Preparation method of organic diazide compound

Abstract

The invention discloses a preparation method of an organic diazide compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: in a reaction system without metal participation, trimethylsilyl azide is used as an azide source, a selective fluorine reagent is used as an activating agent, a carbon-nitrogen bond is constructed, the selective fluorine reagent promotes a substrate compound and trimethylsilyl azide to be subjected to a diazido reaction in acetonitrile in a nitrogen atmosphere, purification is performed after the reaction is completed, and the trimethylsilyl azide is obtained. A product compound is obtained. According to the preparation method of the organic diazide compound, a series of diazide products are synthesized with high separation yield (the highest separation yield can reach 93%), and the method is easy to operate, mild in reaction condition, good in reaction system tolerance and capable of tolerating various substrates.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing an organic bis-azide compound. Background Art

[0002] As one of the most common structural fragments in drug molecules, natural products, and molecular catalysts, o-diamine has attracted the interest of synthetic chemists for decades. Due to the importance of this structural fragment, researchers have been committed to the efficient and direct synthesis of this useful structure. Among the current o-diamine synthesis strategies, the 1,2-diazidation reaction of alkenes is an attractive method. The azide can be reduced to the corresponding amine by a hydrogenation reaction, providing an efficient and convenient route for the synthesis of o-diamine.

[0003] In 2022, the research group of Yumeng Shi utilized the ligand-to-metal charge transfer strategy, used an equivalent amount of iron(III) nitrate nonahydrate, and achieved the diazidation reaction of alkenes under blue light with trimethylsilyl azide as the azide source and acetonitrile as the solvent. In 2019, the research group of Robert H. Dodd successfully achieved the diazidation reaction of alkenes under visible light induction using stable bis(acetoxy)iodosulfate and sodium azide as the azide source. In 2022, the research group of Haichao Xu further reported the copper and electro-cocatalyzed 1,2-diazidation reaction of alkenes. This method uses copper(II) acetylacetonate as the metal catalyst and does not require an exogenous ligand. Although this scheme can obtain the corresponding bis-azide product in good yield, the above-reported 1,2-diazidation methods of alkenes generally have some limitations: these methods usually rely on expensive hypervalent iodine reagents or stoichiometric metal reagents to promote the generation of azide radicals, or require electrocatalysis to activate the azide reagent. Therefore, although these methods have achieved certain success to some extent, they are limited in practical applications due to high costs or complex operations.

[0004] Therefore, it is of great significance to develop a milder and simpler synthetic method to achieve the 1,2-diazidation reaction of alkenes. Summary of the Invention

[0005] In view of the above technical problems, the present invention provides a method for preparing an organic bis-azide compound.

[0006] To achieve the above object, the present invention provides the following technical solutions:

[0007] A method for preparing an organic bis-azide compound, comprising the following steps:

[0008] In a metal-free reaction system, using trimethylsilyl azide as the azide source and a selective fluorine reagent as the activator, a carbon-nitrogen bond is constructed. The selective fluorine reagent promotes the double azide reaction of the substrate compound with trimethylsilyl azide in a nitrogen atmosphere and acetonitrile. After the reaction is complete, purification is carried out to obtain the product compound.

[0009] Optionally, the substrate compound is selected from at least one of but-3-en-1-yl 4-methoxybenzoate, butyl 3-en-1-yl 4-phenoxybenzoate, but-3-en-1-yl 4-methylbenzoate, but-3-en-1-yl benzoate, hex-5-en-1-yl 2-methoxybenzoate, hex-5-en-1-yl 4-methoxybenzoate, hex-5-en-1-yl 4-cyanobenzoate, hex-5-en-1-yl 4-(trifluoromethyl)benzoate, hex-5-en-1-yl 3,5-bis(trifluoromethyl)benzoate, hex-5-en-1-yl 3-fluoro-4-methoxybenzoate, hex-5-en-1-yl 3-fluoro-4-methoxybenzoate, hex-5-en-1-yl tetrahydrofuran-3-carboxylate, hex-5-en-1-yl (1r,3r,5r,7r)-adamantane-2-carboxylate, methyl undec-10-enoate, hex-5-en-1-yl naphthalene-2-sulfonate, hex-5-en-1-yl 4-methylbenzenesulfonate, 2-(hex-5-en-1-yl)isoindoline-1,3-dione, 2-(but-3-en-1-yl)-2H-benzo[d][1,2,3]triazole, but-3-en-1-ylbenzene, allylcyclohexane, dodecene, 11-bromoundec-1-ene, styrene.

[0010] Furthermore, the substrate compound is selected from any one of but-3-en-1-yl 4-methoxybenzoate, butyl 3-en-1-yl 4-phenoxybenzoate, hex-5-en-1-yl 2-methoxybenzoate.

[0011] Furthermore, the molar ratio of the substrate compound, trimethylsilyl azide and the selective fluorine reagent is 2:6:(4 - 5); preferably 2:6:4.6.

[0012] Furthermore, the feeding ratio of the substrate compound to acetonitrile is 1 mmol:10 ml.

[0013] Optionally, the conditions in the double azide reaction process are as follows:

[0014] Under an inert atmosphere, in the solvent acetonitrile, stir and react at 25 - 40 °C for 9 - 24 h.

[0015] Furthermore, the conditions in the double azide reaction process are as follows:

[0016] Under an inert atmosphere, in the solvent acetonitrile, stir and react at 25 °C for 24 h.

[0017] Optionally, the preparation method specifically includes the following steps:

[0018] S1. Add a selective fluorine reagent into a Schlenk reaction tube containing a magnetic stir bar and dried. Fill the Schlenk reaction tube with nitrogen, circulate three times, then add a substrate compound, trimethylsilyl azide, and degassed and dried acetonitrile. Stir and react at 25 °C for 24 h.

[0019] S2. Rotate and evaporate to remove the solvent, and purify by silica gel column chromatography to obtain the product compound.

[0020] Furthermore, the eluent used in the silica gel column chromatography purification process is petroleum ether and ethyl acetate, and the volume ratio of the two is 30:1.

[0021] Compared with the prior art, the present invention has the following advantages and technical effects:

[0022] The present invention discloses a preparation method of an organic bis-azide compound. The specific reaction mechanism is as follows: Through a radical reaction, the selective fluorine reagent single-electron oxidizes TMSN3 (trimethylsilyl azide) to form an azide radical, which then adds to the olefin to form the target product. That is, the preparation method of the present invention synthesizes a series of bis-azide products with a relatively high isolation yield (up to 93% at most). This method is simple to operate, the reaction conditions are mild, and the reaction system has good tolerance and can tolerate a variety of substrates. Specific Embodiments

[0023] Now, various exemplary embodiments of the present invention will be described in detail. This detailed description should not be considered as a limitation of the present invention, but should be understood as a more detailed description of certain aspects, characteristics, and implementation schemes of the present invention.

[0024] It should be understood that the terms described in the present invention are only for describing specific embodiments and are not used to limit the present invention. In addition, for the numerical ranges in the present invention, it should be understood that each intermediate value between the upper and lower limits of the range is also specifically disclosed. Each intermediate value within any stated value or stated range and each smaller range between any other stated value or intermediate value within the stated range are also included in the present invention. The upper and lower limits of these smaller ranges can be independently included or excluded from the range.

[0025] Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. Although this invention only describes preferred methods and materials, any methods and materials similar or equivalent to those described herein can also be used in the practice or testing of this invention. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials related to the said documents. In case of conflict with any incorporated document, the content of this specification shall prevail.

[0026] Without departing from the scope or spirit of this invention, various improvements and changes can be made to the specific embodiments of the description of this invention, which are obvious to those skilled in the art. Other embodiments obtained from the description of this invention are obvious to those skilled in the art. The description and examples of this invention are merely exemplary.

[0027] Regarding "comprising", "including", "having", "containing", etc. used herein, they are all open-ended terms, meaning including but not limited to.

[0028] As used in this invention, "room temperature" refers to 20 - 30 °C unless otherwise specified.

[0029] All raw materials used in this invention are obtained by purchasing from the market. The selective fluorinating reagent was purchased from Energy Chemical, with its CAS: 140681 - 55 - 6.

[0030] The technical solution of this invention is further illustrated by the following examples.

[0031] Example 1

[0032] 0.46 mmol of the selective fluorinating reagent Selectfluor was added to a 25 mL dry Schlenk reaction tube (containing a magnetic stir bar). Nitrogen was filled into the Schlenk tube three times, then 0.2 mmol of but-3-en-1-yl 4-methoxybenzoate (labeled 3a), 0.6 mmol of trimethylsilyl azide TMSN3 and 2 mL of degassed and dried CH3CN as the reaction solvent were added. Stirring was carried out for 24 h under a nitrogen atmosphere at 25 °C. After the reaction was complete, the solvent was removed by a rotary evaporator, and the 1,2-diazidated product of the alkene (labeled 4a) was purified by silica gel column chromatography (the eluent was petroleum ether:ethyl acetate = 30:1).

[0033] The reaction process is as follows:

[0034]

[0035] The corresponding isolated yield reached 89%, the chromatographic yield was 92%, and the conversion rate of the alkene raw material was 98%.

[0036] Among them, the calculation formula for the separation yield is as follows:

[0037]

[0038] Furthermore, based on Example 1, by controlling a single variable and only changing a certain parameter condition (the dosage of the selective fluorine reagent, the reaction temperature, or the reaction time), the following series of tests were carried out. The specific test parameter conditions and the relevant data of the separation yield and conversion rate of the product are shown in Tables 1 - 3.

[0039] Table 1 Only changing the reaction temperature

[0040] Number Temperature / °C Separation Yield / % Conversion Rate / % 1 25 89 98 2 40 90 98

[0041] Table 2 Only changing the dosage of the selective fluorine reagent

[0042]

[0043] Table 3 Only changing the reaction time

[0044] Number Reaction Time / h Separation Yield / % Conversion Rate / % 1 9 80 92 2 12 85 95 3 24 89 98

[0045] Example 2

[0046] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of butyl 3-en-1-yl 4-phenoxybenzoate (3b). The 1,2-bisazide product of the olefin (label 4b) is obtained.

[0047] Example 3

[0048] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of but-3-en-1-yl 4-methylbenzoate (3c). The 1,2-bisazide product of the olefin (label 4c) is obtained.

[0049] Example 4

[0050] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of but-3-en-1-yl benzoate (3d). The 1,2-bisazide product of the olefin (label 4d) is obtained.

[0051] Example 5

[0052] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hexyl 5-en-1-yl 2-methoxybenzoate (3e). The 1,2-bisazide product of the olefin (label 4e) is obtained.

[0053] Example 6

[0054] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl 4-methoxybenzoate (3f). The 1,2-bisazidation product of the alkene (label 4f) is obtained.

[0055] Example 7

[0056] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl 4-cyanobenzoate (3g). The 1,2-bisazidation product of the alkene (label 4g) is obtained.

[0057] Example 8

[0058] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl 4-(trifluoromethyl)benzoate (3h). The 1,2-bisazidation product of the alkene (label 4h) is obtained.

[0059] Example 9

[0060] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl 3,5-bis(trifluoromethyl)benzoate (3i). The 1,2-bisazidation product of the alkene (label 4i) is obtained.

[0061] Example 10

[0062] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl 3-fluoro-4-methoxybenzoate (3j). The 1,2-bisazidation product of the alkene (label 4j) is obtained.

[0063] Example 11

[0064] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl 3-fluoro-4-methoxybenzoate (3k). The 1,2-bisazidation product of the alkene (label 4k) is obtained.

[0065] Example 12

[0066] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate is replaced with an equimolar amount of hex-5-en-1-yl tetrahydrofuran-3-carboxylate (3l). The 1,2-bisazidation product of the alkene (label 4l) is obtained.

[0067] Example 13

[0068] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of hex-5-en-1-yl (1r,3r,5r,7r)-adamantane-2-carboxylate (3m). The 1,2-bisazidation product of the alkene (labeled 4m) was obtained.

[0069] Example 14

[0070] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of methyl undec-10-enoate (3n). The 1,2-bisazidation product of the alkene (labeled 4n) was obtained.

[0071] Example 15

[0072] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of hex-5-en-1-yl naphthalene-2-sulfonate (3o). The 1,2-bisazidation product of the alkene (labeled 4o) was obtained.

[0073] Example 16

[0074] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of hex-5-en-1-yl 4-methylbenzenesulfonate (3p), 0.6 mmol of trimethylsilyl azide TMSN3, and 2 mL of degassed and dried CH3CN as the reaction solvent. The 1,2-bisazidation product of the alkene (labeled 4p) was obtained.

[0075] Example 17

[0076] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of 2-(hex-5-en-1-yl)isoindoline-1,3-dione (3q). The 1,2-bisazidation product of the alkene (labeled 4q) was obtained.

[0077] Example 18

[0078] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of 2-(but-3-en-1-yl)-2H-benzo[d][1,2,3]triazole (3r). The 1,2-bisazidation product of the alkene (labeled 4r) was obtained.

[0079] Example 19

[0080] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of but-3-en-1-ylbenzene (3s). The 1,2-bisazide product of the alkene (label 4s) was obtained.

[0081] Example 20

[0082] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of allylcyclohexane (3t). The 1,2-bisazide product of the alkene (label 4t) was obtained.

[0083] Example 21

[0084] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of dodecene (3u). The 1,2-bisazide product of the alkene (label 4u) was obtained.

[0085] Example 22

[0086] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of 11-bromoundec-1-ene (3v). The 1,2-bisazide product of the alkene (label 4v) was obtained.

[0087] Example 23

[0088] The difference from Example 1 is that but-3-en-1-yl 4-methoxybenzoate was replaced with an equimolar amount of styrene (3w). The 1,2-bisazide product of the alkene (label 4w) was obtained.

[0089] 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n, 3o, 3p, 3q, 3r were synthesized in the laboratory, and the specific method is as follows:

[0090] General method A for synthesizing alkenes: Dissolve 4-dimethylaminopyridine (DMAP) (0.5 mmol), Et3N (10.0 mmol) and alcohol (5.0 mmol) in dichloromethane (12.0 mL), and place it in a 50 mL Schlenk flask. Add acyl chloride (7.5 mmol) dropwise at 0 °C. The solution was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was quenched with water. Then the reaction mixture was washed with brine and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography to obtain products 3a - 3n. The reaction process is as follows:

[0091]

[0092] General method B for synthesizing olefins: Dissolve 4-dimethylaminopyridine (0.5 mmol), Et3N (10.0 mmol), and alcohol (5.0 mmol) in dichloromethane (12.0 mL), and place it in a 50 mL Schlenk flask. Add sulfonyl chloride (7.5 mmol) dropwise at 0 °C. Stir the reaction mixture at room temperature for 2 hours. After the reaction is complete, quench the mixture with water. Then wash the reaction mixture with brine and extract it with EtOAc. Dry the combined organic phases over Na2SO4, filter, and concentrate under vacuum. Purify the residue by silica gel column chromatography to obtain products 3o - 3p. The reaction process is as follows:

[0093]

[0094] General method C for synthesizing olefins: Dissolve amine (10.0 mmol), alkenyl halide (13.0 mmol), and K2CO3 (13.0 mmol) in N,N-dimethylformamide (30.0 mL), and place it in a 100 mL Schlenk flask. Stir the reaction mixture at room temperature and monitor the progress of the reaction by TLC analysis. After 6 hours, judge that the reaction is complete by TLC. Slowly pour the reaction mixture into water (100.0 mL). Extract the aqueous phase with CH2Cl2 (5 × 20.0 mL). Wash the organic extract with water (3 × 40.0 mL) and dry it over Na2SO4. After filtration, evaporate the volatile substances in the filtrate under reduced pressure. Purify the residue by silica gel column chromatography to obtain products 3q, 3r. The reaction process is as follows:

[0095]

[0096] Among them, the above three methods are only for reference in preparing the raw material substrate compounds, not the key points of the invention, and do not limit the specific raw material substrate compounds used in the present invention.

[0097] Perform structural characterization on the product compounds obtained in Examples 1 - 23 to determine the corresponding separation yield (yield). Determine the product structure by 1H NMR, 13C NMR, and high-resolution mass spectrometry (HRMS). 1 1H NMR 13 13C NMR

[0098] The product compound obtained in Example 1 is the 1,2-bisazide product of olefin, named 3,4-diazidobutyl-4-methoxybenzoate, labeled 4a, and its structural formula is as follows:

[0099]

[0100] 3,4-Diazidobutyl 4-methoxybenzoate(4a): 52.2 mg of colorless oil was isolated, yield: 90%. 1 HNMR(400 MHz, Chloroform-d) δ 8.02 - 7.93(m, 2H), 6.97 - 6.88(m, 2H), 4.52 - 4.31(m, 2H), 3.85(s, 3H), 3.76 - 3.66(m, 1H), 3.49(dd, J = 12.7, 4.1 Hz, 1H), 3.41(dd, J = 12.8, 7.2 Hz, 1H), 2.08 - 1.97(m, 1H), 1.95 - 1.84(m, 1H). 13 C NMR(101 MHz, Chloroform-d) δ 166.12, 163.64, 131.70, 122.22, 113.80, 60.86, 59.27, 55.52, 54.94, 31.14. HRMS(ESI) exact mass calculated for [C 12 H 14 N6O3H + : 291.1200, found 291.1201.

[0101] The product compound obtained in Example 2 is the 1,2-bisazide product of an alkene, named 3,4-diazidobutyl 4-phenoxybenzoate, labeled 4b, and its structural formula is as follows:

[0102]

[0103] 3,4-Diazidobutyl 4-phenoxybenzoate(4b): 64.1 mg of colorless oil was isolated, yield: 91%. 1 HNMR(400 MHz, Chloroform-d) δ 8.04 - 7.97(m, 2H), 7.43 - 7.35(m, 2H), 7.23 - 7.16(m, 1H), 7.12 - 7.03(m, 2H), 7.03 - 6.97(m, 2H), 4.52 - 4.37(m, 2H), 3.77 - 3.67(m, 1H), 3.49(dd, J = 12.7, 4.1 Hz, 1H), 3.41(dd, J = 12.7, 7.2 Hz, 1H), 2.09 - 1.98(m, 1H), 1.97 - 1.85(m, 1H). 13CNMR(101MHz,Chloroform-d)δ165.77,162.10,155.50,131.72,130.07,124.62,124.04,120.16,117.33,60.99,59.19,54.84,31.05.HRMS(ESI)exactmass calculated for[C 17 H 16 N6O3Na + :375.1176,found 375.1180.

[0104] The product compound obtained in Example 3 is a 1,2-diazidated product of an alkene, named 3,4-diazidobutyl 4-methylbenzoate, labeled 4c, and its structural formula is as follows:

[0105]

[0106] 3,4-Diazidobutyl 4-methylbenzoate(4c):38.9mg colorless oil wasisolated,yield:71%. 1 HNMR(400MHz,DMSO-d6)δ7.88(d,J=8.2Hz,2H),7.33(d,J=8.0Hz,2H),4.43-4.29(m,2H),3.99-3.88(m,1H),3.67(dd,J=13.0,3.7Hz,1H),3.50(dd,J=13.0,7.4Hz,1H),2.37(s,3H),2.05-1.93(m,1H),1.92-1.80(m,1H). 13 C NMR(101MHz,Chloroform-d)δ166.44,144.03,129.67,129.26,127.12,60.98,59.25,54.95,31.12,21.73.HRMS(ESI)exact mass calculated for[C 12 H 14 N6O2Na + :297.1070,found297.1068.

[0107] The product compound obtained in Example 4 is a 1,2-diazidated product of an alkene, named 3,4-diazidobutyl benzoate, labeled 4d, and its structural formula is as follows:

[0108]

[0109] 3,4-Diazidobutyl benzoate(4d): 42.7 mg of colorless oil was isolated, yield: 82%. 1 H NMR(400 MHz, DMSO-d6) δ 8.00(dd, J = 8.2, 1.1 Hz, 2H), 7.70 - 7.62(m, 1H), 7.57 - 7.50(m, 2H), 4.45 - 4.31(m, 2H), 3.99 - 3.91(m, 1H), 3.68(dd, J = 13.0, 3.7 Hz, 1H), 3.51(dd, J = 13.0, 7.4 Hz, 1H), 2.06 - 1.95(m, 1H), 1.93 - 1.82(m, 1H). 13 C NMR(101 MHz, Chloroform-d) δ 166.38, 133.31, 129.84, 129.64, 128.56, 61.18, 59.21, 54.95, 31.09. HRMS(ESI) exact mass calculated for [C 11 H 12 N6O2Na + : 283.0914, found 283.0915.

[0110] The product compound obtained in Example 5 is a 1,2-diazide product of an alkene, named 5,6-diazidohexyl 2-methoxybenzoate, labeled 4e, and its structural formula is as follows:

[0111]

[0112] 5,6-Diazidohexyl 2-methoxybenzoate(4e): 59.2 mg of colorless oil was isolated, yield: 93%. 1 H NMR(400 MHz, Chloroform-d) δ 7.77(dd, J = 7.9, 1.8 Hz, 1H), 7.53 - 7.40(m, 1H), 7.05 - 6.89(m, 2H), 4.30(t, J = 6.4 Hz, 2H), 3.89(s, 3H), 3.53 - 3.43(m, 1H), 3.39(dd, J = 12.6, 4.1 Hz, 1H), 3.31(dd, J = 12.7, 7.3 Hz, 1H), 1.83 - 1.73(m, 2H), 1.68 - 1.56(m, 3H), 1.55 - 1.47(m, 1H). 13CNMR (101 MHz, Chloroform-d) δ 166.29, 159.16, 133.55, 131.54, 120.22, 120.16, 112.08, 64.29, 61.96, 55.96, 54.84, 31.45, 28.44, 22.61. HRMS (ESI) exact mass calculated for [C 14 H 18 N6O3H + : 319.1513, found 319.1516.

[0113] The product compound obtained in Example 6 is the 1,2-diazidated product of an alkene, named 5,6-diazidohexyl 4-methoxybenzoate, labeled 4f, and its structural formula is as follows:

[0114]

[0115] 5,6-Diazidohexyl 4-methoxybenzoate (4f): 56.0 mg of colorless oil was isolated, yield: 88%. 1 1H NMR (400 MHz, Chloroform-d) δ 8.00 - 7.95 (m, 2H), δ 6.96 - 6.86 (m, 2H), 4.28 (t, J = 6.4 Hz, 2H), 3.83 (s, 3H), 3.52 - 3.43 (m, 1H), 3.39 (dd, J = 12.6, 4.0 Hz, 1H), 3.31 (dd, J = 12.7, 7.3 Hz, 1H), 1.83 - 1.73 (m, 2H), 1.65 - 1.55 (m, 3H), 1.55 - 1.45 (m, 1H). 13 CNMR (101 MHz, Chloroform-d) δ 166.34, 163.40, 131.58, 122.68, 113.66, 64.16, 61.90, 55.45, 54.81, 31.46, 28.50, 22.62. HRMS (ESI) exact mass calculated for [C 14 H 18 N6O3H + : 319.1513, found 319.1514.

[0116] The product compound obtained in Example 7 is the 1,2-diazidated product of an alkene, named 5,6-diazidohexyl 4-cyanobenzoate, labeled 4g, and its structural formula is as follows:

[0117]

[0118] 5,6-Diazidohexyl 4-cyanobenzoate(4g): 52.0 mg colorless oil was isolated, yield: 83%. 1 HNMR(400 MHz, Chloroform-d) δ 8.10 (d, J=8.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 4.34 (t, J=6.5 Hz, 2H), 3.52 - 3.44 (m, 1H), 3.39 (dd, J=12.7, 4.1 Hz, 1H), 3.32 (dd, J=12.7, 7.2 Hz, 1H), 1.85 - 1.75 (m, 2H), 1.65 - 1.55 (m, 3H), 1.55 - 1.45 (m, 1H). 13 C NMR(101 MHz, Chloroform-d) δ 164.88, 134.02, 132.22, 130.03, 117.95, 116.34, 65.25, 61.76, 54.74, 31.36, 28.30, 22.48. HRMS(ESI) exact mass calculated for [C 14 H 15 N7O2Na + : 336.1179, found 336.1179.

[0119] The product compound obtained in Example 8 is a 1,2-diazidated product of an alkene, named 5,6-diazidohexyl 4-(trifluoromethyl)benzoate, labeled 4h, and its structural formula is as follows:

[0120]

[0121] 5,6-Diazidohexyl 4-(trifluoromethyl)benzoate(4h): 49.9 mg colorless oil was isolated, yield: 70%. 11H NMR (400 MHz, Chloroform-d) δ 8.13 (d, J = 8.1 Hz, 2H), 7.69 (d, J = 8.2 Hz, 2H), 4.36 (t, J = 6.5 Hz, 2H), 3.54 - 3.44 (m, 1H), 3.40 (dd, J = 12.7, 4.2 Hz, 1H), 3.33 (dd, J = 12.7, 7.2 Hz, 1H), 1.90 - 1.76 (m, 2H), 1.69 - 1.57 (m, 3H), 1.57 - 1.46 (m, 1H). 13 13C NMR (101 MHz, Chloroform-d) δ 165.39, 134.46 (q, J = 32.6 Hz), 133.55 (d, J = 1.0 Hz), 130.01, 125.48 (q, J = 3.7 Hz), 123.71 (q, J = 272.7 Hz), 65.07, 61.89, 54.85, 31.48, 28.44, 22.60. 19 19F NMR (376 MHz, Chloroform-d) δ -63.12. HRMS (ESI) exact mass calculated for 14 C 15 H + F3N6O2Na

[0122] The product compound obtained in Example 9 is the 1,2-diazidated product of an alkene, named 5,6-diazidohexyl 3,5-bis(trifluoromethyl)benzoate, labeled 4i, and its structural formula is as follows:

[0123]

[0124] 5,6-Diazidohexyl 3,5-bis(trifluoromethyl)benzoate (4i): 67.0 mg colorless oil was isolated, yield: 79%. 1 1H NMR (400 MHz, Chloroform-d) δ 8.47 (s, 2H), 8.06 (s, 1H), 4.42 (t, J = 6.6 Hz, 2H), 3.55 - 3.45 (m, 1H), 3.41 (dd, J = 12.6, 4.2 Hz, 1H), 3.35 (dd, J = 12.6, 7.2 Hz, 1H), 1.91 - 1.81 (m, 2H), 1.69 - 1.58 (m, 3H), 1.58 - 1.50 (m, 1H). 1313C NMR (101 MHz, Chloroform-d) δ 163.99, 132.52, 132.28 (q, J = 34.1 Hz), 129.80 (d, J = 4.0 Hz), 126.45 (dt, J = 3.7 Hz), 122.98 (q, J = 272.9 Hz), 65.77, 61.89, 54.90, 31.51, 28.42, 22.56. 19 19F NMR (376 MHz, Chloroform-d) δ -63.07. HRMS (ESI) exact mass calculated for 15 C 14 12H + 19F6N6O2H

[0125] The product compound obtained in Example 10 is a 1,2-bisazide product of an alkene, named 5,6-diazidohexyl 3-fluoro-4-methoxybenzoate, labeled 4j, and its structural formula is as follows:

[0126]

[0127] 5,6-Diazidohexyl 3-fluoro-4-methoxybenzoate (4j): 47.1 mg of colorless oil was isolated, yield: 70%. 1 1H NMR (400 MHz, Chloroform-d) δ 7.81 - 7.77 (m, 1H), 7.71 (dd, J = 11.7, 2.0 Hz, 1H), 6.96 (t, J = 8.4 Hz, 1H), 4.29 (t, J = 6.5 Hz, 2H), 3.92 (s, 3H), 3.52 - 3.43 (m, 1H), 3.39 (dd, J = 12.7, 4.1 Hz, 1H), 3.32 (dd, J = 12.7, 7.3 Hz, 1H), 1.85 - 1.73 (m, 2H), 1.65 - 1.56 (m, 3H), 1.55 - 1.45 (m, 1H). 1313C NMR (101 MHz, Chloroform-d) δ 165.43 (d, J = 2.6 Hz), 151.75 (d, J = 10.7 Hz), 151.69 (d, J = 246.8 Hz), 126.67 (d, J = 3.4 Hz), 123.02 (d, J = 6.3 Hz), 117.15 (d, J = 19.7 Hz), 112.40 (d, J = 1.9 Hz), 64.54, 61.89, 56.26, 54.83, 31.46, 28.46, 22.59. 19 19F NMR (376 MHz, Chloroform-d) δ -134.64. HRMS (ESI) exact mass calculated for [C 14 H 17 F N6 O3 Na + : 359.1238, found 359.1241.

[0128] The product compound obtained in Example 11 is a 1,2-diazidated product of an alkene, named 5,6-diazidohexyl 3-chloro-4-fluorobenzoate, labeled 4k, and its structural formula is as follows:

[0129]

[0130] 5,6-Diazidohexyl 3-chloro-4-fluorobenzoate (4k): 49.7 mg colorless oil was isolated, yield: 73%. 1 1H NMR (400 MHz, Chloroform-d) δ 8.06 (dd, J = 7.1, 2.2 Hz, 1H), 7.94 - 7.88 (m, 1H), 7.18 (t, J = 8.6 Hz, 1H), 4.31 (t, J = 6.5 Hz, 2H), 3.51 - 3.44 (m, 1H), 3.40 (dd, J = 12.7, 4.1 Hz, 1H), 3.32 (dd, J = 12.7, 7.2 Hz, 1H), 1.83 - 1.74 (m, 2H), 1.64 - 1.56 (m, 3H), 1.55 - 1.46 (m, 1H). 13CNMR(101MHz,Chloroform-d)δ164.59,161.05(d,J=256.2Hz),132.35(d,J=1.0Hz),129.98(d,J=8.4Hz),127.49(d,J=3.6Hz),121.45(d,J=18.3Hz),116.69(d,J=21.7Hz),65.02,61.84,54.82,31.44,28.39,22.55. 19 F NMR(376MHz,Chloroform-d)δ-108.04.HRMS(ESI)exact mass calculated for[C 13 H 14 ClFN6O2Na + :363.0743,found 363.0758.

[0131] The product compound obtained in Example 12 is a 1,2-diazidated product of an alkene, named 5,6-diazidohexyl tetrahydrofuran-3-carboxylate, labeled 4l, and its structural formula is as follows:

[0132]

[0133] 5,6-Diazidohexyl tetrahydrofuran-3-carboxylate(4l):35.0mg colorlessoil was isolated,yield:62%. 1 H NMR(400MHz,Chloroform-d)δ4.10(t,J=6.5Hz,2H),4.00-3.93(m,1H),3.92-3.83(m,2H),3.83-3.76(m,1H),3.50-3.42(m,1H),3.39(dd,J=12.6,4.1Hz,1H),3.32(dd,J=12.6,7.2Hz,1H),3.13-3.02(m,1H),2.24-2.06(m,2H),1.72-1.62(m,2H),1.60-1.48(m,3H),1.46-1.37(m,1H). 13 C NMR(101MHz,Chloroform-d)δ173.92,70.39,68.33,64.43,61.89,54.85,43.88,31.45,29.61,28.36,22.50.HRMS(ESI)exact mass calculated for[C 11 H18 N6O3Na + :305.1333, found 305.1337.

[0134] The product compound obtained in Example 13 is the 1,2-bisazide product of an alkene, named 5,6-diazidohexyl (1R,3R,5R,7R)-adamantane-2-carboxylate, labeled 4m, and its structural formula is as follows:

[0135]

[0136] 5,6-Diazidohexyl(1R,3R,5R,7R)-adamantane-2-carboxylate(4m): 45.0mg colorless oil was isolated, yield: 65%. 1 1H NMR (400 MHz, Chloroform-d) δ 4.04 (t, J = 6.3 Hz, 2H), 3.50 - 3.42 (m, 1H), 3.39 (dd, J = 12.6, 4.0 Hz, 1H), 3.31 (dd, J = 12.6, 7.3 Hz, 1H), 2.03 - 1.96 (m, 3H), 1.86 (d, J = 2.8 Hz, 6H), 1.76 - 1.61 (m, 8H), 1.60 - 1.51 (m, 3H), 1.48 - 1.38 (m, 1H). 13 13C NMR (101 MHz, Chloroform-d) δ 177.75, 63.53, 61.91, 54.86, 40.78, 38.92, 36.55, 31.46, 28.40, 28.00, 22.52. HRMS(ESI) exact mass calculated for [C 17 H 26 N6O2Na + :369.2009, found 369.2021.

[0137] The product compound obtained in Example 14 is the 1,2-bisazide product of an alkene, named methyl 10,11-diazidoundecanoate, labeled 4n, and its structural formula is as follows:

[0138]

[0139] Methyl 10,11-diazidoundecanoate(4n): 36.1mg colorless oil was isolated, yield: 64%. 1HNMR(400MHz,Chloroform-d)δ3.60(s,3H),3.44 - 3.37(m,1H),3.33(dd,J=12.6,4.0Hz,1H),3.25(dd,J=12.7,7.4Hz,1H),2.24(t,J=7.5Hz,2H),1.59 - 1.51(m,2H),1.51 - 1.44(m,2H),1.43 - 1.29(m,2H),1.28 - 1.22(m,8H). 13 C NMR(101MHz,Chloroform-d)δ174.07,61.98,54.74,51.31,33.94,31.65,29.12,29.10,29.02,28.97,25.76,24.81.HRMS(ESI)exact mass calculated for[C 12 H 22 N6O2Na + :305.1696,found 305.1700.

[0140] The product compound obtained in Example 15 is a 1,2 - bis - azide product of an alkene, named 5,6 - diazidohexyl naphthalene - 2 - sulfonate, labeled 4o, and its structural formula is as follows:

[0141]

[0142] 5,6 - Diazidohexyl naphthalene - 2 - sulfonate(4o): 56.1mg colorless oil was isolated, yield: 75%. 1 H NMR(400MHz,Chloroform-d)δ8.48(s,1H),7.98(t,J=8.3Hz,2H),7.92(d,J=8.0Hz,1H),7.85(dd,J=8.7,1.7Hz,1H),7.72 - 7.59(m,2H),4.07(t,J=6.2Hz,2H),3.39 - 3.32(m,1H),3.29(dd,J=12.7,3.9Hz,1H),3.21(dd,J=12.6,7.3Hz,1H),1.71 - 1.62(m,2H),1.51 - 1.34(m,4H). 1313C NMR (101 MHz, Chloroform-d) δ 135.22, 132.65, 131.87, 129.74, 129.66, 129.44, 129.27, 128.00, 127.90, 122.41, 70.31, 61.68, 54.61, 31.00, 28.46, 21.91. HRMS (ESI) exact mass calculated for [C 16 H 18 N6O3SNa + : 397.1053, found 397.1054.

[0143] The product compound obtained in Example 16 is the 1,2-bisazide product of an alkene, named 5,6-diazidohexyl 4-methylbenzenesulfonate, labeled 4p, and its structural formula is as follows:

[0144]

[0145] 5,6-Diazidohexyl 4-methylbenzenesulfonate (4p): 47.3 mg of colorless oil was isolated, yield: 70%. 1 1H NMR (400 MHz, Chloroform-d) δ 7.75 (d, J = 8.2 Hz, 2H), 7.33 (d, J = 8.2 Hz, 2H), 3.99 (t, J = 6.2 Hz, 2H), 3.42 - 3.31 (m, 2H), 3.25 (dd, J = 12.5, 7.2 Hz, 1H), 2.42 (s, 3H), 1.69 - 1.60 (m, 2H), 1.49 - 1.32 (m, 4H). 13 13C NMR (101 MHz, Chloroform-d) δ 144.92, 132.83, 129.89, 127.80, 70.01, 61.72, 54.64, 31.01, 28.42, 21.91, 21.58. HRMS (ESI) exact mass calculated for [C 13 H 18 N6O3SNa + : 361.1053, found 361.1057.

[0146] The product compound obtained in Example 17 is the 1,2-bisazide product of an alkene, named 2-(5,6-diazidohexyl)isoindole-1,3-dione, labeled 4q, and its structural formula is as follows:

[0147]

[0148] 2-(5,6-Diazidohexyl)isoindoline-1,3-dione(4q): 49.5 mg colorless oil was isolated, yield: 79%. 1 H NMR(400 MHz, Chloroform-d) δ 7.87 - 7.78(m, 2H), 7.75 - 7.65(m, 2H), 3.68(t, J = 7.1 Hz, 2H), 3.49 - 3.41(m, 1H), 3.38(dd, J = 12.6, 4.0 Hz, 1H), 3.30(dd, J = 12.6, 7.4 Hz, 1H), 1.75 - 1.66(m, 2H), 1.64 - 1.45(m, 3H), 1.44 - 1.31(m, 1H). 13 C NMR(101 MHz, Chloroform-d) δ 168.45, 134.04, 132.11, 123.30, 61.88, 54.82, 37.53, 31.33, 28.30, 23.21. HRMS(ESI) exact mass calculated for [C 14 H 15 N7O2Na + : 336.1179, found 336.1177.

[0149] The product compound obtained in Example 18 is the 1,2 bis-azide product of an alkene, named 2-(5,6-diazidohexyl)-2H-benzo[d][1,2,3]triazole, labeled 4r, and its structural formula is as follows:

[0150]

[0151] 2-(5,6-Diazidohexyl)-2H-benzo[d][1,2,3]triazole(4r): 45.6 mg colorless oil was isolated, yield: 80%. 11H NMR (400 MHz, Chloroform-d) δ 8.10 (d, J = 8.4 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 4.35 (t, J = 6.5 Hz, 2H), 3.51 - 3.44 (m, 1H), 3.40 (dd, J = 12.6, 4.1 Hz, 1H), 3.32 (dd, J = 12.7, 7.2 Hz, 1H), 1.85 - 1.76 (m, 2H), 1.65 - 1.55 (m, 3H), 1.55 - 1.47 (m, 1H). 13 13C NMR (101 MHz, Chloroform-d) δ 144.37, 126.39, 118.01, 61.70, 56.09, 54.77, 31.17, 29.60, 23.00. HRMS (ESI) exact mass calculated for [C 12 H 15 N9H + : 286.1523, found 286.1519.

[0152] The product compound obtained in Example 19 is the 1,2-bisazide product of an alkene, named (3,4-diazidobutyl)benzene, labeled 4s, and its structural formula is as follows:

[0153]

[0154] (3,4-Diazidobutyl)benzene (4s): 35.0 mg of colorless oil was isolated, yield: 81%. 1 1H NMR (400 MHz, Chloroform-d) δ 7.26 - 7.17 (m, 2H), 7.16 - 7.07 (m, 3H), 3.39 - 3.31 (m, 1H), 3.31 - 3.18 (m, 2H), 2.78 - 2.66 (m, 1H), 2.66 - 2.54 (m, 1H), 1.81 - 1.69 (m, 2H). 13 13C NMR (101 MHz, Chloroform-d) δ 140.46, 128.75, 128.48, 126.44, 61.22, 55.02, 33.49, 32.10. HRMS (ESI) exact mass calculated for [C 10 H 12 N6Na + : 239.1016, found 239.1016.

[0155] The product compound obtained in Example 20 is the 1,2-diazide product of an alkene, named (2,3-diazidopropyl)cyclohexane, labeled 4t, and its structural formula is as follows:

[0156]

[0157] (2,3-Diazidopropyl)cyclohexane(4t): 29.1 mg of colorless oil was isolated, yield: 70%. 1 H NMR(400 MHz, Chloroform-d)δ3.60 - 3.50(m, 1H), 3.38(dd, J = 12.7, 4.0 Hz, 1H), 3.30(dd, J = 12.7, 7.3 Hz, 1H), 1.76 - 1.64(m, 4H), 1.51 - 1.39(m, 2H), 1.38 - 1.08(m, 5H), 1.02 - 0.83(m, 2H). 13 C NMR(101 MHz, Chloroform-d)δ59.61, 55.45, 39.33, 34.40, 33.79, 32.77, 26.48, 26.27, 26.12. HRMS(ESI) exact mass calculated for[C9H 16 N6Na + : 231.1329, found 231.1334.

[0158] The product compound obtained in Example 21 is the 1,2-diazide product of an alkene, named 1,2-diazidododecane, labeled 4u, and its structural formula is as follows:

[0159]

[0160] 1,2-diazidododecane(4u): 34.3 mg of colorless oil was isolated, yield: 68%. 1 H NMR(400 MHz, Chloroform-d)δ3.49 - 3.40(m, 1H), 3.36(dd, J = 12.6, 4.0 Hz, 1H), 3.29(dd, J = 12.7, 7.4 Hz, 1H), 1.53(q, J = 7.2 Hz, 2H), 1.47 - 1.40(m, 1H), 1.35 - 1.20(m, 15H), 0.88(t, J = 6.8 Hz, 3H). 1313C NMR (101 MHz, Chloroform-d) δ 62.13, 54.88, 31.96, 31.82, 29.63, 29.58, 29.47, 29.38, 29.36, 25.93, 22.74, 14.14. HRMS (ESI) exact mass calculated for [C 12 H 24 N6H + : 253.2135, found 253.2147.

[0161] The product compound obtained in Example 22 is the 1,2-bisazide product of an alkene, named 1,2-diazido-11-bromoundecane, labeled 4v, and its structural formula is as follows:

[0162]

[0163] 1,2-Diazido-11-bromoundecane (4v): 38.0 mg of colorless oil was isolated, yield: 60%. 1 1H NMR (400 MHz, Chloroform-d) δ 3.47 - 3.41 (m, 1H), 3.40 - 3.33 (m, 3H), 3.28 (dd, J = 12.7, 7.4 Hz, 1H), 1.87 - 1.78 (m, 2H), 1.56 - 1.47 (m, 2H), 1.46 - 1.33 (m, 4H), 1.32 - 1.24 (m, 8H). 13 13C NMR (101 MHz, Chloroform-d) δ 62.01, 54.79, 34.00, 32.77, 31.70, 29.23, 29.19, 28.65, 28.09, 25.81. HRMS (ESI) exact mass calculated for [C 11 H 21 BrN6H + : 317.1084, found 317.1087.

[0164] The product compound obtained in Example 23 is the 1,2-bisazide product of an alkene, named (1,2-diazoethyl)benzene, labeled 4w, and its structural formula is as follows:

[0165]

[0166] (1,2-Diazidoethyl)benzene(4w): 18.1 mg of colorless oil was isolated, yield: 48%. 1 H NMR(400 MHz, DMSO-d6) δ 7.43(d, J = 4.3 Hz, 4H), 7.40(t, J = 3.8 Hz, 1H), 5.02(dd, 1H), 3.67(d, J = 5.6 Hz, 1H), 3.65(d, J = 3.1 Hz, 1H). 13 C NMR(101 MHz, DMSO-d6) δ 136.54, 128.77, 128.67, 127.26, 64.03, 54.38.

[0167] Then, the separation yields of the product compounds obtained from Examples 1 - 23 using different substrate compounds were statistically analyzed, as shown in Table 1:

[0168] Table 1 Statistical table of separation yields of different substrate compounds

[0169]

[0170]

[0171] In summary, this reaction system has high generality. First, a series of aliphatic terminal alkenes containing benzoyl groups have good tolerance in this system and are successfully converted into the corresponding 1,2-diazide products in high yields. And different functional groups are attached to the benzoyl group, whether electron-withdrawing or electron-donating groups, can obtain satisfactory yields (4a - 4i) under the optimal reaction conditions. At the same time, it is found that the substituents at the ortho and para positions on the benzene ring (4a, 4e) and the substrates with disubstitutions (4j, 4k) can be successfully converted into the target products in good yields under the existing reaction system; when the aryl ring is replaced by other groups (such as tetrahydrofuran, adamantane, heterocycle, cycloalkane), this reaction can also occur smoothly to obtain the corresponding products (4l, 4m, 4q, 4r, 4t); different carbon chain lengths also show excellent reactivity (4u, 4v, 4w).

[0172] Therefore, the present invention adopts the above-mentioned method for preparing an organic bisazide compound to synthesize a series of alkene bisazide products with a high separation yield (up to 93% at most). This method has simple operation, mild reaction conditions, good tolerance of the reaction system, and good substrate applicability.

[0173] The above are only the preferred specific embodiments of the present invention, but the protection scope of the present invention is not limited thereto. Any changes or substitutions that can be easily thought of by those skilled in the art within the technical scope disclosed by the present invention should be covered within the protection scope of the present invention. Therefore, the protection scope of the present invention should be subject to the protection scope of the claims.

Claims

1. A method for preparing an organic bis - azide compound, characterized in that, Comprising the following steps: Under the condition that a selective fluorine reagent is used as an activator, the substrate compound undergoes a diazide reaction with trimethylsilyl azide to construct a carbon-nitrogen bond, and then is purified to obtain an organic diazide compound.

2. The preparation method of an organic bis - azide compound according to claim 1, wherein, The substrate compound is selected from at least one of but-3-en-1-yl 4-methoxybenzoate, butyl 3-en-1-yl 4-phenoxybenzoate, but-3-en-1-yl 4-methylbenzoate, but-3-en-1-yl benzoate, hex-5-en-1-yl 2-methoxybenzoate, hex-5-en-1-yl 4-methoxybenzoate, hex-5-en-1-yl 4-cyanobenzoate, hex-5-en-1-yl 4-(trifluoromethyl)benzoate, hex-5-en-1-yl 3,5-bis(trifluoromethyl)benzoate, hex-5-en-1-yl 3-fluoro-4-methoxybenzoate, hex-5-en-1-yl 3-fluoro-4-methoxybenzoate, hex-5-en-1-yl tetrahydrofuran-3-carboxylate, hex-5-en-1-yl (1r,3r,5r,7r)-adamantane-2-carboxylate, methyl undec-10-enoate, hex-5-en-1-yl naphthalene-2-sulfonate, hex-5-en-1-yl 4-methylbenzenesulfonate, 2-(hex-5-en-1-yl)isoindoline-1,3-dione, 2-(but-3-en-1-yl)-2H-benzo[d][1,2,3]triazole, but-3-en-1-yl benzene, allylcyclohexane, dodecene, 11-bromoundec-1-ene, styrene.

3. The preparation method of an organic bis-azide compound according to claim 2, characterized in that, The substrate compound is selected from any one of but-3-en-1-yl 4-methoxybenzoate, butyl 3-en-1-yl 4-phenoxybenzoate, hex-5-en-1-yl 2-methoxybenzoate.

4. The preparation method of an organic bis-azide compound according to claim 1, wherein, The molar ratio of the substrate compound, trimethylsilyl azide and the selective fluorine reagent is 2∶6∶(4 - 5).

5. The preparation method of an organic bis-azide compound according to claim 4, characterized in that, The molar ratio of the substrate compound, trimethylsilyl azide and the selective fluorine reagent is 2∶6∶4.

6.

6. The preparation method of an organic bis-azide compound according to claim 1, characterized in that, The conditions in the diazide reaction process are as follows: Under an inert atmosphere, in an organic solvent, stirring and reacting at 25 - 40 °C for 9 - 24 h.

7. The preparation method of an organic bis-azide compound according to claim 6, characterized in that, The conditions in the diazide reaction process are as follows: Under an inert atmosphere, in an organic solvent, stirring and reacting at 25 °C for 24 h.

8. The preparation method of an organic bis-azide compound according to claim 6, characterized in that, The feeding ratio of the substrate compound to the organic solvent is 1 mmol∶10 ml.

9. The preparation method of an organic bisazide compound according to claim 6, characterized in that, The organic solvent is acetonitrile.

10. A method for preparing an organic bisazide compound according to claim 1, characterized in that, The preparation method specifically comprises the following steps: S1. Add the selective fluorine reagent into a Schlenk reaction tube containing a magnetic stir bar and dried. Fill the Schlenk reaction tube with nitrogen, circulate three times, and then add the substrate compound, trimethylsilyl azide and degassed and dried acetonitrile for the diazide reaction; S2. Rotate and evaporate to remove the solvent, and purify by silica gel column chromatography to obtain the organic diazide compound.

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