CN111333558A - Visible light promoted α -selenone compound synthesis method - Google Patents
Visible light promoted α -selenone compound synthesis method Download PDFInfo
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- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract
The invention discloses a visible light-promoted α -selenone compound synthesis method which comprises the following steps of A, sequentially adding compounds 1 and 2 into a reactor under an open condition, B, carrying out stirring reaction under a certain temperature condition and light source irradiation, C, carrying out reduced pressure evaporation to remove a solvent after the reaction is finished to obtain a crude product, and D, carrying out column chromatography purification to obtain α -selenone 3.
Description
Technical Field
The invention relates to the technical field of organic synthetic chemistry, in particular to a synthesis method of α -selenone compound promoted by visible light.
Background
Selenium is an essential trace element of the human body, which is closely related to human health ((a) Nogueira, c.w.; Zeni, g.; Rocha, j.b.t., chem.rev.2004, 104, 6255-
((a)Klayman，D.L.；Günther，W.H.H.Organic Selenium Compounds：TheirChemistry and Biology；John Wiley&Sons，New York，1973.；(b)Nogueira，C.W.；Zeni，G.；Rocha，J.B.T.Chem.Rev.2004，104，6255-6286.)
α -selenone compounds are an important class of organic synthetic intermediates ((a) Reich, h.j.; Renga, j.m.; Reich, i.l.j.am.chem.soc.1975, 97, 5434.; b) Movassagh, b.; sharpoor, m.synlett2005, 121.; c) Baudat, r.; petrazaka, m.helv.chem.acta 1979, 62, 1406.; d) Thomas, g.b., russeri, g.k.tetrahedron 1985, 41, 4759.) conventional methods of synthesizing α -selenone generally react with nucleophilic arylseleno anions α -bromocarbonyl compounds ((a) shales, k.b.; lasr, r.f.; teinoc generally by reaction with nucleophilic arylseleno anions α -bromocarbonyl compounds ((a) through extensive reactions with electrophilic substrates, e.t. h.s., t., r.f., 6151, t.h.h.h.1975, 97, 5434, b., 104, h.h.h.h.h.h.h.h.h.h.h.h. h. 1975, h.t. h.h.h.h.26, a.
However, the method for synthesizing α -selenone compound through promotion of visible light by starting from olefin is not reported under the condition of not using a photocatalyst, and still has the need of continuously researching and exploring, which is also the foundation and the power for completing the invention.
Disclosure of Invention
The invention aims to provide a synthesis method of α -selenone compound promoted by visible light, which aims to solve the problems in the background technology.
In order to realize the aim, the invention provides the following technical scheme that the synthesis method of the α -selenone compound promoted by visible light comprises the following steps:
A. sequentially adding a compound 1 and a compound 2 into a reactor;
B. under the open condition, stirring and reacting under the irradiation of a light source under the condition of certain temperature;
C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product;
D. purifying by column chromatography to obtain α -selenone 3.
Preferably, the step A reactor is a round-bottom flask, and α -selenone compound is prepared by a chemical reaction, wherein the reaction equation is as follows:
wherein compound 1 is a mono-or bicyclic heteroaryl ethylene having 5 to 10 ring atoms which may be styrene, substituted styrene, or substituted, said compound 2 being a diaryldiselenide or dialkyldiselenide.
Preferably, the molar ratio of the compounds in the step A is 1: 0.5.
Preferably, the step B is carried out under open conditions and room temperature conditions, and the room temperature reaction is carried out by irradiating white light emitted by a compact fluorescent lamp with 23 watts.
Preferably, the solvent of step C is one of acetonitrile, dichloromethane and ethyl acetate.
Preferably, the eluent used for the column chromatography purification in the step D is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is (4-50) to 1.
Compared with the prior art, the preparation method has the beneficial effects that the α -selenone compound is efficiently synthesized by using olefin and diselenide as raw materials, using one of acetonitrile, dichloromethane and ethyl acetate as a solvent, and under the irradiation of a white fluorescent light source at room temperature.
Drawings
FIG. 1 is a hydrogen spectrum of the product obtained in example 1 of the present invention;
FIG. 2 is a carbon spectrum of the product obtained in example 1 of the present invention;
FIG. 3 is a hydrogen spectrum of the product obtained in example 2 of the present invention;
FIG. 4 is a carbon spectrum of the product obtained in example 2 of the present invention;
FIG. 5 is a hydrogen spectrum of the product obtained in example 3 of the present invention;
FIG. 6 is a carbon spectrum of the product obtained in example 3 of the present invention;
FIG. 7 is a hydrogen spectrum of the product obtained in example 4 of the present invention;
FIG. 8 is a carbon spectrum of the product obtained in example 4 of the present invention;
FIG. 9 is a hydrogen spectrum of the product obtained in example 5 of the present invention;
FIG. 10 is a carbon spectrum of the product obtained in example 5 of the present invention;
FIG. 11 is a hydrogen spectrum of the product obtained in example 6 of the present invention;
FIG. 12 is a carbon spectrum of the product obtained in example 6 of the present invention;
FIG. 13 is a hydrogen spectrum of the product obtained in example 7 of the present invention;
FIG. 14 is a carbon spectrum of the product obtained in example 7 of the present invention;
FIG. 15 is a hydrogen spectrum of the product obtained in example 8 of the present invention;
FIG. 16 is a carbon spectrum of the product obtained in example 8 of the present invention;
FIG. 17 is a hydrogen spectrum of the product obtained in example 9 of the present invention;
FIG. 18 is a carbon spectrum of the product obtained in example 9 of the present invention;
FIG. 19 is a hydrogen spectrum of the product obtained in example 10 of the present invention;
FIG. 20 is a carbon spectrum of the product obtained in example 10 of the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Referring to fig. 1-20, the present invention provides a method for synthesizing α -selenone compound promoted by visible light, comprising the following steps:
A. sequentially adding a compound 1 and a compound 2 into a reactor;
B. under the open condition, stirring and reacting under the irradiation of a light source under the condition of certain temperature;
C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product;
D. purifying by column chromatography to obtain α -selenone 3.
A method for preparing α -selenone comprises the steps of taking olefin 1 as a raw material, taking a selenium source 2 as diaryl diselenide and dialkyl diselenide, filling 10.5 mmol of olefin and 20.25 mmol of diselenide into a 10-ml round-bottom flask filled with 2.0-3.0 ml of acetonitrile, dichloromethane and ethyl acetate at room temperature, placing a 23-watt white compact fluorescent lamp at a position 3 cm away from a reaction tube after adding, reacting at room temperature for 20 hours under an open condition, removing a solvent from a reaction liquid through a rotary evaporator after the reaction is finished, purifying a residue through a silica gel column, wherein the specification of the silica gel is 200-300 meshes, an eluent used for column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is (4-50) to 1 to obtain a target product α -selenone, and the yield is 68-90% according to different reactions.
Example 1
After styrene (0.5 mmol), diphenyl diselenide (0.25 mmol), acetonitrile (3 ml) and addition of 23W white compact fluorescent lamp were charged into a 10 ml round bottom flask equipped with a magnetic stirrer at room temperature, the flask was left to react at room temperature under open conditions for 20 hours, the organic phase was passed through a rotary evaporator to remove the solvent after completion of the reaction, and the residue was purified by a silica gel column (200-300 mesh silica gel, eluent petroleum ether/ethyl acetate: 30: 1) to obtain 115 mg of yellow oily liquid with a yield of 83%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)δ/ppm＝7.83-7.78(m，2H)，7.51-7.43(m，3H)，7.36(t，J＝7.7Hz，2H)，7.23-7.16(m，3H)，4.10(s，2H).13C NMR(100MHz，CDCl3)：δ/ppm＝193.9，134.4，133.0，132.2，128.2，128.0，127.7，127.6，127.1，31.7.
example 2
After 4-tert-butylstyrene (0.5 mmol), diphenyldiselenide (0.25 mmol), acetonitrile (3 ml) and the addition of which were carried out at room temperature in a 10 ml round-bottomed flask equipped with a magnetic stirrer, a 23 w white compact fluorescent lamp was placed at a distance of 3 cm from the round-bottomed flask and reacted at room temperature for 20 hours under open conditions, the organic phase was passed through a rotary evaporator to remove the solvent after the reaction was completed, and the residue was purified by a silica gel column (silica gel specification: 200-300 mesh; eluent: petroleum ether/ethyl acetate: 60: 1) to obtain 142 mg of a yellow oily liquid at a yield of 86%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.75(d，J＝8.5Hz，2H)，7.49-7.44(m，2H)，7.37(d，J＝8.5Hz，2H)，7.23-7.17(m，3H)，4.09(s，2H)，1.26(s，9H).13C NMR(100MHz，CDCl3)：δ/ppm＝193.7，156.1，132.9，131.8，128.2，127.6，126.9，124.6，34.1，31.7，30.0.
example 3
After 4-methylstyrene (0.5 mmol), diphenyldiselenide (0.25 mmol), acetonitrile (3 ml) and the addition of 23W white compact fluorescent lamp were placed 3 cm from the round-bottom flask at room temperature in a 10 ml round-bottom flask equipped with a magnetic stirrer and reacted at room temperature for 20 hours under open conditions, the organic phase was passed through a rotary evaporator to remove the solvent after the reaction was completed, the residue was purified by a silica gel column (silica gel specification of 200-300 mesh; eluent petroleum ether/ethyl acetate: 30: 1) to obtain 130 mg of yellow solid with a yield of 90%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.71(d，J＝8.2Hz，2H)，7.50-7.43(m，2H)，7.24-7.13(m，5H)，4.08(s，2H)，2.33(s，3H).13C NMR(100MHz，CDCl3)：δ/ppm＝193.7，143.2，132.9，131.9，128.3，128.2，128.1，127.8，127.0，31.7，20.7.
example 4
Charging 4-chlorostyrene (0.5 mmol), diphenyl diselenide (0.25 mmol), acetonitrile (3 ml) into a 10 ml round-bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 3 cm from the round-bottom flask, reacting at open air for 20 hours at room temperature, removing the solvent from the organic phase through a rotary evaporator after the reaction is completed, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate-30: 1) to obtain 125 mg of yellow oily liquid with the yield of 81%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.74-7.69(m，2H)，7.46-7.41(m，2H)，7.34-7.29(m，2H)，7.24-7.17(m，3H)，4.05(s，2H).13C NMR(100MHz，CDCl3)：δ/ppm＝192.7，138.7，133.1，132.7，129.1，128.3，127.9，127.7，127.3，31.4.
example 5
After 2-vinyl thiophene (0.5 mmol), diphenyl diselenide (0.25 mmol), acetonitrile (3 ml) and the addition of 23W white compact fluorescent lamp were placed in a 10 ml round bottom flask equipped with a magnetic stirrer at room temperature and reacted at room temperature under an open condition for 20 hours, the organic phase was passed through a rotary evaporator to remove the solvent after the reaction was completed, the residue was purified by a silica gel column (the silica gel specification was 200-300 mesh, and the eluent was petroleum ether/ethyl acetate 15: 1) to obtain 109 mg of yellow oily liquid with a yield of 78%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.56(d，J＝4.9Hz，1H)，7.51-7.47(m，2H)，7.47-7.44(m，1H)，7.23-7.18(m，3H)，7.01-6.97(m，1H)，3.99(s，2H).13C NMR(100MHz，CDCl3)：δ/ppm＝187.3，141.7，133.2，133.1，131.7，128.2，128.1，127.2，127.1，32.1.
example 6
After charging 4-methyl-5-vinyl thiazole (0.5 mmol), diphenyl diselenide (0.25 mmol), acetonitrile (3 ml) into a 10 ml round bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 3 cm from the round bottom flask, reacting at open room temperature for 20 hours, removing the solvent from the organic phase through a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 meshes, and the eluent is petroleum ether/ethyl acetate 5: 1) to obtain 111 mg of yellow solid with a yield of 75%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝8.76(s，1H)，7.50-7.41(m，2H)，7.25-7.17(m，3H)，3.92(s，2H)，2.66(s，3H).13C NMR(100MHz，CDCl3)：δ/ppm＝187.1，133.2，130.5，128.3，128.2，127.4，127.2，126.7，35.7，17.2.
example 7
A10-ml round-bottom flask equipped with a magnetic stirrer was charged with 5- (2, 5-dimethylphenoxy) -2, 2-dimethylpentanoic acid 4-vinylphenol ester (0.5 mmol), diphenyldiselenide (0.25 mmol), acetonitrile (3 ml) at room temperature, after completion of addition, a 23-watt white compact fluorescent lamp was placed at a distance of 3 cm from the round-bottom flask and allowed to react at room temperature for 20 hours under open conditions, after completion of the reaction, the organic phase was passed through a rotary evaporator to remove the solvent, and the residue was purified with a silica gel column (200-300 mesh silica gel, eluent petroleum ether/ethyl acetate 20: 1) to obtain 183 mg of yellow oily liquid with a yield of 70%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.84-7.76(m，2H)，7.48-7.40(m，2H)，7.22-7.15(m，3H)，7.04-6.98(m，2H)，6.92(d，J＝7.4Hz，1H)，6.59(d，J＝7.4Hz，1H)，6.54(s，1H)，4.06(s，2H)，3.90(t，J＝5.2Hz，2H)，2.22(s，3H)，2.09(s，3H)，1.80(s，4H)，1.30(s，6H).13C NMR(100MHz，CDCl3)：δ/ppm＝192.7，174.7，155.8，153.9，135.5，133.0，131.8，129.3，129.3，128.3，127.9，127.1，122.5，120.7，119.8，110.9，66.6，41.6，36.1，31.6，24.2，24.1，20.4，14.8.
example 8
After charging 7-vinylcoumarin (0.5 mmol), diphenyldiselenide (0.25 mmol), acetonitrile (3 ml) into a 10 ml round-bottomed flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 3 cm from the round-bottomed flask, reacting at open air for 20 hours at room temperature, removing the solvent from the organic phase by a rotary evaporator, purifying the residue with a silica gel column (the silica gel specification is 200-300 mesh, and the eluent petroleum ether/ethyl acetate is 4: 1) to obtain 139 mg of yellow solid with a yield of 81%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.71-7.63(m，3H)，7.50-7.40(m，3H)，7.24-7.16(m，3H)，6.45(d，J＝9.6Hz，1H)，4.08(s，2H).13C NMR(100MHz，CDCl3)：δ/ppm＝192.2，159.0，152.7，141.4，136.9，133.2，128.4，127.5，127.3，127.1，123.2，121.2，117.9，116.1，31.5.
example 9
After charging styrene (0.5 mmol), bis (4-chlorophenyl) diselenide (0.25 mmol), acetonitrile (3 ml) into a 10 ml round-bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 3 cm from the round-bottom flask, reacting at open air at room temperature for 20 hours, removing the solvent from the organic phase by a rotary evaporator after the reaction is completed, purifying the residue with a silica gel column (silica gel specification is 200-300 mesh, eluent petroleum ether/ethyl acetate is 60: 1) to obtain 113 mg of white solid with a yield of 73%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.82-7.77(m，2H)，7.53-7.47(m，1H)，7.40-7.33(m，4H)，7.20-7.14(m，2H)，4.08(s，2H).13C NMR(100MHz，CDCl3)：δ/ppm＝193.6，134.4，134.3，133.5，132.4，128.4，127.6，125.9，31.8.
example 10
After charging styrene (0.5 mmol), dibenzyldiselenide (0.25 mmol), acetonitrile (3 ml) into a 10 ml round bottom flask equipped with a magnetic stirrer at room temperature, placing a 23-watt white compact fluorescent lamp at a distance of 3 cm from the round bottom flask, reacting at open room temperature for 20 hours, removing the solvent from the organic phase by a rotary evaporator, purifying the residue with a silica gel column (the specification of the silica gel is 200-300 mesh, and the eluent is petroleum ether/ethyl acetate: 10: 1) to obtain 98 mg of yellow solid with a yield of 68%,
the nuclear magnetic spectrum data of the obtained product are as follows:1H NMR(400MHz，CDCl3)：δ/ppm＝7.89-7.82(m，2H)，7.53-7.47(m，1H)，7.42-7.36(m，2H)，7.31-7.27(m，2H)，7.26-7.21(m，2H)，7.18-7.15(m，1H)，3.80(s，2H)，3.64(s，2H).13C NMR(100MHz，CDCl3)：δ/ppm＝194.0，137.2，134.3，132.2，128.2，127.7，127.6，127.5，126.0，27.6，25.5.
in conclusion, the preparation method takes olefin and diselenide as raw materials, takes one of acetonitrile, dichloromethane and ethyl acetate as a solvent, has the reaction temperature of room temperature, and efficiently synthesizes the α -selenone compound under the irradiation of a white fluorescent light source.
The invention is not described in detail, but is well known to those skilled in the art.
It will be evident to those skilled in the art that the invention is not limited to the details of the foregoing illustrative embodiments, and that the present invention may be embodied in other specific forms without departing from the spirit or essential attributes thereof. The present embodiments are therefore to be considered in all respects as illustrative and not restrictive, the scope of the invention being indicated by the appended claims rather than by the foregoing description, and all changes which come within the meaning and range of equivalency of the claims are therefore intended to be embraced therein. Any reference sign in a claim should not be construed as limiting the claim concerned.
Claims (6)
1. A synthesis method of α -selenone compound promoted by visible light is characterized by comprising the following steps:
A. sequentially adding a compound 1 and a compound 2 into a reactor;
B. under the open condition, stirring and reacting under the irradiation of a light source under the condition of certain temperature;
C. after the reaction is finished, the solvent is evaporated under reduced pressure to obtain a crude product;
D. purifying by column chromatography to obtain α -selenone 3.
2. The method for synthesizing the α -selenone compound promoted by visible light according to claim 1, wherein the step A reactor is a round-bottomed flask, and α -selenone compound is prepared by a chemical reaction, and the reaction equation is as follows:
wherein compound 1 is a mono-or bicyclic heteroaryl ethylene having 5 to 10 ring atoms which may be styrene, substituted styrene, or substituted, said compound 2 being a diaryldiselenide or dialkyldiselenide.
3. The method for synthesizing a α -selenone compound promoted by visible light according to claim 1, wherein the molar ratio of the compound in the step A is 1: 0.5.
4. The method of claim 1, wherein step B is performed under open conditions and at room temperature under irradiation with white light from a 23W compact fluorescent lamp.
5. The method of claim 1, wherein the solvent of step C is one of acetonitrile, dichloromethane, and ethyl acetate.
6. The visible light-promoted α -selenone compound synthesis method according to claim 1, wherein an eluent used in the step D column chromatography purification is a mixed solvent of petroleum ether and ethyl acetate, and the volume ratio of the petroleum ether to the ethyl acetate is (4-50): 1.
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| CN112724058A (en) * | 2020-12-28 | 2021-04-30 | 南通大学 | Synthesis method of visible light-promoted beta-hydroxyselenide compound |
| CN113818034A (en) * | 2021-09-18 | 2021-12-21 | 淮阴工学院 | Electrochemical synthesis method of 2-aryl-1, 2-diphenylethanone |
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| CN113818034A (en) * | 2021-09-18 | 2021-12-21 | 淮阴工学院 | Electrochemical synthesis method of 2-aryl-1, 2-diphenylethanone |
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| CN111333558B (en) | 2021-09-28 |
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