Cyclic biperoxide, synthetic method and application of cyclic biperoxide in preparation of alkyl bifunctional compound

Abstract

The invention relates to a cyclic diperoxide, a synthesis method and an application of the cyclic diperoxide in preparation of an alkyl difunctional compound, naphthenone is adopted as a raw material and is oxidized into bis-peroxy alcohol under the catalysis of hydrogen peroxide and protonic acid, alcoholic hydroxyl group protection is performed through protective agents such as acyl chloride, and a bis-peroxy compound is rapidly prepared; then, ferrous trifluoromethanesulfonate is used as a catalyst, TMSN3 is used as a-N3 source, and the alkyl difunctional compound is prepared under mild conditions, including but not limited to diazotization, dihalogenation, diboronation, diphosphorization and dithiocyanation; according to the invention, the synthesis range of the bifunctional alkane molecule is greatly widened, the synthesis efficiency is improved, the synthesis process is simplified, and the synthesis pollution is reduced; a novel, green and efficient path is provided for synthesis of alkyl bifunctional compounds, and the scope of energetic material preparation technologies is widened.

Description

Technical Field

[0001] The invention belongs to the technical field of energetic materials, and particularly relates to a cyclic double peroxide, a synthesis method and an application thereof in the preparation of an alkyl double functional compound. Background Art

[0002] As a high-performance, high-efficiency, and high-reliability material, energetic materials have broad application prospects in the fields of military, aerospace, petroleum, chemical industry, automobile, electronics, construction, etc. For example, energetic materials are essential damage and power energy materials for various weapon systems (including ballistic missiles and cruise missiles), and are important components of explosives, propellants, and propellant formulations. With the advancement of science and technology and the diversification of people's needs, the application areas of energetic materials are also constantly expanding. In the field of new energy, energetic materials can be used for energy storage and power generation; in the field of environmental protection, they can be used for the harmless treatment of waste and pollutants.

[0003] The azide group (-N3) is a highly reactive functional group that can decompose under certain conditions to release a large amount of energy. This structural feature makes alkylbisazide compounds an important class of energetic materials. Alkylbisazide compounds have a high energy density and can be used as high-energy fuels. During the combustion process, the nitrogen and other gases produced by the decomposition of the azide group can provide a large amount of heat energy, thereby propelling the flight of rockets or other aircraft. In addition, alkylbisazide compounds also play an important role in the field of energetic adhesives. They can be used as components of adhesives to improve the strength and heat resistance of adhesives.

[0004] There are two main industrial preparation methods for alkylbisazide compounds: catalytic azidation and dibromide synthesis. Catalytic azidation refers to the preparation of bisazide compounds by reacting compounds containing carbon-carbon double bonds with azidation reagents (NaN3) in the presence of catalysts and free radical initiators (acyl peroxides, hydroperoxides, dialkyl peroxides). For example, patent application No. 201711026558.7 discloses a method for preparing bisazide compounds, in which raw materials including compounds containing carbon-carbon double bonds and azidation reagents react in the presence of a copper-containing catalyst, an iron catalyst or a trifluoromethanesulfonate anion metal catalyst and a free radical initiator (self-benzoyl peroxide, lauroyl peroxide, isopropylbenzene hydroperoxide, etc.) to prepare the desired bisazide compounds. However, this method needs to be carried out under specific temperature, pressure and catalyst conditions, which are difficult to accurately control, thus affecting the purity and yield of the product, and the types of compounds containing carbon-carbon double bonds are limited, which limits the expansion of the types of alkylbisazide compounds. In addition, manganese salt catalysts can also convert olefin compounds into alkylbisazide compounds in the presence of peroxides such as hydrogen peroxide and benzoyl peroxide. However, this method usually requires the reaction to be carried out at low temperatures, which increases the energy consumption and cost in the production process. At the same time, low-temperature reactions may also lead to a decrease in reaction rate, thereby affecting production efficiency. The dibromide synthesis method refers to the synthesis of alkylbisazides by azidating the corresponding bromohydrocarbons with an azidating agent. During the synthesis process, the reaction conditions need to be strictly controlled to ensure the purity and yield of the product, and the number of dibromide alkyls is small, which limits the diversity of alkylbisazide compounds. Summary of the invention

[0005] In view of the technical problems existing in the preparation of existing alkyl bifunctional compounds, especially alkyl bisazide compounds, the present invention provides a cyclic diperoxide, a synthesis method and the application of the cyclic diperoxide in the preparation of alkyl bifunctional compounds, develops a novel method for continuously generating carbon free radicals, and utilizes abundant metal catalysis to efficiently obtain a series of diazide compounds containing alkyl chains of varying lengths; the present invention greatly enriches the synthesis methods of alkyl bifunctional compounds, especially alkyl bisazide compounds, and has the advantages of low catalyst cost, simple and rapid preparation process, and convenience for industrial production.

[0006] In order to achieve the above object, the technical solution adopted by the present invention is:

[0007] Cyclic double peroxide, its chemical formula is: R represents an aryl group, a n-propyl group, a tert-butyl group, an ethoxy group, an alcoholic hydroxyl group, a halogen atom, a cyano group or a trifluoromethyl group; and n represents 0-10.

[0008] The synthesis method of cyclic double peroxide, the synthesis route is:

[0009]

[0010] In the formula, R includes aryl, n-propyl, tert-butyl, ethyl group, alcohol hydroxyl group, halogen atom, cyano group or trifluoromethyl group; n represents 0-10; R 1 The alkyl groups include acetyl, chloroacetyl, benzoyl, p-fluorobenzoyl, m-fluorobenzoyl, m-chlorobenzoyl, trimethylsilyl, triethylsilyl or triphenylsilyl.

[0011] The synthesis method is specifically as follows: A mmol hydrogen peroxide, B mmol cycloalkanone, and C mmol H2SO4 are mixed in DmL of ethanol, and the mixture is stirred for 1-12h to be converted into E mmol cycloalkyldiperoxy alcohol; wherein, A:B=(4-8):1; B:C=(5-10):1; B:D=(1-2):1; subsequently, the cycloalkyldiperoxy alcohol is dissolved in F mL of dichloromethane, and n-hexane G mL is added, followed by Hmmol of a base, and 1 mmol of an acyl chloride or chlorosilane is dripped in at -30°C, and the mixture is reacted for 30-50min to prepare a diperoxy compound; wherein, E:F=(1-2):1; E:G=1:(10-20); E:H=1:(2-3); and E:I=1:(2-3).

[0012] The cycloalkanone is selected from one of cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, cyclododecanone, cyclopentadecanone, 4-phenylcyclohexanone, 4-methylcyclohexanone, 4,4-difluorocyclohexanone, 4-ethylcyclohexanone, 4-propylcyclohexanone, 2-phenylcyclohexanone, adamantane ketone, 2,2-dimethylcyclopentanone and 2-indanone.

[0013] The base is pyridine, DMAP, triethylamine, sodium carbonate, sodium hydroxide or cesium carbonate.

[0014] The acyl chloride is selected from one of benzoyl chloride, p-fluorobenzoyl chloride, m-fluorobenzoyl chloride, o-fluorobenzoyl chloride, pentafluorobenzoyl chloride, acetyl chloride and chloroacetyl chloride.

[0015] The chlorosilane includes trimethylchlorosilane (TMSCl), triethylchlorosilane (TESCl) or tert-butyldimethylchlorosilane (TBSCl).

[0016] The application of cyclic double peroxide in the preparation of alkyl bifunctional compounds, J mmol trimethylsilyl azide TMSN3, TMSNCS or MgCl2, K mmol catalyst and E mmol double peroxide are mixed uniformly in L mL ethyl acetate or acetonitrile solvent environment, and then heated to 50℃±5℃ under the protection of inert gas to react to prepare the target double azide compound; wherein E:J=1:(2~3); E:K=(10~20):1; E:L=1:(5~10).

[0017] The catalyst is a transition metal, including Fe(OTf)2, FeCl2, FeBr2, Fe(acac)2, Fe(OAc)2, Fe(OTs)2, CuOTf, CuCl, Cu(CH3CN)4PF6, Cu(OAc)2, CuI, CuBr, CuSO4, NiCl2, Ni(OTf)2, NiBr2, Ni(acac)2, Ni(OAc)2, PdCl2, Pd(OAc)2, RuCl2, Co(dppe)Cl2, Co(Ph3P)2Cl2, CoI2, CoBr2, Co(acac)3, Co(acac)2, Co(OAc)2 or CoCl2.

[0018] The inert gas includes nitrogen or helium.

[0019] The reaction time after heating to 50°C±5°C is 3 to 6 hours.

[0020] Compared with the prior art, the present invention has the following beneficial effects:

[0021] 1. The present invention mainly adopts cheap and diverse cycloalkanones as raw materials, oxidizes them into diperoxy alcohols under the catalysis of hydrogen peroxide and protonic acid, and protects the alcohol hydroxyl group by protecting the substrate with protective agents such as acyl chloride, thereby improving the activity of the substrate and quickly preparing diperoxy compounds; the diperoxide prepared by the present invention has good stability and can be stored for a long time in an environment of -20°C, and the preparation is based on cycloalkyl ketones, hydrogen peroxide and acyl chloride, the raw material cost is low, and the atom economy is good.

[0022] 2. The diperoxide prepared by the present invention is then used as a catalyst with ferrous trifluoromethanesulfonate and TMSN3 as a -N3 source to prepare alkyl bifunctional compounds, especially alkyl diazide compounds, under mild conditions; compared with the existing olefin catalytic azidation method or dibromide synthesis method, alkyl diazide can achieve 1, n difunctionalization of alkyl chains under mild conditions through two consecutive catalytic processes of transition metals, including diazidation, dithiocyanate and dihalogenation. In addition, it is also found that it is suitable for the late modification of complex natural products, amino acids and drugs, and asymmetric difunctionalization of alkyl chains is feasible. Compared with traditional methods, the present invention broadens the substrate range, improves the synthesis efficiency, simplifies the synthesis process, and reduces synthesis pollution.

[0023] In summary, the present invention prepares alkyl bifunctional compounds under mild conditions under the catalysis of abundant metals (such as ferrous trifluoromethanesulfonate), and compared with the existing method of catalytic azidation, the preparation method of the present invention has the advantages of wide substrate synthesis range, good functional group tolerance (ester group, amide, alkenyl group, halogen atom, etc.), mild reaction conditions, high reaction efficiency, etc. It has a wide range of uses in organic synthesis, including but not limited to realizing double azidation, double halogenation, double borylation, double phosphation and double thiocyanate, which greatly broadens the synthesis range of double functionalized alkane molecules. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 is the NMR spectrum of the diperoxide compound A of Example 1, wherein: Figure 1 (A) is the hydrogen spectrum, Figure 1 (B) in the figure is the carbon spectrum.

[0025] Figure 2 is the NMR spectrum of the diperoxide compound B of Example 2, wherein: Figure 2 (A) is the hydrogen spectrum, Figure 2 (B) in the figure is the carbon spectrum.

[0026] Figure 3 is the NMR spectrum of the diperoxide compound C of Example 3, wherein: Figure 3 (A) is the hydrogen spectrum, Figure 3 (B) in the figure is the carbon spectrum.

[0027] Figure 4 is the NMR spectrum of the diperoxide compound D of Example 4, wherein: Figure 4 (A) is the hydrogen spectrum, Figure 4 (B) in the figure is the carbon spectrum.

[0028] Figure 5 is the NMR spectrum of the diperoxide compound E of Example 5, wherein: Figure 5 (A) is the hydrogen spectrum, Figure 5 (B) in the figure is the carbon spectrum.

[0029] Figure 6 This is the NMR spectrum of the product 1 alkyl diazide compound of Example 1, wherein: Figure 6 (A) is the hydrogen spectrum, Figure 6 (B) in the figure is the carbon spectrum.

[0030] Figure 7 This is the NMR spectrum of the product 2-alkyl diazide compound of Example 2, wherein: Figure 7 (A) is the hydrogen spectrum, Figure 7 (B) in the figure is the carbon spectrum.

[0031] Figure 8This is the NMR spectrum of the product 3 alkyl diazide compound of Example 3, wherein: Figure 8 (A) is the hydrogen spectrum, Figure 8 (B) in the figure is the carbon spectrum.

[0032] Fig. 9 This is the NMR spectrum of the product 4-alkyl diazide compound of Example 4, wherein: Fig. 9 (A) is the hydrogen spectrum, Fig. 9 (B) in the figure is the carbon spectrum.

[0033] Fig.10 This is the NMR spectrum of the product 5-alkyl diazide compound of Example 5, wherein: Fig.10 (A) is the hydrogen spectrum, Fig.10 (B) in the figure is the carbon spectrum.

[0034] Fig.11 This is the NMR spectrum of the product 6 of Example 6, wherein: Fig.11 (A) is the hydrogen spectrum, Figure 1 (B) in the figure is the carbon spectrum.

[0035] Fig.12 This is the NMR spectrum of the product 7 of Example 7, wherein: Fig.12 (A) is the hydrogen spectrum, Fig.12 (B) in the figure is the carbon spectrum. DETAILED DESCRIPTION

[0036] The preparation method of the present invention is described in detail below in conjunction with the accompanying drawings and the following groups of embodiments, but this should not be used as a limitation to the protection scope of the present invention.

[0037] It should be noted that, unless otherwise specified, the operations used in the embodiments, such as mixing, filtering, etc., are all routine operations in the art.

[0038] The drugs and reagents used in the following examples were all commercially available and of analytical grade.

[0039] Example 1

[0040] 1. This embodiment provides a novel diperoxy compound A: 2-chloroethane-1-peroxy acid-1-[(2-chloroacetyl)peroxy]-4-phenylcyclohexyl ester.

[0041]

[0042] 2. Synthesis steps of diperoxide A.

[0043]

[0044] In a 100mL round-bottom flask equipped with a magnetic particle, first add 10mmol of 4-phenylcyclohexanone, then add 5-10mL of ethanol solvent, add 40-80mmol of hydrogen peroxide during stirring, and gradually add 1-2mmol H2SO4, stir for 12h, add 50-100mL saturated sodium chloride aqueous solution, extract with dichloromethane three times, and quickly obtain by column chromatography (ethyl acetate: petroleum ether = 1:10); then dissolve the synthesized 7.5mmol diperoxy alcohol in 4-8mL dichloromethane, add n-hexane (75-150mL), cool to -30°C in a low-temperature cold trap, then add pyridine (15-23mmol) to the mixture, and add chloroacetyl chloride (15-23mmol) dropwise while stirring, and react at low temperature for 30min; after the reaction, filter the reaction solution with a Buchner funnel, rinse the residue with n-hexane, and concentrate the filtrate in vacuo (temperature below 30°C), and quickly separate by column chromatography to obtain (dichloromethane: petroleum ether = 1:2, total yield of two-step synthesis 41%).

[0045] Reference Figure 1 , the NMR spectrum of 2-chloroethane-1-peroxy acid-1-[(2-chloroacetyl)peroxy]-4-phenylcyclohexyl ester A is illustrated in the figure:

[0046] 1 H NMR (400MHz, CDCl3) δ7.34-7.28(m,2H),7.25-7.19(m,3H),4.12(s,2H),4.10(s,2H),2.66-2.59(m,1H),2.51-2.41(m,2H),1.93-1.75(m,6H);

[0047] 13 C NMR (100MHz, CDCl3) δ164.4,112.9,46.9,38.037.9,32.2,30.0,27.4,23.1ppm;

[0048] 3. Application of the diperoxide compound A in the preparation of alkyl bifunctional compounds, specifically in the preparation of alkyl diazide compounds, more specifically in the preparation of (1,5-diazidepentan-3-yl)benzene 1.

[0049]

[0050] In a 100 mL reaction tube equipped with a magnetic bar, catalyst Fe(OTf)2 (5 mmol%, 53 mg) was added, and then the tube was evacuated and backfilled with nitrogen (three times); subsequently, a solution of diperoxide A (3.0 mmol, 1100 mg) and TMSN3 (9.0 mmol, 1000 mg) mixed in EA (30.0 mL) was added via a syringe; the reaction mixture was stirred at 50 ° C for 3 h; after the reaction was completed, the reaction mixture was concentrated in vacuo and purified by silica gel flash chromatography (PE: DCM = 5: 1) to obtain a colorless, transparent oily product (1,5-diazopentan-3-yl)benzene (yield 62%, 427 mg).

[0051] The separation yield of the present invention by column chromatography was 62%. Figure 6 , the NMR spectrum of (1,5-diazidopentane-3-yl)benzene 1 is shown in the figure:

[0052] 1 H NMR (400MHz, CDCl3) δ7.35-7.31(m,2H),7.26-7.22(m,1H),7.16-7.14(m,2H) ,3.20-3.13(m,2H),3.07-3.00(m,2H),2.84-2.77(m,1H),1.97-1.86(m,4H);

[0053] 13 C NMR (100MHz, CDCl3) δ142.1,128.9,127.5,127.0,49.3,40.2,35.6ppm;

[0054] Example 2

[0055] 1. This example provides the synthesis of a novel diperoxide compound B: 2-chloroethane-1-peroxy acid-2-[(2-chloroacetyl)peroxy]-2,3-dihydro-1H-inden-2-yl ester.

[0056]

[0057] 2. Synthesis steps of diperoxide compound B

[0058]

[0059] In a 100mL round-bottom flask equipped with a magnetic rod, add 10mmol of 2-indanone, then add 5-10mL of ethanol solvent, add 40-80mmol of hydrogen peroxide during stirring, and gradually add 1-2mmol H2SO4, after stirring for 12h, 50-100mL of saturated sodium chloride aqueous solution was added, extracted three times with dichloromethane and quickly obtained by column chromatography (ethyl acetate: petroleum ether = 1:10); then 6.0mmol of the synthesized diperoxy alcohol was dissolved in 3-6mL of dichloromethane, and n-hexane (60-120mL) was added, cooled to -30°C in a low-temperature cold trap, and then pyridine (12-18mmol) was added to the mixed solution, and chloroacetyl chloride (12-18mmol) was added dropwise while stirring, and reacted at low temperature for 30 minutes; after the reaction was completed, the reaction solution was filtered with a Buchner funnel, and the residue was rinsed with n-hexane, and the filtrate was vacuum concentrated (temperature below 30°C), and column chromatography was quickly separated to obtain (dichloromethane: petroleum ether = 1:2, the total yield of the two-step synthesis was 49%).

[0060] Reference Figure 2 , the NMR spectrum of 2-chloroethane-1-peroxy acid-2-[(2-chloroacetyl)peroxy]-2,3-dihydro-1H-inden-2-yl ester B is shown in the figure:

[0061] 1 H NMR (400MHz, CDCl3) δ7.25-7.19(m,4H),4.12(s,4H),3.51(m,4H);

[0062] 13 C NMR (100MHz, CDCl3) δ164.1,137.2,127.6,124.8,121.4,39.8,37.9ppm;

[0063] 3. Application of the diperoxide compound A in the preparation of alkyl bifunctional compounds, specifically in the preparation of alkyl bisazide compounds, more specifically in the preparation of 1,2-bis(azidomethyl)benzene 2.

[0064]

[0065] In a 100 mL reaction tube equipped with a magnet, catalyst Fe(OTf)2 (5 mmol%, 53 mg) was added, and then the tube was evacuated and backfilled with nitrogen (three times); subsequently, a solution of double peroxide B (3.0 mmol, 1000 mg) and TMSN3 (9.0 mmol, 1000 mg) mixed in EA (30.0 mL) was added via a syringe; the reaction mixture was stirred at 50 ° C for 3 h; thereafter, the reaction mixture was concentrated in vacuo and purified by silica gel flash chromatography (PE: DCM = 5: 1) to obtain a colorless, transparent oily product, 1,2-bis(azidomethyl)benzene (yield 46%, 258 mg).

[0066] The separation yield of the present invention by column chromatography was 46%. Figure 7 , the NMR spectrum of 1,2-bis(azidomethyl)benzene 2 is shown in the figure:

[0067] 1 H NMR (400MHz, CDCl3) δ7.41-7.35 (m, 4H), 4.44 (s, 4H);

[0068] 13 C NMR (100MHz, CDCl3) δ133.8, 130.1, 129.0, 52.2ppm;

[0069] Embodiment 3 to Embodiment 5

[0070] The preparation method of cyclic double peroxide is consistent with that of Example 1 and Example 2, as shown in the following table:

[0071]

[0072] Example 6

[0073] 1. This embodiment provides the synthesis steps of a novel diperoxy compound A: 2-chloroethane-1-peroxy acid-1-[(2-chloroacetyl)peroxy]-4-phenylcyclohexyl ester.

[0074]

[0075] 2. The synthesis steps of diperoxide A are the same as those in Example 1.

[0076] 3. Application of the diperoxide compound A in the preparation of an alkyl bifunctional compound, specifically in the preparation of an alkyl dithiocyanate compound, more specifically in the preparation of [5-(cyanothio)-3-phenylpentyl]sulfanecarbonitrile 6:

[0077]

[0078] In a 100mL reaction tube equipped with a magnetic, catalyst Fe(OTf)2 (5mmol%, 53mg) was added, then the tube was evacuated and backfilled with nitrogen (three times); then, a solution of diperoxide A (3.0mmol, 1100mg) and TMSNCS (9.0mmol, 1200mg) mixed in EA (30.0mL) was added via a syringe; the reaction mixture was stirred at 50°C for 3h; after the reaction was completed, the reaction mixture was concentrated in vacuo and purified by silica gel flash chromatography (PE:EA=5:1). A colorless, transparent oily product was obtained (yield 69%, 487mg).

[0079] The separation yield of the present invention by column chromatography was 69%. Fig.11 , the NMR spectrum of (1,5-diazidopentane-3-yl)benzene 6 is shown in the figure:

[0080] 1 H NMR (400MHz, CDCl3) δ7.37-7.33(m,2H),7.29-7.25(m,1H),7.16-7.15(m,2H) ,2.96-2.88(m,1H),2.84-2.77(m,2H),2.68-2.61(m,2H),2.24-2.13(m,4H);

[0081] 13 C NMR (100MHz, CDCl3) δ140.3,129.4,127.7,127.4,111.8,42.7,36.4,31.6ppm;

[0082] Example 7

[0083] 1. This embodiment provides the synthesis steps of a novel diperoxy compound A, which is 2-chloroethane-1-peroxy acid-1-[(2-chloroacetyl)peroxy]-4-phenylcyclohexyl ester.

[0084]

[0085] 2. The synthesis steps of diperoxide A are the same as those in Example 1.

[0086] 3. Application of the diperoxide compound A in the preparation of alkyl bifunctional compounds, specifically in the preparation of alkyl dihalogenated compounds, more specifically in the preparation of (1,5-dichloropentan-3-yl)benzene 7:

[0087]

[0088] In a 100 mL reaction tube equipped with a magnetic bar, catalyst CuOTf (20 mmol%, 127 mg) was added, and then the tube was evacuated and backfilled with nitrogen (three times); subsequently, a solution of diperoxide A (3.0 mmol, 1100 mg) and MgCl2 (9.0 mmol, 855 mg) mixed in CH3CN (30.0 mL) was added via a syringe; the reaction mixture was stirred at 50°C for 3 h; after the reaction was completed, the reaction mixture was concentrated in vacuo and purified by silica gel flash chromatography (PE:DCM=5:1) to obtain a colorless, transparent oily product (yield 60%, 388 mg).

[0089] The separation yield of the present invention by column chromatography was 60%. Fig.12 , the NMR spectrum of ((1,5-dichloropent-3-yl)benzene 7 is shown in the figure:

[0090] 1 H NMR (400MHz, CDCl3) δ7.35-7.30(m,2H),7.25-7.23(m,1H),7.20-7.17(m,2H) ,3.44-3.37(m,2H),3.27-3.21(m,2H),3.12-3.05(m,1H),2.16-2.02(m,4H);

[0091] 13 C NMR (100MHz, CDCl3) δ141.7,128.8,127.7,127.0,42.7,40.1,39.1ppm;

[0092] Universality of the Bisazidation Reaction

[0093] Referring to Examples 1 to 5, by studying the size of different cyclic ketones, from the starting materials of five-membered cyclic ketones to fifteen-membered cyclic ketones, corresponding bis-azidoalkyl groups (products 8-10) were obtained, all of which were obtained in moderate to good yields. In addition, thiophene heterocycles (product 11), alkenyl groups (product 12), and ester groups (products 11-12) were compatible.

[0094]

[0095] The above embodiments provide a detailed description of the present invention, the purpose of which is to enable persons familiar with the technology in this field to understand the contents of the present invention and implement them, and the protection scope of the present invention cannot be limited thereby. Any equivalent changes or modifications made according to the spirit and essence of the present invention should be included in the protection scope of the present invention.

Claims

1. Cyclic double peroxide, characterized in that Its chemical formula is: R represents an aryl group, a n-propyl group, a tert-butyl group, an ethoxy group, an alcoholic hydroxyl group, a halogen atom, a cyano group or a trifluoromethyl group; and n represents 0-10.

2. The method for synthesizing cyclic double peroxide according to claim 1, characterized in that: The synthesis route is: In the formula, R includes aryl, n-propyl, tert-butyl, ethyl group, alcohol hydroxyl group, halogen atom, cyano group or trifluoromethyl group; n represents 0-10; R 1 The alkyl groups include acetyl, chloroacetyl, benzoyl, p-fluorobenzoyl, m-fluorobenzoyl, m-chlorobenzoyl, trimethylsilyl, triethylsilyl or triphenylsilyl.

3. The method for synthesizing cyclic double peroxide according to claim 2, characterized in that: The synthesis method is specifically as follows: A mmol hydrogen peroxide, B mmol cycloalkanone, and C mmol H2SO4 are mixed in D mL ethanol, and the mixture is stirred for 1-12 hours to be converted into E mmol cycloalkyl diperoxy alcohol; A:B=(4-8):1; B:C=(5-10):1; B:D=(1-2):1; subsequently, the cycloalkyl diperoxy alcohol is dissolved in F mL dichloromethane, and n-hexane G mL is added, followed by H mmol alkali, and 1 mmol acyl chloride or chlorosilane is dropped at -30°C, and the reaction is carried out for 30-50 minutes to prepare the diperoxy compound; E:F=(1-2):1; E:G=1:(10-20); E:H=1:(2-3); E:I=1:(2-3).

4. The method for synthesizing cyclic double peroxide according to claim 3, characterized in that: The cycloalkanone is selected from one of cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, cyclododecanone, cyclopentadecanone, 4-phenylcyclohexanone, 4-methylcyclohexanone, 4,4-difluorocyclohexanone, 4-ethylcyclohexanone, 4-propylcyclohexanone, 2-phenylcyclohexanone, adamantane ketone, 2,2-dimethylcyclopentanone and 2-indanone.

5. The method for synthesizing cyclic double peroxide according to claim 3, characterized in that: The base is pyridine, DMAP, triethylamine, sodium carbonate, sodium hydroxide or cesium carbonate.

6. The method for synthesizing cyclic double peroxide according to claim 3, characterized in that: The acyl chloride is selected from one of benzoyl chloride, p-fluorobenzoyl chloride, m-fluorobenzoyl chloride, o-fluorobenzoyl chloride, pentafluorobenzoyl chloride, acetyl chloride and chloroacetyl chloride.

7. The method for synthesizing cyclic double peroxide according to claim 3, characterized in that: The chlorosilane includes trimethylchlorosilane (TMSCl), triethylchlorosilane (TESCl) or tert-butyldimethylchlorosilane (TBSCl).

8. Use of the cyclic diperoxide according to claim 1 in the preparation of an alkyl bifunctional compound, characterized in that: J mmol trimethylsilyl azide TMSN3, TMSNCS or MgCl2, K mmol catalyst and E mmol diperoxide are mixed evenly in L mL ethyl acetate or acetonitrile solvent environment, and then heated to 50°C±5°C under the protection of inert gas to react to prepare the target diazide compound; E:J=1:(2~3); E:K=(10~20):1; E:L=1:(5~10).

9. Use of the cyclic diperoxide according to claim 8 in the preparation of an alkyl bifunctional compound, characterized in that: The catalyst is a transition metal, including Fe(OTf)2, FeCl2, FeBr2, Fe(acac)2, Fe(OAc)2, Fe(OTs)2, CuOTf, CuCl, Cu(CH3CN)4PF6, Cu(OAc)2, CuI, CuBr, CuSO4, NiCl2, Ni(OTf)2, NiBr2, Ni(acac)2, Ni(OAc)2, PdCl2, Pd(OAc)2, RuCl2, Co(dppe)Cl2, Co(Ph3P)2Cl2, CoI2, CoBr2, Co(acac)3, Co(acac)2, Co(OAc)2 or CoCl2.

10. Use of the cyclic diperoxide according to claim 8 in the preparation of an alkyl bifunctional compound, characterized in that: The inert gas includes nitrogen or helium; The reaction time after heating to 50°C±5°C is 3 to 6 hours.

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