Beta-ketosulfone compound and synthesis method thereof
Through electrochemical redox catalysis, β-ketosulfone compounds are synthesized by enol ester compounds and sulfonylhydrazide compounds, which solves the problem of using unstable catalysts and complex starting materials in traditional synthesis methods, and achieves a green and efficient synthesis effect.
Patent Information
- Application Number
- CN202510287510.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-03-12
- Publication Date
- 2025-04-25
- Estimated Expiration
- 2045-03-12
AI Technical Summary
The synthesis method of traditional β-ketosulfone derivatives requires the use of complex starting materials, long reaction steps and the use of unstable, highly active oxidants or transition metal catalysts, resulting in environmental problems, metal residues, and high costs.
The β-ketosulfone compound is synthesized by electrochemical redox catalyzing of enol ester compounds and sulfonylhydrazide compounds, avoiding the use of additional oxidants or reducing agents.
The green and sustainable and efficient synthesis of β-ketosulfone compounds is achieved, with short reaction steps, reducing the generation of chemical waste, complying with the principles of green chemistry, and has high environmental friendliness.
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Figure CN119876974A_ABST
Abstract
Description
Technical Field
[0001] The invention relates to the technical field of chemical synthesis, and in particular to a beta-ketosulfone compound and a synthesis method thereof. Background Art
[0002] Among various sulfone-containing compounds, β-ketosulfone and its related sulfone compounds have attracted much attention due to their good biological activities, such as anti-hepatitis, antibacterial, antifungal and non-nucleoside inhibitors. In addition, β-ketosulfone has multifunctional functional groups, such as sulfonyl, carbonyl and active methylene, which are easy to carry out various synthetic operations. Traditional β-ketosulfone derivatives are synthesized by building CS or CC bonds, such as alkylation of α-haloketones, oxidation of β-carbonyl sulfide or β-hydroxysulfone, etc. However, these methods usually require the use of complex starting materials, long reaction steps and the use of unstable, highly active oxidants or transition metal catalysts, which will lead to environmental problems, metal residues and high costs. Based on the current research status, it is necessary to develop a simple and sustainable catalytic system. Summary of the invention
[0003] The main purpose of the present invention is to propose a β-ketosulfone compound and a synthesis method thereof, which uses an enol ester compound and a sulfonylhydrazide compound to synthesize the β-ketosulfone compound through electrochemical redox catalysis, has the advantages of being green and sustainable, high efficiency and mild conditions, and avoids the use of additional oxidants or reducing agents.
[0004] To achieve the above object, the present invention provides a β-ketosulfone compound, which is synthesized from an enol ester compound and a sulfonylhydrazide compound through electrochemical redox catalysis.
[0005] The structural formula of the β-ketosulfone compound is:
[0006] The structural formula of the enol ester compound is:
[0007] The structural formula of the sulfonylhydrazide compound is:
[0008] Preferably, the synthesis route of the β-ketosulfone compound is as follows:
[0009]
[0010] Preferably, R1 is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group containing nitrogen, oxygen or sulfur atoms; R2 is a hydrogen atom, a methyl group, or an unsubstituted straight-chain alkane; R3 is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group containing nitrogen, oxygen or sulfur atoms, or a substituted or unsubstituted straight-chain alkyl group.
[0011] Preferably, the preparation method of the β-ketosulfone compound comprises the following steps:
[0012] Add enol ester compound, sulfonyl hydrazide compound, electrolyte, sodium carbonate and acetonitrile aqueous solution into a closed system, then install electrodes, graphite as anode and platinum sheet as cathode, perform electrochemical oxidation after the electrodes are installed, and after the reaction is completed, perform post-treatment to obtain β-ketosulfone compound.
[0013] Preferably, the molar ratio of the enol ester compound, the sulfonyl hydrazide compound, the electrolyte, and the sodium carbonate is 1:1.2-2:1-1.2:2.5-3.
[0014] More preferably, the molar ratio of the enol ester compound, the sulfonyl hydrazide compound, the electrolyte, and the sodium carbonate is 1:1.5:1:3.
[0015] Preferably, the electrolyte is at least one of tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium chloride, tetrabutylammonium bromide, tetraethylammonium chloride and tetraethylammonium bromide.
[0016] Preferably, the volume ratio of acetonitrile to water in the acetonitrile aqueous solution is 15-20:1.
[0017] Preferably, during the electrochemical oxidation process, the current is 5-15 mA, the reaction temperature is room temperature, and the reaction time is 3-5 h.
[0018] Compared with the prior art, the present invention has the following beneficial effects:
[0019] The present invention synthesizes a β-ketosulfone compound from an enol ester compound and a sulfonylhydrazide compound through electrochemical redox catalysis, avoids the use of complex starting materials, shortens the reaction steps, and improves the synthesis efficiency. The electrochemical redox catalysis method is adopted to avoid the external oxidant or reductant used in the traditional synthesis, reduces the generation of chemical waste, conforms to the principle of green chemistry, and has high environmental friendliness; the synthesis method of the present invention is suitable for synthesizing β-ketosulfone compounds with various substituents, and expands its application prospects in drug synthesis; it has good application prospects and industrialization potential. BRIEF DESCRIPTION OF THE DRAWINGS
[0020] In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings required for use in the embodiments or the description of the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other related drawings can be obtained based on these drawings without paying creative work.
[0021] Figure 1 The β-ketosulfone compound prepared in Example 1 of the present invention 1 HNMR spectrum;
[0022] Figure 2 The β-ketosulfone compound prepared in Example 1 of the present invention 13 CNMR spectrum;
[0023] Figure 3 The β-ketosulfone compound prepared in Example 2 of the present invention 1 HNMR spectrum;
[0024] Figure 4 The β-ketosulfone compound prepared in Example 2 of the present invention 13 CNMR spectrum;
[0025] Figure 5 The β-ketosulfone compound prepared in Example 3 of the present invention 1 HNMR spectrum;
[0026] Figure 6 The β-ketosulfone compound prepared in Example 3 of the present invention 13 CNMR spectrum;
[0027] Figure 7 The β-ketosulfone compound prepared in Example 4 of the present invention 1 HNMR spectrum;
[0028] Figure 8 The β-ketosulfone compound prepared in Example 4 of the present invention 13 CNMR spectrum;
[0029] Fig. 9 The β-ketosulfone compound prepared in Example 5 of the present invention 1 HNMR spectrum;
[0030] Fig.10 The β-ketosulfone compound prepared in Example 5 of the present invention 13 CNMR spectrum.
[0031] The realization of the purpose, functional features and advantages of the present invention will be further explained in conjunction with embodiments and with reference to the accompanying drawings. DETAILED DESCRIPTION
[0032] To avoid redundancy, the items used in the following examples are all commercially available products unless otherwise specified, and the methods used are all conventional methods unless otherwise specified.
[0033] Example 1
[0034] A method for preparing a β-ketosulfone compound comprises the following steps:
[0035] S1. At -78°C, under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, and then 0.61 g of n-butyl lithium (9.6 mmol) was added dropwise, and the mixture was stirred at -78°C for 30 minutes; then 0.96 g of acetophenone (8 mmol) was added to the reaction mixture, and the mixture was stirred at -78°C for 45 minutes, and then 1.63 g of acetic anhydride (16 mmol) was added, and the reaction mixture was stirred at -78°C for 30 minutes, and then the reaction mixture was reacted at room temperature for 1.5 h. After the reaction was completed, the mixed solution was poured into 100 mL of saturated sodium bicarbonate solution, and the reaction mixture was extracted with 60 mL of ethyl acetate, and the combined organic layer was rinsed with saline, and the organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain an enol ester compound;
[0036] S2. At 0°C and N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to 50 mL of tetrahydrofuran solution containing 2.07 g of 4-methoxybenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether: ethyl acetate = 10:1) to obtain 4-methoxybenzenesulfonyl hydrazide.
[0037] S3, 40.5mg enol ester compound (0.25mmol), 75.81mg 4-methoxybenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN to water is 19:1) are mixed evenly and added to a threaded 10mL small glass bottle, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After the reaction is completed, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times, the organic phase is spin-dried after drying, and petroleum ether / ethyl acetate = 8:1 is used to pass the column at normal pressure to obtain a β-ketosulfone compound.
[0038] The structural formula of the β-ketosulfone compound obtained in this example is The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 1 As shown, 1 HNMR (400MHz, CDCl3) δ7.97–7.92(m,2H),7.76(d,J=8.3Hz,2H),7.65–7.59(m ,1H),7.48(t,J=7.8Hz,2H),7.33(d,J=8.0Hz,2H),4.71(s,2H),2.44(s,3H).
[0039] The β-ketosulfone compound obtained in this example 13 CNMR spectrum Figure 2 As shown, 13 CNMR (100MHz, CDCl3) δ188.1,145.4,135.8,134.3,129.8,129.3,128.8,128.6,63.6,21.7.
[0040] Example 2
[0041] A method for preparing a β-ketosulfone compound comprises the following steps:
[0042] S1. At -80°C, under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, and then 0.61 g of n-butyl lithium (9.6 mmol) was added dropwise, and the mixture was stirred at -80°C for 30 minutes; then 0.96 g of acetophenone (8 mmol) was added to the reaction mixture, and the mixture was stirred at -78°C for 45 minutes, and then 1.63 g of acetic anhydride (16 mmol) was added, and the reaction mixture was stirred at -80°C for 30 minutes, and then the reaction mixture was reacted at room temperature for 1.5 h. After the reaction was completed, the mixed solution was poured into 100 mL of saturated sodium bicarbonate solution, and the reaction mixture was extracted with 60 mL of ethyl acetate, and the combined organic layer was rinsed with saline, and the organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain an enol ester compound;
[0043] S2. At 0°C and N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to 50 mL of tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether: ethyl acetate = 10:1) to obtain 4-methylbenzenesulfonyl hydrazide.
[0044] S3, 40.5mg enol ester compound (0.25mmol), 69.8mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN and water is 15:1) are mixed evenly and added to a threaded 10mL small glass bottle, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After the reaction is completed, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times, the organic phase is spin-dried after drying, and petroleum ether / ethyl acetate = 8:1 is used to pass the column at normal pressure to obtain a β-ketosulfone compound.
[0045] The structural formula of the β-ketosulfone compound obtained in this example is
[0046] The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 3 As shown, 1 HNMR (400MHz, CDCl3) δ7.97–7.92(m,2H),7.76(d,J=8.3Hz,2H),7.65–7.59(m ,1H),7.48(t,J=7.8Hz,2H),7.33(d,J=8.0Hz,2H),4.71(s,2H),2.44(s,3H).
[0047] The β-ketosulfone compound obtained in this example 13 CNMR spectrum Figure 4 As shown, 13 CNMR (100MHz, CDCl3) δ188.1,145.4,135.8,134.3,129.8,129.3,128.8,128.6,63.6,21.7.
[0048] Example 3
[0049] A method for preparing a β-ketosulfone compound comprises the following steps:
[0050] S1, at -78 ℃, N2 atmosphere, add 20mL tetrahydrofuran and 97.8mg diisopropylamine (9.6mmol) in a dry round-bottom flask, then add 0.61g n-butyl lithium (9.6mmol), and stir the mixture at -78 ℃ for 30 minutes. Then add 1.5g 4-(trifluoromethyl) acetophenone (8mmol) to the reaction mixture and stir at -78 ℃ for 45 minutes. Then add 1.63g acetic anhydride (16mmol), and stir the reaction mixture at -78 ℃ for 30 minutes. Then stir the reaction mixture at room temperature for 2h. After the reaction is completed, pour the mixed solution into a saturated sodium bicarbonate (100mL) solution, extract the reaction mixture with ethyl acetate (60mL), and rinse the combined organic layer with brine. After drying the organic layer with anhydrous sodium sulfate, remove the solvent under reduced pressure, and the product is purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to obtain an enol ester compound;
[0051] S2. At 0°C, under N2 atmosphere, add 1.5 g of hydrazine monohydrate (30 mmol) dropwise to 50 mL of tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stir for 1 h. After the reaction is completed, evaporate the solvent, extract the residue with dichloromethane (3×20 mL), wash the combined organic layer with water and saturated brine, and dry with anhydrous sodium sulfate. Evaporate the organic solvent under reduced pressure, and purify on a silica gel column using an eluent (petroleum ether: ethyl acetate = 10:1) to obtain 4-methylbenzenesulfonyl hydrazide;
[0052] S3, 57.5mg enol ester compound (0.25mmol), 69.84mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), MeCN / H2O=20:1 (5mL in total) in a threaded 10mL small glass bottle, add a stirrer, then install electrodes, graphite as anode, platinum sheet as cathode, current 10mA, stir and react at room temperature for 4h. After the reaction is completed, transfer to a 25mL round-bottom flask, spin dry the mixed system, add ethyl acetate, then wash 3 times with water, dry and spin dry the organic phase, use petroleum ether / ethyl acetate=8:1 normal pressure column to obtain β-ketosulfone compound.
[0053] The structural formula of the β-ketosulfone compound obtained in this example is
[0054] The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 5 As shown, 1HNMR (400MHz, CDCl3) δ8.07(d,J=8.2Hz,2H),7.75(d,J=3.5Hz,2H),7.73(d,J=3.5Hz,2H),7.35(d,J=8.0Hz,2H),4.73(s,2H),2.45(s,3H).
[0055] The β-ketosulfone compound obtained in this example 13 CNMR spectrum Figure 6 As shown, 13 CNMR (100MHz, CDCl3) δ 187.4, 145.7, 138.3, 135.4 (t, JC-F = 32.7Hz), 130.0, 129.7, 128.5, 125.9 (q, JC-F = 11.2Hz), 124.7, 124.0, 63.9, 21.7.
[0056] Example 4
[0057] A method for preparing a β-ketosulfone compound comprises the following steps:
[0058] S1. At -78°C, under N2 atmosphere, 20 mL of tetrahydrofuran and 97.8 mg of diisopropylamine (9.6 mmol) were added to a dry round-bottom flask, and then 0.61 g of n-butyl lithium (9.6 mmol) was added dropwise, and the mixture was stirred at -78°C for 30 minutes; then 1.01 g of 2-acetylthiophene (8 mmol) was added to the reaction mixture, and the mixture was stirred at -78°C for 45 minutes, and then 1.63 g of acetic anhydride (16 mmol) was added, and the reaction mixture was stirred at -78°C for 30 minutes, and then the reaction mixture was reacted at room temperature for 1.5 h. After the reaction was completed, the mixed solution was poured into 100 mL of saturated sodium bicarbonate solution, and the reaction mixture was extracted with 60 mL of ethyl acetate, and the combined organic layer was rinsed with brine, and the organic layer was dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The product was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain an enol ester compound;
[0059] S2. At 0°C and N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to 50 mL of tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether: ethyl acetate = 10:1) to obtain 4-methylbenzenesulfonyl hydrazide.
[0060] S3, 42mg enol ester compound (0.25mmol), 69.8mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN and water is 19:1) are mixed evenly and added to a threaded 10mL small glass bottle, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After the reaction is completed, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times, the organic phase is spin-dried after drying, and petroleum ether / ethyl acetate = 8:1 is used to pass the column at normal pressure to obtain a β-ketosulfone compound.
[0061] The structural formula of the β-ketosulfone compound obtained in this example is
[0062] The β-ketosulfone compound obtained in this example 1 HNMR spectrum Figure 7 As shown, 1 HNMR (400MHz, CDCl3) δ7.81(d,J=3.8Hz,1H),7.75(t,J=5.5Hz,3H),7.33(d,J=8.1Hz,2H),7.16(t,J=4.4Hz,1H),4.61(s,2H),2.43(s,3H).
[0063] The β-ketosulfone compound obtained in this example 13 CNMR spectrum Figure 8 As shown, 13 CNMR (100MHz, CDCl3) δ180.3,145.4,143.1,136.4,135.4,135.3,129.8,128.7,128.6,64.6,21.7.
[0064] Example 5
[0065] A method for preparing a β-ketosulfone compound comprises the following steps:
[0066] S1, at -78 ℃, N2 atmosphere, in a dry round-bottom flask, add 20mL tetrahydrofuran and 97.8mg diisopropylamine (9.6mmol), then add 0.61g n-butyl lithium (9.6mmol), and stir the mixture at -78 ℃ for 30 minutes; then add 1.19g 1-tetralone (8mmol) to the reaction mixture, and stir at -78 ℃ for 45 minutes, then add 1.63g acetic anhydride (16mmol), stir the reaction mixture at -78 ℃ for 30 minutes, then react the reaction mixture at room temperature for 1.5h, after the reaction is completed, pour the mixed solution into 100mL saturated sodium bicarbonate solution, extract the reaction mixture with 60mL ethyl acetate, and rinse the combined organic layer with saline, dry the organic layer over anhydrous sodium sulfate, remove the solvent under reduced pressure, and purify the product by (petroleum ether: ethyl acetate = 10:1) silica gel column chromatography to obtain an enol ester compound;
[0067] S2. At 0°C and N2 atmosphere, 1.5 g of hydrazine monohydrate (30 mmol) was added dropwise to 50 mL of tetrahydrofuran solution containing 1.9 g of 4-methylbenzenesulfonyl chloride (10 mmol) and stirred for 1 h. After the reaction was completed, the solvent was evaporated and the residue was extracted with dichloromethane (3×20 mL). The combined organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The organic solvent was evaporated under reduced pressure and purified on a silica gel column using an eluent (petroleum ether: ethyl acetate = 10:1) to obtain 4-methylbenzenesulfonyl hydrazide.
[0068] S3, 47mg enol ester compound (0.25mmol), 75.81mg 4-methylbenzenesulfonyl hydrazide (0.375mmol), 80.57mg tetrabutylammonium tetrafluoroborate (0.25mmol), 79.5mg sodium carbonate (0.75mmol), 5mL MeCN / H2O aqueous solution (the volume ratio of MeCN to water is 19:1) are mixed evenly and added to a threaded 10mL small glass bottle, a stirrer is added, and then electrodes are installed, graphite is anode, platinum sheet is cathode, current is 10mA, and the reaction is stirred at room temperature for 4h. After the reaction is completed, it is transferred to a 25mL round-bottom flask, the mixed system is spin-dried, ethyl acetate is added, and then washed with water 3 times, the organic phase is spin-dried after drying, and petroleum ether / ethyl acetate = 8:1 is used to pass the column at normal pressure to obtain a β-ketosulfone compound.
[0069] The structural formula of the β-ketosulfone compound obtained in this example is The β-ketosulfone compound obtained in this example 1 HNMR spectrum Fig. 9 As shown, 1HNMR (400MHz, CDCl3) δ7.98 (d, J = 7.9 Hz, 1H), 7.79 (d, J = 8.1 Hz, 2H), 7.52 (t, J = 7.5 Hz, 1H), 7.36 (d, J = 8.0 Hz, 2H), 7.31 (t, J = 7.6 Hz, 1H), 7.27 (d, J = 6.8 Hz, 1H), 4.09 (t, J = 5.6 Hz, 1H), 3.57–3.47 (m, 1H), 2.98 (dt, J = 16.9, 5.3 Hz, 1H), 2.87 (dq, J = 16.5, 5.5 Hz, 1H), 2.65 (ddt, J = 14.7, 10.0, 5.0 Hz, 1H), 2.45 (s, 3H). 13 CNMR spectrum Fig.10 As shown, 13 CNMR (100MHz, CDCl3) δ188.7,145.1,143.6,135.9,134.4,131.7,129.6,129.1,128.9,127.9,127.0,69.6,26.5,23.6,21.7.
[0070] The above are only preferred embodiments of the present invention, and do not limit the patent scope of the present invention. For those skilled in the art, the present invention may have various changes and variations. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention shall be included in the patent protection scope of the present invention.
Claims
1. A β-ketosulfone compound, characterized in that: The beta-ketosulfone compound is synthesized from an enol ester compound and a sulfonylhydrazide compound through electrochemical redox catalysis. The structural formula of the β-ketosulfone compound is The structural formula of the enol ester compound is: The structural formula of the sulfonylhydrazide compound is:
2. The β-ketosulfone compound according to claim 1, characterized in that The synthetic route of the β-ketosulfone compound is as follows:
3. The β-ketosulfone compound according to claim 1, characterized in that: The R1 is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group containing nitrogen, oxygen, or sulfur atoms; the R2 is a hydrogen atom, a methyl group, or an unsubstituted straight-chain alkane; the R3 is a substituted or unsubstituted aromatic group, a substituted or unsubstituted heterocyclic group containing nitrogen, oxygen, or sulfur atoms, or a substituted or unsubstituted straight-chain alkyl group.
4. The β-ketosulfone compound according to claim 1, characterized in that The preparation method of the β-ketosulfone compound comprises the following steps: Add enol ester compound, sulfonyl hydrazide compound, electrolyte, sodium carbonate and acetonitrile aqueous solution into a closed system, then install electrodes, graphite as anode and platinum sheet as cathode, perform electrochemical oxidation after the electrodes are installed, and after the reaction is completed, perform post-treatment to obtain β-ketosulfone compound.
5. The β-ketosulfone compound according to claim 4, characterized in that The molar ratio of the enol ester compound, the sulfonyl hydrazide compound, the electrolyte and the sodium carbonate is 1:1.2-2:1-1.2:2.5-3.
6. The β-ketosulfone compound according to claim 5, characterized in that The molar ratio of the enol ester compound, the sulfonyl hydrazide compound, the electrolyte and the sodium carbonate is 1:1.5:1:
3.
7. The β-ketosulfone compound according to claim 5, characterized in that: The electrolyte is at least one of tetrabutylammonium tetrafluoroborate, tetrabutylammonium hexafluorophosphate, tetrabutylammonium chloride, tetrabutylammonium bromide, tetraethylammonium chloride and tetraethylammonium bromide.
8. The β-ketosulfone compound according to claim 5, characterized in that The volume ratio of acetonitrile to water in the acetonitrile aqueous solution is 15-20:
1.
9. The β-ketosulfone compound according to claim 5, characterized in that The current during the electrochemical oxidation process is 5-15 mA.
10. The β-ketosulfone compound according to claim 5, characterized in that: The reaction temperature is room temperature and the reaction time is 3-5h.