A method for preparing 9,10-phenanthrenequinone compounds

Abstract

The invention discloses a preparation method of 9,10-phenanthrenequinone compounds, comprising the following steps: using an enaminone compound as shown in a chemical structure formula (I) as a raw material, under a protective gas environment, in the presence of a small molecule catalyst and an oxidant, reacting for 2 to 12 hours at 30 to 90 ° C in an organic solvent to obtain a reaction product, and then purifying the resulting reaction product to obtain a chemical structure formula (II) as shown in 9,10-phenanthrenequinone compounds. The present invention uses an enaminone compound as a raw material, which is a raw material with simple synthesis and high conversion rate, a wide range of substrate applications, low raw material and catalyst costs, low pollution, few reaction byproducts, and has the characteristics of green environmental protection; in addition, the reaction conditions required for the inventive method are very mild, the number of reactions is small, the operation is simple, and the yield is high.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic compound synthesis, and particularly relates to a method for preparing 9,10-phenanthrenequinone compounds. Background Art

[0002] 9,10-Phenanthrenequinone has been widely used as a functional molecule in chemistry, biology, materials science, and medicine, including as phenanthrenequinone dyes, chelating ligands, organic optoelectronic materials, superconducting materials, and antiarrhythmic drugs. As a multifunctional molecule, 9,10-phenanthrenequinone can serve as the backbone for the anti-inflammatory molecule 5,7-dimethoxy-1,4-phenanthreneanthraquinone (CLLV-1). Phenanthrenequinone can also be used as a novel dye, with the design and synthesis of new, purely organic functional dyes based on a phenanthrenequinone structure containing malononitrile groups. Phenanthrenequinone itself is also a pesticide, capable of inhibiting bacterial growth and reproduction. When applied to wheat seeds as an insecticide, it is effective in controlling wheat smut and head blight. It can replace organic mercury preparations such as "Cilisheng" and "Celisan," which are toxic to humans, difficult to degrade, and harmful to the environment. After treatment with NaOH, 9,10-phenanthrenequinone rearranges into a fluorene derivative, a multifunctional plant growth enhancer (trade name: Aniten or Maintain). 9,10-phenanthrenequinone can be used as a corrosion inhibitor in magnetic recording materials and as a heat transfer agent to improve the thermal stability of color in plastics. Overall, phenanthrenequinone has a wide range of applications and a promising market outlook both domestically and internationally.

[0003] Currently, the industrial method for preparing 9,10-phenanthrenequinone is the oxidation of phenanthrene. However, this method uses potassium dichromate or concentrated sulfuric acid as the oxidant, which is environmentally unfriendly and has limited substrate availability. In recent years, many new methods for synthesizing 9,10-phenanthrenequinone have been developed, such as the oxidation of hydrogenated phenanthrene and phenanthroline phenol, and the intramolecular oxidative coupling of dibenzoyl and 1,1'-diformylbiphenyl. Among them, the raw materials for the oxidation method of hydrogenated phenanthrene and phenanthroline phenol are difficult to prepare, which greatly limits its development. The oxidant used must be quantitative and is harmful to the environment. The intramolecular oxidative coupling method of dibenzoyl and 1,1'-diformylbiphenyl has high raw material and catalyst costs, which further limits the popularity of the substrate. There is also the method disclosed in document 1 (Somai M.; Krishna B.; Xia, L.; et al Chem. Commun. 2015, 51, 8592-8595; Togashi, DM; Nicodem, DESynth. Commun. 1998, 28, 1051-1063), which has harsh reaction conditions, expensive ligands, complex operations, poor atom economy, and is environmentally unfriendly. Summary of the Invention

[0004] In view of the problems existing in the above-mentioned prior art, the purpose of the present invention is to provide a preparation method of 9,10-phenanthrenequinone compounds to solve the many defects existing in the existing synthesis methods, such as high raw material and catalyst costs, expensive ligands, harsh reaction conditions, and poor atom economy.

[0005] In order to achieve the above object, the present invention adopts the following technical solutions:

[0006] The present invention provides a method for preparing a 9,10-phenanthrenequinone compound, comprising the following steps: using an enaminone compound having a general chemical structure as shown in formula (I) as a raw material, reacting in an organic solvent at 30 to 90° C. for 2 to 12 hours in the presence of a small molecule catalyst and an oxidant under a protective gas environment to obtain a reaction product, and then purifying the obtained reaction product to obtain a 9,10-phenanthrenequinone compound having a general chemical structure as shown in formula (II):

[0007]

[0008] Wherein, R is selected from any one of H, CH3, F, Cl, Br, I, OMe, CF3, COOMe, R 1 Any one selected from H, CH3, F, Cl, Br, I, OMe, CF3, COOMe.

[0009] Preferably, the molar ratio of the small molecule catalyst to the enaminone compound is 0.05-0.20:1.

[0010] Preferably, the molar ratio of the oxidant to the enaminone compound is 1.2 to 3.0:1.

[0011] Preferably, the small molecule catalyst is any one of N-chlorosuccinimide, N-bromosuccinimide, iodobenzene acetate, sodium iodide and potassium iodide.

[0012] Preferably, the enaminone compound is selected from (E)-1-([1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-methoxy-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-methyl-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-fluoro-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-1-(4-bromo-[1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one , (E)-3-(dimethylamino)-1-(4'-methyl-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4'-methoxy)-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-1-(4'-chloro-[1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one, (E)-2'-(3-(dimethylamino)acryloyl-[1,1'-biphenyl]-4-carboxylic acid methyl ester.

[0013] Preferably, the oxidant is any one of tert-butyl hydroperoxide, sodium percarbonate, hydrogen peroxide, sodium persulfate, potassium persulfate, ammonium persulfate, activated manganese dioxide, oxygen, N-fluorobenzenesulfonimide, copper acetate and elemental iodine.

[0014] Preferably, the organic solvent is one or a combination of two or more of xylene, acetonitrile, dichloromethane, dichloroethane, chloroform, chlorobenzene, and toluene.

[0015] Preferably, the protective gas is nitrogen or argon.

[0016] Preferably, the reaction product is purified by thin layer chromatography, and the developing solvent system used is petroleum ether / ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate in the developing solvent system is 0.02-0.5:1.

[0017] Compared with the prior art, the present invention has the following beneficial effects:

[0018] The present invention uses enaminones as raw materials, which are simple to synthesize, have high conversion rates, and have a wide range of substrate applications. The raw materials and catalysts used are low-cost, minimally polluting, and produce few reaction byproducts, making them environmentally friendly. Furthermore, the preparation method of the present invention features mild reaction conditions, a limited number of reaction steps, simple operation, and high yield. Due to their widespread distribution in biologically and pharmaceutically active molecules (such as antibacterial agents and herbicides), 9,10-phenanthrenequinone compounds have broad application prospects. BRIEF DESCRIPTION OF THE DRAWINGS

[0019] In order to more clearly illustrate the technical solutions in the embodiments of the present invention, the following briefly introduces the drawings required for use in the embodiments. Obviously, the drawings described below are only some embodiments of the present invention. For ordinary technicians in this field, other drawings can be obtained based on these drawings without paying any creative work.

[0020] Figure 1 The synthetic route of the 9,10-phenanthrenequinone compounds provided by the present invention;

[0021] Figure 2 This is the NMR spectrum of 9,10-phenanthrenequinone prepared in Example 1 of the present invention;

[0022] Figure 3 This is the carbon spectrum of 9,10-phenanthrenequinone prepared in Example 1 of the present invention. DETAILED DESCRIPTION

[0023] In the following description, specific details such as specific system structures and technologies are provided for illustration rather than limitation to facilitate a thorough understanding of the embodiments of the present invention. However, it should be clear to those skilled in the art that the present invention may also be implemented in other embodiments without these specific details.

[0024] Example 1

[0025] Reference Figure 1 , which is a synthetic route for 9,10-phenanthrenequinone compounds, to prepare 9,10-phenanthrenequinone, i.e., compound 1-1:

[0026]

[0027] Acetonitrile, (E)-1-([1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one (chemical structure see Formula 1-1) (0.20 mmol, 0.052 g), N-chlorosuccinimide (0.02 mmol, 0.0027 g), and tert-butyl hydroperoxide (0.3 mmol, 0.027 g) were added to a 10 mL Shrek tube in sequence, and the mixture was stirred at 60°C for 10 h. After the reaction was completed, the product was separated and purified by thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1). The product was a yellow solid substance, namely, compound 1-1, with a yield of 87%.

[0028] 1 HNMR (CDCl3, 400MHz): δ=8.21-8.11(m,2H),8.03-7.94(m,2H),7.75-7.64(m,2H),7.50-7.40(m,2H)ppm; 13 CNMR(CDCl3,100MHz)180.2,136.0,135.8,130.9,130.4,129.5,123.9ppm; HRMS(ESI,m / z):calcd for C 14 H8O2 208.0524, found: 208.0525. Its NMR and C spectrum results are as follows Figure 2 and Figure 3 shown.

[0029] Example 2

[0030]

[0031] Chloroform, (E)-3-(dimethylamino)-1-(4-methyl-[1,1'-biphenyl]-2-yl)propen-2-en-1-one (chemical structure see Formula 1-2) (0.20 mmol, 0.053 g), N-chlorosuccinimide (0.02 mmol, 0.0027 g), and sodium percarbonate (0.3 mmol, 0.047 g) were added to a 10 mL Shrek tube in sequence. The mixture was stirred at 70°C for 8 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product, which was an orange solid compound. 1HNMR (Chloroform-d, 400MHz) δ = 8.11, 8.11, 8.09, 8.09, 7.91, 7.89, 7.83, 7.83, 7.81, 7.81, 7.67, 7.67, 7.67, 7.65,7.65,7.64,7.63,7.63,7.47,7.47,7.45,7.45,7.41,7.41,7.39,7.39,7.38,7.37,7.37,7.26,2.38ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 180.3, 139.9, 136.9, 136.0, 135.9, 133.1, 130.7, 130.7, 130.6, 130.3, 129.1, 123.9, 123.7, 20.9ppm.

[0032] Example 3

[0033]

[0034] To a 10 mL Shrek tube, dichloroethane, (E)-3-(dimethylamino)-1-(4-methoxy-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one (chemical structure see Formula 1-3) (0.20 mmol, 0.056 g), N-chlorosuccinimide (0.01 mmol, 0.0014 g), and sodium percarbonate (0.3 mmol, 0.047 g) were added in sequence. The reaction was stirred at 70°C for 3 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product. The product was an orange solid compound. 1 HNMR (Chloroform-d, 400MHz): δ = 8.12 (d, 1H, J = 7.8Hz), 7.87 (t, 2H, J = 8.7Hz), 7.69–7.63 (m, 1H) ,7.60(d,1H,J=2.9Hz),7.37(t,1H,J=7.6Hz),7.22(ddd,1H,J=8.8,2.9,0.8Hz),3.91(s,2H)ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 180.3, 160.4, 136.2., 136.1, 132.1, 130.5, 123.0, 129.0, 128.6, 125.6, 123.8, 123.4, 112.6, 55.8ppm.

[0035] Example 4

[0036]

[0037] To a 10 mL Shrek tube, dichloromethane, (E)-3-(dimethylamino)-1-(4-fluoro-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one (chemical structure see Formula 1-4) (0.20 mmol, 0.054 g), sodium iodide (0.01 mmol, 0.0015 g), and ammonium persulfate (0.24 mmol, 0.055 g) were added in sequence. The reaction was stirred at 30°C for 12 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product, which was a yellow solid compound. 1 H NMR (Chloroform-d, 400MHz): δ = 8.27 (d, 1H, J = 2.2Hz), 8.18 (dd, 1H, J = 7.8, 1.3Hz), 7.96 (d, 1H, J = 7.7Hz), 7. 88(d,1H,J=8.5Hz),7.81(dd,1H,J=8.5,2.2Hz),7.72(td,1H,J=7.7,1.5Hz),7.49(td,1H,J=7.7,1.0Hz)ppm; 13 19F NMR (377MHz, CHLOROFORM-D) δ = -109.94ppm.

[0038] Example 5

[0039]

[0040] Chloroform, (E)-1-(4-bromo-[1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one (chemical structure see Formula 1-5) (0.20 mmol, 0.066 g), sodium iodide (0.01 mmol, 0.0015 g), and ammonium persulfate (0.24 mmol, 0.055 g) were added to a 10 mL Shrek tube in sequence. The mixture was stirred at 50°C for 10 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product, which was an orange solid compound. 1H NMR (Chloroform-d, 400MHz): δ = 8.17 (dd, 1H, J = 7.8, 1.4Hz), 8.01 (dd, 1H, J = 8.8, 4.8Hz), 7.92 (d, 1H, J = 8.0Hz), 7 .82(dd,1H,J=8.3,2.9Hz),7.71(td,1H,J=7.7,1.5Hz),7.49--7.43(m,1H),7.41(ddd,1H,J=8.8,7.6,2.9Hz)ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 179.4, 164.5, 162.0, 136.4, 135.3, 132.9, 132.4, 130.9, 130.5, 129.7, 126.5, 124.1, 123.6, 116.7, 116.5, 116.5ppm.

[0041] Example 6

[0042]

[0043] To a 10 mL Shrek tube, xylene, (E)-3-(dimethylamino)-1-(4'-methyl-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one (chemical structure see Formula 1-6) (0.20 mmol, 0.053 g), sodium iodide (0.01 mmol, 0.0015 g), and ammonium persulfate (0.48 mmol, 0.11 g) were added in sequence. The reaction was stirred at 90°C for 5 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product. The product was an orange solid compound. 1 HNMR (Chloroform-d, 400MHz): δ = 8.11 (d, 1H, J = 7.7Hz), 7.91 (d, 2H, J = 7.6Hz), 7.83 (d, 1H, J = 8.1Hz),7.66(t,1H,J=7.6Hz),7.47(d,1H,J=8.1Hz),7.40(t,1H,J=7.5Hz),2.39(s,3H)ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 180.3, 139.9, 136.9, 136.0, 133.1, 130.7, 130.7, 130.5, 130.4, 129.1, 123.9, 123.7, 20.9ppm.

[0044] Example 7

[0045]

[0046] To a 10 mL Shrek tube, acetonitrile, (E)-3-(dimethylamino)-1-(4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)propen-2-en-1-one (chemical structure see Formula 1-7) (0.20 mmol, 0.064 g), iodobenzene acetate (0.04 mmol, 0.0129 g), and ammonium persulfate (0.48 mmol, 0.11 g) were added in sequence. The reaction was stirred at 80°C for 8 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product. The product was an orange solid compound. 1 HNMR (Chloroform-d, 400MHz): δ = 8.46 (s, 1H), 8.26 (d, 1H, J = 7.8Hz), 8.19 (d, 1H, J = 8.5Hz), 8 .08(d,1H,J=8.0Hz),7.96(d,1H,J=8.4Hz),7.80(t,1H,J=7.7Hz),7.58(t,1H,J=7.6Hz)ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 179.3, 136.3, 134.3, 132.1, 130.9, 130.8, 129.6, 129.3, 128.9, 128.4, 127.5, 124.7, 124.6, 29.7ppm; 19FNMR (376MHz, CHLOROFORM-D) δ = -63.23ppm.

[0047] Example 8

[0048]

[0049] To a 10 mL Shrek tube, dichloromethane, (E)-3-(dimethylamino)-1-(4'-methoxy-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one (chemical structure see Formula 1-8) (0.20 mmol, 0.056 g), sodium iodide (0.02 mmol, 0.003 g), and ammonium persulfate (0.48 mmol, 0.11 g) were added in sequence. The reaction was stirred at 30°C for 8 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product, which was an orange solid compound. 1HNMR (Chloroform-d, 400MHz): δ = 8.09 (d, 1H, J = 7.7Hz), 7.84 (t, 2H, J = 8.2Hz), 7.64 (t, 1H, J = 7. 7Hz),7.57(d,1H,J=2.5Hz),7.36(t,1H,J=7.5Hz),7.24-7.18(m,1H),3.89(d,3H,J=1.6Hz)ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 180.3, 180.1, 160.4, 136.1, 136.1, 132.1, 130.5, 129.9, 129.0, 128.6, 125.6, 123.7, 123.4, 112.6, 55.7ppm.

[0050] Example 9

[0051]

[0052] Chloroform, (E)-1-(4'-chloro-[1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one (chemical structure see Formula 1-9) (0.20 mmol, 0.057 g), iodobenzene acetate (0.02 mmol, 0.0065 g), active manganese dioxide (0.1 mmol, 0.0087 g), and ammonium persulfate (0.48 mmol, 0.11 g) were added to a 10 mL Shrek tube in sequence. The mixture was stirred at 50°C for 7 h. After the reaction was completed, thin layer chromatography (developing solvent system: petroleum ether / ethyl acetate, the volume of the two was 0.5:1) was used to separate and purify the product, which was an orange solid compound. 1 HNMR (Chloroform-d, 400MHz): δ = 8.17 (dd, 1H, J = 7.8, 1.4Hz), 8.10 (d, 1H, J = 2.4Hz), 7.97-7.91 ( m,2H),7.72(td,1H,J=7.7,1.5Hz),7.65(dd,1H,J=8.6,2.4Hz),7.48(td,1H,J=7.7,0.9Hz)ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 179.2, 136.2, 136.2, 136.1, 135.9, 134.9, 134.2, 131.9, 130.7, 130.7, 130.0, 129.9, 125.5, 124.0ppm.

[0053] Example 10

[0054]

[0055] To a 10 mL Shrek tube, xylene, methyl (E)-2'-(3-(dimethylamino)acryloyl)-[1,1'-biphenyl]-4-carboxylate (chemical formula see Formula 1-10) (0.20 mmol, 0.062 g), iodobenzene acetate (0.02 mmol, 0.0065 g), and activated manganese dioxide (0.1 mmol, 0.0087 g) were added sequentially. The mixture was stirred at 90°C for 8 h. After completion of the reaction, the product was isolated and purified by thin-layer chromatography (developing solvent: petroleum ether / ethyl acetate, 0.5:1 volume ratio) to obtain an orange solid. 1 H NMR (Chloroform-d, 400MHz): δ = 8.81 (d, 1H, J = 1.9Hz), 8.36 (dd, 1H, J = 8.4, 1.9Hz), 8.23 (dd, 1H, J = 7.8, 1.3 Hz), 8.10 (dd, 1H, J = 15.1, 8.2Hz), 7.76 (dd, 1H, J = 7.9, 1.4Hz), 7.55 (td, 1H, J = 7.7, 0.9Hz), 3.98 (s, 3H) ppm; 13 CNMR (Chloroform-d, 100MHz): δ = 179.7, 165.4, 139.4, 136.4, 136.2, 134.7, 131.6, 131.3, 131.1, 130.9, 130.8, 130.6, 124.7, 124.3, 52.6ppm.

[0056] The present invention is not limited to the above-mentioned specific implementation methods. Various changes made by ordinary technicians in this field based on the above-mentioned concept without creative work are all within the scope of protection of the present invention.

Claims

1. A method for preparing 9,10-phenanthrenequinone compounds, characterized in that: The method comprises the following steps: using an enaminone compound represented by a general chemical formula (I) as a raw material, reacting in an organic solvent at 30 to 90° C. for 2 to 12 hours in the presence of a small molecule catalyst and an oxidant under a protective gas environment to obtain a reaction product, and then purifying the obtained reaction product to obtain a 9,10-phenanthrenequinone compound represented by a general structural formula (II): （Ⅰ） （Ⅱ） Wherein, R is selected from any one of H, CH3, F, Cl, Br, I, OMe, CF3, COOMe, R 1 Any one selected from H, CH3, F, Cl, Br, I, OMe, CF3, COOMe; The small molecule catalyst is any one of N-chlorosuccinimide, N-bromosuccinimide, iodobenzene acetate, sodium iodide and potassium iodide; The oxidant is any one of tert-butyl hydroperoxide, sodium percarbonate, sodium persulfate, potassium persulfate, ammonium persulfate, and active manganese dioxide.

2. The method for preparing 9,10-phenanthrenequinone compounds according to claim 1, wherein The molar ratio of the small molecule catalyst to the enaminone compound is 0.05-0.20:

1.

3. The method for preparing 9,10-phenanthrenequinone compounds according to claim 1, wherein The molar ratio of the oxidant to the enaminone compound is 1.2-3.0:

1.

4. The method for preparing 9,10-phenanthrenequinone compounds according to claim 1, wherein The enaminones are selected from (E)-1-([1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-methoxy-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-methyl-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-fluoro-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-1-(4-bromo-[1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4-methyl-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one Any one of (E)-3-(dimethylamino)-1-(4'-methyl-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4'-(trifluoromethyl)-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-3-(dimethylamino)-1-(4'-methoxy)-[1,1'-biphenyl]-2-yl)propyl-2-en-1-one, (E)-1-(4'-chloro-[1,1'-biphenyl]-2-yl)-3-(dimethylamino)propyl-2-en-1-one, and (E)-2'-(3-(dimethylamino)acryloyl-[1,1'-biphenyl]-4-carboxylic acid methyl ester.

5. The method for preparing 9,10-phenanthrenequinone compounds according to claim 1, wherein The organic solvent is one or a combination of two or more of xylene, acetonitrile, dichloromethane, dichloroethane, chloroform, chlorobenzene, and toluene.

6. The method for preparing 9,10-phenanthrenequinone compounds according to claim 1, characterized in that: The protective gas is nitrogen or argon.

7. The method for preparing 9,10-phenanthrenequinone compounds according to claim 1, characterized in that: The reaction product is purified by thin layer chromatography, and the developing solvent system used is petroleum ether / ethyl acetate, and the volume ratio of petroleum ether to ethyl acetate in the developing solvent system is 0.02-0.5:1.

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