A process for the preparation of a beta-amino substituted alpha-branched enone compound

Abstract

The present application belongs to the technical field of preparation of alpha-branched alkenone, and particularly relates to a preparation method of beta-amino substituted alpha-branched alkenone compound. The present application uses beta-acyl allyl sulfide, amine compound and silver carbonate as reaction raw materials, controls reaction temperature and time in a solvent to synthesize the beta-amino substituted alpha-branched alkenone compound. The synthesis method used in the present application can realize the preparation of beta-amino substituted alpha-branched alkenone in only one step. Compared with traditional synthesis reaction, the synthesis method expands the substrate range, shortens the reaction steps, improves the total synthesis yield, reduces the reaction cost, and provides a more economical, efficient and practical synthesis new route for the synthesis of beta-amino substituted alpha-branched alkenone.

Description

Technical Field

[0001] This invention belongs to the field of α-branched ketone preparation technology, specifically relating to a method for preparing β-amino-substituted α-branched ketone compounds. Background Technology

[0002] α-Branched ketones are important structural units found in natural products, pharmaceuticals, and functional materials. Among them, β-amino-substituted α-branched ketones are widely found in molecules with anti-inflammatory, antibacterial, and antitumor biological activities, and are also frequently used as organic synthesis intermediates for constructing nitrogen-containing heterocycles (such as pyridine, quinoline, and pyrrole) and natural product skeletons. Therefore, developing efficient and mild synthetic methods for β-amino-substituted α-branched ketones is of great research value. Currently known synthetic methods for β-amino-α-branched ketones often rely on the aza-Morita–Baylis–Hillman reaction, but this method has limitations such as slow reaction kinetics and a narrow substrate range [see: Chem. Rev. 2013, 113 , 6659-6690; Chem. Rev. 2010, 110, [5447-5674]. Another allyl amination reaction based on Morita–Baylis–Hillman (MBH) derivatives [see: (a)]. Org. Chem. Front. 2025 12 , 2076-2130; (b) Chem. Soc. Rev. ,2012, 41 While highly efficient, conventional desulfurization of thioethers (e.g., 4101–4112) typically requires pre-functionalized carbonates or halides and is limited to strongly nucleophilic nitrogen sources, making it incompatible with weakly nucleophilic amines. β-Acylallyl thioethers, as novel electrophiles, have the potential to construct β-amino-α-branched enones through desulfurization. However, the desulfurization of traditional thioethers relies on strongly nucleophilic amine substrates or harsh reaction conditions (such as strong bases, high temperatures, or noble metal catalysts), while research on efficient conversion of weakly nucleophilic amines remains limited [see: ]. Chem. Soc. Rev. 2020 49 [4307–4359.]. Therefore, how to directly achieve the desulfurization and amination of weakly nucleophilic amine compounds with allyl skeletons using stable and readily available raw materials to efficiently synthesize multifunctional β-amino-α-branched enones remains a significant challenge, and there is an urgent need to develop economical, efficient, and practical new synthetic methods. Summary of the Invention

[0003] In view of this, the purpose of the present invention is to overcome the shortcomings of the prior art and provide a method for preparing β-amino-substituted α-branched ketone compounds.

[0004] To achieve the above objectives, the technical solution of the present invention is as follows: A method for preparing a β-amino-substituted α-branched ketone compound includes the following steps: using β-acyl allyl sulfide, an amine compound, and silver carbonate as reactants, the reaction is carried out in a solvent, and the reaction temperature and time are controlled to synthesize the β-amino-substituted α-branched ketone compound.

[0005] Furthermore, the amine compound is any one of aniline, 2-bromoaniline, 2-methoxyaniline, 2-fluoroaniline, 3-fluoroaniline, 3-aminotrifluorotoluene, and morpholine.

[0006] Furthermore, the solvent is N,N-dimethylformamide (DMF).

[0007] Furthermore, the molar ratio of the β-acyl allyl sulfide, amine compound, and silver carbonate is 1:2:1.

[0008] Furthermore, the reaction is carried out at a temperature of 90 °C for 5-10 hours.

[0009] The technical route of this invention is the desulfurization and amination reaction of β-acyl allyl sulfide with amine compounds, and its chemical equation is as follows:

[0010] Where R represents hydrogen, bromine, fluorine, methoxy, trifluoromethyl, etc.

[0011] The specific reaction principle is as follows: Silver carbonate first coordinates with the sulfur atom of β-acylallyl sulfide to form a silver-sulfur complex, which enhances the electrophilicity of the conjugated olefin through an inductive effect and works synergistically with the inherent electron-withdrawing ability of the carbonyl group. Subsequently, the amine compound undergoes nucleophilic addition to the olefin, followed by deprotonation, to obtain a key anionic intermediate. Finally, silver methyl sulfide (AgSCH3) is eliminated from this intermediate to obtain a β-amino-substituted α-branched ketone compound.

[0012] Compared with the prior art, the beneficial effects of the present invention are as follows: (1) The method used in this invention has readily available raw materials, mild reaction conditions, good substrate universality and functional group compatibility. Amine compounds such as aniline, 2-bromoaniline, 2-methoxyaniline, 2-fluoroaniline, 3-fluoroaniline, 3-aminotrifluorotoluene, and morphine can all react with β-acylallyl sulfide under these reaction conditions and obtain the corresponding target compounds in excellent yields. (2) The synthesis method used in this invention can achieve the preparation of β-amino-substituted α-branched ketones in only one step. Compared with traditional synthesis reactions, it expands the substrate range, shortens the reaction steps, increases the overall synthesis yield, and reduces the reaction cost. (3) This invention realizes the desulfurization and amination reaction of β-acyl allyl thioether with amine compounds, providing a more economical, efficient and practical new synthetic route for the synthesis of α-branched ketones containing β-amino substitution. Attached Figure Description

[0013] Figure 1 The 1H NMR spectrum of 1-phenyl-2-((phenylamino)methyl)prop-2-en-1-one; Figure 2 The carbon spectrum of 1-phenyl-2-((phenylamino)methyl)prop-2-en-1-one; Figure 3 The 1H NMR spectrum is for 2-(((2-bromophenyl)amino)methyl)-1-phenylprop-2-en-1-one; Figure 4 The carbon spectrum of 2-(((2-bromophenyl)amino)methyl)-1-phenylprop-2-en-1-one; Figure 5 The 1H NMR spectrum is for 2-(((2-fluorophenyl)amino)methyl)-1-phenylprop-2-en-1-one; Figure 6 The carbon spectrum of 2-(((2-fluorophenyl)amino)methyl)-1-phenylprop-2-en-1-one; Figure 7 The 1H NMR spectrum of 2-(((2-methoxyphenyl)amino)methyl)-1-phenylprop-2-en-1-one; Figure 8 The carbon spectrum of 2-(((2-methoxyphenyl)amino)methyl)-1-phenylprop-2-en-1-one; Figure 9 The 1H NMR spectrum of 2-((3-fluorophenyl)aminomethyl)-1-phenylprop-2-en-1-one; Figure 10 The carbon spectrum of 2-((3-fluorophenyl)aminomethyl)-1-phenylprop-2-en-1-one; Figure 11 The 1H NMR spectrum of 1-phenyl-2-(((3-(trifluoromethyl)phenyl)amino)methyl)prop-2-en-1-one; Figure 12 The carbon spectrum of 1-phenyl-2-(((3-(trifluoromethyl)phenyl)amino)methyl)prop-2-en-1-one; Figure 13 The 1H NMR spectrum of 2-(morpholinomethyl)-1-phenylprop-2-en-1-one; Figure 14 The carbon spectrum of 2-(morpholinomethyl)-1-phenylprop-2-en-1-one. Detailed Implementation

[0014] To facilitate understanding of the present invention, a more comprehensive description will be given below. However, the present invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a thorough and complete understanding of the disclosure of the present invention.

[0015] In this embodiment of the invention, proton nuclear magnetic resonance spectroscopy (NMR) is used. 1 H NMR, carbon spectrum ( 13 The structure of the β-amino-substituted α-branched ketone skeleton compound was confirmed by 1H NMR and high-resolution mass spectrometry. The instruments used for detection were: an AVANCE III HD 600 MHz NMR spectrometer, with deuterated chloroform as an internal standard (1H NMR, deuterated chloroform: δ 7.26 ppm), and (1H NMR, deuterated chloroform: δ 77 ppm); and a Thermo Scientific Q Exactive high-resolution mass spectrometer.

[0016] Example 1: Synthesis of 1-phenyl-2-((phenylamino)methyl)prop-2-en-1-one

[0017] (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), aniline (0.0466 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 10 hours.

[0018] (2) After the reaction was complete, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 7:1 - 4:1, v / v). The solvent was removed by rotary evaporation, and the residue was dried under an oil pump to obtain 32.5 mg of a yellow oily product, with a yield of 55%. The 1H and 1C spectra are shown below. Figure 1 and Figure 2 As shown, 1H NMR (600 MHz, CDCl3)δ 7.73 – 7.71 (m, 2H), 7.56 – 7.53 (m, 1H), 7.45 – 7.42 (m, 2H), 7.20 – 7.17(m, 2H), 6.74 – 6.72 (m, 1H), 6.65 (d, J = 7.8 Hz, 2H), 6.08 (s, 1H), 5.77 (s,1H), 4.22 (s, 2H), 4.19 (br s, 1H); 13 C NMR (151 MHz, CDCl3) δ 197.8, 147.5,144.8, 137.6, 132.4, 129.4, 129.2, 128.3, 126.8, 117.7, 113.1, 45.3; HRMS(ESI) m / z: [M + H] + Calcd for C 16 H 16 NO 238.1226; Found 238.1224. Example 2: Synthesis of 2-(((2-bromophenyl)amino)methyl)-1-phenylprop-2-en-1-one (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), 2-bromoaniline (0.0860 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 10 hours.

[0019] (2) After the reaction was complete, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 50:1 - 20:1, v / v). The solvent was removed by rotary evaporation, and the residue was dried under an oil pump to obtain 70.8 mg of a yellow oily product, with a yield of 90%. The 1H and 1C spectra are shown below. Figure 3 and Figure 4 As shown, 1 H NMR (600 MHz, CDCl3) δ 7.75 (d, J= 7.8 Hz, 2H), 7.57 – 7.55 (m, 1H), 7.46 – 7.43 (m, 3H), 7.19 – 7.17 (m, 1H), 6.66 (d, J = 8.1 Hz, 1H), 6.60 (t, J = 7.6 Hz, 1H), 6.03(s, 1H), 5.79 (s, 1H), 4.83 (s, 1H), 4.30 (s, 2H); 13 C NMR (151 MHz, CDCl3) δ197.4, 144.2, 144.0, 137.4, 132.50, 132.45, 129.4, 128.4, 128.3, 126.6,118.2, 111.6, 109.8, 44.7; HRMS (ESI) m / z: [M + Na] + Calcd for C 16 H 14 BrNONa338.0151, found 338.0159. Example 3: Synthesis of 2-(((2-fluorophenyl)amino)methyl)-1-phenylprop-2-en-1-one (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), 2-fluoroaniline (0.0556 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 10 hours.

[0020] (2) After the reaction was complete, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 50:1 - 20:1, v / v). The solvent was removed by rotary evaporation, and the residue was dried under an oil pump to obtain 33.6 mg of a yellow oily product, with a yield of 53%. The 1H and 1C spectra are shown below. Figure 5 and Figure 6 As shown, 1 H NMR (600 MHz, CDCl3) δ 7.74 (d, J= 7.9 Hz, 2H), 7.57 – 7.54 (m, 1H), 7.45 – 7.43 (m, 2H), 7.02 – 6.97 (m, 2H), 6.74 – 6.71 (m, 1H), 6.67 – 6.63 (m, 1H), 6.08 (s, 1H),5.79 (s, 1H), 4.43 (br s, 1H), 4.27 (s, 2H); 13 C NMR (151 MHz, CDCl3) δ 197.4,151.6 (d, J = 238.2 Hz), 144.4, 137.4, 135.9, 132.5, 129.4, 128.3, 126.6, 124.5(d, J = 2.8 Hz), 117.1 (d, J = 6.8 Hz), 114.5 (d, J = 18.4 Hz), 112.5, 44.6; HRMS(ESI) m / z: [M + H] + Calcd for C 16 H 15 FNO 256.1132; Found 256.1139. Example 4: Synthesis of 2-(((2-methoxyphenyl)amino)methyl)-1-phenylprop-2-en-1-one (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), 2-methoxyaniline (0.0616 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 5 hours.

[0021] (2) After the reaction was completed, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 50:1 - 20:1, v / v). The solvent was removed by rotary evaporation, and the residue was dried under an oil pump to obtain 32.7 mg of a yellow oily product, with a yield of 49%. The proton and carbon spectra are as follows: Figure 7 and Figure 8 As shown,1 H NMR (600 MHz, CDCl3) δ 7.75 (d, J = 7.0 Hz, 2H), 7.56 – 7.54 (m, 1H), 7.46 – 7.43 (m, 2H), 6.80 (d, J = 7.9 Hz, 1H), 6.80 – 6.79 (m, 1H), 6.72 – 6.69 (m, 1H), 6.64 (d, J =7.8 Hz, 1H), 6.07 (s, 1H), 5.77 (s, 1H), 4.75 (br s, 1H), 4.26 (s, 2H), 3.85(s, 3H); 13 C NMR (151 MHz, CDCl3) δ 197.6, 146.9, 144.8, 137.6, 137.4, 132.3,129.4, 128.2, 126.4, 121.2, 116.8, 110.2, 109.5, 55.4, 44.7; HRMS (ESI) m / z:[M + H] + Calcd for C 17 H 18 NO2268.1332; Found 268.1330. Example 5: Synthesis of 2-((3-fluorophenyl)aminomethyl)-1-phenylprop-2-en-1-one (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), 3-fluoroaniline (0.0556 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 10 hours.

[0022] (2) After the reaction was completed, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 30:1 - 10:1, v / v). The solvent was removed by rotary evaporation, and the residue was dried under an oil pump to obtain 36.5 mg of a yellow oily product, with a yield of 57%. The 1H and 1C spectra are shown below. Figure 9 and Figure 10 As shown, 1 H NMR (600 MHz, CDCl3) δ 7.72 (d, J = 7.8 Hz, 2H), 7.56 – 7.54 (m, 1H), 7.45 – 7.43 (m, 2H), 7.09 (q, J = 7.6 Hz, 1H), 6.41– 6.40 (m, 2H), 6.34 (d, J = 11.5 Hz, 1H), 6.07 (s,1H), 5.79 (s, 1H), 4.32 (br s, 1H), 4.20 (d, J = 5.9 Hz, 2H); 13 C NMR (151 MHz, CDCl3) δ 197.6, 164.1 (d, J = 243.2 Hz), 149.3 (d, J = 10.8 Hz), 144.3, 137.4,132.5, 130.3 (d, J = 10.2 Hz), 129.4, 128.3, 127.0, 109.0 (d, J = 2.1 Hz), 104.2(d, J = 21.6 Hz), 99.7 (d, J = 25.4 Hz), 45.2; HRMS (ESI) m / z: [M + H] + Calcdfor C 16 H 15 FNO 256.1132; Found 256.1140. Example 6: Synthesis of 1-phenyl-2-(((3-(trifluoromethyl)phenyl)amino)methyl)prop-2-en-1-one (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), 3-aminotrifluorotoluene (0.0806 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 10 hours.

[0023] (2) After the reaction was complete, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 30:1 - 10:1, v / v). The solvent was removed by rotary evaporation, and the residue was dried under an oil pump to obtain 42.0 mg of a yellow oily product, with a yield of 55%. The 1H and 1C spectra are shown below. Figure 11 and Figure 12 As shown, 1 H NMR (600 MHz, CDCl3) δ 7.72 (d, J = 7.5 Hz, 2H), 7.57 – 7.54 (m, 1H), 7.45 – 7.43 (m, 2H), 7.27 – 7.25 (m, 1H), 6.96 (d, J = 7.5 Hz, 1H), 6.85 (s, 1H), 6.78 (d, J = 7.7 Hz,1H), 6.08 (s, 1H), 5.80 (s, 1H), 4.44 (br s, 1H), 4.25 (s, 2H); 13 C NMR (151MHz, CDCl3) δ197.5, 147.7, 144.1, 137.3, 132.6, 131.5 (q, J = 31.8 Hz), 129.6,129.4, 128.3, 127.1, 124.3 (q, J = 272.5 Hz), 116.0, 114.1 (q, J = 3.6 Hz), 109.3(q, J = 3.8 Hz), 45.1; HRMS (ESI) m / z: [M - H] - Calcd for C 17 H 13 F3NO 304.0944;Found 304.0950. Example 7: Synthesis of 2-(morpholinomethyl)-1-phenylprop-2-en-1-one (1) β-acylallyl sulfide (0.0481 g, 0.25 mmol), morpholine (0.0436 g, 0.5 mmol, 2 equiv), Ag2CO3 (0.0689 g, 0.25 mmol, 1 equiv), and DMF (1 mL) were stirred evenly in a dry and clean sealed reaction tube and heated to 90 °C for 10 hours.

[0024] (2) After the reaction was completed, the reaction tube was cooled to room temperature. 50 mL of ethyl acetate was added to dilute the reaction solution, which was then transferred to a 100 mL separatory funnel. 10 mL of saturated saline solution was added, the mixture was shaken, and allowed to stand. The organic and aqueous phases were separated. The aqueous phase was extracted twice with 30 mL of ethyl acetate. The resulting organic phases were combined and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate = 100:1 - 30:1, v / v). The solvent was removed by rotary evaporation, and the product was dried under an oil pump to obtain 26.5 mg of a yellow oily product, with a yield of 46%. The 1H and 1C spectra are shown below. Figure 13 and Figure 14 As shown, 1 H NMR (600 MHz, CDCl3) δ 7.78 – 7.77 (m, 2H), 7.56 – 7.54 (m, 1H), 7.46 – 7.43 (m, 2H), 6.01 (s, 1H), 5.74 (s, 1H), 3.68 (t, J = 4.6 Hz, 4H), 3.40 (s, 2H), 2.53 – 2.52 (m,4H); 13 C NMR (151 MHz, CDCl3) δ 197.4, 144.2, 137.4, 132.4, 129.5, 128.3,126.9, 67.0, 59.6, 53.6; HRMS (ESI) m / z: [M + H] + Calcd for C 14 H 18 NO2232.1332; Found 232.1332. The β-amino-substituted α-branched enone compounds prepared in this invention contain both enone and amino functional groups in their structure, and can be used as organic synthesis intermediates or directly as bioactive molecules. Specifically: (1) As a synthetic intermediate: These compounds can be further used to construct nitrogen-containing heterocyclic skeletons. For example, fused heterocyclic systems such as quinoline, indole, and pyrrole can be synthesized through intramolecular cyclization or transition metal-catalyzed coupling reactions. These heterocyclic structures are widely found in natural products and drug molecules.

[0025] (2) As a bioactive molecule: The β-amino-α,β-enone skeleton itself has potential anti-inflammatory, antibacterial and antitumor activities. The compound synthesized in Example 7 of this invention can be used as an important intermediate for subsequent screening of anti-inflammatory activities, providing structurally diverse candidate molecules for drug development.

[0026] The above description is only for better explaining the embodiments of the present invention and is not intended to limit them. Any modifications or equivalent substitutions that do not depart from the spirit and scope of the present invention shall fall within the scope of the present invention.

Claims

1. A method for preparing a β-amino-substituted α-branched enone compound, characterized in that, The process includes the following steps: using β-acyl allyl sulfide, amine compounds, and silver carbonate as reactants, the reaction is carried out in a solvent, with controlled reaction temperature and time, to synthesize the β-amino-substituted α-branched ketone compound.

2. The method for preparing a β-amino-substituted α-branched enone compound according to claim 1, characterized in that, The amine compound is any one of aniline, 2-bromoaniline, 2-methoxyaniline, 2-fluoroaniline, 3-fluoroaniline, 3-aminotrifluorotoluene, and morpholine.

3. The method for preparing a β-amino-substituted α-branched enone compound according to claim 1, characterized in that, The solvent is N,N-dimethylformamide.

4. The method for preparing a β-amino-substituted α-branched enone compound according to claim 1, characterized in that, The molar ratio of the β-acyl allyl sulfide, amine compound, and silver carbonate is 1:2:

1.

5. The method for preparing a β-amino-substituted α-branched ketone compound according to claim 1, characterized in that, The reaction was carried out at a temperature of 90 °C for 5-10 hours.

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