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Method for preparing 2,3-dihydrobenzopyran-4-one derivative

A technology of dihydrobenzopyran and its derivatives, which is applied in the direction of organic chemistry, can solve problems such as damage, environmental pollution, and cumbersome steps, and achieve the effects of mild reaction conditions, simple operation, and low cost

Active Publication Date: 2018-01-16
ZHEJIANG SHENGXIAO CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are many reports on the synthesis of 2,3-dihydrochromen-4-one derivatives, but most of the existing synthesis methods use Lewis acid or transition metal catalyst system, which will inevitably cause great environmental impact. Pollution and destruction with cumbersome steps

Method used

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  • Method for preparing 2,3-dihydrobenzopyran-4-one derivative
  • Method for preparing 2,3-dihydrobenzopyran-4-one derivative
  • Method for preparing 2,3-dihydrobenzopyran-4-one derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Into a 50mL photoreaction tube, add o-propenyloxybenzaldehyde (0.1mmol), benzoin (0.2mmol), dicumyl peroxide (DCP) (0.4mmol), dry benzene (15mL) sequentially, and then Ball bubbling to deoxygenate for 0.5h, then seal the reaction system and irradiate it with 350nm ultraviolet light for 24h. After the reaction was completed, the reaction solvent was concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether with a volume ratio of 50:1: ethyl acetate was used as an eluent for purification and separation by silica gel column chromatography to obtain the corresponding 3 -Benzoylmethyl-2,3-dihydrochromen-4-one, whose structural formula is:

[0022]

[0023] Purity 99%, productive rate 77%, its NMR data analysis is: 1 H NMR (400MHz, CDCl3) δ8.03 (d, J = 7.9Hz, 2H), 7.94 (d, J = 7.8Hz, 1H), 7.61 (t, J = 7.0Hz, 1H), 7.50 (dd, J =10.4,4.8Hz,3H),7.09–6.99(m,2H),4.67(dd,J=11.1,5.3Hz,1H),4.34(t,J=11.4Hz,1H),3.77–3.71(m, 1H), 3.62(ddd, J=1...

Embodiment 2

[0026] Into a 50 mL photoreaction tube, 5-methyl-2-propenyloxybenzaldehyde (0.1 mmol), benzoin (0.3 mmol), dicumyl peroxide (DCP) (0.5 mmol), dry acetonitrile ( 5 mL), deoxygenated by bubbling with a nitrogen balloon for 0.5 h, and then, the reaction system was sealed and irradiated with 350 nm ultraviolet light for 36 h. After the reaction was completed, the reaction solvent was concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether with a volume ratio of 30:1: ethyl acetate was used as an eluent for purification and separation by silica gel column chromatography to obtain the corresponding 3 -Benzoylmethyl-6-methyl-2,3-dihydrochromen-4-one, whose structural formula is:

[0027]

[0028] The purity is 98%, and the yield is 71%. Its NMR data are: 1 H NMR (400MHz, CDCl3) δ8.00(d, J=7.3Hz, 2H), 7.70(s, 1H), 7.59(t, J=7.4Hz, 1H), 7.48(t, J=7.6Hz, 2H ),7.30 (dd, J=8.4,1.9Hz,1H),6.89(d,J=8.4Hz,1H),4.61(dd,J=11.1,5.2Hz,1H),4.28(t,J=11....

Embodiment 3

[0031] Into a 50mL photoreaction tube, add 5-chloro-2-propenyloxybenzaldehyde (0.1mmol), benzoin (0.4mmol), dicumyl peroxide (DCP) (0.6mmol), dry dimethyl After sulfoxide (15 mL), deoxygenation was performed by bubbling a nitrogen balloon for 0.5 h, and then the reaction system was sealed and irradiated with 350 nm ultraviolet light for 30 h. After the reaction was completed, the reaction solvent was concentrated and spin-dried by a rotary evaporator, and then a mixed solution of petroleum ether with a volume ratio of 10:1: ethyl acetate was used as an eluent for purification and separation by silica gel column chromatography to obtain the corresponding 3 -Benzoylmethyl-6-chloro-2,3-dihydrochromen-4-one, whose structural formula is:

[0032]

[0033] The purity is 99%, and the yield is 84%. Its NMR data are: 1 H NMR (400MHz, CDCl3) δ8.00(d, J=7.4Hz, 2H), 7.87(d, J=2.6Hz, 1H), 7.60(t, J=7.4Hz, 1H), 7.49(t, J =7.6Hz, 2H), 7.43(dd, J=8.8, 2.6Hz, 1H), 6.96(d, J=8.8Hz, 1H), 4...

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Abstract

The present invention provides a method for preparing a 2,3-dihydrobenzopyran-4-one derivative, and the method comprises the following steps: under nitrogen atmosphere at room temperature, dissolvinga 2-allyloxybenzaldehyde derivative represented by formula (I) and a benzoin derivative represented by formula (II) in an organic solvent, adding a photosensitizer, evenly mixing, placing under an ultraviolet lamp for light irradiation reaction, removing the solvent by rotary evaporation, and separating and purifying by silica gel column chromatography to obtain the resulting product 2,3-dihydrobenzopyran-4-one derivative. The preparation method solves the problems of cumbersome steps, low yield and poor environmental protection property of the existing synthesis method, can react under normaltemperature and normal pressure, and has the advantages of mild reaction conditions, no need of transition metal catalysis, simple operation, no pollution, safety, environmental protection, low costand the like. R1 and R2 are hydrogen, halogen or alkyl.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of 2,3-dihydrochroman-4-one derivatives. Background technique [0002] The carbon skeleton of dihydrochroman-4-one widely exists in biologically active natural products and some unnatural compounds. Compound 1-4 is a typical biologically active natural product containing a dihydrochromen-4-one carbon skeleton. According to literature reports, a series of 2,3-dihydrochromen-4-one derivatives have various biological activities, such as compounds 5-6 of the following formula, which are a kind of SIRT2 selective inhibitors, so 2,3 - The synthesis of dihydrobenzopyran-4-one derivatives has received extensive attention from chemists. [0003] [0004] At present, there are many reports on the synthesis of 2,3-dihydrochromen-4-one derivatives, but most of the existing synthesis methods use Lewis acid or transition metal catalyst system, which will i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22
Inventor 夏吾炯刘强郭小忠冯永胜徐景祥章丽袁鹏
Owner ZHEJIANG SHENGXIAO CHEM
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