Multifunctional beta-naphthalenone derivative as well as preparation method and application thereof

Abstract

The invention belongs to the technical field of naphthalenone derivatives, and provides a multifunctional beta-naphthalenone derivative as well as a preparation method and application thereof. In the multifunctional beta-naphthalenone derivative disclosed by the invention, R1 is alkyl or aryl; r2 is alkyl, phenyl, naphthyl, thienyl, an aromatic ring connected with an electron withdrawing group or an aromatic ring connected with an electron donating group, and the electron withdrawing group and the electron donating group comprise methyl, methoxyl, trifluoromethyl or halogen; r3 is H, methyl or methoxyl; r4 is H, methyl, phenyl or alkynyl. The preparation method comprises the following steps: by taking a simple and easily available 1, 6-diyne-3-alcohol compound as an initial raw material, potassium chloroaurate as a catalyst and thioanisole as a ligand, carrying out intramolecular 6-endo-dig cyclization, 3, 3-Claisen rearrangement and aromatization reaction, and finally carrying out 1, 3-acyl migration reaction on an aromatic ring, thereby obtaining the multifunctional beta-naphthalenone derivative.

Description

Technical Field

[0001] The present invention relates to the technical field of naphthone derivatives, and particularly relates to a polyfunctionalized β-naphthone derivative, a preparation method thereof, and an application thereof. Background Art

[0002] Due to the unique properties of the naphthone structure, polysubstituted naphthone compounds have a wide range of uses in medicinal chemistry. Among them, the most representative one is the lignan lactone containing a naphthone skeleton, which is a class of natural lignin compounds with biological activity. At present, there is no relevant literature report on the 1,3-acyl migration reaction on the aromatic ring.

[0003] Therefore, it is of great significance to study a method for generating a polyfunctionalized β-naphthone derivative through a gold-catalyzed 1,3-acyl migration reaction on the aromatic ring. Summary of the Invention

[0004] The object of the present invention is to provide a polyfunctionalized β-naphthone derivative, a preparation method thereof, and an application thereof in view of the deficiencies of the prior art.

[0005] In order to achieve the above object of the invention, the present invention provides the following technical solutions: The present invention provides a polyfunctionalized β-naphthone derivative, and the structural formula of the polyfunctionalized β-naphthone derivative is: ; wherein, R 1 is an alkyl group or an aryl group; R 2 is propyl, tert-butyl, n-pentyl, phenyl, naphthyl, thienyl, methylphenyl, methoxyphenyl, trifluoromethylphenyl, chlorophenyl, fluorophenyl or tert-butyldimethylsilyloxy methylene; R 3 is H, methyl or methoxy; R 4 is H, methyl, phenyl or alkynyl. When R 4 is alkynyl, the alkynyl is connected with R 2 .

[0006] Preferably, the structural formula of the polyfunctionalized β-naphthone derivative is: , , , , , , , , , , , , , , , , , , , , , , , , , , , , 。

[0007] The present invention also provides a method for preparing the multi-functionalized β-naphthone derivative, comprising the following steps: Mix potassium chloroaurate, benzyl methyl sulfide, and ethyl acetate to obtain a reaction solution, and react the reaction solution with a 1,6-diyne-3-ol compound to obtain a multi-functionalized β-naphthone derivative; The structural formula of the 1,6-diyne-3-ol compound is: ; wherein, R 1 is an alkyl group or an aryl group; R 2 is propyl, tert-butyl, n-pentyl, phenyl, naphthyl, thiophenyl, methylphenyl, methoxyphenyl, trifluoromethylphenyl, chlorophenyl, fluorophenyl, or tert-butyldimethylsilyloxy methylene; R 3 is H, methyl, or methoxy; R 4 is H, methyl, phenyl, or alkynyl. When R 4 is alkynyl, the alkynyl group is connected to R 2 .

[0008] Preferably, the molar ratio of potassium chloroaurate, benzyl methyl sulfide, and the 1,6-diyne-3-ol compound is 0.04~0.06:0.12~0.17:1.

[0009] Preferably, the molar volume ratio of the 1,6-diyne-3-ol compound and ethyl acetate is 0.2 mmol:2.2~2.6 mL.

[0010] Preferably, the mixing time is 8~12 min; the reaction temperature is 120~140 °C, and the reaction time is 2~12 h.

[0011] Preferably, after the reaction is completed, a crude product is obtained. The crude product is successively subjected to reduced pressure and silica gel column chromatography to obtain a multi-functionalized β-naphthone derivative; the eluent for silica gel column chromatography is petroleum ether and ethyl acetate.

[0012] The present invention also provides the use of the multi-functionalized β-naphthone derivatives in the preparation of drugs.

[0013] The beneficial effects of the present invention include the following points: 1) The present invention uses simple and easily available 1,6-diyn-3-ol compounds as the initial raw materials, potassium tetrachloroaurate (KAuCl4) as the catalyst, and phenyl methyl sulfide (PhSMe) as the ligand. Through intramolecular 6-endo-dig cyclization, 3,3-Claisen rearrangement, and aromatization reactions, and finally through the 1,3-acyl migration reaction on the aromatic ring, multi-functionalized β-naphthone derivatives are obtained. The method of the present invention has mild reaction conditions, high yield, and excellent regioselectivity, and has potential application value in medicinal chemistry. The present invention has successfully synthesized natural naphthyl skeleton lignins Taiwanin C and Justicidin B, demonstrating the important significance of this synthesis method. The reaction yield of the multi-functionalized naphthone derivatives prepared by the present invention is as high as 84%.

[0014] 2) The present invention uses 1,6-diyn-3-ol compounds as the initial raw materials to efficiently synthesize naphthone derivatives. Initially, acyl naphthalene compounds at the α-position of naphthalene are formed, but under the potassium tetrachloroaurate catalyst, the 1,3-acyl migration reaction on the aromatic ring occurs to form acyl naphthalene derivatives at the β-position. Specific Embodiments

[0015] In the present invention, the molar ratio of potassium tetrachloroaurate (KAuCl4), phenyl methyl sulfide (PhSMe), and 1,6-diyn-3-ol compounds is preferably 0.04 - 0.06:0.12 - 0.17:1, more preferably 0.045 - 0.055:0.14 - 0.16:1, and even more preferably 0.05:0.15:1.

[0016] In the present invention, the molar volume ratio of the 1,6-diyn-3-ol compounds and ethyl acetate (EtOAc) is preferably 0.2 mmol:2.2 - 2.6 mL, more preferably 0.2 mmol:2.3 - 2.5 mL, and even more preferably 0.2 mmol:2.4 mL.

[0017] In the present invention, the mixing time is preferably 8 - 12 min, more preferably 9 - 11 min, and even more preferably 10 min; the reaction temperature is preferably 120 - 140 °C, more preferably 125 - 135 °C, and even more preferably 130 °C, and the reaction time is preferably 2 - 12 h, more preferably 4 - 10 h, and even more preferably 6 - 8 h.

[0018] In the present invention, after the reaction is completed, a crude product is obtained. The crude product is preferably subjected to reduced pressure and silica gel column chromatography in sequence to obtain a polyfunctionalized β-naphthone derivative; the eluent for silica gel column chromatography is preferably petroleum ether and ethyl acetate.

[0019] The present invention also provides the application of the polyfunctionalized β-naphthone derivative in the preparation of drugs.

[0020] The technical solutions provided by the present invention will be described in detail below in conjunction with examples, but they should not be construed as limiting the protection scope of the present invention.

[0021] In the examples, KAuCl4 (5 mol%) means that the molar amount of KAuCl4 is 5% of the molar amount of the 1,6-diyne-3-ol compound; benzenemethanethiol PhSMe (15 mol%) means that the molar amount of PhSMe is 15% of the molar amount of the 1,6-diyne-3-ol compound. Potassium tetrachloroaurate was purchased from Shanghai Bide Pharmaceutical Technology Co., Ltd., with a CAS number of 13682-61-6, a purity of 99.9%, and a specification of 1 g. Benzenemethanethiol was purchased from adamas (Shanghai Adamas Reagent Co., Ltd.), with a CAS number of 100-68-5, a purity of 99%, and a specification of 25 g. Ethyl acetate was purchased from Beijing Merida Technology Co., Ltd., with a CAS number of 141-78-6, an AR purity of 99%, and a specification of 25 L. Petroleum ether was purchased from Shanghai Jiazu Industrial Co., Ltd., with a CAS number of 8032-32-4, a purity of 99%, and a specification of 25 L.

[0022] Example 1

[0023] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzenemethanethiol to a 4 mL sample vial, then add 2.4 mL of EtOAc, stir at room temperature for 10 min, and then add 0.2 mmol of 1,5-diphenyl-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyne-3-ol (1a), and react at 130 °C for 8 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 50~25:1) to obtain 1-(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)ethan-1-one (yellow solid product 2a).

[0024] The 2a in this example was 55.6 mg, and the isolated yield was 80%. 1 H NMR(400 MHz, Chloroform- d ) δ8.53 (d, J= 8.2 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H),7.84 (s, 1H), 7.74 – 7.57 (m,4H), 7.52 – 7.36 (m, 8H), 2.30 (s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ205.28, 143.90, 139.87, 136.05, 133.00, 132.20, 131.85, 129.67, 129.29,128.94, 128.77, 128.59, 128.46, 128.01, 127.74, 127.70, 126.74,123.02,117.23, 99.12, 85.12, 32.04.LCMS(ESI+) m / z calculated for C 26 H 18 ONa + [M+Na] + :369.1250, found: 369.1255. Example 2

[0025] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-di-o-tolylpenta-1,4-diyne-3-ol (1b) was added, and the reaction was carried out at 130 °C for 11.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and 1-(3-(o-tolyl)-1-(o-tolylethynyl)naphthalen-2-yl)ethan-1-one (2b) and 1-(2-(o-tolyl)-4-(o-tolylethynyl)naphthalen-1-yl)ethan-1-one (2b’) (brown liquid products 2b and 2b’) were obtained by silica gel column chromatography (volume ratio of petroleum ether to ethyl acetate is 100:1).

[0026] The total mass of 2b and 2b’ in this example was 46.3 mg, and the total isolated yield of 2b and 2b’ was 62% (2b:2b’ = 5.6:1). 1 H NMR(400 MHz, Chloroform- d ) δ 8.61 – 8.52 (m, 1H), 7.87 (d, J= 8.7 Hz, 1H), 7.72 – 7.65 (m, 2H), 7.64 – 7.59 (m, 2H), 7.38 – 7.18 (m, 7H), 2.64 (s, 0.45H, 2b’), 2.60 (s, 2.55H, 2b), 2.28 (s, 2.55H, 2b), 2.25 (s, 0.45H, 2b’), 2.22 (s, 2.55H, 2b), 2.12 (s, 0.45H, 2b’); 13 C NMR(101 MHz, Chloroform - d ) δ 206.20(2b’), 204.69(2b), 144.17(2b), 140.46(2b), 140.39(2b’), 139.24(2b’), 139.03(2b’), 138.99(2b), 136.68(2b), 136.28(2b’), 135.38(2b + 2b’), 132.81(2b), 132.45(2b’), 132.40(2b), 132.27(2b’), 132.23(2b), 131.90(2b’), 130.65(2b’), 130.42(2b), 130.38(2b’), 130.16(2b), 129.77(2b + 2b’), 129.53(2b), 129.16(2b’), 129.00(2b), 128.89(2b’), 128.65(2b’), 128.38(2b), 128.37(2b), 127.89(2b’), 127.63(2b), 127.61(2b), 127.22(2b’), 126.77(2b’), 126.64(2b), 126.00(2b’), 125.87(2b’), 125.82(2b), 125.63(2b), 125.38(2b’), 122.93(2b’), 122.84(2b), 122.53(2b’), 117.11(2b), 98.22(2b), 94.53(2b’), 90.96(2b’), 88.75(2b), 32.40(2b’), 31.76(2b), 21.18(2b’), 21.08(2b), 20.48(2b), 20.45(2b’); LCMS(ESI+) m / z calculated for C 28 H 22 ONa + [M + Na]+ : 397.1563, found: 397.1565. Example 3

[0027] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-di-m-tolylpenta-1,4-diyne-3-ol (1c), and react at 130 °C for 11.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100 - 50:1) to obtain 1-(3-(m-tolyl)-1-(m-tolylethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2c).

[0028] The 2c in this example was 48.4 mg, and the isolated yield was 65%. 1 H NMR(400 MHz, Chloroform- d ) δ8.54 (d, J = 8.3 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.83 (s, 1H), 7.70 – 7.64 (m,1H), 7.63 – 7.58 (m, 1H), 7.47 (d, J = 7.7 Hz, 2H), 7.38 – 7.27 (m, 4H), 7.25 –7.19 (m, 2H),, 2.44 (s, 3H), 2.41 (s, 3H), 2.33 (s, 3H); 13 C NMR(101 MHz,Chloroform- d ) δ 205.37, 143.78, 139.81, 138.39, 138.26, 136.16, 132.96,132.29, 132.12, 129.94, 129.82, 129.48,128.92, 128.72, 128.60, 128.45,128.39, 127.65, 127.57, 126.72, 126.32, 122.79,117.24, 99.30, 84.77, 32.05,21.56, 21.34;LCMS(ESI+) m / z calculated for C 28 H22 ONa + [M+Na] + : 397.1563, found: 397.1567. Example 4

[0029] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-di-p-tolylpenta-1,4-diyne-3-ol (1d), and react at 130 °C for 11.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100 - 50:1) to obtain 1-(3-(p-tolyl)-1-(p-tolylethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2d).

[0030] 2d in this example was 40.6 mg, and the isolated yield was 54%. 1 H NMR(400 MHz, Chloroform- d ) δ8.51 (d, J = 8.2 Hz, 1H), 7.88 (d, J = 8.6 Hz, 1H), 7.81 (s, 1H), 7.66 – 7.57 (m, 2H), 7.53 (d, J = 7.8 Hz, 2H), 7.36 (d, J = 7.9 Hz, 2H), 7.26 (d, J = 7.8 Hz, 2H), 7.21 (d, J = 7.8 Hz, 2H), 2.43 (s, 3H), 2.40 (s, 3H), 2.31 (s, 3H); 13 C NMR(101MHz, Chloroform- d) δ 205.56, 143.76, 139.15, 137.77, 136.98, 136.02, 133.01,132.07, 131.73, 129.47, 129.37, 129.32, 129.12, 128.37, 127.62, 127.49,126.75,119.96, 117.35, 99.33, 84.55, 32.07, 21.70, 21.33; LCMS(ESI+) m / zcalculated for C 28 H 22 ONa + [M+Na] + : 397.1563, found: 397.1567. Example 5

[0031] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-bis(thiophen-2-yl)penta-1,4-diyne-3-ol (1e) was added, and the reaction was carried out at 130 °C for 11.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100 - 50:1) was carried out to obtain 1-(3-thiophen-2-yl)-1-(thiophen-2-ylethynyl)naphthalen-2-yl)ethan-1-one (brown liquid product 2e).

[0032] 2e in this example was 19.0 mg, and the isolated yield was 27%. 1 H NMR(400 MHz, Chloroform- d ) δ8.40 (d, J = 8.2 Hz, 1H), 7.94 (s, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.67 – 7.63 (m,1H), 7.62 – 7.58 (m, 1H), 7.41 – 7.35 (m, 3H), 7.18 – 7.09 (m, 2H), 7.08 –7.03 (m, 1H), 2.40 (s,3H); 13 C NMR(101 MHz, Chloroform- d) δ 205.32, 143.43,140.59, 132.87, 132.82, 132.16, 130.11, 128.51, 128.34, 128.21, 128.17,128.07, 128.05, 127.95, 127.45, 126.67, 126.63,122.74, 117.16, 92.52, 88.57,31.78; LCMS(ESI+) m / z calculated for C 22 H 14 OS2Na + [M+Na] + : 381.0379, found:381.0379. Example 6

[0033] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-bis(4-chlorophenyl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-dien-3-ol (1f) was added, and the reaction was carried out at 130 °C for 11.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100~50:1) was carried out to obtain 1-(3-(4-chlorophenyl)-1-((4-chlorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2f).

[0034] 2f in this example was 47.3 mg, and the isolated yield was 57%. 1 H NMR(400 MHz, Chloroform- d ) δ8.46 (d, J = 8.1 Hz, 1H), 7.89 (d, J = 8.0 Hz, 1H), 7.80 (s, 1H), 7.67 (t, J = 7.5Hz, 1H), 7.61 (t, J = 7.4 Hz, 1H), 7.54 (d, J = 8.2 Hz, 2H), 7.45 – 7.41 (m, 2H),7.41 – 7.35 (m, 4H), 2.30 (s, 3H); 13 C NMR(101 MHz, Chloroform- d) δ 205.05,143.64, 138.13, 135.07, 134.65, 134.31, 132.98, 132.86, 132.12, 130.52,129.82, 128.98, 128.94, 128.48,127.99, 127.93, 126.57, 121.27, 117.03, 98.07,85.84, 32.12;LCMS(ESI+) m / z calculated for C 26 H 16 35 Cl2ONa + [M+Na] + : 437.0471,found: 437.0470; m / z calculated for C 26 H 16 37 Cl2ONa + [M+Na] + : 441.0412, found:441.0421. Example 7

[0035] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 1,5-bis(3-chlorophenyl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyne-3-ol (1 g), and react at 130 °C for 11.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100~50:1) to obtain 1-(3-(3-chlorophenyl)-1-((3-chlorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (2 g of orange solid product).

[0036] The 2 g in this example is 59.6 mg, and the separation yield is 72%. 1 H NMR(400 MHz, Chloroform- d ) δ8.47 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.82 (s, 1H), 7.69 (t, J= 7.5Hz, 1H), 7.65 – 7.58 (m, 2H), 7.53 – 7.47 (m, 2H), 7.43 – 7.30 (m, 5H), 2.34(s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ 204.75, 143.68, 141.46, 134.68,134.48, 134.44, 132.82, 132.24, 131.49, 130.08, 129.98, 129.97,129.84,129.25, 129.17, 128.54, 128.20,128.15, 128.01, 127.55, 126.55, 124.47,116.90, 97.73, 86.00, 32.16;LCMS(ESI+) m / z calculated for C 26 H 16 35 Cl2ONa + [M+Na] + :437.0471, found: 437.0470; m / z calculated for C 26 H 16 37 Cl2ONa + [M+Na] + : 441.0412,found: 441.0423. Example 8

[0037] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-bis(2-chlorophenyl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-dien-3-ol (1h) was added, and the reaction was carried out at 130 °C for 11.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100~50:1) was carried out to obtain 1-(3-(2-chlorophenyl)-1-((2-chlorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2h).

[0038] The 2h in this example was 37.7 mg, and the isolated yield was 45%. 1 H NMR(400 MHz, Chloroform-d ) δ8.65 (d, J J = 7.9 Hz, 1H), 7.89 (d, J J = 8.1 Hz, 1H), 7.79 (s, 1H), 7.73 – 7.67 (m,1H), 7.65 – 7.60 (m, 2H), 7.52 – 7.45 (m, 2H), 7.39 – 7.28 (m, 5H), 2.49 (s,3H); 13 C NMR(101 MHz, Chloroform- d ) δ 204.21, 143.86, 138.20, 136.03, 133.64,133.31, 133.21, 132.66, 132.59, 132.31, 130.97, 130.00, 129.72, 129.57,128.51, 128.21, 127.91,126.85, 126.81, 126.75, 122.98, 116.92, 96.28, 90.05,31.69;LCMS(ESI+) m / z calculated for C 26 H 16 35 Cl2O + [M+Na] + : 437.0471, found:437.0474; m / z calculated for C 26 H 16 37 Cl2O + [M+Na] + : 441.0412, found: 441.0422. Example 9

[0039] To a 4 mL sample vial, 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added. Then, 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-bis(4-fluorophenyl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-dien-3-ol (1i) was added, and the reaction was carried out at 130 °C for 9.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100 - 50:1) was performed to obtain 1-(3-(4-fluorophenyl)-1-((4-fluorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2i).

[0040] In this example, the amount of 2i was 60.7 mg, and the isolated yield was 79%. 1 H NMR(400 MHz, Chloroform- d ) δ8.47 (d, J = 8.3 Hz, 1H), 7.88 (d, J = 8.0 Hz, 1H), 7.80 (s, 1H), 7.69 – 7.57 (m,4H), 7.46 – 7.40 (m, 2H), 7.18 – 7.06 (m, 4H), 2.29 (s, 3H); 13 C NMR(101 MHz,Chloroform- d ) δ 205.30, 163.00 (d, J = 250.5 Hz), 162.76 (d, J = 247.8 Hz),143.75, 135.76 (d, J = 3.3 Hz), 134.86, 133.78 (d, J = 8.5 Hz), 132.92, 132.12,130.97 (d, J = 8.1 Hz), 129.71, 128.45, 127.87, 127.85, 126.62, 118.99 (d, J =3.4 Hz), 117.11, 115.95 (d, J = 22.2 Hz), 115.77 (d, J = 21.5 Hz), 98.13, 84.70,32.06; 19 F NMR(377 MHz, Chloroform- d) δ -109.71, -114.01. LCMS(ESI+) m / z calculated for C 26 H 16 F2ONa + [M+Na] + : 405.1062, found: 405.1062. Example 10

[0041] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-bis(4-(trifluoromethyl)phenyl)penta-1,4-diyne-3-ol (1j) was added, and the reaction was carried out at 130 °C for 9.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100 - 50:1) was carried out to obtain 1-(3-(4-(trifluoromethyl)phenyl)-1-((4-(tetrafluoromethyl)phenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2j).

[0042] 2j in this example was 76.8 mg, and the isolated yield was 80%. 1 H NMR(400 MHz, Chloroform- d ) δ 8.49 (dd, J = 8.3, 1.2 Hz, 1H), 7.92 (dd, J = 8.1, 1.6 Hz, 1H), 7.86 (s, 1H), 7.75 – 7.68 (m, 5H), 7.67 – 7.62 (m, 3H), 7.59 (d, J = 8.0 Hz, 2H), 2.33 (s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ 204.76, 143.85, 143.32, 134.54, 132.87, 132.37, 132.07, 130.73 (q, J = 32.8 Hz), 130.30 (q, J = 32.4 Hz), 130.46, 129.65, 128.68, 128.43, 128.21, 126.56, 126.52, 125.78 (q,J = 3.7 Hz), 125.58 (q, J = 3.7 Hz), 124.21 (q, J = 273.7 Hz), 123.98 (q, J = 272.3 Hz), 116.88, 97.84, 87.10, 32.23; 19 F NMR(377 MHz, Chloroform- d ) δ -62.52, -62.83. LCMS(ESI+) m / z calculated for C 28 H 16 F6ONa + [M+Na] + : 505.0998, found: 505.0998. Example 11

[0043] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-bis(2-(trifluoromethyl)phenyl)penta-1,4-diyne-3-ol (1k) was added, and the reaction was carried out at 130 °C for 5.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100~50:1) was carried out to obtain 1-(3-(2-(trifluoromethyl)phenyl)-1-((2-(trifluoromethyl)phenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2k).

[0044] 2k in this example was 79.1 mg, and the isolated yield was 82%. 1 H NMR(400 MHz, Chloroform- d ) δ 8.55 (d, J = 8.4 Hz, 1H), 7.87 (d, J = 8.1 Hz, 1H), 7.82 – 7.78 (m, 2H), 7.77 – 7.69 (m, 3H), 7.65 – 7.61 (m, 1H), 7.60 – 7.50 (m, 3H), 7.47 (t, J = 7.7 Hz, 1H), 7.40 (d, J= 7.5 Hz, 1H), 2.37 (s, 3H); 13 C NMR (151 MHz, Chloroform- d ) δ204.34, 144.03, 137.54, 134.51, 133.49, 132.66, 132.55, 132.16, 131.74,131.28, 131.21 (q, J = 30.7 Hz), 130.92, 128.93 (d, J = 29.8 Hz), 128.75, 128.60,128.38, 128.36, 128.02, 126.51, 126.38 (q, J = 5.2 Hz), 126.13 (q, J = 5.1 Hz),124.18 (d, J = 273.9 Hz), 123.73 (d, J = 273.4 Hz), 121.09 (d, J = 2.1 Hz), 116.43,95.09, 90.48, 31.74; 19 F NMR(377 MHz, Chloroform- d ) δ -56.95, -61.89.LCMS(ESI+)m / z calculated for C 28 H 16 F6ONa + [M+Na] + : 505.0998, found: 505.1001. Example 12

[0045] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, and then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-bis(naphthalen-1-yl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyne-3-ol (1l) was added, and the reaction was carried out at 130 °C for 8 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100 - 50:1) was carried out to obtain 1-(4'-(naphthalen-1-yl ethynyl)-[1,2'-binaphthalene]-3'-yl)ethan-1-one (brown solid product 2l).

[0046] In this example, 2l is 50.4 mg and the separation yield is 56%. 1 H NMR(400 MHz, Chloroform- d ) δ8.75 (d, J = 8.4 Hz, 1H), 8.54 (d, J = 8.2 Hz, 1H), 7.96 (s, 1H), 7.95 – 7.87 (m,6H), 7.81 – 7.74 (m, 2H), 7.71 – 7.64 (m, 2H), 7.57 (t, J = 7.2 Hz, 2H), 7.55 –7.44 (m, 4H), 2.20 (s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ 204.89, 144.94,136.88, 134.05, 133.76, 133.42, 133.34, 132.78, 132.52, 132.23, 131.08,131.03, 129.51, 128.68, 128.53,128.44, 128.41, 127.96, 127.83, 127.28,126.79, 126.71, 126.59, 126.40, 126.24, 126.22, 125.37, 125.29, 120.66,117.34, 97.64, 89.72, 31.76;LCMS(ESI+) m / z calculated for C 34 H 22 ONa + [M+Na] + :469.1563, found: 469.1560. Example 13

[0047] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 1,5-bis(naphthalen-2-yl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyne-3-ol (1m), and react at 130 °C for 8 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100 - 50:1) to obtain 1-(4-(naphthalen-2-ylethynyl)-[2,2'-binaphthalene]-3-yl)ethan-1-one (yellow solid product 2m).

[0048] In this example, the amount of 2m is 42.3 mg, and the separation yield is 47%. R f = 0.20 (petroleum ether / ethyl acetate = 25 / 1); 1 1H NMR(400 MHz, Chloroform- d ) δ 8.63 (d, J = 8.2 Hz, 1H), 8.17 (s, 1H), 7.99 –7.91 (m, 6H), 7.89 – 7.84 (m, 3H), 7.75 – 7.68 (m, 2H), 7.67 –7.61 (m, 2H),7.59 – 7.50 (m, 4H), 2.34 (s, 3H); 13 13C NMR(101 MHz, Chloroform- d ) δ 205.42,144.03, 137.31, 135.98, 133.38, 133.19, 133.11, 133.05, 132.81, 132.25,131.84, 130.01,128.52, 128.39, 128.29, 128.02, 127.95, 127.87, 127.83,127.81, 127.17, 127.07, 126.82, 126.71, 126.58, 120.26, 117.40, 99.65, 85.49,32.18; LCMS(ESI+) m / z calculated for C 34 H 22 ONa + [M+Na] + : 469.1563, found:469.1560. Example 14

[0049] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-(4-methoxy-2-(prop-1-yn-1-yl)phenyl)-1,5-diphenyl-1,4-diyne-3-ol (1n), and react at 130 °C for 5.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and obtain 1-(6-methoxy-3-phenyl-1-(phenylethynyl)naphthalen-2-yl)ethan-1-one (yellow solid product 2n) by silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100~50:1).

[0050] The 2n in this example is 28.6 mg, and the isolated yield is 38%. 1 H NMR(400 MHz, Chloroform- d ) δ8.41 (d, J = 9.1 Hz, 1H), 7.72 (s, 1H), 7.66 – 7.59 (m, 2H), 7.48 – 7.36 (m,8H), 7.34 – 7.27 (m, 1H), 7.17(s, 1H), 3.95 (s, 3H), 2.27 (s, 3H); 13 C NMR(101MHz, Chloroform- d ) δ 205.46, 159.09, 141.69, 140.10, 136.73, 134.44, 131.84,129.20, 128.91, 128.75, 128.57, 128.52, 128.42, 127.96,127.62, 123.02,120.48, 117.23, 106.21, 98.73, 85.29, 55.56, 32.14;LCMS(ESI+) m / z calculatedfor C 27 H 20 O2Na + [M+Na] + : 399.1356, found: 399.1357. Example 15

[0051] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-(5-methyl-2-(prop-1-yn-1-yl)phenyl)-1,5-diphenyl-1,4-diyne-3-ol (1o), and react at 130 °C for 5.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100~50:1) to obtain 1-(7-methyl-3-phenyl-1-(phenylethynyl)naphthalen-2-yl)ethan-1-one (orange liquid product 2o).

[0052] In this example, the amount of 2o is 44.7 mg, and the isolated yield is 62%. 1 H NMR(400 MHz, Chloroform- d ) δ8.30 – 8.27 (m, 1H), 7.79 (t, J = 4.2 Hz, 2H), 7.69 – 7.64 (m, 2H), 7.51 – 7.38(m, 9H), 2.63 (s, 3H), 2.31 (s,3H); 13 C NMR(101 MHz, Chloroform- d ) δ 205.56,143.90, 139.95, 137.75, 135.06, 132.32, 131.79, 131.23, 129.99, 129.46,129.24, 128.84, 128.70, 128.55, 128.26, 127.85, 125.61,123.09, 116.34, 98.84,85.28, 32.04, 22.23;LCMS(ESI+) m / z calculated for C 27 H 20 ONa + [M+Na] + : 383.1407,found: 383.1410. Example 16

[0053] To a 4 mL sample vial, 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 8-(2-(prop-1-yn-1-yl)phenyl)pentadeca-6,9-dien-8-ol (1p) was added, and the reaction was carried out at 130 °C for 6 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100 - 50:1) was performed to obtain 1-(1-(hept-1-en-1-yl)-3-pentylnaphthalen-2-yl)ethan-1-one (2p) and 1-(4-(hept-1-yn-1-yl)-2-pentylnaphthalen-1-yl)ethan-1-one (2p’) (orange liquid products 2p and 2p’).

[0054] The total mass of 2p and 2p’ in this example was 56.2 mg, and the total isolated yield of 2p and 2p’ was 84% (2p:2p’ = 5:1). 1 HNMR(400 MHz, Chloroform- d ) δ 8.37 – 8.34 (m, 1H), 8.33 – 8.29 (m, 1H), 7.78 –7.73 (m, 1H), 7.61 (s, 1H), 7.55 – 7.46 (m, 3H), 2.69 (s, 3H), 2.68(s, 0H),2.66 – 2.62 (m, 2H), 2.56 (t, J = 7.1 Hz, 3H), 1.74 – 1.61 (m, 5H), 1.54 – 1.45(m, 2H), 1.44 – 1.33 (m, 8H), 0.99 – 0.86 (m, 8H); 1 H NMR(400 MHz, Chloroform- d ) δ 8.37 – 8.34 (m, 0.2H, 2p’), 8.33 – 8.29 (m, 1H, 2p), 7.78 – 7.73 (m,1H),7.61 (s, 1H), 7.55 – 7.46 (m, 3H), 2.69 (s, 2.92H, 2p), 2.68 (s, 0.53H,2p’), 2.66 – 2.62 (m, 2H), 2.56 (t, J = 7.1 Hz, 2H), 1.74 – 1.61 (m, 5H),1.54 – 1.45(m, 2H), 1.44 – 1.33 (m, 7H), 0.99 – 0.86 (m, 7H); 1313C NMR (101 MHz, Chloroform- d ) δ 207.90 (2p’), 206.77 (2p), 144.18 (2p), 138.30 (2p’), 135.42 (2p), 134.65 (2p’), 133.10 (2p), 132.00 (2p’), 131.79 (2p), 131.51 (2p’), 128.93 (2p’), 127.86 (2p), 127.73 (2p), 127.22 (2p’), 127.05 (2p), 126.82 (2p’), 126.55 (2p), 126.27 (2p), 126.15 (2p’), 124.40 (2p’), 122.93 (2p’), 117.33 (2p), 101.16 (2p), 96.33 (2p’), 78.34 (2p’), 76.46 (2p), 33.55 (2p’), 33.40 (2p’), 33.31 (2p), 32.26 (2p), 31.89 (2p’), 31.80 (2p), 31.35 (2p’), 31.27 (2p), 31.02 (2p), 28.67 (2p’), 28.45 (2p), 22.61, 22.37 (2p’), 22.33 (2p), 19.90 (2p), 19.82 (2p’), 14.11; LCMS (ESI+) m / z calculated for C 24 H 30 ONa + [M+Na] + : 357.2189, found: 357.2194. Example 17

[0055] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample bottle, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 2,2,8,8-tetramethyl-5-(2-(prop-1-yn-1-yl)phenyl)nona-3,6-diyne-5-ol (1q), and react at 130 °C for 5.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100~50:1) to obtain 1-(3-(tert-butyl)-1-(3,3-dimethylbut-1-yn-1-yl)naphthalen-2-yl)ethan-1-one (yellow liquid product 2q).

[0056] In this example, 2q is 41.5 mg and the separation yield is 68%. 1 H NMR(600 MHz, Chloroform- d ) δ8.26 (d, J = 8.2 Hz, 1H), 7.83 (s, 1H), 7.78 (d, J = 8.0 Hz, 1H), 7.52 (dt, J =22.4, 7.2 Hz, 2H), 2.79 (s, 3H), 1.45 (s, 9H), 1.41 (s, 9H); 13 C NMR(151 MHz,Chloroform- d ) δ 208.38, 144.38, 143.63, 132.62, 131.45, 128.23, 126.96,126.90, 125.83, 125.70, 117.92, 109.50,75.52, 36.15, 33.64, 31.86, 30.86,28.66;LCMS(ESI+) m / z calculated for C 22 H 26 ONa + [M+Na] + : 329.1876, found:329.1880. Example 18

[0057] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 1,5-dicyclopropyl-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-dien-3-ol (1r), and react at 130 °C for 5.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100~50:1) to obtain 1-(3-cyclopropyl-1-(cyclopropylethynyl)naphthalen-2-yl)ethan-1-one (2r) and 1-(2-cyclopropyl-4-(cyclopropylethynyl)naphthalen-1-yl)ethan-1-one (2r’) (orange liquid products 2r and 2r’).

[0058] The total mass of 2r and 2r’ in this example is 38.2 mg, and the total separation yield of 2r and 2r’ is 70% (2r:2r’ = 1:0.25). 11H NMR (400 MHz, Chloroform- d ) δ 8.30 – 8.26 (m, 0.25H, 2r’), 8.26 – 8.21 (m, 1H, 2r), 7.73 – 7.69 (m, 1H, 2r), 7.62 – 7.57 (m, 0.25H, 2r’), 7.55 – 7.45 (m, 2.5H), 7.39 (s, 1H, 2r), 7.16 (s, 0.25H, 2r’), 2.70 (s, 3H, 2r), 2.68 (s, 0.75H, 2r’), 2.03 – 1.95 (m, 1H, 2r), 1.94 – 1.89 (m, 0.25H, 2r’), 1.64 – 1.55 (m, 1.25H), 1.07 – 1.00 (m, 0.50H, 2r’), 1.00 – 0.92 (m, 4.5H), 0.92 – 0.86 (m, 2H, 2r), 0.86 – 0.82 (m, 0.50H, 2r’), 0.79 – 0.73 (m, 2H, 2r); 13 13C NMR (101 MHz, Chloroform- d ) δ 208.16 (2r’), 206.81 (2r), 145.47 (2r), 139.09 (2r’), 135.89 (2r), 134.99 (2r’), 133.07 (2r), 131.99 (2r’), 131.82 (2r), 128.70 (2r’), 127.83 (2r), 127.41 (2r’), 127.10 (2r), 127.05 (2r’), 126.72 (2r’), 126.62 (2r), 126.23 (2r), 126.12 (2r’), 124.50 (2r), 124.11 (2r’), 123.04 (2r’), 116.86 (2r), 103.99 (2r), 99.35 (2r’), 73.60 (2r’), 71.30 (2r), 33.38 (2r’), 31.99 (2r), 13.47 (2r), 13.27 (2r’), 9.11 (2r), 9.08 (2r’), 8.70 (2r’), 7.86 (2r), 0.73 (2r), 0.58 (2r’); LCMS (ESI+) m / z calculated for C 20 H 18 ONa+ [M+Na] + : 297.1250, found: 297.1253. Example 19

[0059] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-phenyl-1-(2-(prop-1-yn-1-yl)phenyl)prop-2-en-1-ol (1s), and react at 130 °C for 5.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100 - 50:1) to obtain 1-(3-phenylnaphthalen-2-yl)ethan-1-one (orange liquid product 2s).

[0060] The amount of 2s in this example is 16 mg, and the isolated yield is 32%. 1 H NMR(400 MHz, Chloroform- d ) δ 8.12(s, 1H), 7.95 (d, J = 7.9 Hz, 1H), 7.88 (d, J = 7.9 Hz, 1H), 7.85 (s, 1H), 7.63 –7.50 (m, 2H), 7.50 – 7.42 (m, 5H), 2.15 (s, 3H); 13 C NMR(101 MHz, Chloroform- d )δ 204.08, 140.97, 139.29, 137.46, 134.12, 131.80, 129.47, 128.96, 128.75,128.72, 128.54, 128.03, 127.83, 127.71,126.83, 30.46;LCMS(ESI+) m / zcalculated for C 18 H 14 ONa + [M+Na] + : 269.0937, found: 269.0935. Example 20 Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 4-phenyl-2-(2-(prop-1-yn-1-yl)phenyl)but-3-yn-2-ol (1t), and react at 130 °C for 5.5 h. After the reaction is complete, remove EtOAc under reduced pressure and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100:1) to obtain 1-(1-methyl-3-phenylnaphthalen-2-yl)ethan-1-one (2t) and 1-(4-methyl-2-phenylnaphthalen-1-yl)ethan-1-one (2t’) (yellow liquid products 2t and 2t’).

[0061] The total mass of 2t and 2t’ in this example is 46.9 mg, and the total separation yield of 2t and 2t’ is 90% (2t:2t’ = 2:1). 1 HNMR(400 MHz, Chloroform- d ) δ 8.13 – 8.09 (m, 1H, 2t), 8.09 – 8.06 (m, 0.55H,2t’), 7.93 – 7.88 (m, 0.55H, 2t’), 7.89 – 7.85 (m, 1H, 2t), 7.73 (s, 1H,2t),7.63 – 7.54 (m, 3H), 7.50 – 7.37 (m, 8.4H), 2.77 (s, 1.65H, 2t’), 2.66 (s,3H, 2t), 2.09 (s, 1.65H, 2t’), 2.04 (s, 3H, 2t); 13 C NMR(101 MHz, Chloroform- d)δ 208.43(2t), 207.86(2t’), 140.69(2t), 140.61(2t’), 140.03(2t), 136.94(2t’),136.15(2t’), 135.84(2t’),135.81(2t), 133.14(2t), 131.86(2t’), 131.80(2t),129.83(2t), 129.43(2t’), 129.35(2t), 129.16(2t’), 128.82(2t’), 128.78(2t),128.71(2t), 128.31(2t’),128.03(2t’), 127.77(2t), 127.48(2t), 127.19(2t’),126.92(2t), 126.78(2t), 126.29(2t’), 125.50(2t’), 124.69(2t), 124.48(2t’),33.00(2t’), 32.88(2t),19.78(2t’), 15.72(2t);LCMS(ESI+) m / z calculated forC 19 H 16 ONa + [M+Na] + : 283.1094, found: 283.1097. Example 21

[0062] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 1,3-diphenyl-1-(2-(prop-1-en-1-yl)phenyl)prop-2-en-1-ol (1u), and react at 130 °C for 8 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100~50:1) to obtain 1-(1,3-diphenylnaphthalen-2-yl)ethan-1-one (yellow solid product 2u).

[0063] The 2u in this example is 40.5 mg, and the isolated yield is 63%. 1 H NMR(400 MHz, Chloroform- d ) δ7.93 (d, J= 8.2 Hz, 1H), 7.89 (s, 1H), 7.61 – 7.37 (m, 13H), 1.87 (s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ 206.23, 140.56, 140.18, 137.67, 136.28, 136.01,133.19, 131.58, 130.76, 129.40, 128.92, 128.60,128.33, 128.15, 127.98,127.72, 127.09, 126.95, 126.79, 33.02; LCMS(ESI+) m / z calculated for C 24 H 18 ONa + [M+Na] + : 345.1250, found: 345.1255. Example 22 To a 4 mL sample vial was added 0.01 mmol KAuCl4 and 0.03 mmol benzyl mercaptan, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 1,3-diphenyl-1-(2-(prop-1-en-1-yl)phenyl)prop-2-en-1-ol (1v) was added, and the reaction was carried out at 130 °C for 9 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (volume ratio of petroleum ether to ethyl acetate was 100~50:1) was carried out to obtain 1-(1-(3,3-dimethylbut-1-yn-1-yl)-3-phenylnaphthalen-2-yl)ethan-1-one (2v-1) and 1-(3-(tert-butyl)-1-(phenylethynyl)naphthalen-2-yl)ethan-1-one (2v-2) (yellow liquid products 2v-1 and 2v-2).

[0064] The total mass of 2v-1 and 2v-2 in this example was 43.5 mg, and the total separation yield of 2v-1 and 2v-2 was 67% (2v-1:2v-2 = 3.4:1). 1 H NMR(400 MHz, Chloroform- d) δ 8.44 – 8.34 (m, 1H), 7.92 (s,0.21H), 7.88 – 7.80 (m, 1H), 7.76 (s, 0.71H), 7.68 (s, 0.08H), 7.65 – 7.35(m,7H), 2.86 (s, 0.62H, 2v-2), 2.26 (s, 2.12H, 2v-1), 2.08 (s, 0.24H), 1.48(s,1.87H, 2v-2), 1.45 (s, 0.72H), 1.42 (s, 6.38H, 2v-1); 13 C NMR(101 MHz,Chloroform- d ) δ 208.12(2v-2), 205.63(2v-1), 144.90(2v-2), 143.80(2v-2),143.63(2v-1), 140.01(2v-1), 135.87(2v-1), 132.91(2v-1),132.66(2v-2), 132.27(2v-1), 131.64(2v-1), , 129.27(2v-1), 128.91(2v-2), 128.86(2v-2), 128.86(2v-1), 128.65(2v-1), 128.63 (2v-1), 128.37(2v-2),128.31(2v-1), 127.85(2v-1),127.49(2v-1), 127.39(2v-1), 127.22(2v-1), 126.71(2v-1), 126.67 (2v-2), 125.81(2v-1), , 123.03(2v-2), 117.82(2v-1),117.20(2v-2), 108.89(2v-1), 99.97(2v-2),85.63(2v-2), 74.94(2v-1), 36.26, 33.75, 31.93, 31.90, 30.92(2v-1), 28.65;LCMS(ESI+) m / z calculated for C 24 H 22 ONa + [M+Na] + : 349.1563, found: 349.1562. Example 23

[0065] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-(2-(hept-1-yn-1-yl)phenyl)-1,5-diphenylpenta-1,4-diyne-3-ol (1w), and react at 130 °C for 9.5 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 100 - 50:1) to obtain 1-(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)hexan-1-one (brown liquid product 2w).

[0066] The 2w in this example was 62.2 mg, and the isolated yield was 77%. 1 H NMR(400 MHz, Chloroform- d ) δ8.53 (d, J = 8.3 Hz, 1H), 7.90 (d, J = 8.0 Hz, 1H), 7.84 (s, 1H), 7.70 – 7.57 (m,4H), 7.52 – 7.37 (m, 8H), 2.47 (t, J = 7.2 Hz, 2H), 1.52 (p, J = 7.2 Hz, 2H),1.19 – 1.08 (m, 4H), 0.77 (t, J = 6.8 Hz, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ207.90, 144.00, 139.77, 136.03, 132.91, 132.18, 131.81, 129.53, 129.43,128.85, 128.67, 128.54, 128.43, 127.96,127.62, 127.59, 126.67, 123.05,117.32, 98.79, 85.22, 44.42, 31.21, 23.29, 22.41, 13.93;LCMS(ESI+) m / zcalculated for C 30 H 26 ONa + [M+Na] + : 425.1876, found: 425.1879. Example 24

[0067] 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, and then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(cyclopropyl ethynyl)phenyl)-1,5-diphenylpenta-1,4-diyne-3-ol (1x) was added, and the reaction was carried out at 130 °C for 9.5 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 100 - 50:1) was carried out to obtain cyclopropyl(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)methanone (yellow solid product 2x).

[0068] The 2x in this example was 20.8 mg, and the isolated yield was 28%. 1 H NMR(400 MHz, Chloroform- d ) δ8.55 (d, J = 8.2 Hz, 1H), 7.90 (d, J = 8.1 Hz, 1H), 7.86 (s, 1H), 7.72 – 7.58 (m,4H), 7.50 (d, J = 7.4 Hz, 2H), 7.47 – 7.37 (m, 6H), 2.23 – 2.13 (m, 1H), 1.21 –1.13 (m, 2H),0.95 – 0.80 (m, 2H); 13 C NMR(101 MHz, Chloroform- d ) δ 207.34,144.27, 140.10, 136.71, 133.06, 132.22, 131.79, 129.60, 129.49, 128.80,128.55, 128.44, 127.76, 127.67, 127.58,126.75, 123.23, 117.78, 99.05, 85.59,24.03, 13.17;LCMS(ESI+) m / z calculated for C 28 H 20 ONa + [M+Na] + : 395.1407, found:395.1409. Example 25

[0069] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 3-(2-((4-methoxyphenyl)ethynyl)phenyl)-1,5-diphenylpenta-1,4-diyne-3-ol (1y), and react at 130 °C for 8 h. After the reaction is completed, remove EtOAc under reduced pressure, and obtain (4-methoxyphenyl)(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)methanone (brown liquid product 2y) by silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 50 - 25:1).

[0070] For 2y in this example, it was 16.6 mg, and the isolated yield was 19%. 1 H NMR(400 MHz, Chloroform- d ) δ8.55 (d, J = 8.3 Hz, 1H), 7.88 (s, 1H), 7.74 (d, J = 8.5 Hz, 1H), 7.71 – 7.67 (m,2H), 7.65 – 7.60 (m, 3H), 7.52 – 7.47 (m, 1H), 7.45 – 7.38 (m, 5H), 7.28 –7.19 (m, 3H), 6.73 (d, J = 8.9 Hz, 2H), 3.77 (s, 3H); 13 C NMR(101 MHz,Chloroform- d ) δ 197.65, 163.89, 139.73, 136.86, 136.59, 132.31, 132.18,132.07, 131.90, 131.09, 130.83, 129.48, 128.83, 128.65,128.39, 127.73,127.71, 127.19, 126.59, 126.23, 123.22, 122.43, 113.79, 95.39, 87.21, 55.53;LCMS(ESI+) m / z calculated for C 32 H 22 O2Na + [M+Na] + : 461.1512, found: 461.1509. Example 26 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan were added to a 4 mL sample vial, and then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 4-((tert-butyldimethylsilyl)oxy)-1-(4,5-dimethoxy-2-(prop-1-yn-1-yl)phenyl)-1-phenylbut-2-yn-1-ol (1z) was added, and the reaction was carried out at 130 °C for 8 h. After the reaction was completed, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 50~25:1) was carried out to obtain 1-(3-((tert-butyldimethylsilyl)oxy)methyl)-6,7-dimethoxy-1-phenylnaphthalen-2-yl)ethan-1-one (yellow liquid product 2z).

[0071] In this example, the amount of 2z was 55.9 mg, and the isolated yield was 62%. 1 H NMR(600 MHz, Chloroform- d ) δ7.74 (s, 1H), 7.51 – 7.42 (m, 3H), 7.39 – 7.35 (m, 2H), 7.15 (s, 1H), 6.92(s, 1H), 4.82 (s, 2H), 4.02 (s, 3H), 3.74(s, 3H), 1.89 (s, 3H), 0.95 (s, 9H),0.12 (s, 6H); 13 C NMR(151 MHz, Chloroform- d ) δ 207.39, 150.23, 149.92, 138.18,137.38, 134.70, 133.10, 130.92, 129.48, 128.67, 128.14, 126.85,124.90,106.59, 105.32, 63.93, 56.07, 55.76, 32.30, 26.17, 18.67, -5.21;LCMS(ESI+) m / z calculated for C 27 H 34 O4SiNa + [M+Na] + : 473.2119, found: 473.2125. Dissolve 0.1 mmol of compound 2z in 2.3 mL of dry tetrahydrofuran, cool to 0 °C, add tetrabutylammonium fluoride TBAF (1 mol / L, 0.12 mmol), and react at 0 °C for 3.5 h. After the reaction is complete, quench with saturated aqueous NH4Cl solution, extract with EtOAc, wash the combined organic phases with saturated aqueous NaCl solution, dry over anhydrous Na2SO4, filter by suction, and concentrate under reduced pressure to dryness. Purify the residue by silica gel chromatography (eluent: petroleum ether and ethyl acetate in a volume ratio of 2:1) to obtain yellow solid 3z, 30.9 mg, with a separation yield of 92%.

[0072] In a reaction kettle, dissolve 0.55 mmol of compound 3z in 13.8 mL of DMSO, successively add 0.22 mmol of CuCl2, 0.22 mmol of 1,10-phenanthroline, 1.1 mmol of NIS (N-iodosuccinimide), 2.75 mmol of K2CO3, and 275 mg of 4 Å molecular sieve, and react at 100 °C for 6 h under an O2 atmosphere of 0.5 MPa. After the reaction is complete, quench with saturated aqueous NH4Cl solution, extract with EtOAc, wash the combined organic phases with saturated aqueous NaCl solution, dry over anhydrous Na2SO4, filter by suction, and concentrate under reduced pressure to dryness. Perform silica gel column chromatography (volume ratio of petroleum ether to ethyl acetate is 3:1) to obtain 6,7-dimethoxy-9-phenylnaphtho[2,3-c]furan-1(3H)-one (orange solid 4z).

[0073] 4z in this example is 108.1 mg, with a separation yield of 62%. 1 H NMR(400 MHz, Chloroform- d ) δ7.72 (s, 1H), 7.56 – 7.48 (m, 3H), 7.42 – 7.36 (m, 2H), 7.20 (s, 1H), 7.04(s, 1H), 5.38 (s, 2H), 4.05 (s, 3H), 3.75(s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ 170.09, 151.91, 150.16, 140.17, 139.66, 135.04, 133.28, 130.00, 128.71,128.35, 128.22, 118.45, 106.14, 106.01, 68.19, 56.19,55.82;LCMS(ESI+) m / zcalculated for C 20 H 16 O4Na +[M+Na] + : 343.0941, found: 343.0945. Example 27

[0074] Add 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan to a 4 mL sample vial, then add 2.4 mL of EtOAc. After stirring at room temperature for 10 min, add 0.2 mmol of 1-(benzo[d][1,3]dioxol-5-yl)-4-((tert-butyldimethylsilyl)oxy)-1-(6-(prop-1-yn-1-yl)benzo[d][1,3]dioxol-5-yl)but-2-yn-1-ol (1aa), and react at 130 °C for 8 h. After the reaction is completed, remove EtOAc under reduced pressure, and perform silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate is 50 - 25:1) to obtain 1-(5-(benzo[d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)methyl)naphtho[2,3-d][1,3]dioxol-6-yl)ethan-1-one (yellow solid product 2aa).

[0075] 2aa in this example was 54.7 mg, and the isolated yield was 57%. R f = 0.23 (Petrolether / Ethylacetate = 5 / 1); 1 H NMR(400 MHz, Chloroform- d ) δ 7.68 (s, 1H), 7.14 (s, 1H),6.97 (s, 1H), 6.90 (d, J = 7.9 Hz, 1H), 6.81 (s, 1H), 6.75 (d, J = 7.9 Hz, 1H),6.05 (d, J = 5.9 Hz, 2H), 6.02 (d, J = 2.8 Hz, 2H), 4.78 (s, 2H), 1.99 (s, 3H),0.94 (s, 9H), 0.11 (s, 6H); 13 C NMR(101 MHz, Chloroform- d) δ 207.10, 148.39,148.30, 147.83, 147.64, 137.67, 134.76, 133.24, 131.56,130.81, 128.64,125.55, 124.75, 111.35, 108.66, 104.19, 102.95, 101.44, 101.39, 63.82, 32.38,26.16, 18.68, -5.21;LCMS(ESI+) m / z calculated for C 27 H 30 O6SiNa + [M+Na] + :501.1704, found: 501.1711. Dissolve 0.1 mmol of compound 2aa in 2.3 mL of dry THF, cool to 0 °C, add TBAF (1 mol / L, 0.12 mmol), and react at 0 °C for 3.5 h. After completion of the reaction, quench with saturated aqueous NH4Cl solution, extract with EtOAc, wash the combined organic phases with saturated aqueous NaCl solution, dry over anhydrous Na2SO4, filter by suction, and concentrate under reduced pressure to dryness. Purify the residue by silica gel chromatography (eluent: petroleum ether / ethyl acetate = 2:1, v / v) to obtain yellow liquid 3aa, 36.0 mg, with a separation yield of 99%.

[0076] In a reaction kettle, dissolve 0.26 mmol of compound 3aa in 6.5 mL of DMSO, and successively add 0.104 mmol of CuCl2, 0.104 mmol of 1,10-phenanthroline, 0.52 mmol of NIS, 1.3 mmol of K2CO3, and 130 mg of 4 Å molecular sieve. React at 100 °C for 6 h under an O2 atmosphere of 0.5 MPa. After completion of the reaction, quench with saturated aqueous NH4Cl solution, extract with EtOAc, wash the combined organic phases with saturated aqueous NaCl solution, dry over anhydrous Na2SO4, filter by suction, and concentrate under reduced pressure to dryness. Perform silica gel column chromatography (petroleum ether / ethyl acetate = 3 - 2:1, v / v) to obtain 5-(benzo[d][1,3]dioxol-5-yl)furo[3',4':6,7]naphtho[2,3-d][1,3]dioxin-6(8H)-one (white solid Taiwanin C).

[0077] The Taiwanin C in this example is 23.5 mg, with a separation yield of 26%. 1 H NMR(400 MHz, DMSO- d6) δ 7.94 (s, 1H), 7.52 (s, 1H), 7.04 (d, J = 7.9 Hz, 1H), 6.90 (s, 1H), 6.88 (d, J = 1.6 Hz, 1H), 6.75 (dd, J = 7.9, 1.6 Hz, 1H), 6.18 (d, J = 2.4 Hz, 2H), 6.14 (s, 1H), 6.11 (s, 1H), 5.43 (s, 2H); 13 C NMR(151 MHz, DMSO - d 6) δ 169.26, 149.61, 148.45, 147.00, 147.00, 140.30, 138.70, 134.32, 129.41, 128.37, 123.35, 119.61, 118.48, 110.51, 108.01, 103.77, 102.18, 102.14, 101.18, 68.01; LCMS(ESI+) m / z calculated for C 20 H 12 O6Na + [M + Na] + : 371.0527, found: 371.0530. Example 28

[0078] To a 4 mL sample vial was added 0.01 mmol of KAuCl4 and 0.03 mmol of benzyl mercaptan, then 2.4 mL of EtOAc was added. After stirring at room temperature for 10 min, 0.2 mmol of 1-(benzo[D][1,3]dioxol - 5 - yl)-4-((tert - butyldimethylsilyl)oxy)-1-(4,5 - dimethoxy - 2-(prop - 1 - yn - 1 - yl)phenyl)but - 2 - yn - 1 - ol (1ab) was added, and the reaction was carried out at 130 °C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 50 - 25:1) was carried out to obtain 1-(1-(benzo[D][1,3]dioxol - 5 - yl)-3-((tert - butyldimethylsilyl)oxymethyl)-6,7 - dimethoxynaphthalen - 2 - yl)ethan - 1 - one (yellow liquid product 2ab).

[0079] The total mass of 2ab and 2ab' in this example is 65.0 mg, and the total separation yield of 2ab and 2ab' is 66% (2ab:2ab' = 5:1). R f = 0.21 (Petrolether / Ethyl acetate = 5 / 1); 1 H NMR(400 MHz, Chloroform- d )δ 7.74 (s, 1H), 7.29 (s, 1H), 7.17 (s, 1H), 7.00 (s, 1H), 6.98 – 6.92 (m,1H), 6.88 (s, 1H), 6.84 (d, J = 8.0 Hz, 1H), 6.11 (s, 1H), 6.08 – 6.05 (m,1.4H), 4.85 (s, 0.4H, 2ab’), 4.83 (s, 2H, 2ab),4.05 (s, 3H, 2ab), 3.99 (s,0.6H, 2ab’), 3.86 (s, 0.6H, 2ab’), 3.83 (s, 3H, 2ab), 2.73 (s, 0.6H, 2ab’),2.02 (s, 3H, 2ab), 0.97 (s, 9H, 2ab), 0.96 (s, 1.5H, 2ab’),0.15 (s, 7.2H); 13 CNMR(101 MHz, Chloroform- d) δ 207.27 (2ab), 150.28 (2ab), 149.98 (2ab), 147.89(2ab), 147.60 (2ab), 137.52 (2ab), 134.22 (2ab), 133.10 (2ab), 131.68 (2ab),129.52 (2ab), 127.08 (2ab), 124.89 (2ab), 124.71 (2ab), 123.28 (2ab’), 111.28(2ab), 110.36 (2ab’), 108.67 (2ab), 108.51 (2ab’), 106.66 (2ab), 105.33(2ab’),105.28 (2ab), 103.37 (2ab’), 101.44 (2ab), 101.34 (2ab’), 63.92 (2ab),63.77 (2ab’), 56.09 (2ab), 56.00 (2ab’), 55.92 (2ab), 33.33 (2ab’), 32.38(2ab), 26.18 (2ab),26.10 (2ab’), 18.69 (2ab), -5.19 (2ab); LCMS(ESI+) m / zcalculated for C 28 H 34 O6SiNa + [M+Na] + : 517.2017, found: 517.2023. Dissolve 0.1 mmol of compound 2ab in 2.3 mL of dry THF, cool to 0 °C, add TBAF (1 mol / L, 0.12 mmol), and react at 0 °C for 3.5 h. After completion of the reaction, quench with saturated aqueous NH4Cl, extract with EtOAc, wash the combined organic phases with saturated aqueous NaCl, dry over anhydrous Na2SO4, filter by suction, and concentrate under reduced pressure to dryness. Purify the residue by silica gel chromatography (eluent: petroleum ether and ethyl acetate in a volume ratio of 2:1) to obtain 37.2 mg of yellow solid 3ab, with a separation yield of 98%.

[0080] In a reaction kettle, 0.28 mmol of compound 3ab was dissolved in 7.0 mL of DMSO. Then, 0.112 mmol of CuCl2, 0.112 mmol of 1,10-phenanthroline, 0.56 mmol of NIS, 1.4 mmol of K2CO3, and 140 mg of 4Å molecular sieve were added successively. The reaction was carried out at 100 °C for 6 h under an O2 atmosphere of 0.5 MPa. After the reaction was completed, it was quenched with saturated NH4Cl aqueous solution, extracted with EtOAc. The combined organic phases were washed with saturated NaCl, dried over anhydrous Na2SO4, filtered by suction, and concentrated under reduced pressure to dryness. Through silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 3 - 2:1), 9-(benzo[d][1,3]dioxol-5-yl)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one (orange solid Justicidin B) was obtained.

[0081] In this example, the amount of Justicidin B obtained was 26.2 mg, and the isolated yield was 26%. 1 H NMR(400 MHz,Chloroform- d ) δ 7.70 (s, 1H), 7.19 (s, 1H), 7.11 (s, 1H), 6.97 (d, J = 7.8 Hz,1H), 6.88 – 6.80 (m, 2H), 6.11 – 6.08 (m, 1H), 6.05 (d, J = 1.8 Hz, 1H), 5.38(s, 2H), 4.05 (s, 3H), 3.82 (s, 3H); 13 C NMR(101 MHz, Chloroform- d ) δ 170.10,151.97, 150.23, 147.73, 147.69, 139.80, 139.67, 133.32, 129.00, 128.55,123.62, 118.67, 118.41, 110.72, 108.36, 106.16, 106.01,101.39, 68.18, 56.21,55.97;LCMS(ESI+) m / z calculated for C 21 H 16 O6Na + [M+Na] + : 387.0840, found:387.0844. Multifunctionalized β - naphthyl ethyl ketone is a very important class of organic small - molecule compounds. It is not only the core skeleton of natural lignan lactones (such as Justicidin B, Taiwanin C, Chinensin, and Daurinol, etc.), but also a key intermediate in pharmaceuticals, having potential application value in drug synthesis. It can also be used in the fragrance formulations of toiletries and industrial products.

[0082] The above are only the preferred embodiments of the present invention. It should be noted that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and refinements can be made, and these improvements and refinements should also be regarded as the protection scope of the present invention.

Claims

1. A multi-functionalized β-naphthone derivative, characterized in that, The structural formula of the polyfunctionalized β-naphthone derivative is as follows: ； Among them, R 1 is alkyl or aryl; R 2 is propyl, tert-butyl, n-pentyl, phenyl, naphthyl, thienyl, methylphenyl, methoxyphenyl, trifluoromethylphenyl, chlorophenyl, fluorophenyl or tert-butyldimethylsilyloxy methylene; R 3 is H, methyl or methoxy; R 4 is H, methyl, phenyl or alkynyl. When R 4 is alkynyl, the alkynyl is attached to R 2 .

2. The polyfunctionalized β-naphthone derivative according to claim 1, wherein The structural formula of the polyfunctionalized β-naphthone derivative is as follows: 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 。 3. A method for preparing the polyfunctionalized β-naphthone derivative according to claim 1 or 2, characterized in that, It includes the following steps: Mix potassium chloroaurate, benzyl methyl sulfide, and ethyl acetate to obtain a reaction solution, and react the reaction solution with a 1,6-diyne-3-ol compound to obtain a polyfunctionalized β-naphthone derivative; The structural formula of the 1,6-diyne-3-ol compound is as follows: ； wherein, R 1 is an alkyl or aryl group; R 2 is propyl, tert-butyl, n-pentyl, phenyl, naphthyl, thienyl, methylphenyl, methoxyphenyl, trifluoromethylphenyl, chlorophenyl, fluorophenyl or tert-butyldimethylsilyloxy methylene; R 3 is H, methyl or methoxy; R 4 is H, methyl, phenyl or alkynyl. When R 4 is alkynyl, the alkynyl is connected to R 2 .

4. The method for preparing the polyfunctionalized β-naphthone derivative according to claim 3, characterized in that, The molar ratio of the potassium chloroaurate, benzyl methyl sulfide, and 1,6-diyne-3-ol compound is 0.04~0.06:0.12~0.17:

1.

5. The method for preparing a polyfunctionalized β-naphthone derivative according to claim 3 or 4, characterized in that, The molar volume ratio of the 1,6-diyne-3-ol compound and ethyl acetate is 0.2 mmol:2.2~2.6 mL.

6. The preparation method of the polyfunctionalized β-naphthone derivative according to claim 5, characterized in that, The mixing time is 8~12 min; the reaction temperature is 120~140 °C, and the reaction time is 2~12 h.

7. The preparation method of the polyfunctionalized β-naphthone derivative according to claim 6, characterized in that, After the reaction is completed, a crude product is obtained. The crude product is successively subjected to reduced pressure and silica gel column chromatography to obtain a polyfunctionalized β-naphthone derivative; the eluent for silica gel column chromatography is petroleum ether and ethyl acetate.

8. Use of the polyfunctionalized β-naphthone derivative according to claim 1 or 2 in the preparation of a drug.

Images