CN107382640B - β -aryl phenylpropanone compound synthesis method - Google Patents

β -aryl phenylpropanone compound synthesis method Download PDF

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CN107382640B
CN107382640B CN201710683627.5A CN201710683627A CN107382640B CN 107382640 B CN107382640 B CN 107382640B CN 201710683627 A CN201710683627 A CN 201710683627A CN 107382640 B CN107382640 B CN 107382640B
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吴华悦
李鸿辰
刘妙昌
黄小波
高文霞
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Wenzhou University
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    • C07—ORGANIC CHEMISTRY
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    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
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Abstract

The invention discloses a synthesis method of β -aryl phenylpropanone compounds, which is characterized in that chalcone compounds are used as reaction substrates in an organic solvent under the condition of nitrogen, and carbon-carbon double bonds in the reaction substrates are reduced in a chemoselectivity manner at the temperature of 100 ℃ and 160 ℃ under the combined promotion action of inorganic alkali and elemental selenium to obtain β -aryl phenylpropanone compounds.

Description

β -aryl phenylpropanone compound synthesis method
Technical Field
The invention relates to a synthesis method of a compound, in particular to a synthesis method of β -aryl propiophenone compounds, belonging to the technical field of organic compound synthesis.
Background
β -aryl ketone organic compounds are widely present in drug molecules, physiologically active inhibitors and functional molecules of materials, for example, satabacin isolated from Bacillus, which is believed to have biological activity against herpes simplex virus type 1(HSV1), inhibits the growth of VZV, ar-turmerone, a main ingredient of turmeric, an antioxidant common in dye structure, anagesic activity having analgesic activity, and cyclooxygenase inhibitors (inhibitor of cyclo-oxygenase), etc.
The following are chemical structural formulas of several common β -aryl ketone drug molecules:
Figure BDA0001376106180000011
the traditional method for synthesizing β -aryl ketone compounds is mainly obtained by nucleophilic addition reaction of lithium reagent and Grignard reagent with strong nucleophilic ability and α -unsaturated ketone, however, the substrate contains functional groups sensitive to alkali such as hydroxyl and carboxyl with poor tolerance due to strong alkalinity of the nucleophilic reagent used in the reaction, the current development is mature that noble metals such as transition metal palladium, rhodium and the like catalyze 1, 4-addition reaction of aryl boron reagent, aryl silicon reagent, aryl bismuth reagent and α -unsaturated ketone, but the price of metal catalyst and arylation reagent is expensive, so that industrial production is inhibited.
Because β -aryl ketone compounds are so important, people have carried out a great deal of research on the synthesis of the compounds, especially for the synthesis of β -aryl phenylpropanone compounds, α -unsaturated ketone compound raw materials are obtained through aldol condensation reaction, and then carbon-carbon double bonds in the structure of the compounds are selectively reduced to simply obtain β -aryl phenylpropanone compounds, and a plurality of synthetic routes and methods, such as transition metal catalytic hydrogenation, selective hydrogenation reaction taking metal cyanide as a reducing agent and hydrogen transfer reduction reaction catalyzed by organic micromolecules, are explored at present.
However, many of the prior art have the defects of complicated experimental operation, expensive noble metal price, more side reactions, severe reaction conditions, poor functional group tolerance and the like.
Disclosure of Invention
In order to solve the defects of the prior art, the invention aims to provide a synthesis method of β -aryl propiophenone compounds, which has the advantages of mild reaction conditions, simple and convenient operation, good functional group tolerance and reasonable price.
In order to achieve the above object, the present invention adopts the following technical solutions:
β -aryl phenylpropanone compound synthesis method, characterized in that, in organic solvent, under nitrogen condition, chalcone compound with structure shown in formula (I) is used as reaction substrate, under the common promotion effect of inorganic base and simple substance selenium, carbon-carbon double bond in the reaction substrate is reduced in chemoselectivity at 100-160 ℃ to obtain β -aryl phenylpropanone compound with structure shown in formula (II), the reaction equation is as follows:
Figure BDA0001376106180000031
wherein R is1Hydrogen, methyl, dimethylamino, methylthio, methoxy or fluoro R2Hydrogen or methyl.
The synthesis method of the β -aryl propiophenone compound is characterized by comprising the following steps:
step 1: adding a reaction substrate, elemental selenium and inorganic base into a reaction container, and continuously performing extraction-nitrogen filling operation on the reaction container for 3 times;
step 2: adding an organic solvent, and carrying out a heating reduction reaction in an oil bath to reduce the carbon-carbon double bond in the reaction substrate in a chemoselective manner until the reaction is finished (the reaction time is not particularly limited, and the reaction time is determined by detecting the residual percentage of the target product or raw material by a gas chromatograph, and is usually 12-36h, preferably 24 h);
step 3: the reaction product is isolated and purified (by isolation and purification methods known to those skilled in the art, such as extraction, column chromatography, distillation, filtration, centrifugation, washing, fractionation or adsorption, or a combination of at least two methods), to obtain a purer final product (of course, if necessary, the obtained reaction mixture can be directly introduced into other processes for direct reaction, thereby producing other products, and before introduction into other processes, the reaction mixture can be pretreated, such as concentration, extraction, distillation under reduced pressure, to obtain a crude product or a pure product, and then introduced into other processes).
The synthesis method of the β -aryl propiophenone compound is characterized in that in Step3, the method for separating and purifying the reaction product is as follows:
(1) cooling the reaction liquid, adding ethyl acetate for dilution, and then concentrating under reduced pressure;
(2) separating the concentrate by column chromatography, and separating with petroleum ether and diethyl ether at a volume ratio of 9-10: 1, taking the mixed solution as an eluent, and collecting the eluent;
(3) and (5) removing the solvent by spinning off to obtain the product.
The synthesis method of β -arylphenylpropanone compounds is characterized in that 300-400 mesh silica gel is used for the column chromatography.
The β -aryl phenylpropanone compound synthesis method is characterized in that the organic solvent is any one of alcohol, ether, amide, chloralkane, aromatic hydrocarbon, dimethyl sulfoxide, ester, heterocyclic aromatic hydrocarbon and aliphatic hydrocarbon, or any combination of any several of the above, wherein the alcohol can be monohydric alcohol, or polymer of monohydric alcohol, or C1-C4 straight-chain or branched-chain alkyl alcohol including but not limited to methanol, ethanol, N-propanol, isopropanol, N-butanol and polyethylene glycol, the ether can be simple ether, or mixed ether, or cyclic ether including but not limited to diethyl ether, the amide includes but not limited to N, N-dimethylformamide (preferred), N-dimethylacetamide, N-dimethylpropionamide, N-diethylformamide and N-methylformanilide, the chloralkane includes but not limited to chloroform and carbon tetrachloride, the aromatic hydrocarbon includes but not limited to benzene, chlorobenzene, o-dichlorobenzene and xylene, the ester includes but not limited to ethyl acetate, the heterocyclic aromatic hydrocarbon includes but not limited to pyridine, and the aliphatic hydrocarbon includes but not limited to N-hexane.
The synthesis method of β -aryl phenylpropanone compounds is characterized in that the ratio of the amount of the inorganic base to the amount of the reaction substrate is 2-4:1, preferably 2:1, by mole.
The β -arylhydrocinnamanes compound synthesis method is characterized in that the inorganic base is any one of lithium carbonate, potassium phosphate, cesium fluoride, sodium phosphate, potassium acetate, barium acetate, silver acetate, sodium nitrite and ammonium acetate, and preferably potassium acetate is used.
The synthesis method of the β -aryl propiophenone compound is characterized in that the ratio of the amount of the elemental selenium to the amount of the reaction substrate is 1-3:1 by mol.
The invention has the advantages that:
(1) the carbon-carbon double bond in the reaction substrate is reduced in chemical selectivity at the temperature of 100-160 ℃, and the reaction condition is mild;
(2) the reaction thermal method is adopted, the operation is simple and convenient, the reaction is efficient, the yield and the purity are high, the post-treatment is simple, and the method is suitable for large-scale industrial production;
(3) the reaction substrate has wide range, good functional group tolerance and easy preparation;
(4) simple substance selenium is used as a catalyst, is cheap and easy to obtain, does not have a metal catalyst required by the traditional reduction reaction, and has reasonable price.
Detailed Description
The present invention will be described in detail with reference to the following embodiments.
Example 1
β Synthesis of Phenylpropiophenone:
Figure BDA0001376106180000051
chalcone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube at room temperature, followed by evacuation-replacement with nitrogen three times, addition of 2mL DMF, stirring at a reaction temperature of 150 ℃, monitoring the completion of the reaction by thin layer chromatography (about 24 hours), cooling the reaction mixture, then adding ethyl acetate for dilution, concentrating under reduced pressure, and separating by column chromatography to obtain a product (eluent: petroleum ether and diethyl ether mixed at a volume ratio of 10: 1) which is a white solid, weighing 81.4mg, yield 97%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.93(d,J＝7.5Hz,2H),7.52(t,J＝7.5Hz,1H),7.42(t,J＝7.5Hz,2H),7.29-7.17(m,5H),3.27(t,J＝7.5Hz,2H),3.05(t,J＝7.5Hz,2H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ199.2,141.3,136.9,133.1,128.6,128.5,128.4,128.1,126.2,40.4,30.2。
example 2
Synthesis of 1-phenyl-3- (p-tolyl) -acetone:
Figure BDA0001376106180000061
at room temperature, (E) -1-phenyl-3- (p-tolyl) -2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, followed by evacuation-replacement with nitrogen three times, addition of 2mL of DMF, stirring at a reaction temperature of 150 ℃, monitoring by thin layer chromatography after the reaction was completed (about 24h), cooling the reaction mixture, then adding ethyl acetate for dilution, distillation under reduced pressure, and separation by column chromatography to obtain a product (eluent: petroleum ether and diethyl ether mixed at a volume ratio of 10: 1) as a pale yellow solid, weighing 82.4mg, yield 92%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.95(d,J＝7.0Hz,2H),7.53(t,J＝7.5Hz,1H),7.43(t,J＝7.5Hz,2H),7.15-7.09(m,4H),3.27(t,J＝7.5Hz,2H),3.02(t,J＝7.5Hz,2H),2.31(s,3H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ199.3,138.2,137.0,135.6,133.0,129.2,128.6,128.3,128.1,40.6,29.8,21.0。
example 3
Synthesis of 3-phenyl-1- (p-tolyl) -acetone:
Figure BDA0001376106180000071
at room temperature, (E) -3-phenyl-1- (p-tolyl) -2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, followed by evacuation-replacement with nitrogen three times, addition of 2mL of DMF, stirring at a reaction temperature of 150 ℃, monitoring by thin layer chromatography after the reaction was completed (about 24h), cooling the reaction mixture, then adding ethyl acetate for dilution, distillation under reduced pressure, and separation by column chromatography to obtain a product (eluent: petroleum ether and diethyl ether mixed at a volume ratio of 10: 1) as a pale yellow solid, weighing 86.2mg, yield 96%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.84(d,J＝8.0Hz,2H),7.28(t,J＝7.5Hz,2H),7.23(t,J＝7.0Hz,4H),7.18(t,J＝7.0Hz,1H),3.25(t,J＝7.5Hz,2H),3.04(t,J＝7.5Hz,2H),2.38(s,3H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ198.9,143.8,141.4,134.5,129.3,128.5,128.4,128.2,126.1,40.3,30.2,21.7。
example 4
Synthesis of 3- (-4- (dimethylamino) phenyl) -1-p-tolyl-acetone:
Figure BDA0001376106180000081
at room temperature, (E) -3- (-4- (dimethylamino) phenyl) -1-phenyl-2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, then air-suction-nitrogen-substitution was performed three times, 2mL of DMF was added, stirring was performed at a reaction temperature of 150 ℃, after completion of the reaction was monitored by thin layer chromatography (about 24 hours), the reaction mixture was cooled, then ethyl acetate was added for dilution, distillation under reduced pressure was performed, and the product was obtained by column chromatography separation (eluent: petroleum ether and diethyl ether were mixed at a volume ratio of 9: 1), the product was a yellow solid, 82.7mg in weight, and yield 81%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.94(d,J＝7.5Hz,2H),7.52(t,J＝7.0Hz,1H),7.42(t,J＝8.0Hz,2H),7.12(d,J＝8.5Hz,2H),6.69(d,J＝8.5Hz,2H),3.24(t,J＝7.5Hz,2H),2.97(t,J＝7.5Hz,2H),2.89(s,6H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ199.7,149.3,137.1,132.9,129.3,129.0,128.6,128.1,113.1,40.9,40.8,29.3。
example 5
Synthesis of 3- (2- (5-methylfuran)) -1-phenyl-acetone:
Figure BDA0001376106180000082
at room temperature, (E) -3- (2- (5-methylfuran)) -1-phenyl-2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, then evacuated-replaced with nitrogen three times, 2mL of DMF was added, stirring was carried out at a reaction temperature of 150 ℃, after completion of the reaction was monitored by thin layer chromatography (about 24h), the reaction mixture was cooled, then ethyl acetate was added for dilution, distillation under reduced pressure was carried out, and the product was isolated by column chromatography (eluent: petroleum ether and diethyl ether were mixed at a volume ratio of 9: 1) as a dark brown solid, weighing 76.3mg, yield 89%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.96(d,J＝8.0Hz,2H),7.54(t,J＝7.5Hz,1H),7.44(t,J＝7.5Hz,2H),5.90(s,1H),5.84(s,1H),3.02(t,J＝7.5Hz,2H),2.30(t,J＝7.5Hz,2H),2.24(s,3H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ198.8,152.9,150.5,136.9,133.0,128.6,128.0,106.0,105.9,37.2,22.7,13.5。
example 6
Synthesis of 3- (p-methylthiophenyl) -1-phenyl-acetone:
Figure BDA0001376106180000091
the data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.93(d,J＝8.0Hz,2H),7.53(t,J＝7.5Hz,1H),7.43(t,J＝7.5Hz,2H),7.18(q,J1＝15.0Hz,J2＝8.0Hz,4H),3.25(t,J＝7.5Hz,2H),3.01(t,J＝7.5Hz,2H),2.43(s,3H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ199.1,138.4,136.9,135.8,133.1,129.0,128.6,128.0,127.3,40.3,29.6,16.3。
example 7
Synthesis of 3- (p-methoxyphenyl) -1-phenyl-acetone:
Figure BDA0001376106180000101
at room temperature, (E) -3- (p-methoxyphenyl) -1-phenyl-2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, then air-suction-nitrogen replacement was performed three times, 2mL of DMF was added, stirring was performed at a reaction temperature of 150 ℃, after completion of the reaction (about 24 hours) was monitored by thin layer chromatography, the reaction mixture was cooled, then ethyl acetate was added for dilution, distillation under reduced pressure was performed, and a product was obtained by column chromatography (eluent: petroleum ether and diethyl ether were mixed at a volume ratio of 10: 1), which was a pale yellow solid, 49.9mg in weight, and 52% yield.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.95(d,J＝7.5Hz,2H),7.54(t,J＝7.0Hz,1H),7.44(t,J＝8.0Hz,2H),7.16(d,J＝8.5Hz,2H),6.84(,J＝8.5Hz,2H),3.78(s,3H),3.26(t,J＝7.5Hz,2H),3.01(t,J＝7.5Hz,2H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ199.4,158.0,136.9,133.3,133.0,129.3,128.6,128.0,114.0,55.3,40.7,29.3。
example 8
Synthesis of 3- (p-fluorophenyl) -1-phenyl-acetone:
Figure BDA0001376106180000111
at room temperature, (E) -3- (p-fluorophenyl) -1-phenyl-2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, followed by evacuation-replacement with nitrogen gas three times, addition of 2mL of DMF, stirring at a reaction temperature of 150 ℃, monitoring by thin layer chromatography after the reaction was completed (about 24h), cooling the reaction mixture, then adding ethyl acetate for dilution, distillation under reduced pressure, and separation by column chromatography to obtain a product (eluent: petroleum ether and diethyl ether mixed at a volume ratio of 9: 1) as a pale yellow solid, weighing 51.1mg, yield 56%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.95(d,J＝7.5Hz,2H),7.55(t,J＝7.0Hz,1H),7.45(t,J＝8.0Hz,2H),7.20(d,J＝6.0Hz,2H),6.79(t,J＝8.5Hz,2H),3.27(t,J＝7.5Hz,2H),3.04(t,J＝7.5Hz,2H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ198.9,162.4,160.5,136.9(d,JF＝6.3Hz),133.1,129.8(d,JF＝7.5Hz),128.6,128.0,115.2(d,JF＝21.3Hz),40.4,29.3。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
19F NMR(470MHz,CDCl3):δ-117.3。
example 9
Synthesis of 3- (1-methylpyrrole) -1-phenyl-acetone:
Figure BDA0001376106180000121
at room temperature, (E) -3- (1- (methylpyrrole)) -1-phenyl-2-propenone (0.4mmol,1equiv), selenium powder (1.2mmol,3equiv) and KOAc (0.8mmol,2equiv) were added to a reaction tube, then air-suction-nitrogen substitution was performed three times, 2mL of DMF was added, stirring was performed at a reaction temperature of 150 ℃, after completion of the reaction was monitored by thin layer chromatography (about 36 hours), the reaction mixture was cooled, then ethyl acetate was added to dilute, and distillation under reduced pressure was performed to obtain a product by column chromatography (eluent: petroleum ether and diethyl ether were mixed at a volume ratio of 9: 1), which was a dark brown solid, having a weight of 70.2mg, and a yield of 83%.
The data of the nuclear magnetic resonance hydrogen spectrum of the obtained product are as follows:
1H NMR(500MHz,CDCl3):δ7.98(d,J＝8.0Hz,2H),7.55(t,J＝7.0Hz,1H),7.46(t,J＝7.5Hz,2H),6.56(s,1H),6.06(t,J＝7.5Hz,2H),5.92(s,1H),3.56(s,3H),3.32(t,J＝7.5Hz,2H),2.98(t,J＝7.5Hz,2H)。
the data of the nuclear magnetic resonance carbon spectrum of the obtained product are as follows:
13C NMR(125MHz,CDCl3):δ199.1,136.9,133.2,132.1,128.7,128.1,121.5,106.8,105.4,37.8,33.6,20.7。
examples 10 to 17
Examples 10 to 17 were each carried out in the same manner as in example 1 except that the reaction solvents N, N-methylformamide were each replaced with the following organic solvents, and the yields of the organic solvents used and the corresponding products were as shown in the following tables.
Figure BDA0001376106180000122
Figure BDA0001376106180000131
As can be seen from the above table, when other organic solvents are used, the reaction can occur in a strongly polar solvent, but the yield is reduced; while in non-polar and lower boiling solvents there may be no product.
In conclusion, when the method is adopted and a composite reaction system is formed by inorganic base and a proper organic solvent (especially N, N-dimethylformamide), a novel reducing agent, namely elemental selenium is used, so that chalcone compounds can be subjected to selective carbon-carbon double bond reduction reaction, and β -phenylpropanoid compounds can be synthesized with high yield and high purity.
It should be noted that the above-mentioned embodiments do not limit the present invention in any way, and all technical solutions obtained by using equivalent alternatives or equivalent variations fall within the protection scope of the present invention.

Claims (6)

  1. The synthesis method of the 1, β -aryl phenylpropanone compound is characterized in that chalcone compound with the structure shown in the formula (I) is used as a reaction substrate in an organic solvent under the condition of nitrogen, and under the common promotion action of inorganic base and elemental selenium, carbon-carbon double bonds in the reaction substrate are reduced in a chemoselective manner at the temperature of 100-160 ℃, so that the β -aryl phenylpropanone compound with the structure shown in the formula (II) is obtained, wherein the reaction equation is as follows:
    Figure FDA0002396557790000011
    wherein R is1Hydrogen, methyl, dimethylamino, methylthio, methoxy or fluoro, R2Hydrogen or methyl, the organic solvent is DMF, and the inorganic base is KOAc.
  2. 2. The synthesis method of β -arylphenylpropanone compounds according to claim 1, which comprises the following steps:
    step 1: adding a reaction substrate, elemental selenium and inorganic base into a reaction container, and continuously performing extraction-nitrogen filling operation on the reaction container for 3 times;
    step 2: adding an organic solvent, and carrying out heating reduction reaction in an oil bath to ensure that the carbon-carbon double bond in the reaction substrate is reduced in chemical selectivity until the reaction is finished;
    step 3: and separating and purifying the reaction product.
  3. 3. The method for synthesizing β -arylphenylpropanone compounds according to claim 2, wherein the method for separating and purifying the reaction product in Step3 comprises the steps of:
    (1) cooling the reaction liquid, adding ethyl acetate for dilution, and then concentrating under reduced pressure;
    (2) separating the concentrate by column chromatography, and separating with petroleum ether and diethyl ether at a volume ratio of 9-10: 1, taking the mixed solution as an eluent, and collecting the eluent;
    (3) and (5) removing the solvent by spinning off to obtain the product.
  4. 4. The method for synthesizing β -arylphenylpropanone compounds according to claim 3, wherein the column chromatography is performed using 300-400 mesh silica gel.
  5. 5. The method for synthesizing β -arylphenylpropanone compounds according to claim 1 or 2, wherein the ratio of the amount of the inorganic base to the amount of the reaction substrate is 2-4:1 in terms of molar amount.
  6. 6. The method for synthesizing β -arylphenylpropanone compounds according to claim 1 or 2, wherein the ratio of the amount of elemental selenium to the amount of reaction substrate is 1-3:1 by mole.
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2,4,5-Trisubstituted thiazole derivatives: A novel and potent class of non-nucleoside inhibitors of wild type and mutant HIV-1 reverse transcriptase;ZhongliangXu;《European Journal of Medicinal Chemistry》;20141006;第86卷(第6期);27-42 *
A robust Ru-PNNP catalyst system for the asymmetric hydrogenation of α,β-unsaturated ketones to allylic alcohol;Sheng-MeiLu;《Tetrahedron Letters》;20131218;第54卷(第51期);7013-7016 *
Catalytic asymmetric hydrogenation using a [2.2]paracyclophane based chiral 1,2,3-triazol-5-ylidene–Pd complex under ambient conditions and 1 atmosphere of H2;Ayan Dasgupta;《RSC Advances》;20150217;21558–21561 *

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