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        以丹皮酚為前體催化合成一氯查爾酮及黃酮的研究
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        陜西理工大學 陜西省催化基礎與應用重點實驗室 陜西漢中 723000

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        O626.41

        基金項目:

        陜西省科技廳社會發展科技攻關項目(2021SF-382);2022年研究生創新(SLGYCX2227)和國家級大學生創新創業訓練計劃項目(202210720017)。


        Study on the Synthesis of monochlorchalone and flavone catalyzed by paeonol as precursor
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        Shaanxi Key Laboratory for Catalysis,Shaanxi University of Technology

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          摘要:

          探索以丹皮酚為前體催化合成一氯代查爾酮及其黃酮的工藝,開拓合成氯代查爾酮和黃酮的新途徑。讓丹皮酚和不同位次的一氯代苯甲醛通過克萊森-斯密特反應堿催化合成一氯代的查爾酮Ⅰ、Ⅱ和Ⅲ,進而對三種查爾酮分別進行碘催化關環合成出來了一氯代的黃酮Ⅳ、Ⅴ和Ⅵ,測試產物的1H NMR、13C NMR、135° DEPT、FTIR以及其紫外和熒光性能,氯代黃酮Ⅳ、Ⅴ、Ⅵ的收率分別為88.6%、87.7%、86.1%,在熒光峰(λex/λem)220/415 nm處熒光強度分別為400、500、600。合成查爾酮是關鍵步驟,以合成查爾酮Ⅰ為例,通過考察堿、溫度、溶劑等單因素對查爾酮產率的影響,經響應面法優化其合成工藝條件:一氯代苯甲醛的用量3.6 mmol、丹皮酚3 mmol、乙醇15 mL、NaOH 0.239 g、70 ℃下回流10 h,查爾酮Ⅰ的收率高達93.7%,同樣條件下,查爾酮Ⅱ、Ⅲ的收率為92.3%、92.1%。該文合成一氯代查爾酮及其黃酮的工序簡單、綠色環保,可實現規?;可a。

          Abstract:

          To explore the catalytic synthesis process of chlorchalcone and its flavones with different substitutions using paeonol as precursor, and to explore a new way to synthesize chlorchalcone and its flavones. ChalconeⅠ, Ⅱ and Ⅲ were synthesized by paeonol and chlorobenzaldehyde catalyzed by Clason-Smit reaction base, and then the chlorobenzone Ⅳ, Ⅴ and Ⅵ were synthesized by iodine catalytic cycloclosure of the three chalcone respectively. 1H NMR, 13CNMR, 135°DEPT, FTIR and UV and fluorescence properties of the products were tested. The yield of chlorinated flavonoids Ⅳ, Ⅴ and Ⅵ were 88.6%, 87.7% and 86.1%, respectively. The fluorescence intensity at the fluorescence peak (λex/ λEM) 220/415 nm was 400, 500 and 600, respectively. The synthesis of chalcone Ⅰ is the key step. Taking the synthesis of chalcone Ⅰ as an example, the effects of single factors such as base, temperature and solvent on the yield of chalcone were investigated, and the synthesis process conditions were optimized by response surface method. With benzaldehyde dosage of 3.6 mmol, paeonol 3 mmol, ethanol 15 mL, NaOH 0.239 g and reflux at 70 ℃ for 10 h, the yield of chalcone Ⅰ was up to 93.7%. Under the same conditions, the yield of chalcone Ⅱ and chalcone Ⅲ was 92.3% and 92.1%, respectively. The synthesis process of chlorinated chalcone and flavone is simple, green and environmentally friendly, and can achieve

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        安超娜,王乙穎,劉萌,鄒肖,劉存芳,田光輝.以丹皮酚為前體催化合成一氯查爾酮及黃酮的研究[J].精細化工,2023,40(7):

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        • 收稿日期:2022-10-27
        • 最后修改日期:2022-12-21
        • 錄用日期:2022-12-22
        • 在線發布日期: 2023-05-11
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