CN113429272A - Aryl aldehyde ketone and synthetic method thereof - Google Patents

Aryl aldehyde ketone and synthetic method thereof Download PDF

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CN113429272A
CN113429272A CN202110684283.6A CN202110684283A CN113429272A CN 113429272 A CN113429272 A CN 113429272A CN 202110684283 A CN202110684283 A CN 202110684283A CN 113429272 A CN113429272 A CN 113429272A
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aryl
ethyl acetate
crude product
additive
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徐骏
张怡岚
岳晓光
章鹏飞
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Hangzhou Normal University
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Abstract

The invention discloses aryl aldehyde ketone and a synthesis method thereof, which are used for synthesizing aryl aldehyde and ketone compounds by taking cheap olefin as a raw material, and particularly used for synthesizing aldehyde and ketone by taking commercially available cheap olefin as a raw material, ether as an additive, molecular oxygen as a unique oxidant and water as a solvent, reacting under a photocatalysis condition and carrying out column chromatography. The method has the advantages of mild reaction conditions, environment-friendly method, simple experimental operation, good reaction selectivity, high product yield and the like.

Description

Aryl aldehyde ketone and synthetic method thereof
Technical Field
The invention belongs to the technical field of pharmaceutical and chemical intermediate synthesis, and particularly relates to aryl aldehyde ketone and a synthesis method thereof.
Background
Aldehydes and ketones are very important intermediates due to their widespread existence and wide use in the fragrance, food additives, pharmaceuticals, agrochemical and other chemical industries. For example, the compound (III) represented by the formula (III) can be used as a perfume, for preparing a floral essence, for foods and cosmetics, soap, etc.; can be used as intermediate of antihistaminic drugs, such as antibiotic hydroxyaminobenzylpenicillin. The compound (IV) of formula (IV) is an intermediate of ultraviolet absorber, organic pigment, medicine, perfume, insecticide, and is used for producing dicyclohexylpiperidine, diphenhydramine hydrochloride, etc. in the pharmaceutical industry. The compound (V) represented by the formula (V) is fenofibrate, a drug for treating hyperlipidemia in which the dietary control therapy for adults is not ideal. The application values of the aldehyde ketone and the derivative thereof in other fields are reflected.
Figure 829065DEST_PATH_IMAGE001
Currently, there are many methods available for the oxidative cleavage of olefins to synthesize aldehydes and ketones, mainly including: decomposing ozone; adding some metal oxide (KMnO)4、OsO4、RuO4Etc.); transition metals are used as catalysts in combination with peroxides, peroxy acids and other oxidizing agents; an electrochemical method; organic molecules are used in combination with an oxidizing agent and oxygen, and the like. These processes often present safety hazards, such as the use of expensive toxic metals or the use of excess oxidants, some of which are expensive and may even produce large amounts of by-products, greatly reducing the atomic economy of the reaction.
Therefore, there is a great interest in developing new methods for the simple, economical and green synthesis of aldehydes, ketones and their derivatives. The photocatalytic organic synthesis has the advantages of mild reaction conditions, renewable energy sources, high reaction efficiency and the like. The invention uses cheap and easily obtained olefin as raw material and ether as additive, and obtains a series of aryl aldehyde ketone and its derivatives with high selectivity and high yield by light irradiation. The compounds are important intermediates in organic synthesis, and have good research and application values.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides a simple, convenient and efficient aryl aldehyde ketone and a synthetic method thereof.
The aryl aldehyde ketone is characterized in that the structural formula is shown as the formula (II):
Figure 685026DEST_PATH_IMAGE002
wherein: r is hydrogen, alkyl, phenyl, 4-methylphenyl; ar is aryl, and the aryl is substituted phenyl, furyl, pyridyl or thienyl.
Further, the present invention defines the substituents in the substituted phenyl as alkyl, halogen, trifluoromethyl, phenyl or nitro.
The invention further defines a synthesis method of the aryl aldehyde ketone, which is characterized in that the method takes the olefin shown in the formula (I) as a raw material, takes ether as an additive, takes water as a solvent, and synthesizes the aldehyde or ketone shown in the formula (II) under the action of molecular oxygen and photocatalysis, wherein the reaction equation is as follows:
Figure 382724DEST_PATH_IMAGE003
wherein: r is hydrogen, alkyl, phenyl, 4-methylphenyl; ar is aryl, and the aryl is substituted phenyl, furyl, pyridyl or thienyl.
Furthermore, the invention also defines that the additive is any one of tetrahydrofuran, 1, 4-dioxane, diethylene glycol dimethyl ether, 1, 2-dimethoxyethane, 2, 5-dimethyl tetrahydrofuran and 2-chloromethyl tetrahydrofuran, and the feeding molar ratio of the additive to olefin is 0.3-1: 1, preferably 0.5: 1.
Further, the invention also defines the molecular oxygen as reacting in air and oxygen atmosphere, preferably oxygen; the reaction time is 12 to 48 hours, preferably 12 to 36 hours, and most preferably 18 hours.
Furthermore, the invention also defines the light wavelength of 360-.
Furthermore, the invention also defines a synthesis method of the aryl aldehyde ketone, which specifically comprises the following steps:
placing olefin shown as a formula (I) in a reaction bottle, adding an additive and solvent water, carrying out visible light catalytic reaction for 12-36 hours at room temperature under the action of molecular oxygen, adding ethyl acetate for extraction and layering after the reaction is finished, drying an organic layer by anhydrous magnesium sulfate or anhydrous sodium sulfate, filtering and concentrating to obtain a crude product, purifying the crude product by silica gel column chromatography, wherein the solvent used by the silica gel column chromatography is a mixed solution of ethyl acetate and petroleum ether in a volume ratio of 1:10 to obtain a target product, and the additive is further defined to be any one of tetrahydrofuran, 1, 4-dioxane, diethylene glycol dimethyl ether, 1, 2-dimethoxyethane, 2, 5-dimethyltetrahydrofuran and 2-chloromethyl tetrahydrofuran.
By adopting the technology, compared with the prior art, the invention has the following beneficial effects:
according to the invention, a series of aryl aldehyde ketones are synthesized by adopting a limited method, and the reaction conditions are mild through visible light catalytic reaction, so that the method has the advantages of energy regeneration, high reaction efficiency and the like; the invention takes cheap and easily obtained olefin as raw material, under the action of molecular oxygen and ether, a series of aryl aldehyde ketone and derivatives thereof are obtained with high selectivity and high yield by light irradiation.
Detailed Description
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
example 1:
Figure 742161DEST_PATH_IMAGE004
adding p-methoxystyrene (670 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) into a 100 mL reaction bottle, irradiating by an LED lamp (400 plus 405 nm) in an oxygen atmosphere, stirring for reacting for 18 hours, adding ethyl acetate for extraction after the reaction is finished, fully stirring, standing for layering, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product, and purifying the crude product by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 531 mg of colorless liquid, wherein the yield is 78%.1H NMR (500 MHz, CDCl3) δ 9.89 (s, 1H), 7.84 (d, J = 8.9 Hz, 2H), 7.03 – 6.98 (m, 2H), 3.89 (s, 3H)。
Example 2:
Figure 132691DEST_PATH_IMAGE005
adding 4-vinylbiphenyl (901 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) into a 100 mL reaction bottle, irradiating by an LED lamp (400-405 nm) in an oxygen atmosphere, stirring for reacting for 18 hours, adding ethyl acetate for extraction after the reaction is finished, fully stirring, standing for layering, drying an organic layer by anhydrous magnesium sulfate, filtering and concentrating to obtain a crude product, and purifying the crude product by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 683 mg of a white solid, wherein the yield is 75%.1H NMR (500 MHz, CDCl3) δ 10.09 (s, 1H), 7.99 (d, J = 8.3 Hz, 2H), 7.79 (d, J = 8.3 Hz, 2H), 7.67 (d, J = 7.1 Hz, 2H), 7.52 (t, J = 7.5 Hz, 2H), 7.45 (t, J = 7.3 Hz, 1H) 。
Example 3:
Figure 210368DEST_PATH_IMAGE006
4-trifluoromethylstyrene (930 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were put into a 100 mL reaction flask, and stirred under the molecular oxygen atmosphere with an LED lamp (400-405 nm) for 18 hours. After the reaction, ethyl acetate was added to extract, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 605 mg of a colorless liquid with a yield of 70%.1H NMR (500 MHz, CDCl3) δ 10.11 (s, 1H), 8.02 (d, J = 8.0 Hz, 2H), 7.81 (d, J = 8.2 Hz, 2H) 。
Example 4:
Figure 977336DEST_PATH_IMAGE007
3-fluorostyrene (611 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were added to a 100 mL reaction flask, and the mixture was stirred and reacted for 18 hours under an oxygen atmosphere by irradiation with an LED lamp (400 and 405 nm). After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 455 mg of a pale yellow liquid with a yield of 73%.1H NMR (500 MHz, CDCl3) δ 10.01 (s, 1H), 7.70 (d, J = 7.6 Hz, 1H), 7.61 – 7.51 (m, 2H), 7.35 (td, J = 8.3, 2.7 Hz, 1H) 。
Example 5:
Figure 253596DEST_PATH_IMAGE008
2-methylstyrene (591 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were charged into a 100 mL reaction flask, and the mixture was stirred and reacted for 18 hours under an oxygen atmosphere by irradiation with an LED lamp (410 and 415 nm). After the reaction, ethyl acetate was added to extract, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 418 mg of a colorless liquid with a yield of 70%.1H NMR (500 MHz, CDCl3) δ 10.29 (s, 1H), 7.82 (d, J = 7.6 Hz, 1H), 7.50 (t, J = 7.5 Hz, 1H), 7.38 (t, J = 7.5 Hz, 1H), 7.28 (d, J = 7.6 Hz, 1H), 2.70 (s, 3H) 。
Example 6:
Figure 690394DEST_PATH_IMAGE009
2-Vinylnaphthalene (771 mg, 5.0 mmol), 1, 4-dioxane (220 mg, 50% mol), water (30 mL) were addedIn a 100 mL reaction flask, the reaction was stirred for 24 hours under the molecular oxygen atmosphere by the illumination of an LED lamp (400-405 nm). After the reaction, ethyl acetate was added to extract, the mixture was fully stirred and then was allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 479 mg of a white solid with a yield of 61%.1H NMR (500 MHz, CDCl3) δ 10.15 (s, 1H), 8.33 (s, 1H), 7.99 (d, J = 8.1 Hz, 1H), 7.96 – 7.88 (m, 3H), 7.63 (dd, J = 12.2, 4.0 Hz, 1H), 7.58 (t, J = 7.5 Hz, 1H) 。
Example 7:
Figure 114422DEST_PATH_IMAGE010
2-vinylpyridine (526 mg, 5.0 mmol), 1, 4-dioxane (220 mg, 50% mol) and water (30 mL) were added to a 100 mL reaction flask, and the mixture was irradiated under an oxygen atmosphere with an LED lamp (400-405 nm) and stirred for reaction for 18 hours. After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 258 mg of a pale yellow liquid with a yield of 48%.1H NMR (500 MHz, CDCl3) δ 10.09 (s, 1H), 8.81 (dd, J = 6.0, 2.4 Hz, 1H), 8.02 – 7.94 (m, 1H), 7.89 (dd, J = 2.3, 1.6 Hz, 1H), 7.58 – 7.50 (m, 1H) 。
Example 8:
Figure 294868DEST_PATH_IMAGE011
1-isopropenyl-4-methoxybenzene (741 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), water (30 mL) and water (3.0 mL) were put into a 100 mL reaction flask, and the reaction was stirred for 12 hours under irradiation with an LED lamp (400 and 405 nm) under an oxygen atmosphere. After the reaction is finished, adding ethyl acetate for extraction, and fully stirringStirring, standing, layering, drying the organic layer with anhydrous magnesium sulfate, filtering, concentrating to obtain crude product, and purifying by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 630 mg of white solid with yield of 84%.1H NMR (500 MHz, CDCl3) δ 7.95 (d, J = 8.9 Hz, 2H), 6.94 (d, J = 8.8 Hz, 2H), 3.88 (s, 3H), 2.57 (s, 3H) 。
Example 9:
Figure 425635DEST_PATH_IMAGE012
4-chloro-alpha-methylstyrene (763 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were placed in a 100 mL reaction flask, and the mixture was irradiated with an LED lamp (400-405 nm) under an oxygen atmosphere, followed by stirring and reacting for 18 hours. After the reaction, ethyl acetate was added to extract, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 629 mg of a colorless liquid with a yield of 81%.1H NMR (500 MHz, CDCl3) δ 7.89 (dd, J = 8.6, 1.0 Hz, 2H), 7.42 (dd, J = 8.5, 1.2 Hz, 2H), 2.58 (s, 3H) 。
Example 10:
Figure 160897DEST_PATH_IMAGE013
4-nitro-alpha-methylstyrene (815 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were placed in a 100 mL reaction flask, and the mixture was irradiated with LED lamp (420-425 nm) under oxygen atmosphere, and stirred for reaction for 36 hours. After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 287 mg of a pale yellow solid with a yield of 35%.1H NMR (500 MHz, CDCl3) δ 8.30 (d, J = 6.9 Hz, 2H), 8.10 (d, J = 8.9 Hz, 2H), 2.67 (s, 3H) 。
Example 11:
Figure 213167DEST_PATH_IMAGE014
alpha-ethylstyrene (660 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were put in a 100 mL reaction flask, and the mixture was irradiated with an LED lamp (400-405 nm) under an oxygen atmosphere, and stirred for reaction for 18 hours. After the reaction, ethyl acetate was added for extraction, the mixture was sufficiently stirred and then allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 557 mg of a colorless liquid with a yield of 81%.1H NMR (500 MHz, CDCl3) δ 7.98 (dd, J = 8.3, 1.1 Hz, 2H), 7.56 (t, J = 7.4 Hz, 1H), 7.47 (t, J = 7.6 Hz, 2H), 3.02 (q, J = 7.2 Hz, 2H), 1.25 (t, J = 7.3 Hz, 3H) 。
Example 12:
Figure 790779DEST_PATH_IMAGE015
1-methylene-1, 2,3, 4-tetrahydronaphthalene (720 mg, 5.0 mmol), diethylene glycol dimethyl ether (335 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 36 hours under irradiation with an LED lamp (400 and 405 nm) under an oxygen atmosphere. After the reaction, ethyl acetate was added for extraction, the mixture was sufficiently stirred and then allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 406 mg of a colorless liquid with a yield of 58%.1H NMR (500 MHz, CDCl3) δ 8.05 (d, J = 7.8 Hz, 1H), 7.48 (t, J = 7.4 Hz, 1H), 7.32 (t, J = 7.5 Hz, 1H), 7.27 (d, J = 7.6 Hz, 1H), 2.98 (t, J = 6.1 Hz, 2H), 2.70 – 2.65 (m, 2H), 2.18 – 2.12 (m, 2H) 。
Example 13:
Figure 244894DEST_PATH_IMAGE016
2-isopropenylfuran (540 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were put into a 100 mL reaction flask, and the reaction was stirred for 18 hours under an oxygen atmosphere by irradiation with an LED lamp (410 and 415 nm). After the reaction, ethyl acetate was added to extract, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 268 mg of a colorless liquid with a yield of 49%.1H NMR (500 MHz, CDCl3) δ 7.61 – 7.57 (m, 1H), 7.18 (d, J = 3.6 Hz, 1H), 6.55 – 6.52 (m, 1H), 2.48 (s, 3H) 。
Example 14:
Figure 820232DEST_PATH_IMAGE017
4- (1-methyl-1-propenyl) -pyridine (596 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 36 hours under irradiation with an LED lamp (420-425 nm) under an oxygen atmosphere. After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 333 mg of a pale yellow liquid with a yield of 48%.1H NMR (500 MHz, CDCl3) δ 8.72 – 8.66 (m, 1H), 8.04 (dd, J = 7.9, 1.0 Hz, 1H), 7.84 (dt, J = 9.4, 4.7 Hz, 1H), 7.50 – 7.43 (m, 1H), 2.73 (s, 3H) 。
Example 15:
Figure 484431DEST_PATH_IMAGE018
2-isopropenylthiophene (621 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were added to a 100 mL reaction flask, and the mixture was irradiated under an oxygen atmosphere with an LED lamp (400-405 nm) and stirred for reaction for 36 hours. After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 375 mg of a pale yellow liquid with a yield of 60%.1H NMR (500 MHz, CDCl3) δ 7.70 (d, J = 3.7 Hz, 1H), 7.63 (d, J = 4.9 Hz, 1H), 7.16 – 7.10 (m, 1H), 2.56 (s, 3H) 。
Example 16:
Figure 6679DEST_PATH_IMAGE019
1, 1-stilbene (901 mg, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol) and water (30 mL) were put into a 100 mL reaction flask, and the reaction was stirred for 18 hours under an oxygen atmosphere by irradiation with an LED lamp (400-405 nm). After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 724 mg of a yellow liquid with a yield of 80%.1H NMR (500 MHz, CDCl3) δ 7.83 – 7.78 (m, 4H), 7.59 (t, J = 7.4 Hz, 2H), 7.48 (t, J = 7.7 Hz, 4H) 。
Example 17:
Figure 174355DEST_PATH_IMAGE020
1-iodo-4- (1-phenylvinyl) benzene (1.5 g, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 18 hours under irradiation with an LED lamp (400 and 405 nm) under an oxygen atmosphere. After the reaction is finished, ethyl acetate is added for extraction, and then the mixture is filledStirring, standing for layering, drying the organic layer with anhydrous magnesium sulfate, filtering, concentrating to obtain crude product, and purifying by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 1059 mg of white solid with yield of 69%.1H NMR (500 MHz, CDCl3) δ 7.76 (d, J = 8.5 Hz, 2H), 7.68 (dd, J = 8.2, 1.2 Hz, 2H), 7.51 (t, J = 7.4 Hz, 1H), 7.44 – 7.37 (m, 4H) 。
Example 18:
Figure 123857DEST_PATH_IMAGE021
1, 2-dichloro-4- (1-1-phenylvinyl) benzene (1.2 g, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 36 hours under irradiation with an LED lamp (400-405 nm) under an oxygen atmosphere. After the reaction, ethyl acetate was added for extraction, the mixture was fully stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 830 mg of a white solid with a yield of 66%.1H NMR (500 MHz, CDCl3) δ 7.81 (d, J = 1.9 Hz, 1H), 7.71 – 7.67 (m, 2H), 7.54 (dt, J = 8.9, 4.6 Hz, 2H), 7.48 (d, J = 8.3 Hz, 1H), 7.42 (t, J = 7.8 Hz, 2H) 。
Example 19:
Figure 681877DEST_PATH_IMAGE022
1-bromo-4- (1- (p-tolyl) vinyl) benzene (1.4 g, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were charged in a 100 mL reaction flask, and the reaction was stirred for 36 hours under irradiation with an LED lamp (400 and 405 nm) under an oxygen atmosphere. Extracting with ethyl acetate, stirring, standing for layering, drying the organic layer with anhydrous magnesium sulfate, filtering, concentrating to obtain crude product, and performing silica gel column chromatography (ethyl acetate: petroleum ether)= 1: 10) to obtain 853 mg of white solid with a yield of 68%.1H NMR (500 MHz, CDCl3) δ 7.73 (d, J = 8.6 Hz, 2H), 7.69 (d, J = 8.1 Hz, 2H), 7.44 (d, J = 8.6 Hz, 2H), 7.28 (d, J = 7.9 Hz, 2H), 2.44 (s, 3H) 。
Example 20:
Figure 132450DEST_PATH_IMAGE023
2- (1- (p-tolyl) vinyl) thiophene (1.0 g, 5.0 mmol), 1, 4-dioxane (220 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 18 hours under irradiation with an LED lamp (400 and 405 nm) under an oxygen atmosphere. After the reaction, ethyl acetate was added for extraction, the mixture was sufficiently stirred and then allowed to stand for layering, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 689 mg of a yellow liquid with a yield of 68%.1H NMR (500 MHz, CDCl3) δ 7.79 (d, J = 8.1 Hz, 2H), 7.70 (dd, J = 4.9, 1.0 Hz, 1H), 7.65 (dd, J = 3.8, 1.0 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.16 (dd, J = 4.9, 3.8 Hz, 1H), 2.45 (s, 3H) 。
Example 21:
Figure 29999DEST_PATH_IMAGE024
compound (VI) (1.8 g, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 18 hours under an oxygen atmosphere by irradiation with an LED lamp (400-405 nm). After the reaction, ethyl acetate was added to extract, the mixture was fully stirred and then allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 1.3 g of a white solid product (V) with a yield of 70%.1H NMR (500 MHz, CDCl3) δ 7.73 (d, J = 8.9 Hz, 2H), 7.70 (d, J = 8.6 Hz, 2H), 7.45 (d, J = 8.6 Hz, 2H), 6.87 (d, J = 8.9 Hz, 2H), 5.13 – 5.05 (m, 1H), 1.66 (s, 6H), 1.21 (d, J = 6.3 Hz, 6H) 。
Example 22:
Figure 275036DEST_PATH_IMAGE025
compound (VIII) (1.6 g, 5.0 mmol), tetrahydrofuran (180 mg, 50% mol), and water (30 mL) were charged into a 100 mL reaction flask, and the reaction was stirred for 18 hours under irradiation with an LED lamp (400-405 nm) under an oxygen atmosphere. After the reaction, ethyl acetate was added to extract, the mixture was sufficiently stirred and then allowed to stand for delamination, the organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain a crude product, and the crude product was purified by silica gel column chromatography (ethyl acetate: petroleum ether = 1: 10) to obtain 1.2 g of a yellow liquid product (VII) with a yield of 68%.1H NMR (500 MHz, CDCl3) δ 7.90 (d, J = 7.5 Hz, 2H), 7.57 (t, J= 7.4 Hz, 1H), 7.45 (t, J = 7.7 Hz, 2H), 7.15 (d, J = 8.0 Hz, 2H), 7.04 (d, J= 8.0 Hz, 2H), 4.55 – 4.48 (m, 2H), 3.66 (q, J = 7.2 Hz, 1H), 3.26 – 3.21 (m, 2H), 2.42 (d, J = 7.2 Hz, 2H), 1.83 (dd, J = 13.5, 6.7 Hz, 1H), 1.46 (d, J = 7.2 Hz, 3H), 0.88 (d, J = 6.6 Hz, 6H); 13C NMR (126 MHz, CDCl3) δ 197.1, 174.7, 140.5, 137.6, 136.7, 133.4, 129.3, 128.7, 128.1, 127.1, 60.1, 45.1, 45.0, 37.3, 30.2, 22.4, 18.5; HRMS (ESI+): Calculated for C22H26O3Na: [M + Na]+361.1774, Found 361.1777。
Example 23:
the reaction additive was replaced with 1, 4-dioxane, and the same operations as in example 1 were carried out to give 436 mg of a colorless liquid in a yield of 64%.
Example 24:
the reaction additive was changed to diethylene glycol dimethyl ether, and the other operations were performed in the same manner as in example 1 to obtain 477 mg of a colorless liquid with a yield of 70%.
Example 25:
the mass ratio of tetrahydrofuran to p-methoxystyrene charged was 0.3:1, and the other operations were the same as in example 1, giving 449 mg of a yellow solid with a yield of 66%.
Example 26:
the feed mass ratio of tetrahydrofuran to p-methoxystyrene was 1:1, and the other operations were the same as in example 1, whereby 524 mg of a colorless liquid was obtained with a yield of 77%.
Example 27:
the reaction time was changed to 12 hours, and the other operations were carried out in the same manner as in example 1 to obtain 354 mg of a colorless liquid with a yield of 52%.
Example 28:
the reaction time was changed to 24 hours, and the other operations were carried out in the same manner as in example 1 to obtain 456 mg of a colorless liquid in a yield of 67%.
Example 29:
the wavelength of the reaction catalyst light was changed to 360-365 nm, and other operations were performed as in example 1 to obtain 265 mg of colorless liquid with a yield of 39%.
The aryl aldehyde ketone derivative obtained by the embodiment of the invention has potential application prospects in the fields of pharmaceutical chemicals, materials, dyes and the like.

Claims (8)

1. An aryl aldehyde ketone characterized by the structural formula shown in formula (II):
Figure 220702DEST_PATH_IMAGE001
wherein: r is hydrogen, alkyl, phenyl, 4-methylphenyl; ar is aryl, and the aryl is substituted phenyl, furyl, pyridyl or thienyl.
2. An aryl aldehyde ketone according to claim 1 wherein the substituent in the substituted phenyl group is an alkyl group, a halogen, a trifluoromethyl group, a phenyl group or a nitro group.
3. The method for synthesizing aryl aldehyde ketone according to claim 1, wherein the method comprises the steps of taking olefin as shown in formula (I) as a raw material, taking ether as an additive, taking water as a solvent, and synthesizing aldehyde or ketone as shown in formula (II) under the action of molecular oxygen under photocatalysis, wherein the reaction equation is as follows:
Figure 256791DEST_PATH_IMAGE002
wherein: r is hydrogen, alkyl, phenyl, 4-methylphenyl; ar is aryl, and the aryl is substituted phenyl, furyl, pyridyl or thienyl.
4. The method for synthesizing aryl aldehyde ketone according to claim 3, wherein the additive is any one of tetrahydrofuran, 1, 4-dioxane, diethylene glycol dimethyl ether, 1, 2-dimethoxyethane, 2, 5-dimethyltetrahydrofuran and 2-chloromethyl tetrahydrofuran, and the feeding molar ratio of the additive to the olefin is 0.3-1: 1, preferably 0.5: 1.
5. The method for synthesizing aryl aldehyde ketone according to claim 3, wherein the molecular oxygen is a reaction in air or oxygen atmosphere, preferably oxygen; the reaction time is 12 to 48 hours, preferably 12 to 36 hours, and most preferably 18 hours.
6. The method as claimed in claim 3, wherein the light wavelength in the photocatalysis is 360-365 nm, 395-400 nm, 400-405 nm, 410-415 nm or 420-425 nm, and most preferably 400-405 nm.
7. The method for synthesizing aryl aldehyde ketone according to claim 3, comprising the steps of:
placing olefin shown as a formula (I) in a reaction bottle, adding an additive and solvent water, carrying out visible light catalytic reaction for 12-36 hours at room temperature under the action of molecular oxygen, adding ethyl acetate for extraction and layering after the reaction is finished, drying an organic layer by anhydrous magnesium sulfate or anhydrous sodium sulfate, filtering and concentrating to obtain a crude product, purifying the crude product by silica gel column chromatography, wherein the solvent used by the silica gel column chromatography is a mixed solution of ethyl acetate and petroleum ether in a volume ratio of 1:10, and obtaining a target product.
8. The method according to claim 7, wherein the additive is any one of tetrahydrofuran, 1, 4-dioxane, diethylene glycol dimethyl ether, 1, 2-dimethoxyethane, 2, 5-dimethyltetrahydrofuran, and 2-chloromethyltetrahydrofuran.
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