A multifunctional β-naphthone derivative and its preparation method and application

Abstract

The present invention belongs to the technical field of naphthalene ketone derivatives and provides a multifunctional β-naphthalene ketone derivative and its preparation method and application. In the multifunctional β-naphthalene ketone derivative of the present invention, R 1 is an alkyl group or an aryl group; R 2 is an alkyl group, a phenyl group, a naphthyl group, a thienyl group, an aromatic ring connected to an electron-withdrawing group, or an aromatic ring connected to an electron-donating group, wherein the electron-withdrawing group and the electron-donating group include methyl, methoxy, trifluoromethyl, or halogen; R 3 is H, methyl or methoxy; R 4 The invention uses readily available 1,6-diyne-3-alcohol compounds as starting materials, potassium chloroaurate as a catalyst, and thioanisole as a ligand to obtain multifunctionalized β-naphthone derivatives through intramolecular 6-endo-dig cyclization, 3,3-Claisen rearrangement, aromatization, and finally a 1,3-acyl migration reaction on the aromatic ring.

Description

Technical Field

[0001] The present invention relates to the technical field of naphthone derivatives, in particular to a multifunctionalized beta-naphthone derivative and a preparation method and application thereof. Background Art

[0002] Due to the unique properties of the naphthone structure, polysubstituted naphthone compounds have a wide range of applications in medicinal chemistry. Among these, the most representative are lignan lactones containing a naphthone skeleton, a class of naturally occurring lignin compounds with biological activity. However, there are currently no reports on 1,3-acyl migration reactions on aromatic rings.

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

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

[0005] In order to achieve the above-mentioned object of the invention, the present invention provides the following technical solutions:

[0006] The present invention provides a multifunctional β-naphthone derivative, the structural formula of the multifunctional β-naphthone derivative is:

[0007] ;

[0008] Among them, 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-butyldimethylsilyloxymethylidene;

[0009] R 3 is H, methyl or methoxy;

[0010] R 4 is H, methyl, phenyl or alkynyl, when R 4 When it is an alkynyl group, the alkynyl group is connected to R 2 .

[0011] Preferably, the structural formula of the multifunctionalized β-naphthone derivative is:

[0012] 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 .

[0013] The present invention also provides a method for preparing the multifunctionalized β-naphthone derivative, comprising the following steps:

[0014] Potassium chloroaurate, thioanisole, and ethyl acetate are mixed to obtain a reaction solution, and the reaction solution is reacted with a 1,6-diyn-3-ol compound to obtain a multifunctional β-naphthone derivative;

[0015] The structural formula of 1,6-diyne-3-ol compounds is:

[0016] ;

[0017] Among them, 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-butyldimethylsilyloxymethylidene;

[0018] R 3 is H, methyl or methoxy;

[0019] R 4 is H, methyl, phenyl or alkynyl, when R 4 When it is an alkynyl group, the alkynyl group is connected to R 2 .

[0020] Preferably, the molar ratio of the potassium chloroaurate, thioanisole and 1,6-diyn-3-ol compound is 0.04-0.06:0.12-0.17:1.

[0021] Preferably, the molar volume ratio of the 1,6-diyn-3-ol compound to ethyl acetate is 0.2 mmol: 2.2-2.6 mL.

[0022] Preferably, the mixing time is 8 to 12 minutes; the reaction temperature is 120 to 140° C., and the reaction time is 2 to 12 hours.

[0023] Preferably, after the reaction is completed, a crude product is obtained, and the crude product is subjected to decompression and silica gel column chromatography in sequence to obtain a multifunctional β-naphthone derivative; the eluent for the silica gel column chromatography is petroleum ether and ethyl acetate.

[0024] The present invention also provides the use of the multifunctionalized beta-naphthone derivative in preparing medicines.

[0025] The beneficial effects of the present invention include the following:

[0026] 1) This method uses readily available 1,6-diyne-3-ol compounds as starting materials, potassium chloroaurate (KAuCl4) as a catalyst, and thioanisole (PhSMe) as a ligand. Through intramolecular 6-endo-dig cyclization, 3,3-Claisen rearrangement, aromatization, and finally a 1,3-acyl migration reaction on the aromatic ring, multifunctionalized β-naphthone derivatives are obtained. This method exhibits mild reaction conditions, high yields, and excellent regioselectivity, and has potential applications in medicinal chemistry. The natural naphthyl-based lignins Taiwanin C and Justicidin B were successfully synthesized, demonstrating the significance of this synthetic method. The multifunctionalized naphthalenone derivatives obtained in this method exhibit a yield of up to 84%.

[0027] 2) The present invention uses 1,6-diyne-3-ol compounds as starting materials to efficiently synthesize naphthone derivatives. Initially, acyl naphthalene compounds at the α-position of naphthalene are generated. However, under the catalyst of potassium chloroaurate, a 1,3-acyl migration reaction on the aromatic ring occurs to generate acyl naphthalene derivatives at the β-position. DETAILED DESCRIPTION

[0028] In the present invention, the molar ratio of potassium chloroaurate (KAuCl4), thioanisole (PhSMe) and 1,6-diyn-3-ol compound is preferably 0.04-0.06:0.12-0.17:1, more preferably 0.045-0.055:0.14-0.16:1, and more preferably 0.05:0.15:1.

[0029] In the present invention, the molar volume ratio of the 1,6-diyn-3-ol compound to 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.

[0030] In the present invention, the mixing time is preferably 8 to 12 minutes, more preferably 9 to 11 minutes, and more preferably 10 minutes; the reaction temperature is preferably 120 to 140°C, more preferably 125 to 135°C, and more preferably 130°C; the reaction time is preferably 2 to 12 hours, more preferably 4 to 10 hours, and more preferably 6 to 8 hours.

[0031] In the present invention, a crude product is obtained after the reaction is completed. The crude product is preferably subjected to decompression and silica gel column chromatography in sequence to obtain a multifunctional β-naphthone derivative; the eluent for silica gel column chromatography is preferably petroleum ether and ethyl acetate.

[0032] The present invention also provides the use of the multifunctionalized beta-naphthone derivative in preparing medicines.

[0033] The technical solutions provided by the present invention are described in detail below with reference to the embodiments, but they should not be construed as limiting the scope of protection of the present invention.

[0034] In the examples, KAuCl4 (5 mol%) means that the molar amount of KAuCl4 is 5% of the molar amount of the 1,6-diyn-3-ol compound; thioanisole PhSMe (15 mol%) means that the molar amount of PhSMe is 15% of the molar amount of the 1,6-diyn-3-ol compound;

[0035] Potassium chloroaurate was purchased from Shanghai Bid Pharmaceutical Technology Co., Ltd. with CAS number 13682-61-6, purity 99.9%, and specification 1 g.

[0036] Thioanisole was purchased from Adamas (Shanghai Adamas Reagent Co., Ltd.), CAS number 100-68-5, purity 99%, specification 25g;

[0037] Ethyl acetate was purchased from Beijing Mairuida Technology Co., Ltd. with a CAS number of 141-78-6, a purity AR of 99%, and a specification of 25 L;

[0038] Petroleum ether was purchased from Shanghai Jiazu Industrial Co., Ltd. with CAS number 8032-32-4, purity of 99%, and specification of 25L.

[0039] Example 1

[0040]

[0041] To a 4 mL sample vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-diphenyl-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyn-3-ol (1a) was added and the mixture was reacted at 130°C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 50-25:1) to obtain 1-(3-phenyl-1-(phenylynyl)naphthalen-2-yl)ethan-1-one (yellow solid product 2a).

[0042] The amount of 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.

[0043] Example 2

[0044]

[0045] To a 4 mL sample vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. 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-diyn-3-ol (1b) was added and the reaction was continued at 130°C for 11.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (volume ratio of petroleum ether to ethyl acetate: 100:1) to give 1-(3-(o-tolyl)-1-(o-tolylethynyl)naphthalen-2-yl)ethan-1-one (2b) and 1-(2-(o-tolyl)-4-(o-tolynyl)naphthalen-1-yl)ethan-1-one (2b') (brown liquid products 2b and 2b').

[0046] The total mass of 2b and 2b' in this example is 46.3 mg, and the total isolated yield of 2b and 2b' is 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) δ206.20(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 / zcalculated for C 28 H 22 ONa + [M+Na] + : 397.1563, found: 397.1565.

[0047] Example 3

[0048]

[0049] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-di-m-tolylpenta-1,4-diyn-3-ol (1c) was added and the mixture was allowed to react at 130°C for 11.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100-50:1) to afford 1-(3-(m-tolyl)-1-(m-tolylethynyl)naphthalen-2-yl)ethan-1-one (product 2c) as an orange solid.

[0050] The amount of 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 H 22 ONa + [M+Na] + : 397.1563, found:397.1567.

[0051] Example 4

[0052]

[0053] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-di-p-tolylpenta-1,4-diyn-3-ol (1d) was added. The mixture was reacted at 130°C for 11.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(3-(p-tolyl)-1-(p-tolylethynyl)naphthalen-2-yl)ethan-1-one (product 2d) as an orange solid.

[0054] The amount of 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 (101 MHz, 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.

[0055] Example 5

[0056]

[0057] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. The mixture was stirred at room temperature for 10 min, followed by the addition of 0.2 mmol of 3-(2-(prop-1-yn-1-yl)phenyl)-1,5-di(thiophen-2-yl)penta-1,4-diyn-3-ol (1e). The reaction was continued at 130°C for 11.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to afford 1-(3-thiophen-2-yl)-1-(thiophen-2-ylethynyl)naphthalen-2-yl)ethan-1-one (brown liquid product 2e).

[0058] The amount of 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.

[0059] Example 6

[0060]

[0061] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 minutes, 0.2 mmol of 1,5-bis(4-chlorophenyl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyn-3-ol (1f) was added. The mixture was reacted at 130°C for 11.5 hours. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(3-(4-chlorophenyl)-1-((4-chlorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (product 2f) as an orange solid.

[0062] The amount of 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 35Cl2ONa + [M+Na] + : 437.0471,found: 437.0470; m / z calculated for C 26 H 16 37 Cl2ONa + [M+Na] + : 441.0412, found:441.0421.

[0063] Example 7

[0064]

[0065] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 minutes, 0.2 mmol of 1,5-bis(3-chlorophenyl)-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyn-3-ol (1 g) was added and the mixture was allowed to react at 130°C for 11.5 hours. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100-50:1) to obtain 1-(3-(3-chlorophenyl)-1-((3-chlorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (2 g of an orange solid).

[0066] 2g in this example is 59.6mg, and the isolated 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.

[0067] Example 8

[0068]

[0069] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. 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-diyn-3-ol (1h) was added. The mixture was allowed to react at 130°C for 11.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100-50:1) to obtain 1-(3-(2-chlorophenyl)-1-((2-chlorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2h).

[0070] The amount of 2h in this example is 37.7 mg, and the isolated yield is 45%. 1 H NMR (400 MHz, Chloroform- d ) δ8.65 (d, J = 7.9 Hz, 1H), 7.89 (d, 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.

[0071] Example 9

[0072]

[0073] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. 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-diyn-3-ol (1i) was added and the mixture was reacted at 130°C for 9.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:100-50:1) to afford 1-(3-(4-fluorophenyl)-1-((4-fluorophenyl)ethynyl)naphthalen-2-yl)ethan-1-one (product 2i) as an orange solid.

[0074] The amount of 2i in this example 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 / zcalculated for C 26 H 16 F2ONa + [M+Na] + : 405.1062, found: 405.1062.

[0075] Example 10

[0076]

[0077] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. 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-diyn-3-ol (1j) was added and the mixture was reacted at 130°C for 9.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(3-(4-(trifluoromethyl)phenyl)-1-((4-(tetrafluoromethyl)phenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2j).

[0078] The amount of 2j in this example was 76.8 mg, and the isolated yield was 80%. 1 H NMR (400 MHz, Chloroform- d ) δ8.49 (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 / zcalculated for C 28 H 16 F6ON + [M+Na] + : 505.0998, found: 505.0998.

[0079] Example 11

[0080]

[0081] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. 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-diyn-3-ol (1k) was added and the mixture was reacted at 130°C for 5.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100-50:1) to obtain 1-(3-(2-(trifluoromethyl)phenyl)-1-((2-(trifluoromethyl)phenyl)ethynyl)naphthalen-2-yl)ethan-1-one (orange solid product 2k).

[0082] The amount of 2k in this example was 79.1 mg, and the isolated yield was 82%. 1 H NMR (400 MHz, Chloroform- d ) δ8.55 (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 F6ON + [M+Na] + : 505.0998, found: 505.1001.

[0083] Example 12

[0084]

[0085] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-di(naphthalen-1-yl)-3-(2-(prop-1-yn-1-yl)phenyl)pent-1,4-diyn-3-ol (1L) was added and the mixture was reacted at 130°C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(4'-(naphthalen-1-ylethynyl)-[1,2'-binaphthyl]-3'-yl)ethan-1-one (brown solid product 2L).

[0086] The amount of 21 in this example was 50.4 mg, and the isolated yield was 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.

[0087] Example 13

[0088]

[0089] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-di(naphthalen-2-yl)-3-(2-(prop-1-yn-1-yl)phenyl)pent-1,4-diyn-3-ol (1 m) was added and the mixture was reacted at 130°C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(4-(naphthalen-2-ylethynyl)-[2,2'-binaphthyl]-3-yl)ethan-1-one (yellow solid product 2 m).

[0090] The amount of 2m in this example is 42.3 mg, and the isolated yield is 47%. f= 0.20 (petroleum ether / ethyl acetate = 25 / 1); 1 HNMR (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 C 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.

[0091] Example 14

[0092]

[0093] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 3-(4-methoxy-2-(prop-1-yn-1-yl)phenyl)-1,5-diphenyl-1,4-diyn-3-ol (1n) was added and the mixture was allowed to react at 130°C for 5.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(6-methoxy-3-phenyl-1-(phenylethynyl)naphthalen-2-yl)ethan-1-one (yellow solid product 2n).

[0094] The amount of 2n in this example was 28.6 mg, and the isolated yield was 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 (101 MHz, 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 calculated for C 27 H 20 O2Na + [M+Na] + : 399.1356, found: 399.1357.

[0095] Example 15

[0096]

[0097] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 3-(5-methyl-2-(prop-1-yn-1-yl)phenyl)-1,5-diphenyl-1,4-diyn-3-ol (1o) was added and the mixture was allowed to react at 130°C for 5.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:100-50:1) to afford 1-(7-methyl-3-phenyl-1-(phenylethynyl)naphthalen-2-yl)ethan-1-one (orange liquid product 2o).

[0098] The amount of 2o in this example 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.

[0099] Example 16

[0100]

[0101] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole 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-diyn-8-ol (1p) was added and the mixture was allowed to react at 130°C for 6 h. After completion of the reaction, EtOAc was removed under reduced pressure. The mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to afford 1-(1-(hept-1-en-1-yl)-3-pentylnaphth-2-yl)ethan-1-one (2p) and 1-(4-(hept-1-yn-1-yl)-2-pentylnaphth-1-yl)ethan-1-one (2p') (orange liquid products 2p and 2p').

[0102] The total mass of 2p and 2p' in this example is 56.2 mg, and the total isolated yield of 2p and 2p' is 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); 13 C 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.

[0103] Example 17

[0104]

[0105] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 2,2,8,8-tetramethyl-5-(2-(prop-1-yn-1-yl)phenyl)nona-3,6-diyn-5-ol (1q) was added. The reaction was continued at 130°C for 5.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 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).

[0106] The amount of 2q in this example was 41.5 mg, and the isolated yield was 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.

[0107] Example 18

[0108]

[0109] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 1,5-dicyclopropyl-3-(2-(prop-1-yn-1-yl)phenyl)penta-1,4-diyn-3-ol (1r) was added and the mixture was allowed to react at 130°C for 5.5 h. After completion of the reaction, EtOAc was removed under reduced pressure. The mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to afford 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').

[0110] The total mass of 2r and 2r' in this example is 38.2 mg, and the total isolated yield of 2r and 2r' is 70% (2r:2r'=1:0.25).1 H 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 C 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 18ONa + [M+Na] + : 297.1250,found: 297.1253.

[0111] Example 19

[0112]

[0113] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 minutes, 0.2 mmol of 3-phenyl-1-(2-(prop-1-yn-1-yl)phenyl)prop-2-en-1-ol (1s) was added and the mixture was allowed to react at 130°C for 5.5 hours. After completion of the reaction, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(3-phenylnaphthalen-2-yl)ethan-1-one (orange liquid product 2s).

[0114] The amount of 2s in this example was 16 mg, and the isolated yield was 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.

[0115] Example 20

[0116]

[0117] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 4-phenyl-2-(2-(prop-1-yn-1-yl)phenyl)but-3-yn-2-ol (1t) was added, and the mixture was reacted at 130°C for 5.5 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:1) to afford 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').

[0118] The total mass of 2t and 2t' in this example is 46.9 mg, and the total isolated yield of 2t and 2t' is 90% (2t:2t'=2:1). 1 H NMR (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 / zcalculated for C 19 H 16 ONa + [M+Na] + : 283.1094, found: 283.1097.

[0119] Example 21

[0120]

[0121] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 minutes, 0.2 mmol of 1,3-diphenyl-1-(2-(prop-1-en-1-yl)phenyl)prop-2-en-1-ol (1u) was added and the mixture was reacted at 130°C for 8 hours. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(1,3-diphenylnaphthalen-2-yl)ethan-1-one (yellow solid product 2u).

[0122] The amount of 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 CNMR(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.

[0123] Example 22

[0124]

[0125] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. 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. The mixture was allowed to react at 130°C for 9 h. After completion of the reaction, EtOAc was removed under reduced pressure. The mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to afford 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).

[0126] The total mass of 2v-1 and 2v-2 in this example is 43.5 mg, and the total isolated yield of 2v-1 and 2v-2 is 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.

[0127] Example 23

[0128]

[0129] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 minutes, 0.2 mmol of 3-(2-(hept-1-yn-1-yl)phenyl)-1,5-diphenylpenta-1,4-diyn-3-ol (1w) was added. The mixture was reacted at 130°C for 9.5 hours. After completion of the reaction, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100:50:1) to obtain 1-(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)hexan-1-one (brown liquid product, 2w).

[0130] The amount of 2w in this embodiment is 62.2 mg, and the isolated yield is 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.

[0131] Example 24

[0132]

[0133] To a 4 mL vial, add 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole, followed by 2.4 mL of EtOAc. Stir at room temperature for 10 minutes, then add 0.2 mmol of 3-(2-(cyclopropylethynyl)phenyl)-1,5-diphenylpenta-1,4-diyn-3-ol (1x). React at 130°C for 9.5 hours. After completion of the reaction, remove the EtOAc under reduced pressure, and purify by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 100-50:1) to obtain cyclopropyl(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)methanone (2x) as a yellow solid.

[0134] The amount of 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.

[0135] Example 25

[0136]

[0137] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. After stirring at room temperature for 10 min, 0.2 mmol of 3-(2-((4-methoxyphenyl)ethynyl)phenyl)-1,5-diphenylpenta-1,4-diyn-3-ol (1y) was added and the mixture was reacted at 130°C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio: 50-25:1) to afford (4-methoxyphenyl)(3-phenyl-1-(phenylethynyl)naphthalen-2-yl)methanone (brown liquid product 2y).

[0138] The amount of 2y in this example 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.

[0139] Example 26

[0140]

[0141] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. The mixture was stirred at room temperature for 10 min, followed by the addition of 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). The reaction was continued at 130°C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:50-25:1) to afford 1-(3-((tert-butyldimethylsilyl)oxy)methyl)-6,7-dimethoxy-1-phenylnaphthalen-2-yl)ethan-1-one (yellow liquid product 2z).

[0142] The amount of 2z in this example 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.

[0143] 0.1 mmol of compound 2z was dissolved in 2.3 mL of dry tetrahydrofuran, cooled to 0°C, and tetrabutylammonium fluoride (TBAF) (1 mol / L, 0.12 mmol) was added. The mixture was allowed to react at 0°C for 3.5 h. After completion, the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography (eluent: petroleum ether: ethyl acetate (2:1, by volume)) to afford 3z as a yellow solid (30.9 mg, 92% yield).

[0144] In a reaction vessel, 0.55 mmol of compound 3z was dissolved in 13.8 mL of DMSO. Then, 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 4Å molecular sieves were added sequentially. The mixture was reacted at 100°C for 6 h under an atmosphere of 0.5 MPa of O₂. After completion, the reaction was quenched with saturated aqueous NH₄Cl and extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried over anhydrous Na₂SO₄, filtered, and concentrated to dryness under reduced pressure. Silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:3:1) afforded 6,7-dimethoxy-9-phenylnaphtho[2,3-c]furan-1(3H)-one (4z) as an orange solid.

[0145] The amount of 4z in this example was 108.1 mg, and the isolated yield was 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.

[0146] Example 27

[0147]

[0148] To a 4 mL sample vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. The mixture was stirred at room temperature for 10 min, and then 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) was added. The mixture was reacted at 130 °C for 8 h. After the reaction was completed, EtOAc was removed under reduced pressure, and the product was purified by silica gel column chromatography (volume ratio of petroleum ether and ethyl acetate was 50-25:1) to obtain 1-(5-(benzo[d][1,3]dioxol-5-yl)-7-((tert-butyldimethylsilyl)oxy)methyl)naphthol[2,3-d][1,3]dioxol-6-yl)ethan-1-one (yellow solid product 2aa).

[0149] The amount of 2aa in this example was 54.7 mg, and the isolated yield was 57%. 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.

[0150] 0.1 mmol of compound 2aa was dissolved in 2.3 mL of dry THF, cooled to 0°C, and TBAF (1 mol / L, 0.12 mmol) was added. The mixture was allowed to react at 0°C for 3.5 h. After completion, the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography (eluent: petroleum ether: ethyl acetate in a 2:1 volume ratio) to afford 3aa, a yellow liquid (36.0 mg, 99% yield).

[0151] In a reaction vessel, 0.26 mmol of compound 3aa was dissolved in 6.5 mL of DMSO. 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 4Å molecular sieves were added sequentially. The reaction was incubated at 100°C under an atmosphere of 0.5 MPa of O₂ for 6 h. After completion, the reaction was quenched with saturated aqueous NH₄Cl and extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried over anhydrous Na₂SO₄, filtered, and concentrated to dryness under reduced pressure. Silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:3:2:1) afforded 5-(benzo[d][1,3]dioxol-5-yl)furo[3',4':6,7]naphtho[2,3-d][1,3]dioxin-6(8H)-one (Taiwanin C), a white solid.

[0152] The amount of Taiwanin C in this example was 23.5 mg, and the isolated yield was 26%. 1 H NMR (400 MHz, DMSO- d6) δ7.94 (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.

[0153] Example 28

[0154]

[0155] To a 4 mL vial, 0.01 mmol of KAuCl4 and 0.03 mmol of thioanisole were added, followed by 2.4 mL of EtOAc. The mixture was stirred at room temperature for 10 min, followed by the addition of 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). The reaction was continued at 130°C for 8 h. After completion of the reaction, EtOAc was removed under reduced pressure, and the mixture was purified by silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:50-25:1) to afford 1-(1-(benzo[D][1,3]dioxol-5-yl)-3-((tert-butyldimethylsilyl)oxy)methyl)-6,7-dimethoxynaphthalen-2-yl)ethan-1-one (yellow liquid product 2ab).

[0156] The total mass of 2ab and 2ab' in this example is 65.0 mg, and the total isolated yield of 2ab and 2ab' is 66% (2ab:2ab'=5:1). 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.

[0157] 0.1 mmol of compound 2ab was dissolved in 2.3 mL of dry THF, cooled to 0°C, and TBAF (1 mol / L, 0.12 mmol) was added. The reaction was allowed to react at 0°C for 3.5 h. After completion, the reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure. The residue was purified by silica gel chromatography (eluent: petroleum ether: ethyl acetate in a 2:1 volume ratio) to afford 3ab as a yellow solid (37.2 mg, 98% yield).

[0158] In a reaction vessel, 0.28 mmol of compound 3ab was dissolved in 7.0 mL of DMSO. 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 sieves were added sequentially. The mixture was reacted at 100°C under an atmosphere of 0.5 MPa of O₂ for 6 h. After completion, the reaction was quenched with saturated aqueous NH₄Cl and extracted with EtOAc. The combined organic phases were washed with saturated NaCl, dried over anhydrous Na₂SO₄, filtered, and concentrated to dryness under reduced pressure. Silica gel column chromatography (petroleum ether:ethyl acetate, volume ratio:3:2:1) afforded 9-(benzo[d][1,3]dioxolan-5-yl)-6,7-dimethoxynaphtho[2,3-c]furan-1(3H)-one (Justicidin B) as an orange solid.

[0159] The amount of Justicidin B in this example 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.

[0160] Polyfunctionalized β-acetonaphthone 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), but also a key pharmaceutical intermediate. It has potential application value in drug synthesis and can also be used in the formulation of toiletries and industrial product fragrances.

[0161] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principles of the present invention. These improvements and modifications should also be regarded as within the scope of protection of the present invention.

Claims

1. A method for preparing a multifunctional β-naphthone derivative, characterized in that: The following steps are included: Potassium chloroaurate, thioanisole, and ethyl acetate are mixed to obtain a reaction solution, and the reaction solution is reacted with a 1,6-diyn-3-ol compound to obtain a multifunctional β-naphthone derivative; The structural formula of the 1,6-diyne-3-ol compound is: ； Among them, 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-butyldimethylsilyloxymethylidene; R 3 is H, methyl or methoxy; R 4 is H, methyl, phenyl or alkynyl, when R 4 When it is an alkynyl group, the alkynyl group is connected to R 2 ; The structural formula of the multifunctionalized β-naphthone derivative is: ; Among them, 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-butyldimethylsilyloxymethylidene; R 3 is H, methyl or methoxy; R 4 is H, methyl, phenyl or alkynyl, when R 4 When it is an alkynyl group, the alkynyl group is connected to R 2 .

2. The method for preparing a multifunctional β-naphthone derivative according to claim 1, wherein: The structural formula of the multifunctionalized β-naphthone derivative is: 。 3. The method for preparing a multifunctional β-naphthone derivative according to claim 1, wherein: The molar ratio of the potassium chloroaurate, thioanisole and 1,6-diyn-3-ol compound is 0.04-0.06:0.12-0.17:

1.

4. The method for preparing a multifunctional β-naphthone derivative according to claim 3, wherein: The molar volume ratio of the 1,6-diyn-3-ol compound and ethyl acetate is 0.2 mmol: 2.2-2.6 mL.

5. The method for preparing a multifunctional β-naphthone derivative according to claim 4, wherein: The mixing time is 8 to 12 minutes; the reaction temperature is 120 to 140° C., and the reaction time is 2 to 12 hours.

6. The method for preparing a multifunctional β-naphthone derivative according to claim 5, wherein: After the reaction is completed, a crude product is obtained, and the crude product is subjected to decompression and silica gel column chromatography in sequence to obtain a multifunctional β-naphthone derivative; the eluents for the silica gel column chromatography are petroleum ether and ethyl acetate.

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