CN107586285B - Preparation method of 2, 3-dihydrobenzopyran-4-one derivative - Google Patents
Preparation method of 2, 3-dihydrobenzopyran-4-one derivative Download PDFInfo
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Abstract
The invention provides a preparation method of a 2, 3-dihydrobenzopyran-4-ketone derivative, which comprises the following steps: dissolving the o-propenyloxybenzaldehyde derivative shown in the formula (I) and the benzoin derivative shown in the formula (II) in an organic solvent under the atmosphere of nitrogen at room temperature, adding a photosensitizer, uniformly mixing, placing under an ultraviolet lamp for illumination reaction, performing rotary evaporation to remove the solvent, and performing silica gel column chromatography separation and purification to obtain the product, namely the 2, 3-dihydrobenzopyran-4-one derivative. The preparation method solves the problems of complicated steps, low yield and poor environmental protection of the existing synthesis method, can react at normal temperature and normal pressure, has mild reaction conditions, does not need transition metal catalysis, and has the advantages of simple operation, no pollution, safety, environmental protection, low cost and the like.
Wherein R is1、R2Is hydrogen, halogen or alkyl.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of a 2, 3-dihydrobenzopyran-4-one derivative.
Background
The dihydrobenzopyran-4-one carbon skeleton is widely present in natural products having biological activity as well as in some non-natural compounds. As shown in the following formula, the compounds 1-4 are typical natural products with biological activity containing a carbon skeleton of dihydrobenzopyran-4-one. A series of 2, 3-dihydrobenzopyran-4-one derivatives have been reported in the literature to have various biological activities, such as the following compounds 5-6, which are selective SIRT2 inhibitors, so that the synthesis of 2, 3-dihydrobenzopyran-4-one derivatives is of great interest to chemists.
At present, the synthesis of 2, 3-dihydrobenzopyran-4-ketone derivatives is reported more, but most of the existing synthesis methods adopt Lewis acid or transition metal catalytic systems, which inevitably causes great pollution and damage to the environment and has complicated steps. Therefore, the problem to be solved at present is to find a synthetic method of 2, 3-dihydrobenzopyran-4-one derivatives which is green and environment-friendly, simple in method, few in steps and high in yield.
Disclosure of Invention
The invention provides a method for preparing 2, 3-dihydrobenzopyran-4-ketone derivatives, which comprises the following steps:
dissolving an o-propenyloxybenzaldehyde derivative shown in a formula (I) and a benzoin derivative shown in a formula (II) in an organic solvent at room temperature under the atmosphere of nitrogen, adding a photosensitizer, uniformly mixing, placing under an ultraviolet lamp for illumination reaction, performing rotary evaporation to remove the solvent, and performing silica gel column chromatography separation and purification to obtain a product, namely the 2, 3-dihydrobenzopyran-4-one derivative (shown in a formula (III)), wherein the reaction formula is as follows:
wherein R is1、R2Is hydrogen, halogen or alkyl.
Preferably, the photosensitizer is benzophenone or dicumyl peroxide.
Preferably, the organic solvent is one selected from acetonitrile, benzene, toluene, dimethyl sulfoxide, and N, N-dimethylformamide.
More preferably, the organic solvent is benzene, and when benzene is selected as the solvent, the product yield is highest.
Preferably, the time of the ultraviolet irradiation reaction is 24-48h, and if the ultraviolet irradiation time is too short, the reaction is incomplete; the irradiation time is too long, the product is degraded, and the purity and yield of the product are reduced.
Preferably, the solvent used for separation and purification by silica gel column chromatography is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10-50: 1.
Preferably, the o-propenyloxybenzaldehyde derivative, benzoin derivative compound and photosensitizer are fed in a molar ratio of 1: 2-4: 4-8.
More preferably, the o-propenyloxybenzaldehyde derivative, benzoin derivative compound and photosensitizer are fed in a molar ratio of 1: 2: 4.
preferably, the organic solvent is charged in a volume of 50 to 150mL/mol of the o-propenyloxybenzaldehyde derivative.
The invention has the beneficial effects that:
the invention provides a simple method for synthesizing a 2, 3-dihydrobenzopyran-4-ketone derivative in one step, which solves the problems of complicated synthesis steps, low yield and poor environmental protection of the existing 2, 3-dihydrobenzopyran-4-ketone derivative.
Detailed Description
The technical solution of the present invention will be further specifically described below by way of specific examples.
Example 1
After successively adding o-acryloyloxybenzaldehyde (0.1mmol), benzoin (0.2mmol), dicumyl peroxide (DCP) (0.4mmol) and dry benzene (15mL) to a 50mL photoreaction tube, the reaction system was sealed and irradiated under 350nm ultraviolet light for 24 hours after deoxygenation by bubbling with a nitrogen balloon for 0.5 hours. After the reaction is finished, concentrating and spin-drying the reaction solvent by a rotary evaporator, and then mixing the reaction solvent with petroleum ether: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-phenacyl-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 99%, yield 77%, with nmr data analysis:1H NMR(400MHz,CDCl3)8.03(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＝12.0,8.6,4.6Hz,1H),3.05(dd,J＝18.0,8.3Hz,1H)ppm.
13C NMR(150MHz,CDCl3)197.03,193.48,161.86,136.43,136.05,133.51,128.74,128.18,127.42,121.49,120.66,117.92,70.42,41.86,34.36
example 2
After 5-methyl-2-propenyloxybenzaldehyde (0.1mmol), benzoin (0.3mmol), dicumyl peroxide (DCP) (0.5mmol) and dry acetonitrile (5mL) were added in this order to a 50mL photoreaction tube, oxygen was removed by bubbling with a nitrogen balloon for 0.5h, and then the reaction was sealed and irradiated under 350nm UV light for 36 h. After the reaction is finished, concentrating and spin-drying the reaction solvent by a rotary evaporator, and then mixing the reaction solvent with petroleum ether: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-phenacyl-6-methyl-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 98% and yield 71%. The nuclear magnetic data are:1H NMR(400MHz,CDCl3)8.00(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＝11.3Hz,1H),3.70(dd,J＝18.0,3.7Hz,1H),3.61–3.52(m,1H),3.02(dd,J＝18.0,8.4Hz,1H),2.31(s,3H)ppm.
13C NMR(150MHz,CDCl3)197.11,193.72,159.93,137.13,136.46,133.48,130.93,128.73,128.18,126.95,120.26,117.69,70.42,41.90,34.46,20.45
example 3
After 5-chloro-2-propenyloxybenzaldehyde (0.1mmol), benzoin (0.4mmol), dicumyl peroxide (DCP) (0.6mmol) and dried dimethyl sulfoxide (15mL) were added in this order to a 50mL photoreaction tube, the reaction system was sealed and irradiated under 350nm UV light for 30h after deoxygenation by bubbling with a nitrogen balloon for 0.5 h. After the reaction is finished, concentrating and spin-drying a reaction solvent by a rotary evaporator, and then mixing the reaction solvent with petroleum ether in a volume ratio of 10: 1: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-phenacyl-6-chloro-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 99%, yield 84%. The nuclear magnetic data are:1H NMR(400MHz,CDCl3)8.00(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),4.65(dd,J＝11.1,5.3Hz,1H),4.31(t,J＝11.5Hz,1H),3.70(dd,J＝18.1,3.6Hz,1H),3.63–3.54(m,1H),3.05(dd,J＝18.1,8.2Hz,1H)ppm.
13C NMR(151MHz,CDCl3)196.74,192.41,160.31,136.30,135.86,133.61,128.77,128.17,127.02,126.71,121.44,119.68,70.53,41.64,34.26ppm.
example 4
After 5-bromo-2-acryloyloxybenzaldehyde (0.1mmol), benzoin (0.2mmol), benzophenone (DCP) (0.8mmol), and dry N, N-dimethylformamide (10mL) were sequentially added to a 50mL photoreaction tube, oxygen was removed by bubbling with a nitrogen balloon for 0.5h, and then the reaction was sealed and irradiated under 350nm ultraviolet light for 24 h. After the reaction is finished, concentrating and spin-drying the reaction solvent by a rotary evaporator, and then mixing the reaction solvent with petroleum ether: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-phenacyl-6-bromo-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 99%, yield 50%. The nuclear magnetic data are: 1H NMR (400MHz, CDCl3)8.03(d, J ═ 8.9Hz,3H),7.61(t, J ═ 17.3,8.8Hz,2H),7.51(t, J ═ 7.6Hz,2H),6.93(d, J ═ 8.9Hz,1H),4.68(dd, J ═ 11.1,5.2Hz,1H),4.34(t, J ═ 11.4Hz,1H), 3.77-3.69 (m,1H), 3.65-3.56 (m,1H),3.07(dd, J ═ 18.2,8.1Hz,1H) ppm.
13C NMR(150MHz,CDCl3)196.72,192.27,160.77,138.64,136.30,133.62,129.84,128.78,128.17,121.93,120.03,114.16,70.50,41.59,34.26ppm.
Example 5
After 3, 5-dimethyl-2-propenyloxybenzaldehyde (0.1mmol), benzoin (0.3mmol), benzophenone (0.8mmol) and dry benzene (15mL) were added in this order to a 50mL photoreaction tube, oxygen was removed by bubbling with a nitrogen balloon for 0.5h, and then the reaction was sealed and irradiated under 350nm UV light for 48 h. After the reaction is finished, concentrating and spin-drying the reaction solvent by a rotary evaporator, and then mixing the reaction solvent with petroleum ether: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-phenacyl-6, 8-dimethyl-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 97.5%, yield 58%. The nuclear magnetic data are: 1H NMR (400MHz, CDCl3)8.03(d, J ═ 7.7Hz,2H),7.61(t,2H),7.50(t, J ═ 7.5Hz,2H),7.20(s,1H),4.68(dd, J ═ 10.9,5.1Hz,1H),4.29(t, J ═ 11.2Hz,1H),3.73(d, J ═ 18.1Hz,1H), 3.61-3.52 (m,1H),3.03(dd, J ═ 17.9,8.5Hz,1H),2.30(s,3H),2.24(s,3H) ppm.13c NMR (150MHz, CDCl3)197.18,194.08,158.22,138.10,136.51,133.44,130.17,128.70,128.18,126.92,124.47,119.92,70.28,41.74,34.49,20.42,15.55ppm.
Example 6
After 2-acryloyloxybenzaldehyde (0.1mmol), 4' -dimethyl-substituted benzoin (0.4mmol), dicumyl peroxide (DCP) (0.4mmol) and dried benzene (15mL) were sequentially added to a 50mL photoreaction tube, oxygen was removed by bubbling with a nitrogen balloon for 0.5h, and then the reaction was sealed and irradiated under 350nm ultraviolet light for 24 h. After the reaction is finished, the reaction solvent is concentrated and dried by a rotary evaporator and then is subjected to volume ratio
40:1 petroleum ether: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-p-methylbenzoylmethyl-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 98.2%, yield 64%. The nuclear magnetic data are: 1H NMR (400MHz, CDCl3)7.93(d, J ═ 6.3Hz,3H),7.51(t, J ═ 7.6Hz,1H),7.30(d, J ═ 8.8Hz,2H), 7.09-6.99 (m,2H),4.67(dd, J ═ 11.1,5.3Hz,1H),4.33(t, J ═ 11.3Hz,1H),3.72(d, J ═ 18.1Hz,1H), 3.66-3.56 (m,1H),3.03(dd, J ═ 17.8,8.5Hz,1H),2.45(s,3H) ppm.
13C NMR(150MHz,CDCl3)196.64,193.57,161.87,144.37,136.01,133.98,129.41,128.30,127.42,121.46,120.69,117.91,70.46,41.88,34.24,21.72ppm.
Example 7
After 2-acryloyloxybenzaldehyde (0.1mmol), 4' -dibromo-substituted benzoin (0.2mmol), dicumyl peroxide (DCP) (0.4mmol), and dried benzene (15mL) were sequentially added to a 50mL photoreaction tube, oxygen was removed by bubbling with a nitrogen balloon for 0.5h, and then the reaction was sealed and irradiated under 350nm ultraviolet light for 24 h. After the reaction is finished, concentrating and spin-drying the reaction solvent by a rotary evaporator, and then mixing the reaction solvent with petroleum ether: the mixed solution of ethyl acetate is used as eluent to carry out silica gel column chromatography purification and separation to obtain corresponding 3-p-bromobenzoyl methyl-2, 3-dihydrobenzopyran-4-ketone, and the structural formula is as follows:
purity 96.3% yield 84%. The nuclear magnetic data are: 1H NMR (600MHz, CDCl3)7.91(dd, J ═ 7.8,1.2Hz,1H),7.87(d, J ═ 8.5Hz,2H),7.63(d, J ═ 8.5Hz,2H), 7.52-7.48 (m,1H),7.04(t, J ═ 7.5Hz,1H),7.00(d, J ═ 8.3Hz,1H),4.64(dd, J ═ 11.1,5.3Hz,1H),4.31(t, J ═ 11.4Hz,1H),3.67(dd, J ═ 17.9,3.9Hz,1H), 3.63-3.57 (m,1H),2.97(dd, J ═ 17.9,8.0, 1H), 3.1H, 3.70 ppm, 36.34, 36 ppm, 41.85 ppm.
The above-described embodiments are only preferred embodiments of the present invention, and are not intended to limit the present invention in any way, and other variations and modifications may be made without departing from the spirit of the invention as set forth in the claims.
Claims (7)
1. A method for producing a 2, 3-dihydrobenzopyran-4-one derivative represented by the formula (III), characterized by comprising the steps of:
dissolving an o-propenyloxybenzaldehyde derivative shown in a formula (I) and a benzoin derivative shown in a formula (II) in an organic solvent at room temperature under the atmosphere of nitrogen, adding a photosensitizer, uniformly mixing, placing under an ultraviolet lamp for illumination reaction, performing rotary evaporation to remove the solvent, and performing silica gel column chromatography separation and purification to obtain a product, namely the 2, 3-dihydrobenzopyran-4-one derivative shown in the formula (III);
wherein R is1、R2Is hydrogen or halogenAn alkyl or a biotin group;
the photosensitizer is benzophenone or dicumyl peroxide.
2. The process for producing a 2, 3-dihydrobenzopyran-4-one derivative according to claim 1, wherein the organic solvent is one selected from the group consisting of acetonitrile, benzene, toluene, dimethyl sulfoxide and N, N-dimethylformamide.
3. The process for producing 2, 3-dihydrobenzopyran-4-one derivatives according to claim 1, wherein the reaction time of the ultraviolet irradiation is 24 to 48 hours.
4. The method for preparing 2, 3-dihydrobenzopyran-4-one derivatives according to claim 1, wherein the solvent used for the separation and purification by silica gel column chromatography is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is 10-50: 1.
5. The method for preparing 2, 3-dihydrobenzopyran-4-one derivatives according to claim 1, wherein the o-propenyloxybenzaldehyde derivative, benzoin derivative compound and photosensitizer are dosed in a molar ratio of 1: 2-4: 4-8.
6. The method for preparing 2, 3-dihydrobenzopyran-4-one derivatives according to claim 5, wherein the o-propenyloxybenzaldehyde derivative, benzoin derivative compound and photosensitizer are dosed in a molar ratio of 1: 2: 4.
7. the method for producing a 2, 3-dihydrobenzopyran-4-one derivative according to claim 1, wherein the organic solvent is fed in a volume of 50 to 150mL/mmol of the o-propenyloxybenzaldehyde derivative.
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| CN112759586B (en) * | 2019-11-01 | 2022-05-17 | 河南大学 | Chiral thiochroman-4-ketone compound, and preparation method and application thereof |
| CN112759580B (en) * | 2019-11-01 | 2022-05-17 | 河南大学 | Preparation method of chroman-4-one and derivatives thereof |
| CN111484469B (en) * | 2020-05-14 | 2022-07-05 | 遵义医科大学 | Synthesis method and application of pyran subunit malononitrile photosensitizer lead compound |
| CN114478449B (en) * | 2022-01-19 | 2023-10-27 | 江苏海洋大学 | Polysubstituted selenium-containing dihydroisobenzofuran derivative and preparation method thereof |
| CN114853707B (en) * | 2022-06-13 | 2024-01-26 | 上饶师范学院 | Method for synthesizing difluoro hydrogen methylation 2, 3-dihydro benzopyran-4-ketone derivative |
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