.46mL (24.56mmol) of 1-bromo-3-methyl-2-butene in 30mL of dry acetone (Acetone), under stirring conditions, Slowly add 3.4g (24.54mmol) potassium carbonate (K 2 CO 3 ) and 1.23g (8.18mmol) sodium iodide were reacted at room temperature for 4h. After the reaction was completed, ultrapure water was added to the reaction liquid to terminate the reaction, acetone was removed under reduced pressure, extracted with ethyl acetate (30 mL×3), the organic phases were combined, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and separated by silica gel column chromatography to obtain 1.50 g of 4-(3-methyl-2-butenyloxy)benzaldehyde (2) as a colorless liquid with a yield of 96.4%.
Embodiment 2
[0030] Example 2 Synthesis of 3-(3-methyl-3-buten-2-yl)-4-[(4hydrogen-2H-pyran-2-yl)oxy]benzaldehyde (3)
[0031] Dissolve 1.3g (6.84mmol) of 4-(3-methyl-2-butenyloxy)benzaldehyde (2) in 30mL of dry N,N-diethylaniline, and slowly heat up the sand bath to 200°C for reaction 6h. The reaction solution was cooled to room temperature, and after adding 30 mL of ultrapure water, the pH value was adjusted to 7 with hydrochloric acid. Continue to extract with ethyl acetate (30 mL×3), combine the organic phases, wash with saturated sodium chloride solution, and dry over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and separated by silica gel column chromatography to obtain 0.85 g of a colorless transparent liquid. Dissolve the entire liquid in 15 mL of dichloromethane (CH 2 Cl 2 ), slowly add 0.5mL of 3,4-dihydro-2H-pyran and 0.05g of catalyst pyridinium p-toluenesulfonate under rapid stirring. The reaction was carried out at room...
Embodiment 3
[0032] Synthesis of embodiment 3 chalcones 4a~4j (taking 4a as an example)
[0033] 0.01g (0.364mmol) 3-(3-methyl-3-buten-2-yl)-4-[(4 hydrogen-2H-pyran-2-yl)oxy]benzaldehyde (3) and 0.05g (0.41mmol) of 4-methoxyacetophenone was dissolved in 10mL of ethanol-water (2:1), and 0.005mg of potassium hydroxide (KOH) was slowly added under stirring conditions, and the reaction system was stirred overnight at room temperature. After the reaction was over, an excess of ice water was added to the system until a yellow precipitate was precipitated. Suction filtration, the filter cake was washed with a small amount of ice water and then sucked dry. The filter cake was dissolved in 5 mL of methanol (MeOH), and 0.5 mL of 6.0 mol / L hydrochloric acid was slowly added dropwise at room temperature. The reaction lasted for 30 min. After the reaction, ice water was added to the reaction solution until a yellow precipitate was precipitated. Filtered, the filter cake was washed with ice water and ...
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