Preparation method of tetralone compound

Abstract

The invention provides a novel preparation method of a tetralone compound, which comprises the following steps: reacting a 1, 6-eneyne compound with water under the synergistic catalysis of transition metal and an amine nucleophilic reagent to generate the tetralone compound. The synthesis method is simple and rapid in preparation process, low in catalyst price and wide in substrate applicability, so that the synthesis method is expected to be used for industrial production. # imgabs0 #

Description

Technical Field

[0001] The invention belongs to the field of organic chemical synthesis, and specifically relates to a preparation method of a tetralone compound. Background Art

[0002] The preparation methods of tetralone compounds currently available in the literature are exemplified as follows.

[0003] Method 1 (Synthesis.2016,48,2050-2056):

[0004]

[0005] Method 2 (Korean J.Chem.Eng.2017,34,701-705):

[0006]

[0007] Method 3 (Org. Biomol. Chem., 2023, 21, 910–924):

[0008]

[0009] Method 4: (The Journal of Organic Chemistry 2024,89,13575-13584):

[0010]

[0011] Among the above methods for preparing tetralone compounds, method 1 has a narrower applicability to substrates; the chromium catalyst used in method 2 is a toxic heavy metal; method 3 requires multi-step synthesis, and has poor step economy and atom economy; method 4 requires consumption of 3 equivalents of hydrazone reagent, and the conversion process releases gas, which may cause explosion hazard if amplified, and is not conducive to safe production. Summary of the invention

[0012] In order to overcome the shortcomings and deficiencies of the prior art, the present invention aims to provide a method for preparing a tetralone compound. In this method, the raw materials are cheap and readily available, and the product synthesis method is simple and efficient.

[0013] The present invention is achieved through the following technical solutions:

[0014] The method for preparing a tetralone compound of the present invention comprises the following steps:

[0015] Under nitrogen protection, a 1,6-enyne compound is dissolved in a solvent, a transition metal catalyst and a nucleophilic catalyst are added, and then an organic acid additive and water are added. After the reaction, the compound is separated and purified to obtain a tetralone compound.

[0016] Where R 1 Selected from hydrogen atoms, C1~C 12 One of alkyl, aryl, and heteroaryl; wherein R 1 Any one or more hydrogen atoms of the aromatic ring may be replaced by a substituent;

[0017] R 2 Selected from C1~C 12 One of alkyl, aryl, and heteroaryl; wherein R 1 Any one or more hydrogen atoms of the aromatic ring may be replaced by a substituent;

[0018] R 3 Selected from hydrogen atom, halogen, C1~C 12 Alkyl or heteroaromatic ring;

[0019] R 4 Selected from hydrogen atom or C1~C 12 alkyl.

[0020] Substituent Definitions and General Terms:

[0021] The term "aryl" used in the present invention refers to a monocyclic or bicyclic carbon ring system containing 6-10 ring atoms, wherein at least one ring system is aromatic, and examples of aryl may include phenyl and naphthyl. The alkyl group may be independently unsubstituted or substituted with one or more substituents described in the present invention.

[0022] The term "alkyl" used in the present invention refers to a group containing 1 to 12 carbon atoms. The alkyl group may be a straight chain or a branched chain, and may be independently unsubstituted or substituted with one or more substituents described in the present invention.

[0023] The term "halogen" refers to fluorine, chlorine, bromine, iodine.

[0024] The transition metal catalyst is one of Cu(OAc)2·H2O, Cu(OAc)2·H2O, Cu(OAc)2, CuSO4·5H2O, AgOTf, CuSO4, CuCl2, CuO, CuCl, CuBr, and CuI, preferably Cu(OAc)2·H2O.

[0025] The molar ratio of the transition metal catalyst to the 1,6-enyne compound is 0.01 to 1:1, preferably 0.1 to 0.2:1.

[0026] The nucleophilic catalyst is selected from C1 to C12 One of alkylamine, aniline, piperidine and triethylamine, preferably alkylamine, more preferably n-butylamine.

[0027] The molar ratio of the nucleophilic reagent to the 1,6-enyne compound is 0.01 to 1:1, preferably 0.2:1.

[0028] The organic acid additive is selected from C1 to C 12 One of an alkyl carboxylic acid and phosphoric acid, preferably acetic acid.

[0029] The molar ratio of the organic acid reagent to the 1,6-enyne compound is 0.01 to 10:1, preferably 10:1.

[0030] The molar ratio of water to 1,6-enyne compound is 1 to 100:1, preferably 20:1.

[0031] The solvent is selected from 1,1-dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, trifluorotoluene, 1,4-dioxane, acetonitrile, toluene, chlorobenzene and xylene, preferably 1,2-dichloroethane.

[0032] The ratio of the solvent to the 1,6-enyne compound is 1-40 mL:1 mmol, preferably 20 mL:1 mmol.

[0033] The conditions are 25°C to 120°C for reaction for 2h to 48h, and the preferred conditions are 80°C for reaction for 4h.

[0034] The 1,6-enyne compound can be prepared by referring to known literature (eg Angew. Chem. Int. Ed. 2011, 50, 8968).

[0035]

[0036] Tetralone skeleton is a basic component of organic synthesis, and these structures are widely present in natural products, medicines, and bioactive substances, such as CYP27A1 inhibitor, Sertraline, 10-norparvulenone, etc. The present invention provides a convenient, simple and efficient method for constructing a tetralone skeleton.

[0037] The following bioactive molecules contain a tetralone skeleton, illustrating the potential application value of this method.

[0038] The tetralone compounds that can be prepared by the present invention are exemplified as follows:

[0039]

[0040] Compared with the prior art, the present invention has the following advantages and effects:

[0041] The preparation process of the invention is simple and quick, and the tetralone compound can be efficiently synthesized in only one simple step. The operation is simple, the raw materials used are easy to prepare, the catalyst used is small in amount and is cheap and easily available, and the prepared tetralone compound has strong substrate compatibility and is simple to purify. BRIEF DESCRIPTION OF THE DRAWINGS

[0042] Figure 1 The catalyst in the figure is equivalent to transition metal catalysis + nucleophilic catalyst; 1,6-enyne is equivalent to A, and tetralone is equivalent to B. DETAILED DESCRIPTION

[0043] The present invention is further described below in conjunction with specific examples, but the examples do not limit the present invention in any form. Unless otherwise specified, the reagents, methods and equipment used in the present invention are conventional reagents, methods and equipment in the art and can be directly purchased or synthesized by known literature methods.

[0044] Example 1

[0045]

[0046] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1a (61.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain product 2a (58 mg, 89%) as a white solid with a melting point of 152-153°C. 1 H NMR(400MHz, CDCl3)δ8.21(dd,J=6.9,2.4Hz,1H),7.57–7.51(m,2H),7.48–7.38(m,3H),7.27(s,1H),7.25–7.08(m,7 H),5.30(d,J=4.6Hz,1H),3.96(dt,J=14.6,4.4Hz,1H),3.80(dd,J=17.2,14.5Hz,1H),2.83(dd,J=17.1,4.2Hz,1H); 13C NMR (101MHz, CDCl3) δ199.6,197.8,141.5,140.2,137.6,133.6,133.1,132.9,128 .8,128.5,128.4,128.2,128.12,128.10,127.6,51.6,44.2,38.6; HRMS(ESI)Calcd for C23H18O2Na(M+Na)+349.1199,found349.1205.

[0047] Example 2

[0048]

[0049] Take a dry Schlenk tube with a stirrer, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1b (65.2 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2b (60 mg, 87%) as a white solid with a melting point of 132-133°C. 1 H NMR(400MHz, CDCl3)δ8.20(dd,J=6.7,2.7Hz,1H),7.63–7.53(m,2H),7.50–7.39(m,3H),7.29(t,J=7.8Hz,2H),7.21–7.08(m,3H),6 .94–6.78(m,2H),5.28(d,J=4.7Hz,1H),3.94(dt,J=14.5,4.5Hz,1H),3.76(dd,J=17.2,14.5Hz,1H),2.81(dd,J=17.2,4.3Hz,1H); 13 C NMR(101MHz,CDCl3)δ199.4,197.4,162.0(d, 1 J C-F =247.5Hz),141.2,137.4,136.0(d, 4 J C-F =3.0Hz),133.6,133.3,132.8,129.2,129.1,128.5(d, 3 J C-F =3.0Hz),128.2,128.1,115.6(d, 2 J C-F=22.2Hz),51.4,43.4,38.8; 19 F NMR(376MHz, CDCl3)δ-114.77; HRMS(ESI)Calcd for C 23 H 17 O2FNa(M+Na) + 367.1105, found 367.1115.

[0050] Example 3

[0051]

[0052] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1c (68.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain product 2c (48 mg, 67%) as a yellow solid with a melting point of 161-162°C. 1 H NMR(400MHz, CDCl3)δ8.20(dd,1H),7.59(d,J=7.1Hz,2H),7.51–7.40(m,3H),7.31(t,J=7.8Hz,2H),7.18–7 .09(m,5H),5.28(d,J=4.8Hz,1H),3.93(dt,J=14.5,4.4Hz,1H),3.77(dd,1H),2.80(dd,J=17.1,4.2Hz,1H); 13 C NMR (101MHz, CDCl3) δ199.3,197.3,141.1,138.7,137.4,133.6,133.4,133.3, 132.8,128.92,128.85,128.6,128.5,128.2,51.1,43.5,38.7; HRMS(ESI)Calcd for C 23 H 17 O2NaCl(M+Na) + 383.0809, found 383.0814.

[0053] Example 4

[0054]

[0055] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1d (77.4 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2d (61 mg, 76%) as a white solid with a melting point of 155-156°C. 1 H NMR(400MHz, CDCl3)δ8.20(dd,J=7.3,2.0Hz,1H),7.64–7.55(m,2H),7.51–7.40(m,3H),7.35–7.26(m,4H),7.15–7.04( m,3H),5.28(d,J=4.6Hz,1H),3.91(dt,J=14.5,4.4Hz,1H),3.77(dd,J=17.1,14.4Hz,1H),2.80(dd,J=17.1,4.2Hz,1H); 13 C NMR (101MHz, CDCl3) δ199.3,197.3,141.1,139.3,137.4,133.6,133.4,132.8,131 .8,129.3,128.6,128.5,128.20,128.17,121.4,51.1,43.6,38.6; HRMS(ESI)Calcd for C 23 H 17 O2NaBr(M+Na) + 427.0304, found 427.0312.

[0056] Example 5

[0057]

[0058] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1e (66.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 5:1) to obtain the product 2e (30 mg, 43%) as a reddish brown solid with a melting point of >300°C. 1H NMR (400MHz, CDCl3) δ8.21(dd,J=7.0,2.3Hz,1H),7.59(d,J=7.0Hz,2H),7.52–7.42(m,5H),7.32(dd,J=14.5,8.0Hz,4H),7.13(dd, J=6.6,2.1Hz,1H),5.30(d,J=4.6Hz,1H),4.01(dt,J=14.4,4.5Hz,1H),3.81(dd,J=17.1,14.3Hz,1H),2.83(dd,J=17.1,4.3Hz,1H); 13 C NMR (101MHz, CDCl3) δ198.8,196.6,145.5,140.6,137.1,133.8,133.7,132.7,132.5,128 .7,128.5,128.39,128.37,128.3,128.2,118.4,111.4,50.5,44.0,38.2; HRMS(ESI)Calcd for C 24 H 17 NO2Na(M+Na) + 374.1151, found 374.1153.

[0059] Example 6

[0060]

[0061] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1f (64.4 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2f (42 mg, 62%) as a white solid with a melting point of 163-164°C. 1H NMR (400MHz, CDCl3) δ8.23–8.17(m,1H),7.55(d,J=7.3Hz,2H),7.46–7.40(m,3H),7.26(t,2H),7.10(d,J=8.1Hz,3H),6.98(d ,J=8.1Hz,2H),5.28(d,J=4.5Hz,1H),3.92(dt,J=14.5,4.3Hz,1H),3.78(dd,1H),2.81(dd,J=17.1,4.1Hz,1H),2.21(s,3H); 13 CNMR(101MHz,CDCl3)δ199.8,198.0,141.5,137.7,137.2,137.1,133.5,133.0,132.9,1 29.3,128.6,128.3,128.2,128.1,128.0,127.4,51.7,43.9,38.8,21.0; HRMS(ESI)Calcd for C 24 H 20 O2Na(M+Na) + 363.1356, found 363.1364.

[0062] Example 7

[0063]

[0064] Take a dry Schlenk tube with a stirrer, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1g (67.2 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain 2 g (45 mg, 64%) of the product as a brown solid with a melting point of 149-151°C. 1H NMR (400MHz, CDCl3) δ8.20(dd,J=7.1Hz,1H),7.57(d,J=7.4Hz,2H),7.47–7.39(m,3H),7.28(s,1H),7.24–7.09(m,2H),6.74(d,J=27.2 Hz,3H),5.27(d,J=4.7Hz,1H),3.86(dt,J=14.6,4.4Hz,1H),3.70(dd,J=17.1,14.7Hz,1H),2.80(dd,J=17.2,4.2Hz,1H),2.13(s,6H); 13 C NMR (101MHz, CDCl3) δ199.6,198.0,141.7,139.9,138.2,137.8,133.5,133.1,132.9,128 .9,128.4,128.2,128.1,128.04,128.01,125.4,51.7,44.2,38.7,21.2; HRMS(ESI)Calcd for C 25 H 22 O2Na(M+Na) + 377.1512, found 377.1517.

[0065] Example 8

[0066]

[0067] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace with nitrogen three times, add 1h (71.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100 ° C for 4 h. The reaction is complete, the solvent is removed by rotation, and the product is purified by flash column chromatography (eluent is petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2h (39 mg, 52%) as a yellow solid with a melting point of 143-144 ° C. 1H NMR(400MHz, CDCl3)δ8.25(dd,J=15.8,8.2Hz,2H),7.86(d,J=8.2Hz,1H),7.67(t,J=7.7Hz,1H),7.60–7.44(m,4H),7.25–7.21(m,1H),7.20–7.0 8(m,5H),6.96(t,J=7.5Hz,2H),5.56(d,J=4.7Hz,1H),4.82(dt,J=14.5,4.5Hz,1H),3.96(dd,J=16.9,14.5Hz,1H),2.90(dd,J=17.0,3.9Hz,1H); 13 C NMR (101MHz, CDCl3) δ199.1,198.0,141.7,137.2,135.2,134.0,133.6,133.2,132.9,131.2,129.5 ,128.4,128.2,128.1,128.00,127.96,127.9,126.9,125.7,125.3,124.2,122.1,49.7,38.7,38.6.

[0068] Example 9

[0069]

[0070] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1i (71.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL), stir at 80 ° C for 4 h, the reaction is complete, the solvent is removed by rotation, and the product is purified by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2i (44 mg, 59%) as a white solid with a melting point of 189-190 ° C. 1 H NMR (400MHz, CDCl3) δ8.23(dd,1H),7.74–7.62(m,4H),7.54(d,J=6.9Hz,2H),7.49–7.34(m,5H),7.32–7.26(m,1H),7.18–7. 08(m,3H),5.41(d,J=4.6Hz,1H),4.12(dt,J=14.6,4.4Hz,1H),3.95(dd,J=17.2,14.5Hz,1H),2.93(dd,J=17.2,4.2Hz,1H); 13CNMR(101MHz, CDCl3)δ199.7,197.7,141.5,137.6,137.5,133.6,133.3,133.00,132.94,132.6,128 .5,128.4,128.3,128.2,128.1,127.8,127.5,126.3,126.2,125.9,125.8,115.1,51.4,44.3,38.9.

[0071] Example 10

[0072]

[0073] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1j (59.6 mg, 0.2 mmol), n-butylamine (29.2 mg, 0.4 mmol), acetic acid (0.24 mL, 2 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2j (62 mg, 99%, cis:trans=50:50), a brown oily liquid. 11H NMR (400 MHz, CDCl3) for mixture: δ 8.18 (dd, J = 7.6, 1.4 Hz, 1H), 8.12 (dd, 1H), 8.10 (s, 1H), 8.08 (s, 1H), 7.80 (s, 1H), 7.78 (s, 1H), 7.64 (t, J = 7.4 Hz, 1H), 7.56 (t, 1H), 7.54–7.52 (m, 1H), 7.52–7.48 (m, 1H), 7.48–7.41 (m, 3H), 7.40–7.34 (m, 3H), 7.27 (s, 1H), 7.17 (s, 1H), 7.15 (d, 1H), 7.06 (d, J = 7.6 Hz, 1H), 6.16 (dd, J = 3.3, 1.9 Hz, 1H), 6.09 (dd, J = 3.3, 1.9 Hz, 1H), 5.99 (d, J = 3.2 Hz, 1H), 5.97 (d, J = 3.3 Hz, 1H), 5.52 (d, J = 4.7 Hz, 1H), 5.45 (d, J = 5.3 Hz, 1H), 4.03 (dd, J = 5.1 Hz, 1H), 3.98 (dd, J = 10.9, 5.4 Hz, 1H), 3.49 (dd, J = 17.8, 14.2 Hz, 1H), 3.11 (dd, J = 17.2, 5.0 Hz, 1H), 2.97 (dd, J = 17.2, 6.6 Hz, 1H), 2.87 (dd, J = 17.8, 4.8 Hz, 1H); 13 13C NMR (101 MHz, CDCl3) for mixture: δ 199.8, 198.8, 196.7, 195.8, 154.3, 153.6, 141.9, 141.6, 140.6, 139.9, 137.0, 136.4, 134.0, 133.8, 133.6, 133.2, 133.1, 132.7, 129.1, 129.0, 128.8, 128.5, 128.40, 128.36, 128.2, 128.0, 127.9, 127.3, 110.4, 106.8, 106.4, 50.4, 48.8, 39.4, 37.6, 37.3, 37.1; HRMS (ESI) Calcd for C 21 H 16 O3Na (M+Na) + 339.0992, found 339.1000.

[0074] Example 11

[0075]

[0076] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1k (66.8 mg, 0.2 mmol), n-butylamine (29.2 mg, 0.4 mmol), acetic acid (0.24 mL, 2 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2k (62 mg, 88%, cis: trans = 40:60), a brown oily liquid. 1 H NMR(400MHz,CDCl3)for cis-isomer:δ8.18–8.16(m,1H),8.05–8.03(m,2H),7.66–7.62(m,1H),7 .55–7.53(m,1H),7.51–7.47(m,3H),7.25–7.21(m,4H),7.18–7.13(m,2H) ,6.53(d,J=15.7Hz,1H),6.00(dd,J=15.7,8.4Hz,1H),5.27(d,J=4.8Hz, 1H),3.52–3.46(m,1H),3.28(dd,J=17.6,13.1Hz,1H),2.73–2.69(m,1H); 13 C NMR(101MHz,CDCl3)for cis-isomer:δ2199.3,197.1,141.0,137.6,136.5,133.6,133.5,133.1,132. 9,129.6,128.9,128.5,128.4,128.0,127.9,127.7,126.3,50.0,42.3,39.7; 1 HNMR(400MHz,CDCl3)for trans-isomer: δ8.16–8.13(m,1H),8.03–8.00(m,2H),7.62–7.56(m,1H),7.53–7.51(m,1H),7.46–7.37(m,3H),7.21–7.18(m,4H),7.11–7.06(m,2 H),6.44(d,J=15.8Hz,1H),6.14(dd,J=15.8,7.8Hz,1H),5.02(d,J=6.2Hz ,1H),3.58–3.52(m,1H),3.03(dd,J=17.0,4.6Hz,1H),2.77–2.73(m,1H); 13C NMR(101MHz,CDCl3)for trans-isomer: δ200.2,196.2,140.5,136.9,136.4,134.1,133.7,132.0,131.8,129.5,1 29.1,128.9,128.8,128.5,127.9,127.8,127.4,126.3,52.5,41.7,41.6; HRMS(ESI)Calcd forC 25 H 20 O2Na(M+Na) + 375.1356, found 375.1363.

[0077] Example 12

[0078]

[0079] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1l (64.4 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2l (58 mg, 86%) as a white solid with a melting point of 166-167°C. 1 H NMR(400MHz, CDCl3)δ8.20(dd,J=6.5,2.9Hz,1H),7.49–7.38(m,4H),7.25–7.15(m,4H),7.15–7.08(m,2H),7.05(d,J=8.0Hz,2H ),5.26(d,J=4.6Hz,1H),3.94(dt,J=14.5,4.3Hz,1H),3.82(dd,J=16.9,14.5Hz,1H),2.83(dd,J=16.9,3.9Hz,1H),2.32(s,3H); 13 C NMR (101MHz, CDCl3) δ199.1,197.9,144.0,141.7,140.3,135.1,133.5,132.9,129.1,128. 70,128.68,128.12,128.08,128.0,127.6,127.5,51.3,44.3,38.7,21.6; HRMS(ESI)Calcd for C 24 H 20O2Na(M+Na) + 363.1356, found 363.1364.

[0080] Example 13

[0081]

[0082] Take a dry Schlenk tube with a stirrer, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1m (64.4 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2m (51 mg, 75%) as a white solid with a melting point of 119-120°C. 1 H NMR(400MHz, CDCl3)δ8.21(dd,J=7.3,2.0Hz,1H),7.47–7.39(m,2H),7.33(d,J=7.8Hz,1H),7.29(s,1H),7.25–7.16(m,5H),7.16–7.07 (m,3H),5.27(d,J=4.6Hz,1H),3.95(dt,J=14.6,4.4Hz,1H),3.79(dd,J=17.1,14.6Hz,1H),2.83(dd,J=17.3,4.2Hz,1H),2.25(s,3H); 13 C NMR (101MHz, CDCl3) δ199.7,197.9,141.6,140.3,138.1,137.6,133.8,133.5,132.9,129.1,128 .7,128.2,128.14,128.08,128.0,127.6,127.5,125.7,51.8,44.3,38.6,21.2; HRMS(ESI)Calcd for C 24 H 20 O2Na(M+Na) + 363.1356, found 363.1364.

[0083] Embodiment 14

[0084]

[0085] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1n (67.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2n (35 mg, 49%) as a white solid with a melting point of 167-168°C. 1 H NMR(400MHz, CDCl3)δ8.20(dd,J=7.1,2.2Hz,1H),7.60–7.50(m,2H),7.47–7.37(m,2H),7.25–7.15(m,4H),7.15–7.08(m,2H) ,6.73(d,J=9.0Hz,2H),5.23(d,J=4.6Hz,1H),3.93(dt,J=14.5,4.3Hz,1H),3.89–3.73(m,4H),2.81(dd,J=16.9,4.0Hz,1H); 13 CNMR(101MHz, CDCl3)δ197.9,197.7,163.5,141.8,140.4,133.4,133.0,130.9,130.6, 128.7,128.1,128.0,127.6,127.5,113.6,55.4,51.2,44.3,38.8; HRMS(ESI)Calcdfor C 24 H 20 O3Na(M+Na) + 379.1305, found 379.1313.

[0086] Embodiment 15

[0087]

[0088] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1o (65.2 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 100°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2o (47 mg, 69%) as a white solid with a melting point of 185-186°C.1 H NMR(400MHz, CDCl3)δ8.21(dd,J=7.4,2.0Hz,1H),7.60–7.52(m,2H),7.49–7.41(m,2H),7.23–7.06(m,6H),6.95–6.86( m,2H),5.24(d,J=4.8Hz,1H),3.96(dt,J=14.5,4.5Hz,1H),3.74(dd,J=17.3,14.6Hz,1H),2.83(dd,J=17.3,4.3Hz,1H); 13 C NMR (101MHz, CDCl3) δ197.9,197.6,165.6(d, 1 J C-F =256.5Hz),141.3,140.1,134.0(d, 4 J C-F =3.0Hz),133.6,133.0,131.2(d, 3 J C-F =9.1Hz),128.8,128.2,128.14,128.05,127.7,127.5,115.5(d, 2 J C-F =22.2Hz),51.7,44.2,38.5; 19 F NMR(376MHz, CDCl3)δ-104.74; HRMS(ESI)Calcd for C 23 H 17 O2FNa(M+Na) + 367.1105, found 367.1115.

[0089] Example 16

[0090]

[0091] Take a dry Schlenk tube with a stirrer, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1p (68.6 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2p (59 mg, 82%) as a white solid with a melting point of 165-166°C. 1H NMR(400MHz, CDCl3)δ8.21(dd,1H),7.50–7.40(m,4H),7.25–7.12(m,7H),7.11–7.05(m,1H),5.22(d,J =4.7Hz,1H),3.96(dt,J=14.5,4.5Hz,1H),3.74(dd,J=17.3,14.5Hz,1H),2.83(dd,J=17.4,4.3Hz,1H); 13 C NMR (101MHz, CDCl3) δ198.4,197.5,141.2,140.0,139.7,135.9,133.6,132.9,129.8, 128.8,128.7,128.22,128.17,128.0,127.7,127.5,51.8,44.2,38.5; HRMS(ESI)Calcd for C 23 H 17 O2NaCl(M+Na) + 383.0809, found 383.0814.

[0092] Embodiment 17

[0093]

[0094] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1q (77.4 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2q (65 mg, 80%) as a white solid with a melting point of 164-165°C. 1 H NMR (400MHz, CDCl3) δ8.20 (dd, J=6.5, 2.8Hz, 1H), 7.50–7.33 (m, 6H), 7.24–7.12 (m, 5H), 7.12–7.03 (m, 1H), 5. 21(d,J=4.7Hz,1H), 3.95(dt,J=14.5,4.5Hz,1H), 3.74(dd,J=17.3,14.5Hz,1H), 2.83(dd,J=17.3,4.3Hz,1H); 13C NMR (101MHz, CDCl3) δ198.6,197.5,141.1,140.0,136.3,133.6,132.9,131.7,129.9, 128.9,128.5,128.23,128.17,128.1,127.7,127.5,51.8,44.2,38.5; HRMS(ESI)Calcd for C 23 H 17 O2NaBr(M+Na) + 427.0304, found 427.0312.

[0095] Embodiment 18

[0096]

[0097] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1r (75.2 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2r (55 mg, 70%) as a white solid with a melting point of 110-111°C. 1 H NMR (400MHz, CDCl3) δ8.22(dd,1H),7.59(d,J=8.2Hz,2H),7.55–7.40(m,4H),7.23–7.04(m,6H),5.27(d, J=4.7Hz,1H),3.99(dt,J=14.5,4.5Hz,1H),3.73(dd,J=17.4,14.5Hz,1H),2.86(dd,J=17.2,4.2Hz,1H); 13 C NMR (101MHz, CDCl3) δ199.0,197.4,140.8,140.3,139.8,134.3,134.0,133.7,132.9,128 .9,128.7,128.4,128.2,128.1,127.8,127.5,125.4(q,4JC-F=4.0Hz),52.3,44.2,38.3; 19 F NMR(376MHz, CDCl3)δ-62.99; HRMS(ESI)Calcd for C 24 H 17 O2NaF3(M+Na)+ 417.1073, found 417.1080.

[0098] Embodiment 19

[0099]

[0100] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1s (61.8 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 2:1) to obtain the product 2s (28 mg, 43%) as a white solid with a melting point of 181-182°C. 1 H NMR (400MHz, CDCl3) δ8.68(d,J=43.6Hz,2H),8.22(dd,J=6.9,2.4Hz,1H),7.81(dt,J=8.0,1.9Hz,1H),7.51–7.43(m,2H),7.26 –7.08(m,7H),5.26(d,J=4.8Hz,1H),4.00(dt,J=14.5,4.5Hz,1H),3.70(dd,J=17.4,14.6Hz,1H),2.86(dd,J=17.3,4.0Hz,1H); 13 C NMR (101MHz, CDCl3) δ198.6,197.3,153.3,149.7,140.6,139.7,135.6,133.7,133.0 ,129.0,128.4,128.2,128.1,127.9,127.4,123.3,52.4,44.1,38.3; HRMS(ESI)Calcd for C 22 H 18 NO2(MH) - 328.1332, found 328.1339.

[0101] Embodiment 20

[0102]

[0103] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1t (62.8 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2t (37 mg, 56%) as a white solid with a melting point of 177-178°C. 1 H NMR(400MHz, CDCl3)δ8.20(dd,J=7.6,1.6Hz,1H),7.58(d,J=1.7Hz,1H),7.50–7.41(m,2H),7.26–7.10(m,8H),5 .01(d,J=4.6Hz,1H),3.93(dt,J=14.6,4.4Hz,1H),3.74(dd,J=17.2,14.6Hz,1H),2.82(dd,J=17.3,4.2Hz,1H); 13 C NMR (101MHz, CDCl3) δ197.7,193.0,143.0,141.3,140.3,133.6,133.2,132.9,128.7, 128.19,128.15,128.0,127.6,127.5,127.0,126.2,54.2,44.3,38.6; HRMS(ESI)Calcd for C 21 H 16 O2NaS(M+Na) + 355.0763, found 355.0772.

[0104] Embodiment 21

[0105]

[0106] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1u (63.2 mg, 0.2 mmol), n-butylamine (2.29 mg, 0.4 mmol), acetic acid (0.24 mL, 2 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 120°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent is petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2u (40 mg, 60%, cis:trans=37:63), a white oily liquid. 1H NMR(400MHz,CDCl3)for cis-isomer:δ8.16(d,J=7.9Hz,1H),7.55–7.52(m,1H),7.45–7.41(m,2H),7.34–7.29(m,4H),7.19–7.16(m,1H),4.38(d,J=4.7Hz,1H),3.84–3.76(m,2H),3.09–2.96(m,2H),2.39(ddd,J=17.8,8.2,6.4Hz,2H),1.50–1.43(m,2H),1.23–1.17(m,5H),0.87–0.84(m,3H); 13 C NMR(101MHz,CDCl3)for cis-isomer:δ209.4,197.6,140.9,140.3,133.6,132.4,129.0,128.1,128.0,127.9,127.7,127.5,57.6,46.0,43.2,38.0,31.4,28.4,22.7,22.4,14.0; 1 H NMR(400MHz,CDCl3)fortrans-isomer:δ8.13(d,J=7.8Hz,1H),7.52–7.47(m,1H),7.41–7.35(m,2H),7.29–7.27(m,1H),7.25–7.19(m,3H),7.06(d,J=7.7Hz,1H),4.35(d,J=8.7Hz,1H),3.78–3.71(m,1H),3.65(dd,J=17.0,14.5Hz,1H),2.98–2.72(m,2H),2.33–2.13(m,2H),1.75(ddd,J=17.9,8.4,6.2Hz,1H),1.43–1.30(m,2H),1.14–1.06(m,4H),0.84–0.78(m,3H); 13 C NMR(101MHz,CDCl3)for trans-isomer:δ209.4,197.6,140.9,140.3,133.6,132.4,129.0,128.1,128.0,127.9,127.7,127.5,57.6,46.0,43.2,38.0,31.4,28.4,22.7,22.4,14.0;HRMS(ESI)Calcd for C 23 H 26 O2Na(M+Na) + 357.1825,found 357.1832.

[0107] Embodiment 22

[0108]

[0109] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1v (65.2 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2v (42 mg, 61%) as a brown solid with a melting point of 173-174°C. 1 H NMR (400MHz, CDCl3) δ8.24(dd,J=8.8,6.0Hz,1H),7.57–7.49(m,2H),7.44(t,J=7.4Hz,1H),7.28(s,1H),7.24(s,1H),7.23–7.06(m,6H),6. 79(dd,J=8.8,2.5Hz,1H),5.26(d,J=4.7Hz,1H),3.95(dt,J=14.5,4.5Hz,1H),3.75(dd,J=17.3,14.5Hz,1H),2.82(dd,J=17.4,4.4Hz,1H); 13 C NMR (101MHz, CDCl3) δ198.9,196.3,165.5(d, 1 J C-F =256.5Hz),144.2(d, 3 J C-F =9.1Hz),139.7,137.3,133.3,131.1(d, 3 J C-F =10.1Hz),129.7(d, 4 J C-F =3.0Hz),128.8,128.5,128.4,127.7,127.5,115.6(d, 2 J C-F =22.2Hz),114.7(d, 2 J C-F =22.2Hz),51.6,44.2,38.4; 19 F NMR(376MHz, CDCl3)δ-104.29; HRMS(ESI)Calcd for C23 H 17 O2FNa(M+Na) + 367.1105, found 367.1115.

[0110] Embodiment 23

[0111]

[0112] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1w (64.4 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2w (54 mg, 80%) as a white solid with a melting point of 140-141°C. 1 H NMR (400MHz, CDCl3) δ8.10(d,J=8.0Hz,1H),7.54(d,J=7.8Hz,2H),7.45–7.26(m,2H),7.25–7.13(m,6H),7.13–7.06(m,1H),6.89(s ,1H),5.25(d,J=4.7Hz,1H),3.93(dt,J=14.5,4.5Hz,1H),3.75(dd,J=17.2,14.5Hz,1H),2.79(dd,J=17.2,4.2Hz,1H),2.30(s,3H); 13 C NMR (101MHz, CDCl3) δ199.6,197.6,144.5,141.6,140.2,137.6,133.0,130.7,129.1,12 8.7,128.6,128.5,128.3,128.2,127.6,127.5,51.5,44.4,38.6,21.7; HRMS(ESI)Calcd for C 24 H 20 O2Na(M+Na) + 363.1356, found 363.1364.

[0113] Embodiment 24

[0114]

[0115] Take a dry Schlenk tube with a stirring bar, add Cu(OAc)2·H2O (8 mg, 20% mmol), replace the atmosphere with nitrogen three times, add 1x (36.8 mg, 0.2 mmol), n-butylamine (2.9 mg, 20% mmol), acetic acid (0.12 mL, 1 mmol), water (36 mg, 2 mmol) and 1,2-dichloroethane (4 mL) and stir at 80°C for 4 h. After the reaction is complete, remove the solvent and purify by flash column chromatography (eluent: petroleum ether: ethyl acetate volume ratio 10:1) to obtain the product 2x (33 mg, 45%, cis:trans=50:50), a white oily liquid. 1 H NMR(400MHz,CDCl3)for mixture:δ8.14(s,1H),8.12(s,1H),8.10–8.05(m,2H),8.05–8.00(m,2H),7.68–7.64(m,1H),7.64–7.61(m,1 H),7.58–7.50(m,4H),7.49–7.42(m,2H),7.42–7.35(m,2H),7.13–7.09(m,1H),7.04(dd,J=7.6,1.3Hz,1H),5. 12–5.08(m,1H),5.08–5.05(m,1H),2.81(ddd,J=12.1,6.7,5.0Hz,1H),2.78–2.69(m,1H),2.46(ddd,J=13.8,5 .0,3.1Hz,1H),2.41–2.32(m,2H),2.26(td,J=13.4,11.8Hz,1H),1.31(d,J=6.7Hz,3H),1.20(d,J=6.8Hz,3H); 13 C NMR(101MHz,CDCl3)for mixture:δ201.3,199.8,199.7,199.2,142.3,141.1,136.7,135.9,133.73,133.67,133.5,133.3,133.2,132.7,129.03,129.01 ,128.98,128.9,128.7,128.3,127.9,127.83,127.77,127.5,47.7,45.9,42.0,37.7,35.7,34.4,15.42,15.35; HRMS(ESI)Calcd for C 18 H 16 O2Na(M+Na) + 287.1043, found 287.1051.

[0116] The above embodiments are preferred implementation modes of the present invention, but the implementation modes of the present invention are not limited to the above embodiments. Any other changes, modifications, substitutions, combinations, and simplifications that do not deviate from the spirit and principles of the present invention should be equivalent replacement methods and are included in the protection scope of the present invention.

Claims

1. A method for preparing a tetralone compound, characterized in that: Its structural formula is as follows: Where: R 1 For hydrogen atoms, C1~C 12 One of alkyl, aryl, and heteroaryl; wherein R 1 Any one or more hydrogen atoms of the aromatic ring may be replaced by a substituent; R 2 C1~C 12 One of alkyl, aryl, and heteroaryl; wherein R 1 Any one or more hydrogen atoms of the aromatic ring may be replaced by a substituent; R 3 For hydrogen atoms, halogens, C1~C 12 Alkyl or heteroaromatic ring; R 4 A hydrogen atom or a C1~C 12 alkyl.

2. The method for preparing a tetralone compound according to claim 1, characterized in that: The steps include: Under nitrogen protection, the 1,6-enyne compound is dissolved in a solvent, a catalyst and a nucleophilic reagent are added, and then an acid and water are added. After the reaction, the tetralone compound is separated and purified to obtain the tetralone compound.

3. The preparation method according to claim 2, characterized in that: The 1,6-enyne compound has the following structural formula: Where: R 1 Selected from hydrogen atoms, C1~C 12 One of alkyl, aryl, and heteroaryl; wherein R 1 Any one or more hydrogen atoms of the aromatic ring may be replaced by a substituent; R 2 Selected from C1~C 12 One of alkyl, aryl, and heteroaryl; wherein R 1 Any one or more hydrogen atoms of the aromatic ring may be replaced by a substituent; R 3 Selected from hydrogen atom, halogen, C1~C 12 Alkyl or heteroaromatic ring; R 4 Selected from hydrogen atom or C1~C 12 alkyl.

4. The preparation method according to claim 2, characterized in that: The transition metal catalyst is one of Cu(OAc)2·H2O, Cu(OAc)2, CuSO4·5H2O, AgOTf, CuSO4, CuCl2, CuO, CuCl, CuBr, and CuI; the nucleophilic reagent is selected from C1 to C 12 One of alkylamine, aniline, piperidine and triethylamine.

5. The preparation method according to claim 2, characterized in that: The acid reagent is selected from C1~C 12 One of alkyl carboxylic acids, phosphoric acid, and trifluoroacetic acid.

6. The preparation method according to claim 2, characterized in that: The solvent is selected from one of 1,1-dichloromethane, 1,2-dichloroethane, chloroform, carbon tetrachloride, trifluorotoluene, 1,4-dioxane, acetonitrile, toluene, chlorobenzene and xylene.

7. The preparation method according to claim 2, characterized in that: The reaction is carried out at 25°C to 150°C for 0.5h to 48h to obtain a tetralone compound.

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