Method for synthesizing diaryl ketone derivative by catalyzing C-O fracture of isochroman derivative through tetradentate manganese complex

Abstract

The invention discloses a method for synthesizing a diaryl ketone derivative by catalyzing C-O breakage of an isochroman derivative by a tetradentate manganese complex, which comprises the following steps: stirring and reacting at room temperature by taking ligand complex manganese with bipiperidine as a skeleton as a catalyst and H2O2 as an oxidant to obtain an oxidation product, namely the diaryl ketone derivative. The method has the advantages of small catalyst dosage, short reaction time, mild reaction conditions, wide substrate range, good product selectivity, high yield, low industrial cost and the like.

Description

Technical Field

[0001] The present invention belongs to the technical field of oxidative cleavage of carbon-oxygen bonds in organic compounds, and specifically relates to a method for generating diaryl ketone derivatives from isochroman derivatives under the action of a tetradentate manganese catalyst and H2O2. Background Art

[0002] Diaryl ketone derivatives are very useful intermediates in synthetic chemistry. Several classes of biologically active compounds can be synthesized from them, including isochromans, benzodiazepines, 1-aryl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones, (2-hydroxyethyl)benzophenone derivatives, and neuroprotectant analogs such as GYKI52466, LY300164, and Tfisopam. Tofisopane and dextrotofisopane are commonly used drugs for the treatment of familial dysautonomia and irritable bowel syndrome, both of which have a strong global market. 2,3-Benzodiazepine derivatives are an important class of antiepileptic drugs that exhibit anticonvulsant properties in epileptic seizures and block the (R,S)-2-amino-3-(3-hydroxy-5-methyl-4-isoxazolyl)propionic acid glutamate receptor (AMPA) in a noncompetitive manner. These 2,3-benzodiazepine derivatives can interact with AMPA and act as AMPA receptor antagonists. They are potential drugs for treating many neurological diseases, such as epilepsy, stroke, and amyotrophic lateral sclerosis (ALS).

[0003] Common methods for synthesizing diaryl ketone derivatives include carbon-carbon double bond oxidation and Grignard reagent addition, enzymatic oxidation, and strong oxidant oxidation. Due to the strong bond energy of the CO bond, strong oxidants are typically required for oxidative cleavage. However, strong oxidants can result in multiple oxidation sites, resulting in poor reaction selectivity. Therefore, the use of mild oxidants under catalytic conditions is key to selective CO bond oxidation. In nature, iron- and manganese-containing metallooxidases are well-known for their high activity and selectivity in catalyzing oxidation in organisms. For example, bacteria driven by iron-containing oxidases can oxidatively degrade ether bonds in agrochemicals, detergents, and lignin. Inspired by nature, a variety of biomimetic iron- and manganese-containing metallocatalysts have been designed and synthesized over the past few decades. These catalysts have played an important role in the selective oxidation of various carbon-hydrogen bonds. However, iron and manganese catalysts have rarely been used for the selective oxidation of ether bonds, and even fewer for the oxidative cleavage of CO bonds in ether bonds. Summary of the Invention

[0004] The present invention aims to provide a method for synthesizing benzophenone derivatives by catalyzing the selective oxidative cleavage of the CO bond of an isochroman derivative using H2O2 as an oxidant and a tetradentate manganese complex as a catalyst.

[0005] The technical solution provided by the present invention comprises the following steps: uniformly mixing an isochroman derivative, a tetradentate manganese complex and acetonitrile, injecting a hydrogen peroxide acetonitrile solution by using a flow injection pump at room temperature and under stirring conditions, continuing to stir and react for 3 to 8 hours after the injection, and separating and purifying the product after the reaction to obtain a diaryl ketone derivative.

[0006] When the above-mentioned isochroman derivative is a compound of formula I, a diaryl ketone derivative represented by formula I' is obtained.

[0007]

[0008] When the above-mentioned isochroman derivative is a compound of formula II, a diaryl ketone derivative represented by formula II' is obtained.

[0009]

[0010] When the above-mentioned isochroman derivative is a compound of formula III, a diaryl ketone derivative represented by formula III′ is obtained.

[0011]

[0012] When the above-mentioned isochroman derivative is a compound of formula IV, a diaryl ketone derivative represented by formula IV' is obtained.

[0013]

[0014] In the above structural formula, R1 and R2 independently represent any one of C1~C6 alkyl, C1~C6 alkoxy, hydroxyl, nitro, fluorine, methyl formate, and cyano; w represents the number of substitutions of R1, and x represents the number of substitutions of R2. The values ​​of w and x are integers of 0 to 2 respectively, each R1 is the same or different, and each R2 is the same or different.

[0015] The structural formula of the above tetradentate manganese complex is shown below:

[0016]

[0017] Furthermore, in the above synthesis method, the amount of the tetradentate manganese complex added is preferably 1% to 5% of the molar amount of the isochroman derivative.

[0018] Furthermore, in the above synthesis method, the molar ratio of the isochroman derivative to H2O2 in hydrogen peroxide is preferably 1:4-6.

[0019] Furthermore, in the above synthesis method, the mass concentration of H2O2 in the hydrogen peroxide is preferably 20% to 30%.

[0020] Furthermore, in the above synthesis method, the volume ratio of hydrogen peroxide to acetonitrile in the hydrogen peroxide acetonitrile solution is preferably 1:10 to 20.

[0021] Furthermore, in the above synthesis method, the flow rate of the hydrogen peroxide acetonitrile solution is preferably 0.02 to 0.05 mL / min.

[0022] The beneficial effects of the present invention are as follows:

[0023] The present invention uses a tetradentate manganese complex as a catalyst and clean, environmentally friendly hydrogen peroxide as an oxidant to catalyze the oxidation of isochroman derivatives to synthesize diaryl ketone derivatives. Compared with existing methods, the present invention has the advantages of low catalyst price, simple preparation method, readily available raw materials, small catalyst dosage, wide substrate range, mild reaction conditions, simple operation, green and environmental protection, short reaction time, high yield, good selectivity, low industrialization cost, and the like. DETAILED DESCRIPTION

[0024] The present invention will be further described in detail below with reference to the embodiments, but the protection scope of the present invention is not limited to these embodiments.

[0025] Example 1

[0026] Synthesize diaryl ketone derivatives with the following structural formula

[0027]

[0028] 7.59 mg (0.01 mmol) of (2R, 2'R) 1,1'-bis-(2-methylpyridine)-2,2'-bispiperidine manganese catalyst (rac-1) and 82 mg (0.5 mmol) of 6,7-dimethoxy-1-phenylisochroman (Compound I) were added to a reaction tube, and then 1.5 mL of acetonitrile was added and stirred evenly; 125 μL of 30% hydrogen peroxide (H2O2 is 2.5 mmol) was diluted with 1.5 mL of acetonitrile and injected into the above reaction tube at a flow rate of 0.025 mL / min at room temperature with stirring using a flow syringe pump. After the injection, the reaction was continued with stirring for 4 hours. Then, solid sodium sulfite was added to the reaction solution to quench the remaining hydrogen peroxide. The reaction was filtered, rotary evaporated, and separated by column chromatography to obtain a white solid Compound I' with a yield of 87%. The spectral data are as follows: 1 H NMR (400MHz, CDCl3): δ = 7.79 (d, J = 7.1Hz, 2H), 7.58 (t, J = 7.4Hz, 1H), 7.45 (t, J = 7.8Hz, 2H), 6.87 (s ,1H),6.84(s,1H),3.94(s,3H),3.89-3.83(m,2H),3.74(s,3H),3.39(s,1H),2.91(t,J=6.1Hz,2H);13 C NMR (100 MHz, CDC13): δ = 198.0, 151.5, 146.4, 138.2, 133.8, 133.2, 130.6, 130.4, 128.4, 113.6, 113.4, 64.1, 56.2, 56.0, 36.1; HRMS (ESI) m / z C 17 H 18 O4[M+Na] + : Theoretical 309.1097, Found 309.1085.

[0029] Example 2

[0030] Synthesis of the diaryl ketone derivative of the following structure

[0031]

[0032] In this example, 6,7-dimethoxy-l-(4-methoxyphenyl)isochroman was used to replace 6,7-dimethoxy-l-phenylisochroman in Example 1, and other steps were the same as Example 1, to obtain the target product with a yield of 87%, and the spectral data were as follows: 1 H NMR (400 MHz, CDC13): δ = 7.78 (d, J = 8.4 Hz, 2H), 6.95 (s, 1H), 6.93 (s, 1H), 6.85 (d, J = 9.2 Hz, 2H), 3.93 (s, 3H), 3.88 (s, 3H), 3.85 (m, 2H, m), 3.79 (s, 3H), 3.48 (brs, 1H), 2.86 (t, J = 6.0 Hz, 2H); 13 C NMR (100 MHz, CDC13): δ = 196.8, 163.8, 151.1, 146.3, 133.2, 133.0, 131.0, 130.7, 113.7, 113.4, 112.9, 64.0, 56.2, 56.0 (2C), 36.0; HRMS (ESI) m / z C 18 H 20 O5[M+Na] + : Theoretical 339.1203, Found 339.1214.

[0033] Example 3

[0034] Synthesis of the diaryl ketone derivative of the following structure

[0035]

[0036] In this example, 6,7-dimethoxy-1-(4-methylphenyl)isochroman was used to replace the 6,7-dimethoxy-1-phenylisochroman in Example 1. The other steps were the same as in Example 1 to obtain the target product with a yield of 90%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 7.70 (d, J = 7.8Hz, 2H), 7.25 (d, J = 7.8Hz, 2H), 6.87 (s, 1H), 6.84 (s, 1H) ),3.94(s,3H),3.85(m,2H),3.76(s,3H),3.54(brs,1H),2.89(d,J=6.0Hz,2H),2.42(s,3H); 13 C NMR (100MHz, CDCl3): δ=197.7,151.2,146.2,144.1,135.4,133.4,130.7,129.1,113.4,113.2,63.9,56.1,56.0,36.0,21.6; HRMS (ESI) m / z C 18 H 20 O4[M+Na] + :Theoretical value 323.1254, measured value 323.1250.

[0037] Example 4

[0038] Synthesize diaryl ketone derivatives with the following structural formula

[0039]

[0040] In this example, 6,7-dimethoxy-1-(4-tert-butylphenyl)isochroman was used to replace the 6,7-dimethoxy-1-phenylisochroman in Example 1. The other steps were the same as in Example 1 to obtain the target product with a yield of 91%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 7.75 (d, J = 8.2Hz, 2H), 7.47 (d, J = 8.2Hz, 2H), 6.87 (s, 2H), 3.95 (s, 3H),3.88(t,J=6.0Hz,2H),3.78(s,3H),3.47(brs,1H),2.90(t,J=6.0Hz,2H),1.35(s,9H); 13C NMR (100MHz, CDCl3): δ=197.6,157.2,151.3,146.3,135.3,133.6,130.7,125.5,113.5,113.3,64.1,56.3,56.1,36.1,35.2,31.1; HRMS (ESI) m / zC 21 H 26 O4[M+Na] + :Theoretical value 365.1723, measured value 365.1718.

[0041] Example 5

[0042] Synthesize diaryl ketone derivatives with the following structural formula

[0043]

[0044] In this example, 6,7-dimethoxy-1-(3,4-dimethoxyphenyl)isochroman was used to replace the 6,7-dimethoxy-1-phenylisochroman in Example 1. The other steps were the same as in Example 1 to obtain the target product with a yield of 86%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 7.49 (s, 1H), 7.30-7.26 (m, 1H), 6.85-6.82 (m, 3H), 3.92 (s, 3H), 3.90(s,3H),3.84(s,3H),3.79(s,2H),3.76(s,3H),3.52(s,1H),2.85(t,J=6.0Hz,2H); 13 C NMR (100MHz, CDCl3): δ=196.6,153.5,151.0,149.0,146.2,133.0,130.7,126.2,113.3,112.8,111.9,109.8,63.8,56.0,55.9,35.9; HRMS (ESI) m / z C 19 H 22 O6[M+Na] + :Theoretical value 369.1309, measured value 369.1300.

[0045] Example 6

[0046] Synthesize diaryl ketone derivatives with the following structural formula

[0047]

[0048] In this example, 6,7-dimethoxy-1-phenylisochroman in Example 1 was replaced with an equal molar amount of (E)-6,7-dimethoxy-1-(1-phenylpropenyl)isochroman. The other steps were the same as in Example 1 to obtain the target product with a yield of 89%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ=7.40-7.39(m,4H),7.36-7.33(m,1H),7.17(s,1H),6.88(s,1H),6.85(s,1H) ),3.94(s,3H),3.87(t,J=6.1Hz,2H),3.84(s,3H),3.25(s,1H),2.86(d,J=6.1Hz,2H),2.26(s,3H); 13 C NMR (100MHz, CDCl3): δ=201.1,150.9,146.6,144.6,138.2,132.4,131.3,12 9.9,129.0,128.6,113.3,112.5,63.9,56.2,56.0,36.1,13.8; HRMS(ESI)m / z C 20 H 22 O4[M+Na] + :Theoretical value 349.1410, measured value 349.1406.

[0049] Example 7

[0050] Synthesize diaryl ketone derivatives with the following structural formula

[0051]

[0052] In this example, 7-(4-nitrophenyl)-4,7-dihydro-5H-thieno[2,3-c]pyran was used to replace the 6,7-dimethoxy-1-phenylisochroman in Example 1. The other steps were the same as in Example 1 to obtain the target product with a yield of 53%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 8.33 (d, J = 8.6Hz, 2H), 7.98 (d, J = 8.7Hz, 2H), 7.64 (d, J = 5.0 Hz,1H),7.20(d,J=5.0Hz,1H),3.97(brs,2H),3.29(d,J=6.2Hz,2H),2.38(brs,1H); 13C NMR (100MHz, CDCl3): δ = 187.9, 150.2, 149.6, 145.0, 134.7, 132.9, 132.2, 130.2, 123.6, 63.2, 33.5; HRMS (ESI) m / z C 13 H 11 NO4[M+Na] + :Theoretical value 300.0301, measured value 300.0293.

[0053] Example 8

[0054] Synthesize diaryl ketone derivatives with the following structural formula

[0055]

[0056] In this example, 6,7-dimethoxy-1-phenylisochroman in Example 1 was replaced with an equal molar amount of 6-hydroxy-1-phenylisochroman. The other steps were the same as in Example 1 to obtain the target product with a yield of 99%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 10.03 (s, 1H), 7.68-7.62 (m, 3H), 7.52 (t, J = 7.5Hz, 2H), 7.13 (d, J = 8.4Hz, 1H), 6 .80(d,J=1.9Hz,1H),6.69-6.67(m,1H),4.60(d,J=5.2Hz,1H),3.54-3.49(m,2H),2.81(t,J=7.0Hz,2H); 13 C NMR (100MHz, CDCl3): δ=196.9,159.4,141.6,138.5,132.6,131.9,129.6,129.0,128.4,117.9,112.4,62.1,36.5; HRMS (ESI) m / z C 15 H 14 O3[M+Na] + :Theoretical value 265.0835, measured value 265.0833.

[0057] Example 9

[0058] Synthesize diaryl ketone derivatives with the following structural formula

[0059]

[0060] In this example, 6,7-dimethoxy-1-phenylisochroman in Example 1 was replaced with an equal molar amount of 6-hydroxy-1-(4-cyanophenyl)isochroman. The other steps were the same as in Example 1 to obtain the target product with a yield of 98%. The spectral data were as follows: 1 HNMR (400MHz, CDCl3): δ = 10.20 (s, 1H), 7.99 (d, J = 8.1Hz, 2H), 7.79 (d, J = 8.0Hz, 2H), 7.15 (d, J = 8.5Hz, 1H), 6.82 ( d,J=1.9Hz,1H),6.68(dd,J=8.4,2.1Hz,1H),4.60(t,J=5.2Hz,1H),3.53(q,J=6.6Hz,2H),2.86(t,J=6.8Hz,2H); 13 C NMR (100MHz, CDCl3): δ=195.5,160.2,142.6,142.5,132.8,132.5,130.0,127.8,118.3,114.4,112.3,62.0,36.5; HRMS (ESI) m / z C 16 H 13 NO3[M+Na] + :Theoretical value 290.0788, measured value 290.0785.

[0061] Example 10

[0062] Synthesize diaryl ketone derivatives with the following structural formula

[0063]

[0064] In this example, 6,7-dimethoxy-1-phenylisochroman in Example 1 was replaced with an equal molar amount of 6-hydroxy-1-(4-methylphenyl)isochroman. The other steps were the same as in Example 1 to obtain the target product with a yield of 98%. The spectral data were as follows: 1 HNMR (400MHz, CDCl3): δ = 9.97 (s, 1H), 7.58 (d, J = 7.8Hz, 2H), 7.32 (d, J = 7.8Hz, 2H), 7.13 (d, J = 8.3Hz, 1H), 6.79(s,1H),6.66(d,J=8.3Hz,1H),4.58(s,1H),3.50(t,J=7.0Hz,2H),2.77(t,J=7.0Hz,2H),2.39(s,3H); 13C NMR (100MHz, CDCl3): δ = 196.6, 159.2, 143.1, 141.2, 135.8, 131.4, 129.8, 129.3, 129.0, 117.8, 112.1, 62.1, 36.5, 21.1; HRMS (ESI) m / zC 16 H 16 O3[M+Na] + :Theoretical value 279.0992, measured value 279.0996.

[0065] Example 11

[0066] Synthesize diaryl ketone derivatives with the following structural formula

[0067]

[0068] In this example, 6,7-dimethoxy-1-phenylisochroman in Example 1 was replaced with an equal molar amount of 6-hydroxy-1-(4-methoxyphenyl)isochroman. The other steps were the same as in Example 1 to obtain the target product with a yield of 95%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 9.92 (s, 1H), 7.66 (d, J = 8.7Hz, 2H), 7.10-7.03 (m, 3H), 6.78 (s, 1H), 6.66 (dd ,J=8.3,2.2Hz,1H),4.58(t,J=4.8Hz,1H),3.83(s,3H),3.48(d,J=5.1Hz,2H),2.74(t,J=6.9Hz,2H); 13 C NMR (100MHz, CDCl3): δ=200.9,168.2,164.2,146.0,137.3,136.1,134.9,122.9,119.0,117.3,67.4,60.8,41.7; HRMS (ESI) m / z C 16 H 16 O4[M+Na] + :Theoretical value 295.0941, measured value 295.0945.

[0069] Example 12

[0070] Synthesize diaryl ketone derivatives with the following structural formula

[0071]

[0072] In this example, 6,7-dihydroxy-1-phenylisochroman was used to replace the 6,7-dimethoxy-1-phenylisochroman in Example 1. The other steps were the same as in Example 1 to obtain the target product with a yield of 98%. The spectral data were as follows: 1 HNMR (400MHz, CDCl3): δ = 9.51 (s, 1H), 9.07 (s, 1H), 7.53 (d, J = 7.5Hz, 3H), 7.52 (d, J = 7 .5Hz,2H),6.78(s,1H),6.70(s,1H),4.54(s,1H),3.47(s,2H),2.71(t,J=7.1Hz,2H); 13 CNMR (100MHz, CDCl3): δ = 196.8, 147.8, 142.4, 138.7, 132.5, 131.2, 129.6, 128.7, 128.4, 118.3, 117.4, 62.5, 35.9; HRMS (ESI) m / z C 15 H 14 O4[M+Na] + : Theoretical value 281.0784, measured value 281.0790.

[0073] Example 13

[0074] Synthesize diaryl ketone derivatives with the following structural formula

[0075]

[0076] In this example, 5-methoxy-1-phenyl-1,3-dihydroisobenzofuran was used in place of 6,7-dimethoxy-1-phenylisochroman in Example 1. The other steps were the same as in Example 1 to obtain the target product with a yield of 92%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 10.11 (s, 1H), 7.82 (d, J = 8.1Hz, 2H), 7.62 (td, J = 8.4, 1.1Hz, 1H), 7.55-7.47 (m, 4H), 7.16-7.14 (m, 1H), 3.95 (s, 3H); 13 C NMR (100MHz, CDCl3): δ = 195.5, 190.8, 161.8, 138.6, 137.7, 133.7, 133.4, 132.1, 130.2, 128.6, 119.0, 112.7, 55.8; HRMS (ESI) m / z C 15 H 12 O3[M+Na] + :Theoretical value 263.0679, measured value 263.0680.

[0077] Example 14

[0078] Synthesize diaryl ketone derivatives with the following structural formula

[0079]

[0080] In this example, 5,7-dimethoxy-1-phenyl-1,3-dihydroisobenzofuran was used in place of 6,7-dimethoxy-1-phenylisochroman in Example 1 in an equal molar amount. The other steps were the same as in Example 1 to obtain the target product with a yield of 85%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 9.82 (s, 1H), 7.79 (d, J = 8.2Hz, 2H), 7.57 (td, J = 7.7, 1.1Hz, 1H ),7.43(t,J=7.4Hz,2H),7.09(m,1H),6.76(t,J=1.9Hz,1H),3.92(s,3H),3.72(s,3H); 13 C NMR (100MHz, CDCl3): δ = 195.4, 190.0, 161.8, 158.5, 138.0, 136.4, 133.5, 129.3, 128.6, 104.5, 104.3, 56.1, 55.8; HRMS (ESI) m / z C 16 H 14 O4[M+Na] + :Theoretical value 293.0784, measured value 293.0782.

[0081] Example 15

[0082] Synthesize diaryl ketone derivatives with the following structural formula

[0083]

[0084] In this example, 6,7-dimethoxy-1-phenylisochroman in Example 1 was replaced with an equal molar amount of 5-cyano-1-phenyl-1,3-dihydroisobenzofuran. The other steps were the same as in Example 1 to obtain the target product with a yield of 92%. The spectral data were as follows: 1 H NMR (400MHz, CDCl3): δ = 9.98 (s, 1H), 8.29 (s, 1H), 7.98-7.96 (m, 1H), 7.80-7.77 (m, 2H), 7.60 (td, J = 7.6, 1.1Hz, 1H), 7.18-7.13 (m, 2H); 13 C NMR (100MHz, CDCl3): δ = 193.0, 188.3, ​​166.4 (d, JC-F =256.0Hz),144.4,136.4,133.9,132.6(d,J C-F =9.7Hz),129.4,116.9,116.4(d,J C-F =20.0Hz),115.0; HRMS(ESI)m / z C 15 H8FNO2[M+Na] + :Theoretical value 276.0431, measured value 276.0436.

Claims

1. A method for synthesizing diaryl ketone derivatives by CO cleavage of an isochroman derivative catalyzed by a tetradentate manganese complex, characterized in that: The isochroman derivative, the tetradentate manganese complex, and acetonitrile are stirred and mixed uniformly, and a hydrogen peroxide acetonitrile solution is injected using a flow injection pump at room temperature and under stirring conditions. After the injection, the stirring reaction is continued for 3 to 8 hours. After the reaction is completed, the product is separated and purified to obtain a diaryl ketone derivative. When the above-mentioned isochroman derivative is a compound of formula I, a diaryl ketone derivative represented by formula I′ is obtained; When the above-mentioned isochroman derivative is a compound of formula II, a diaryl ketone derivative represented by formula II′ is obtained; When the above-mentioned isochroman derivative is a compound of formula III, a diaryl ketone derivative represented by formula III′ is obtained; When the above-mentioned isochroman derivative is a compound of formula IV, a diaryl ketone derivative represented by formula IV′ is obtained; In the above structural formula, R1 and R2 each independently represent any one of a C1-C6 alkyl group, a C1-C6 alkoxy group, a hydroxyl group, a nitro group, a fluoro group, a methyl formate group, and a cyano group; w represents the number of substitutions of R1, and x represents the number of substitutions of R2, and the values ​​of w and x are integers of 0 to 2, each R1 is the same or different, and each R2 is the same or different; The structural formula of the above tetradentate manganese complex is shown below:

2. The method for synthesizing diaryl ketone derivatives by CO cleavage of an isochroman derivative catalyzed by a tetradentate manganese complex according to claim 1, characterized in that: The added amount of the tetradentate manganese complex is 1% to 5% of the molar amount of the isochroman derivative.

3. The method for synthesizing diaryl ketone derivatives by CO cleavage of an isochroman derivative catalyzed by a tetradentate manganese complex according to claim 1, characterized in that: The molar ratio of the isochroman derivative to H2O2 in hydrogen peroxide is 1:4-6.

4. The method for synthesizing diaryl ketone derivatives by CO cleavage of an isochroman derivative catalyzed by a tetradentate manganese complex according to claim 1 or 3, characterized in that: The mass concentration of H2O2 in the hydrogen peroxide is 20% to 30%.

5. The method for synthesizing diaryl ketone derivatives by CO cleavage of an isochroman derivative catalyzed by a tetradentate manganese complex according to claim 4, characterized in that: The volume ratio of hydrogen peroxide to acetonitrile in the hydrogen peroxide acetonitrile solution is 1:10-20.

6. The method for synthesizing diaryl ketone derivatives by CO cleavage of an isochroman derivative catalyzed by a tetradentate manganese complex according to claim 1 or 5, characterized in that: The flow rate of the hydrogen peroxide acetonitrile solution is 0.02 to 0.05 mL / min.

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