Vinyl ether compound with strigolactone activity and application thereof
A compound and an independent technology, applied in the field of plant growth regulators, can solve the problems of inability to realize large-scale preparation, restrict large-scale promotion and application, and difficult to synthesize, achieve excellent plant growth regulation activity, and facilitate large-scale production and application , the preparation method is simple and feasible
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Embodiment 1
[0058] Example 1, Preparation of 3-((4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)-2-acrylonitrile (compound 1)
[0059] Weigh 5g (42.68mmol) of phenylacetonitrile into a 250mL round-bottomed flask, pressurize and pump 10mL of anhydrous N,N-dimethylformamide with magnetic stirring to dissolve, add 30mL of methyl formate, and slowly add NaH2.1g (53.35mmol), the reaction system was returned to room temperature for reaction. TLC[V 石油醚 : V 乙酸乙酯 =4:1] Monitor the reaction, after 16 hours the reaction is over, add 30mL of 10% dilute hydrochloric acid at 0°C, extract 10mL×3 with dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate; filter with suction, concentrate under reduced pressure, and Purified by column chromatography, V 石油醚 : V 乙酸乙酯 =4:1, a yellow solid was obtained, yield: 83.87%.
[0060] Weigh 1g (6.89mmol) of the reaction product from the previous step, add 20ml of anhydrous N,N-dimethylformamide, stir magnetically to dissolve it, and then add 5...
Embodiment 2
[0061] Example 2, 3-((4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxy)-2-(p-methyl)acrylonitrile (compound 7)
[0062] Weigh 5g (38.12mmol) of p-tolueneacetonitrile into a 250mL round-bottomed flask, add 30mL of methyl formate and 10mL of anhydrous N,N-dimethylformamide, and dissolve it under magnetic stirring. 1.91 g NaH (47.65 mmol) was added slowly. The system was returned to room temperature for reaction. TLC[V 石油醚 : V 乙酸乙酯 =4:1] to monitor the reaction, after 16 hours the reaction was completed, 30mL of 10% dilute hydrochloric acid was added at 0°C, 30mL×3 of dichloromethane was extracted, the organic phase was combined, dried with anhydrous sodium sulfate, suction filtered, concentrated under reduced pressure, Purified by column chromatography, V 石油醚 : V 乙酸乙酯 =4:1. Yield: 94.89%.
[0063] Weigh 1 g (6.28 mmol) of the product after enolization of p-toluene acetonitrile, dissolve it in anhydrous N,N-dimethylformamide (20 ml), add 5-bromo-3-methyl-2- (5H)-furanone 1.67g (9...
Embodiment 3
[0071] Embodiment 3, compound promotes the biological activity assay of sunflower rowang seed germination
[0072] Sunflower rowdang seeds were sterilized successively with 70% (v / v) ethanol and 0.5% sodium hypochlorite for 1 min and 15 min, respectively. Then rinse it several times with sterile water and dry it naturally in an ultra-clean workbench. The filter paper was placed in a Petri dish (diameter d=9 cm) and 1 ml of sterile water was added. Place three pieces of glass fiber filter paper with a diameter of d=13mm on the filter paper, and drop the test solution on the glass fiber filter paper. In all experiments, GR24rac was used as a positive control, and ethanol was used as a negative control, wherein GR24rac was a mixture of racemic isomers of (2'r) and (2's), and 6 replicates were set for each treatment. Place 30-80 sunflower leydang seeds on each piece of glass fiber filter paper, and then cultivate them in the dark at 25-26°C. On the 10th day, the number of radic...
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