Functionalized silacyclohexene compound as well as preparation method and application thereof

Abstract

The invention discloses a functionalized silacyclohexene compound as well as a preparation method and application thereof. The functionalized silacyclohexene compound is shown as a formula (I). The preparation method comprises the following step: synthesizing the borate-substituted silacyclohexene compound with high regioselectivity from halomethyl allene silane and diborate through a copper-catalyzed allene intramolecular boronation cyclization reaction. Compared with a traditional synthesis method using alkyl halogenated hydrocarbon, chlorosilane and a metal reagent as raw materials, the method has the characteristics of mild reaction conditions, simple preparation method, commercially available catalyst and the like, and can be used for obtaining various functionalized silacyclohexene compounds with different substituent groups; and a novel method is provided for synthesis of different functionalized organosilane compounds.

Description

Technical Field

[0001] This invention relates to a functionalized silane heterocyclohexene compound, its preparation method and application, belonging to the field of silane compound chemical synthesis technology. Background Technology

[0002] Compared to carbon atoms, silicon atoms have lower electronegativity, larger atomic radius, and available 3d empty orbitals. These characteristics lead to significant differences in the chemical reactivity and physical properties of silicon-containing compounds. Therefore, introducing silicon atoms into organic molecules can effectively regulate the electron cloud distribution, spatial configuration, and reactivity of molecules, thereby endowing silicon-containing compounds with unique properties and application potential.

[0003] Among them, the silane six-membered ring skeleton has shown important value in the fields of organic chemistry, medicinal chemistry and materials science due to its special electronic effects and spatial configuration. Specifically, it is reflected in: (1) Enhanced bioactivity: Studies have shown that the introduction of silane six-membered ring structure into drug molecules can significantly enhance key bioactivity such as lipophilicity and metabolic stability. For example, silane faracin and compound (-)-sila-mesembranol both show better antidepressant effects than their parent carbon compounds; (2) Regulation of material properties: The silane six-membered ring skeleton plays an important role in the field of materials science. For example, compounds containing this structure can be applied to liquid crystal materials and organic dye systems. The introduction of silicon atoms can effectively regulate the stability and optical properties of materials; (3) Expansion of chemical diversity: Replacing quaternary carbon atoms in organic molecules with silicon atoms is an effective strategy for expanding chemical diversity. For example, silane herbalone obtained by replacing the quaternary carbon center in the fragrance molecule herbalone with silicon atoms exhibits a richer aroma characteristic than the parent herbalone. Traditional methods for synthesizing silane-hexa-membered ring compounds typically rely on nucleophilic cyclization reactions between dichlorosilanes and 1,5-bisGrignard reagents. However, this method, due to the use of chlorosilanes and metal reagents that are highly sensitive to water and oxygen, is incompatible with active functional groups, making it impossible to synthesize functionalized silane-hexa-membered ring compounds. To overcome this limitation, researchers have developed several alternative strategies, including ring-expansion reactions of silane-hexa-butanes with unsaturated hydrocarbons. For example, Utimoto, Hayashi, Song, Xu, Zhang, Wang, and others have developed a series of rhodium or palladium-catalyzed enantioselective cyclization reactions of silane-hexa-butanes with functionalized alkynes or allenes, achieving highly enantioselective construction of 1-silane-2-cyclohexene compounds with silicon steric centers. On the other hand, intramolecular cyclization using difunctionalized silanes as substrates has become an effective way to construct such skeletons. For example, Song et al. successfully synthesized siloxane compounds by using divinylsilane and allylamine derivatives as raw materials through a rhodium-catalyzed cyclization reaction; Yu et al. used silicon-bridged dialdehydes as raw materials to synthesize formyl-substituted siloxanes by intramolecular Aldol condensation under chiral amine catalysis; List et al. developed an intramolecular cyclization strategy of diallylsilane catalyzed by a superacid to synthesize siloxane derivatives containing silicon stereocenters.

[0004] Nevertheless, existing methods for catalytically constructing functionalized silicon hetero six-membered rings still have significant drawbacks, including dependence on noble metals or highly supported organic catalysts, limited product structural diversity, and insufficient ability for subsequent derivatization of functional groups, which severely restrict the further development and application of such compounds in functional organosilicon materials. Summary of the Invention

[0005] The purpose of this invention is to overcome the shortcomings of existing technologies and provide a functionalized silane-heterocyclohexene, its preparation method, and its applications. The preparation method uses a class of halomethyl allenylsilanes as starting materials, and under mild conditions, a copper-catalyzed allenyl borylation cyclization reaction can yield various functionalized silane-heterocyclohexenes with different substituents. Based on the structural characteristics of these compounds, a series of transformation methods have been subsequently developed to achieve the efficient synthesis of a series of functionalized silane-heterocyclohexenes.

[0006] This invention is achieved through the following technical solution: In a first aspect, the present invention provides a functionalized silane-hexene compound having a structure as shown in formula (I): In equation (I), R 1 R is methyl, substituted or unsubstituted aryl or tert-butoxy. 2 B(OR) is a methyl or substituted or unsubstituted aryl group. 3)2 is an o-diol-derived alkoxyboronic acid ester. The substituent is methyl, methoxy, ethyl, tert-butyl, or benzyloxy.

[0007] As a preferred option, B(OR) 3 )2 forms one of the following structures: .

[0008] Preferably, the functionalized silane heterocyclohexene compound is selected from one of the following B1 to B21: .

[0009] Secondly, the present invention provides a method for preparing the above-mentioned functionalized silane-heterocyclohexene compound, comprising the following steps: under an inert gas protection environment, a halomethyl allenyl silane compound of formula (II), an alloboronate ester of formula (III), a copper catalyst, a phosphine ligand, a base, and a solvent are mixed and stirred, and a functionalized silane-heterocyclohexene compound (I) is constructed by a copper-catalyzed allenyl borylation cyclization reaction, as shown in the following reaction formula: In formula (II) R 1 and R 2 The definition is the same as in equation (I).

[0010] This invention utilizes halomethyl allenylsilane compounds and commercially available pinacol diboronate as raw materials to efficiently synthesize a series of functionalized silanecyclohexene compounds via a transition metal-catalyzed boronization and cyclization reaction of allenes. The reaction is easy to synthesize, simple to operate, convenient to post-process, and yields good results.

[0011] Preferably, the phosphine ligand is one of the following formulas: Preferably, the copper catalyst is one of cuprous chloride, cuprous bromide, cuprous iodide, cuprous acetate, cuprous cyanide, and cuprous thiophene-2-carboxylate, and more preferably cuprous iodide, which can improve the reaction selectivity.

[0012] Preferably, the alkali is one of lithium tert-butoxide, sodium tert-butoxide, cesium carbonate, and potassium tert-butoxide.

[0013] Preferably, the solvent is selected from one of 1,4-dioxane, tetrahydrofuran, diethyl ether, toluene, dichloromethane, and N,N-dimethylformamide, and the amount used is sufficient to allow the solute to react completely; more preferably, it is 1,4-dioxane, in which case the reaction yield is the highest.

[0014] Preferably, the molar ratio of the compound shown in formula (II) to the compound shown in formula (III) is 0.5:1.0 to 1.0:2.0, and more preferably 1.0:1.0, at which point the reaction yield is the highest. The concentrations of the compounds shown in formula (II) and (III) in the solvent are 0.10 mol / L to 0.20 mol / L.

[0015] Preferably, the reaction temperature is 0~90 ℃ and the reaction time is 8~24 h; the reaction temperature is further preferably 70~90 ℃ and the reaction time is further preferably 16 h, at which point the reaction can be fully completed to obtain the highest yield and selectivity.

[0016] Preferably, the functionalized silanecyclohexene compound is obtained after post-treatment following the reaction. The post-treatment includes: filtering the reaction solution through diatomaceous earth, drying the organic phase and removing the solvent by rotary evaporation, and separating and purifying the crude product by silica gel column chromatography.

[0017] Thirdly, the present invention provides the application of the above-mentioned functionalized silanehexene compounds in organic synthesis, materials science and bioactive drug synthesis.

[0018] The borate ester group introduced in the compounds of this invention can serve as a universal synthetic site, and further molecular derivatization can be achieved through various means such as halogenation and catalytic coupling, providing a new route for the efficient catalytic synthesis of novel silicon-based functional molecules, as shown below: Compared with the prior art, the beneficial technical effects of the present invention are as follows: (1) This invention provides a novel borate ester-functionalized silane-hexene compound. The borate ester functional group introduced in this compound can be used as a reactive group in various transmetalation reactions and metal-catalyzed coupling reactions. The obtained functionalized silane-hexene can be used as a precursor in the derivatization preparation of various silicon-based heterocyclic molecules and drug molecules, and has substantial application value.

[0019] (2) This invention proposes a method for the direct catalytic synthesis of functionalized silanecyclohexene compounds, solving the problem of preparing borate-functionalized silanecyclohexene compounds that are difficult to obtain by conventional methods. This invention uses halomethyl allenylsilane as a raw material and achieves the simultaneous construction of a silane-hexene six-membered ring structure by introducing a borate functional group through a copper-catalyzed intramolecular borylation cyclization reaction. The reaction conditions are mild, using inexpensive and readily available copper catalysts and commercial phosphine ligands as the catalytic system, avoiding the use of precious metal reagents, thereby reducing the synthesis cost and operability, and exhibiting good yield, chemoselectivity, and regioselectivity.

[0020] Meanwhile, this technology achieves gram-scale production of functionalized silanecyclohexene, and compared with other methods, the method of this invention has greater potential for large-scale production. Attached Figure Description

[0021] Figure 1 This is the 1H NMR spectrum of compound B1.

[0022] Figure 2 This is the carbon NMR spectrum of compound B1. Detailed Implementation

[0023] The technical solutions in the embodiments of the present invention will be clearly and completely described below. These described embodiments are only a part of the examples of the present invention, and not all of them. All other embodiments obtained by those skilled in the art based on the embodiments of the present invention without creative effort are within the scope of protection of the present invention.

[0024] Example 1: This example provides a method for synthesizing functionalized silane compounds (B1-B21) using halomethyl allenyl silane compounds (A1-A21) as precursor compounds, to further illustrate the present invention.

[0025] 1) Preparation of compound B1, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A1 (164.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was complete, the mixture was filtered through diatomaceous earth, and the filtrate was concentrated under vacuum. The crude product was then purified by silica gel column chromatography (200-300 mesh) to obtain 97 mg of compound B1 as a white solid, with a yield of 58%. Its 1H NMR spectrum is shown below. Figure 1 As shown, the carbon spectrum is as follows Figure 2 As shown.

[0026] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.55 – 7.51 (m,4H), 7.39 – 7.33 (m, 6H), 6.94 (td, J = 5.5, 2.8 Hz, 1H), 2.53 – 2.45 (m, 2H), 1.96 (d, J = 5.4 Hz, 2H), 1.28 (s, 12H), 1.23 – 1.19 (m, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 142.7, 136.5, 134.7, 129.3, 127.8,83.1, 24.8, 23.1, 13.7, 8.6, 1.0. HRMS(ESI): m / z: [M + Na] + Calculated for C 23 H 29 BO2Si: 399.1922, Found:399.1919. 2) Preparation of compound B2, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A2 (220.8 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 125 mg of compound B2 as a white solid, with a yield of 51%.

[0027] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.47 – 7.44 (m,4H), 7.37 (d, J = 8.2 Hz, 4H), 6.91 (t, J = 5.6 Hz, 1H), 2.48 – 2.42 (m, 2H), 1.92 (d, J = 5.6 Hz, 2H), 1.31 (s, 18H), 1.26 (s, 12H), 1.16 (dd, J = 7.7, 5.7Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 152.1, 143.1, 134.5, 133.2, 124.8,83.1, 34.6, 31.2, 24.8, 23.1, 14.0, 8.89. HRMS (ESI): m / z: [M + Na] + Calculated for C 31 H 45 BO2Si: 510.3210, Found:510.3211. 3) Preparation of compound B3, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A3 (192.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 131.2 mg of compound B3 as a white solid, with a yield of 61%.

[0028] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.48 – 7.43 (m,4H), 7.22 – 7.18 (m, 4H), 6.97 – 6.90 (m, 1H), 2.66 (q, J = 7.7 Hz, 4H), 2.50 –2.44 (m, 2H), 1.94 (d, J = 5.6 Hz, 2H), 1.28 (d, J = 2.9 Hz, 12H), 1.24 (d, J = 7.6Hz, 6H), 1.18 (dd, J = 7.5, 6.0 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 145.3, 143.0, 134.7, 133.4, 127.4,83.0, 28.8, 24.8, 23.148, 15.3, 14.0, 8.8, 1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 27 H 37 BO2Si: 454.2584, Found:454.2585. 4) Preparation of compound B4, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A4 (194.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 110.2 mg of compound B4 as a white solid, with a yield of 51%.

[0029] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.45 – 7.40 (m,4H), 6.92 – 6.87 (m, 5H), 3.80 (s, 6H), 2.47 – 2.40 (m, 2H), 1.91 – 1.85 (m,2H), 1.26 (s, 12H), 1.13 (ddd, J = 8.2, 6.0, 1.5 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 160.5, 142.9, 136.1, 127.6, 113.6,83.1, 55.0, 24.8, 23.2, 14.3, 9.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 25 H 33 BO4Si: 458.2170, Found:458.2170. 5) Preparation of compound B5, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A5 (194.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 110.4 mg of compound B5 as a white solid, with a yield of 51%.

[0030] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.45 – 7.40 (m, 4H), 6.92 – 6.87 (m, 5H), 3.80 (s, 6H), 2.47 – 2.40 (m, 2H), 1.91 – 1.85 (m, 2H), 1.26 (s, 12H), 1.13 (ddd, J = 8.2, 6.0, 1.5 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 160.5, 142.9, 136.1, 127.6, 113.6,83.1, 55.0, 24.8, 23.2, 14.3, 9.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 25 H 33 BO4Si: 458.2170, Found:458.2170. 6) Preparation of compound B6, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A6 (178.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 103 mg of compound B6 as a white solid, with a yield of 51%.

[0031] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.43 – 7.40 (m,4H), 7.17 (d, J = 7.6 Hz, 4H), 6.92 (tt, J = 5.7, 1.5 Hz, 1H), 2.48 – 2.43 (m,2H), 2.35 (s, 6H), 1.91 (d, J = 5.4 Hz, 2H), 1.26 (s, 12H), 1.18 – 1.14 (m,2H). 13 C NMR (101 MHz, Chloroform- d ) δ 142.9, 139.1, 134.7, 133.1, 128.7,83.1, 24.8, 23.2, 21.5, 14.0, 8.8, 1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 25 H 33 BO2Si: 426.2271, Found:426.2269. 7) Preparation of compound B7, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A7 (192.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 102.3 mg of compound B7 as a white solid, with a yield of 47%.

[0032] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.15 (s, 4H), 7.03(s, 2H), 6.96 – 6.91 (m, 1H), 2.49 – 2.45 (m, 2H), 2.32 (s, 12H), 1.95 (d, J =5.6 Hz, 2H), 1.29 (s, 12H), 1.19 (dd, J = 7.4, 6.0 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.1, 137.0, 136.5, 132.3, 131.0,83.0, 24.8, 23.1, 21.4, 13.9, 8.7, 1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 27 H 37 BO2Si: 454.2584, Found:454.2583. 8) Preparation of compound B8, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A8 (206.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 113 mg of compound B8 as a white solid, with a yield of 49%.

[0033] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.47 (d, J = 7.7 Hz, 4H), 7.23 (d, J = 7.7 Hz, 4H), 6.95 (t, J = 5.6 Hz, 1H), 2.91 (p, J = 6.9 Hz, 2H), 2.48 (t, J = 6.8 Hz, 2H), 1.95 (d, J = 5.6 Hz, 2H), 1.29 (s, 12H), 1.28 (s, 6H), 1.26 (s, 6H), 1.19 (t, J = 6.7 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.9, 143.0, 134.7, 133.6, 126.0,83.0, 34.0, 24.8, 23.8, 23.1, 14.0, 8.9, 1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 29 H 41 BO2Si: 482.2897, Found:482.2990. 9) Preparation of compound B9, the reaction formula is as follows: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A9 (102.6 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 31 mg of compound B9 as a colorless liquid, with a yield of 25%.

[0034] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 6.77 (t, J = 5.7 Hz,1H), 2.29 – 2.24 (m, 2H), 1.35 (d, J = 5.7 Hz, 2H), 1.24 (s, 12H), 0.58 – 0.55(m, 2H), 0.02 (s, 6H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.9, 82.9, 24.8, 23.0, 16.0, 10.4,1.0, -2.1. HRMS (ESI): m / z: [M + Na] + Calculated for C 13 H 25 BO2Si: 274.1645, Found:274.1640. 10) The preparation of compound B10 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A10 (158.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 101 mg of compound B10 as a colorless liquid, with a yield of 56%.

[0035] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.01 (s, 1H), 7.82 (dd, J = 9.2, 6.9 Hz, 3H), 7.59 (dd, J = 8.2, 1.0 Hz, 1H), 7.48 (dd, J = 6.3, 3.2Hz, 2H), 6.90 (t, J = 5.7 Hz, 1H), 2.43 (t, J = 7.0 Hz, 2H), 1.80 (dd, J = 16.6, 5.5 Hz, 1H), 1.66 (d, J = 5.8 Hz, 1H), 1.27 (s, 12H), 1.03 (dt, J = 13.8, 6.7 Hz, 1H), 0.86 (dt, J = 14.1, 6.8 Hz, 1H), 0.39 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.3, 136.2, 134.3, 133.7, 132.8,130.0, 128.0, 127.7, 127.0, 126.3, 125.9, 83.1, 24.8, 23.2, 15.0, 9.7, 1.0, -3.4. HRMS (ESI): m / z: [M + Na] + Calculated for C 22 H 29 BO2Si: 386.1958, Found:386.1952. 11) The preparation of compound B11 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A11 (155.6 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 101 mg of compound B11 as a colorless liquid, with a yield of 56%.

[0036] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.01 – 6.95 (m,2H), 6.87 – 6.81 (m, 2H), 5.93 (s, 2H), 2.42 – 2.33 (m, 2H), 1.65 (dd, J =16.4, 5.6 Hz, 1H), 1.54 (dd, J = 16.5, 5.8 Hz, 1H), 1.26 (s, 12H), 0.88 (dt, J =13.7, 6.7 Hz, 1H), 0.81 – 0.72 (m, 1H), 0.27 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 148.4, 147.3, 143.3, 131.7, 127.7,113.1, 108.6, 100.5, 83.0, 24.8, 23.2, 15.2, 9.9, 1.0, -3.3. HRMS (ESI): m / z: [M + Na] + Calculated for C 19 H 27 BO4Si: 380.1700, Found:380.1691. 12) The preparation of compound B12 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A12 (133.6 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 86 mg of compound B12 as a colorless liquid, with a yield of 55%.

[0037] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.54 (dd, J = 6.7, 3.0 Hz, 2H), 7.36 (dd, J = 5.0, 1.9 Hz, 3H), 6.89 (td, J = 5.7, 1.4 Hz, 1H), 2.41(tt, J = 6.6, 1.3 Hz, 2H), 1.75 – 1.69 (m, 1H), 1.62 – 1.56 (m, 1H), 1.28 (s,12H), 0.96 (dt, J = 13.8, 6.7 Hz, 1H), 0.81 (dt, J = 13.7, 6.8 Hz, 1H), 0.33 (s,3H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.3, 138.7, 133.7, 129.0, 127.7,83.0, 24.8, 23.1, 14.9, 9.66, 1.0, -3.5. HRMS (ESI): m / z: [M + Na] + Calculated for C 18 H 27 BO2Si: 336.1802, Found:336.1799. 13) The preparation of compound B13 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A13 (140.6 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 96 mg of compound B13 as a colorless liquid, with a yield of 58%.

[0038] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.44 (d, J = 7.7 Hz, 2H), 7.19 (d, J = 7.5 Hz, 2H), 6.88 (t, J = 5.7 Hz, 1H), 2.43 – 2.38 (m, 2H), 2.36 (s, 3H), 1.71 (dd, J = 16.5, 5.3 Hz, 1H), 1.58 (dd, J = 16.5, 5.8 Hz, 1H),1.28 (s, 12H), 0.95 (dt, J = 13.9, 6.8 Hz, 1H), 0.80 (dd, J = 14.2, 7.1 Hz, 1H),0.31 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.4, 138.9, 135.0, 133.8, 128.6,83.0, 24.8, 23.1, 21.4, 15.1, 9.75, 1.0, -3.4. HRMS (ESI): m / z: [M + Na] + Calculated for C 19 H 29 BO2Si: 350.1958, Found:350.1961. 14) The preparation of compound B14 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A14 (154.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 85 mg of compound B14 as a colorless liquid, with a yield of 48%.

[0039] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.48 – 7.45 (m,2H), 7.23 (d, J = 7.8 Hz, 2H), 6.92 – 6.84 (m, 1H), 2.93 – 2.86 (m, 1H), 2.44 –2.35 (m, 2H), 1.73 – 1.67 (m, 1H), 1.56 (dd, J = 16.5, 6.0 Hz, 1H), 1.28 (s,12H), 1.27 (s, 3H), 1.25 (s, 3H), 0.94 (dt, J = 13.8, 6.6 Hz, 1H), 0.82 – 0.74(m, 1H), 0.30 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.8, 143.5, 135.6, 133.8, 126.0,83.0, 34.0, 24.8, 23.9, 23.2, 15.1, 9.8, 1.0, -3.5. HRMS (ESI): m / z: [M + Na] + Calculated for C 21 H 33 BO2Si: 378.2271, Found:378.2273. 15) The preparation of compound B15 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (127 mg) and 2-(dicyclohexylphosphino)biphenyl (8.8 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (4.8 mg) and potassium tert-butoxide (67.3 mg) were weighed in a glove box. Then, 2.5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A15 (147.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 85 mg of compound B15 as a colorless liquid, with a yield of 50%.

[0040] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.15 (s, 2H), 7.02(s, 1H), 6.89 (t, J = 5.6 Hz, 1H), 2.41 (dt, J = 8.0, 4.0 Hz, 2H), 2.33 (s, 6H), 1.75 – 1.68 (m, 1H), 1.58 (dd, J = 16.5, 5.9 Hz, 1H), 1.29 (s, 12H), 0.96 (dt, J = 13.9, 6.8 Hz, 1H), 0.79 (dt, J = 14.2, 6.7 Hz, 1H), 0.30 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.5, 138.5, 137.1, 131.4, 130.8,83.0, 24.8, 23.1, 21.3, 15.2, 9.7, 1.0, -3.4. HRMS (ESI): m / z: [M + Na] + Calculated for C 20 H 31 BO2Si: 364.2115, Found:364.2115. 16) The preparation of compound B16 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (253.9 mg) and 2-(dicyclohexylphosphino)biphenyl (17.5 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (9.5 mg) and potassium tert-butoxide (134.7 mg) were weighed in a glove box. Then, 5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A16 (263.3 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 151 mg of compound B16 as a colorless liquid, with a yield of 49%.

[0041] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 6.74 – 6.69 (m,1H), 2.40 – 2.28 (m, 2H), 1.50 (dd, J = 14.5, 5.5 Hz, 2H), 1.25 (s, 9H), 1.24(s, 12H), 0.74 – 0.67 (m, 1H), 0.59 (ddd, J = 14.2, 8.3, 5.4 Hz, 1H), 0.15 (s,3H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.5, 83.0, 72.3, 32.1, 31.2, 24.8,23.5, 18.9, 12.3, 0.6. HRMS (ESI): m / z: [M + Na] + Calculated for C 16 H 31 BO3Si: 332.2064, Found:332.2065. 17) The preparation of compound B17 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (253.9 mg) and 2-(dicyclohexylphosphino)biphenyl (17.5 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (9.5 mg) and potassium tert-butoxide (134.7 mg) were weighed in a glove box. Then, 5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A17 (325.3 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 214 mg of compound B17 as a white solid, with a yield of 58%.

[0042] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.62 – 7.58 (m,2H), 7.34 (dd, J = 5.9, 1.5 Hz, 3H), 6.81 (t, J = 5.6 Hz, 1H), 2.53 – 2.32 (m,2H), 1.78 (dd, J = 13.4, 5.6 Hz, 2H), 1.25 (s, 9H), 1.24 (s, 12H), 0.95 (t, J =6.8 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.1, 139.0, 133.8, 129.2, 127.6,83.0, 73.0, 32.1, 24.8, 23.5, 17.7, 11.4, 1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 21 H 33 BO3Si: 394.2221, Found: 394.2215. 18) The preparation of compound B18 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (253.9 mg) and 2-(dicyclohexylphosphino)biphenyl (17.5 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (9.5 mg) and potassium tert-butoxide (134.7 mg) were weighed in a glove box. Then, 5 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A18 (325.3 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 200 mg of compound B18 as a white solid, with a yield of 54%.

[0043] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.44 – 7.41 (m,2H), 7.30 (dd, J = 8.4, 6.9 Hz, 2H), 7.23 – 7.18 (m, 1H), 6.73 – 6.67 (m, 1H), 2.39 – 2.25 (m, 2H), 1.58 (s, 6H), 1.50 – 1.40 (m, 2H), 1.25 (s, 12H), 0.75 –0.68 (m, 1H), 0.57 (ddd, J = 14.3, 8.2, 5.5 Hz, 1H), 0.13 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 149.7, 143.3, 127.9, 126.3, 124.6,83.0, 75.3, 32.6, 32.5, 24.8, 12.1, 0.3. HRMS (ESI): m / z: [M + Na] + Calculated for C 21 H 33 BO3Si: 394.2221, Found: 394.2220. 19) The preparation of compound B19 is shown in the following reaction formula: Under a nitrogen atmosphere, pinacol diboronate (64.7 mg) and 2-(dicyclohexylphosphino)biphenyl (3.5 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (1.9 mg) and potassium tert-butoxide (26.9 mg) were weighed in a glove box. Then, 1 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A19 (64.7 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 45 mg of compound B19 as a white solid, with a yield of 60%.

[0044] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 8.07 – 8.01 (m,1H), 7.81 (d, J = 7.9 Hz, 1H), 7.50 – 7.44 (m, 2H), 7.34 – 7.30 (m, 1H), 6.89(t, J = 5.7 Hz, 1H), 2.45 – 2.37 (m, 2H), 1.76 (dd, J = 16.6, 5.5 Hz, 1H), 1.63(d, J = 4.6 Hz, 1H), 1.27 (s, 12H), 1.00 (dt, J = 13.8, 6.7 Hz, 1H), 0.88 – 0.81(m, 1H), 0.37 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 143.2, 140.1, 139.6, 134.2, 129.0,127.9, 126.9, 123.8, 123.1, 83.1, 24.8, 23.2, 15.1, 9.9, 1.0, -3.2. HRMS (ESI): m / z: [M + Na] + Calculated for C 20 H 27 BO2SSi: 392.1523, Found: 392.1530. 20) The preparation of compound B20 is shown in the following reaction formula: Under a nitrogen atmosphere, bis(2,4-dimethyl-2,4-pentanediol)borate (56.4 mg) and 2-(dicyclohexylphosphino)biphenyl (3.5 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (1.9 mg) and potassium tert-butoxide (26.9 mg) were weighed in a glove box. Then, 1 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A1 (65.9 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth, the filtrate was concentrated under vacuum, and the crude product was purified by silica gel column chromatography with a mesh size of 200-300 to obtain 41 mg of compound B20 as a colorless oil, with a yield of 52%.

[0045] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.55 – 7.51 (m,4H), 7.37 – 7.33 (m, 6H), 6.82 (t, J = 5.5 Hz, 1H), 2.44 (t, J = 6.6 Hz, 2H), 1.91 (d, J = 5.5 Hz, 2H), 1.80 (s, 2H), 1.34 (s, 12H), 1.17 (t, J = 6.8 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 138.4, 137.0, 134.7, 129.1, 127.8,70.3, 48.8, 31.8, 22.4, 13.3, 8.7, 1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 24 H 31 BO2Si: 412.2115, Found: 412.2113. 21) The preparation of compound B21 is shown in the following reaction formula: Under a nitrogen atmosphere, bis[(-)pinenediol]diboron ester (71.6 mg) and 2-(dicyclohexylphosphino)biphenyl (3.5 mg) were added to a 25 mL dry high-pressure tube. Cuprous iodide (1.9 mg) and potassium tert-butoxide (26.9 mg) were weighed in a glove box. Then, 1 mL of anhydrous 1,4-dioxane was added. After pre-stirring at room temperature for 30 minutes, compound A1 (65.9 mg) was added. The reaction was carried out at 70 °C for 16 h. After the reaction was completed, the mixture was filtered with diatomaceous earth. The filtrate was concentrated under vacuum and then purified by silica gel column chromatography with a mesh size of 200-300 to obtain 39 mg of compound B21 as a colorless oil, with a yield of 45%.

[0046] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.52 (dt, J = 7.8,1.8 Hz, 4H), 7.39 – 7.34 (m, 6H), 6.92 (t, J = 5.4 Hz, 1H), 4.31 (dd, J = 8.8, 1.9 Hz, 1H), 2.48 (t, J = 6.0 Hz, 2H), 2.38 – 2.32 (m, 1H), 2.21 (ddd, J = 12.0,5.8, 3.8 Hz, 1H), 2.07 (t, J = 5.4 Hz, 1H), 1.96 (d, J = 5.6 Hz, 2H), 1.90 (d, J =3.6 Hz, 1H), 1.41 (s, 3H), 1.26 (d, J = 7.0 Hz, 1H), 1.23 – 1.19 (m, 2H), 1.16(d, J = 10.8 Hz, 1H), 0.08 (s, 6H). 13 C NMR (101 MHz, Chloroform- d ) δ 142.5, 136.5, 134.7, 129.3, 127.83,87.5, 77.8, 51.4, 39.5, 38.1, 35.6, 28.7, 27.1, 26.4, 24.0, 23.2, 13.8, 8.7,1.0. HRMS (ESI): m / z: [M + Na] + Calculated for C 27 H 33 BO2Si: 450.2271, Found:450.2273. Example 2: In this embodiment, the obtained functionalized silanecyclohexene compound was applied to a further conversion reaction to synthesize halogen-substituted silanecyclohexene compounds (C1-C3). The specific reaction formula is as follows: 1) Preparation of compound C1, the reaction formula is as follows: B1 (75.3 mg), CuCl2 (80.7 mg), and methanol / water (1 mL / 1 mL) were added to a 25 mL test tube under a nitrogen atmosphere. The mixture was stirred at 70 °C for 12 h, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated. The crude product was then purified by silica gel column chromatography (200-300 mesh) to give 43 mg of compound C1 as a white solid, with a yield of 75%.

[0047] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.52 (dd, J = 7.7,1.7 Hz, 4H), 7.45 – 7.36 (m, 6H), 6.10 (t, J = 5.3 Hz, 1H), 2.68 (td, J = 7.0, 1.9 Hz, 2H), 1.86 (dt, J = 4.7, 2.1 Hz, 2H), 1.41 (t, J = 7.0 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 134.8, 134.7, 134.5, 129.7, 128.1,123.2, 31.3, 11.5, 8.7. HRMS (ESI): m / z: [M + Na] + Calculated for C 17 H 17 ClSi: 307.0680, Found: 307.0690. 2) Preparation of compound C2, the reaction formula is as follows: B1 (75.3 mg), CuBr2 (134 mg), and methanol / water (1 mL / 1 mL) were added to a 25 mL test tube under a nitrogen atmosphere. The mixture was stirred at 70 °C for 12 h, diluted with water, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated. The crude product was then purified by silica gel column chromatography (200-300 mesh) to give 37 mg of compound C2 as a white solid, with a yield of 56%.

[0048] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.52 (td, J = 5.5,2.7 Hz, 4H), 7.45 – 7.35 (m, 6H), 6.40 – 6.30 (m, 1H), 2.82 (ddt, J = 6.8, 4.4,2.5 Hz, 2H), 1.85 (dt, J = 4.8, 2.5 Hz, 2H), 1.45 – 1.39 (m, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 134.8, 134.5, 129.7, 128.1, 127.5,125.7, 33.7, 13.2, 9.7. HRMS (ESI): m / z: [M + Na] + Calculated for C 17 H 17 BrSi: 351.0175, Found: 351.0189. 3) Preparation of compound C3, the reaction formula is as follows: B1 (75.3 mg) was dissolved in 1.2 mL of tetrahydrofuran, and NaOH solution (480 mg) dissolved in 3.6 mL of H2O was added dropwise. The mixture was stirred vigorously for 3 hours in the dark. Iodine solution (101.5 mg) was then added dropwise to 0.8 mL of tetrahydrofuran. Stirring continued for 5 hours. After the reaction was complete, the mixture was quenched with sodium thiosulfate solution, washed with sodium bicarbonate solution, extracted with diethyl ether, dried over anhydrous sodium sulfate, and concentrated. The crude product was then purified by silica gel column chromatography (200-300 mesh) to obtain 37 mg of compound C3 as a white solid, with a yield of 49%.

[0049] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.51 (dd, J = 7.8,1.7 Hz, 4H), 7.45 – 7.33 (m, 6H), 6.65 (t, J = 5.4 Hz, 1H), 2.91 (td, J = 6.9, 1.9 Hz, 2H), 1.87 (dt, J = 5.4, 2.1 Hz, 2H), 1.37 (t, J = 6.9 Hz, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 136.1, 134.9, 134.5, 129.7, 128.1,101.1, 38.2, 15.3, 10.7. HRMS (ESI): m / z: [M + Na] + Calculated for C 17 H 17 ISi: 399.0036, Found: 399.0029. Example 3: In this embodiment, the obtained functionalized silicone compounds were applied to an oxidation reaction to synthesize silicone compounds (D1-D5). The specific reaction formulas are as follows: 1) Preparation of compound D1, the reaction formula is as follows: Add 2 mL of an aqueous solution of NaBO3·4H2O (123.1 mg) to a 2 mL tetrahydrofuran solution of B1 (75.3 mg). Stir the resulting heterogeneous mixture vigorously at room temperature for 12 h. After the reaction is complete, extract the aqueous phase with diethyl ether. Dry the combined organic phase extract with magnesium sulfate, filter, and concentrate under reduced pressure. Purify the crude product by silica gel column chromatography (200–300 mesh) to give 41 mg of compound D1 as a white solid, yield 76%.

[0050] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.61 – 7.55 (m,4H), 7.47 – 7.38 (m, 6H), 2.76 – 2.57 (m, 4H), 1.60 – 1.51 (m, 4H). 13 C NMR (101 MHz, Chloroform- d ) δ 214.0, 134.4, 134.3, 129.9, 128.2,37.9, 8.7. HRMS (ESI): m / z: [M + Na] + Calculated for C 17 H 18 OSi: 289.1019, Found: 289.1020. 2) Preparation of compound D2, the reaction formula is as follows: Add 1 mL of an aqueous solution of NaBO3·4H2O (120.0 mg) to a 1 mL tetrahydrofuran solution of B4 (67.9 mg). Stir the resulting heterogeneous mixture vigorously at room temperature for 12 h. After the reaction is complete, extract the aqueous phase with diethyl ether. Dry the combined organic phase extract with magnesium sulfate, filter, and concentrate under reduced pressure. Purify the crude product by silica gel column chromatography (200–300 mesh) to give 44 mg of compound D2 as a white solid, in 86% yield.

[0051] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.40 (ddd, J = 8.5,7.3, 1.8 Hz, 2H), 7.30 (dd, J= 7.2, 1.8 Hz, 2H), 6.95 (td, J = 7.4, 0.8 Hz, 2H), 6.88 (d, J = 8.3 Hz, 2H), 3.76 (s, 6H), 2.67 – 2.60 (m, 4H), 1.55 – 1.50 (m, 4H). 13 C NMR (101 MHz, Chloroform- d ) δ 216.2, 164.4, 136.2, 131.4, 123.0,120.7, 109.7, 55.0, 38.0, 7.6. HRMS (ESI): m / z: [M + Na] + Calculated for C 19 H 22 O3Si:349.1230, Found:349.1232. 3) Preparation of compound D3, the reaction formula is as follows: Add 1 mL of an aqueous solution of NaBO3·4H2O (87.7 mg) to a 1 mL tetrahydrofuran solution of B8 (47.5 mg). Stir the resulting heterogeneous mixture vigorously at room temperature for 12 h. After the reaction is complete, extract the aqueous phase with diethyl ether. Dry the combined organic phase extract with magnesium sulfate, filter, and concentrate under reduced pressure. Purify the crude product by silica gel column chromatography (200–300 mesh) to give 27 mg of compound E3 as a colorless oil, in 77% yield.

[0052] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.42 (d, J = 7.9 Hz,4H), 7.20 – 7.17 (m, 4H), 2.83 (p, J = 6.9 Hz, 2H), 2.60 – 2.52 (m, 4H), 1.46 –1.40 (m, 4H), 1.18 (d, J = 7.0 Hz, 12H). 13 C NMR (101 MHz, Chloroform- d) δ 214.1, 150.3, 134.3, 131.0, 126.1,37.8, 33.8, 23.5, 8.6. HRMS (ESI): m / z: [M + Na] + Calculated for C 23 H 30 OSi:373.1958, Found:373.1960. 4) Preparation of compound D4, the reaction formula is as follows: Add 1 mL of an aqueous solution of NaBO3·4H2O (121.5 mg) to a tetrahydrofuran solution of B7 (68.3 mg). Stir the resulting heterogeneous mixture vigorously at room temperature for 12 h. After the reaction is complete, extract the aqueous phase with diethyl ether. Dry the combined organic phase extract with magnesium sulfate, filter, and concentrate under reduced pressure. Purify the crude product by silica gel column chromatography (200–300 mesh) to give 39 mg of compound D4 as a white solid, in 76% yield.

[0053] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.16 (s, 4H), 7.07(s, 2H), 2.68 – 2.60 (m, 4H), 2.32 (s, 12H), 1.54 – 1.46 (m, 4H). 13 C NMR (101 MHz, Chloroform- d ) δ 214.5, 137.5, 134.3, 132.1, 131.6,38.1, 21.4, 8.8. HRMS (ESI): m / z: [M + Na] + Calculated for C 21 H 26 OSi:345.1645, Found:345.1647. 5) Preparation of compound D5, the reaction formula is as follows: A 12 mL aqueous solution of NaBO3·4H2O (1.1 g) was added to a 12 mL tetrahydrofuran solution of B15 (427.5 mg). The resulting heterogeneous mixture was stirred vigorously at room temperature for 12 h. After the reaction was complete, the aqueous phase was extracted with diethyl ether. The combined organic phase extract was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was then purified by silica gel column chromatography (200–300 mesh) to give 257 mg of compound D5 as a colorless oil, in 81% yield.

[0054] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.16 (s, 2H), 7.06(s, 1H), 2.59 (t, J = 7.3 Hz, 4H), 2.34 (s, 6H), 1.35 – 1.27 (m, 2H), 1.16 –1.07 (m, 2H), 0.39 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 214.8, 137.5, 136.2, 131.4, 131.3,37.9, 21.3, 9.6, -3.9. HRMS (ESI): m / z: [M + Na] + Calculated for C 14 H 20 OSi:255.1176, Found:255.1178. Example 4: In this embodiment, the obtained functionalized silane-hexene compounds were applied to a palladium-catalyzed Suzuki-Miyaura coupling reaction to synthesize aryl-substituted silane-hexene compound E1 and alkenyl-substituted silane-hexene compound E2. The specific reaction formulas are as follows: 1) The preparation of compound E1 is shown in the following reaction formula: Iodobenzene was added to a THF solution of B1 (75.3 mg), Pd2(dba)3 (9.2 mg), PPh3 (5.2 mg), and Cs2CO3 (130.3 mg). The mixture was stirred at 65°C for 24 hours. After cooling to room temperature, the mixture was filtered through diatomaceous earth and concentrated under vacuum. The crude product was then purified by silica gel column chromatography (200-300 mesh) to give 33 mg of compound E1 as a colorless oil, in 50% yield.

[0055] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.47 (dd, J = 7.6, 1.9 Hz, 4H), 7.27 (qd, J = 8.4, 7.4, 3.0 Hz, 8H), 7.21 (t, J = 7.6 Hz, 2H), 7.12(t, J = 7.1 Hz, 1H), 6.16 (t, J = 5.8 Hz, 1H), 2.72 – 2.65 (m, 2H), 1.92 (d, J =5.8 Hz, 2H), 1.33 – 1.27 (m, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 144.3, 142.0, 136.2, 134.7, 129.4,128.2, 127.9, 126.4, 125.6, 124.1, 26.3, 12.6, 9.3. HRMS (ESI): m / z: [M + H] + Calculated for C 23 H 22 Si: 327.1564, Found: 327.1576. 2) Preparation of compound E2, the reaction formula is as follows: A solution of NaOH (0.12 g) in H₂O (1 mL) was added to a THF (3 mL) solution of B1 (75.3 mg), Pd₂(dba)₃, and Sphos, followed by a THF (1 mL) solution of 1-bromo-2-methylpropene. The reaction was carried out at 60 °C for 19 h. The solution was diluted with water and extracted with ethyl acetate. The crude product was then purified by silica gel column chromatography (200–300 mesh) to give 37 mg of compound E2 as a colorless oil, with a yield of 47%.

[0056] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.56 (dd, J= 7.6, 1.9 Hz, 4H), 7.38 (dqt, J = 8.5, 6.5, 2.2 Hz, 6H), 5.78 (t, J = 5.0 Hz, 1H), 5.65(s, 1H), 2.37 (t, J = 7.0 Hz, 2H), 1.91 (d, J = 7.3 Hz, 2H), 1.75 (d, J = 8.0 Hz, 6H), 1.29 – 1.25 (m, 2H). 13 C NMR (101 MHz, Chloroform- d ) δ 139.6, 136.5, 134.7, 132.2, 129.3,128.5, 127.8, 123.4, 27.1, 26.5 19.6, 11.7, 8.7. HRMS (ESI): m / z: [M + K] + Calculated for C 21 H 24 OSi: 343.1279, Found: 343.1271. Example 5: The functionalized silyrocyclohexene compound obtained in this embodiment can be applied to the derivatization of the commercially available drug estrone via a palladium-catalyzed Suzuki-Miyaura coupling reaction, synthesizing a silyrocyclohexene-substituted estrone derivative G. The specific reaction formula is as follows: F (80.1 mg) was added to a solution of B1 (75.3 mg), Pd(PPh3)4 (11.6 mg), and K2CO3 (130.3 mg) in DME (1.6 mL) / H2O (1.6 mL), and nitrogen gas was introduced. The mixture was stirred at 80 °C for 6 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate and concentrated under vacuum. The crude product was then purified by silica gel column chromatography (200–300 mesh) to give 54 mg of compound G as a white solid, with a yield of 53%.

[0057] The physicochemical properties of this product are as follows: 1 H NMR (400 MHz, Chloroform- d ) δ 7.55 (dd, J= 7.7,1.7 Hz, 4H), 7.40 – 7.33 (m, 6H), 7.23 (s, 1H), 7.16 (dd, J = 8.2, 2.0 Hz, 1H), 7.10 (d, J = 2.0 Hz, 1H), 6.23 (t, J = 5.8 Hz, 1H), 2.95 – 2.88 (m, 2H), 2.79 –2.72 (m, 2H), 2.55 – 2.42 (m, 2H), 2.31 (d, J = 9.5 Hz, 1H), 2.22 – 2.07 (m,2H), 2.04 – 1.95 (m, 4H), 1.63 (dd, J = 11.7, 8.8 Hz, 2H), 1.51 (ddd, J = 9.8,4.0, 2.1 Hz, 2H), 1.40 – 1.35 (m, 2H), 1.31 – 1.21 (m, 2H), 0.91 (s, 3H). 13 C NMR (101 MHz, Chloroform- d ) δ 141.9, 141.7, 138.0, 136.3, 136.2,134.8, 129.4, 128.0, 126.3, 125.3, 123.6, 123.2, 50.5, 48.1, 44.4, 38.3,35.9, 31.6, 29.6, 26.6, 26.3, 25.8, 21.6, 13.9, 12.7, 9.4. HRMS (ESI): m / z: [M + Na] + Calculated for C 35 H 38 OSi:525.2584, Found:252.2584. Comparative Example 1: This embodiment discusses the reaction conditions (ligands, leaving groups, copper salt catalyst, solvent type, temperature, time, reactant ratio and concentration ratio, base type, etc.) for the synthesis of functionalized silicon heterocyclic six-membered ring compound B1 in Example 1, in order to further illustrate the technical solution of the present invention.

[0058] The specific reactions involved are as follows: (1) Effect of copper catalyst on the reaction As shown in Table 1 below, copper catalysts were screened, including cuprous chloride, cuprous bromide, cuprous iodide, cuprous acetate, cuprous cyanide, and cuprous thiophene-2-carboxylate. It was confirmed that when cuprous iodide was used as a catalyst, the reaction had good chemoselectivity and regioselectivity to obtain the target product B1.

[0059] Table 1. Screening of copper catalysts based on their conditions (2) Effect of ligands on the reaction As shown in Table 2 below, different ligands have a significant impact on the catalytic efficiency and chemoselectivity of this reaction. 2-(dicyclohexylphosphino)biphenyl (L26) was identified as the optimal ligand, and the reaction yielded the silane-heterocyclic six-membered ring compound B1 with a yield of 68% and a regioselectivity of 96:4.

[0060] Table 2. Conditional screening of ligands (3) Effect of solvent on reaction As shown in Table 3 below, after determining the copper salt and ligand, in order to further improve the reaction yield and selectivity, commonly used solvents in the laboratory were investigated, and 1,4-dioxane was finally identified as the optimal solvent.

[0061] Table 3 Solvent Condition Optimization (4) Effects of reactant ratio and reaction time on the reaction As shown in Table 4, when using 1.0 equivalent of pinacol diboronate, the reactant can be completely converted and the yield reaches its maximum after a reaction time of 16 hours. Extending the reaction time further will actually decrease the yield. Therefore, 16 hours is selected as the optimal reaction time.

[0062] The specific reactions involved are as follows: Table 4 Optimization of reactant ratio and reaction time (5) Effects of reaction temperature and base on the reaction As shown in Table 5, different reaction temperatures have a significant impact on the regioselectivity of the reaction. The regioselectivity shows a marked improvement as the temperature increases from 0℃ to 90℃. Ultimately, 70℃ was determined to be the optimal reaction temperature, yielding the silane-containing six-membered ring product in 70% yield and with a regioselectivity of 99:1. Finally, the base was screened, replacing potassium tert-butoxide with sodium tert-butoxide, lithium tert-butoxide, or cesium carbonate. Ultimately, 1.2 equivalents of potassium tert-butoxide as the base was determined to be the optimal condition.

[0063] Table 5. Optimization of temperature and inorganic base conditions Unless otherwise specified, the raw materials and equipment used in this invention are all commonly used in the field. Unless otherwise specified, the methods used in this invention are all conventional methods in the field.

[0064] The above description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, improvements, etc., made within the spirit and principles of the present invention should be included within the protection scope of the present invention.

Claims

1. A functionalized silane-hexene compound, characterized in that, Its structural formula is shown in equation (I): In equation (I), R 1 R is methyl, substituted or unsubstituted aryl or tert-butoxy. 2 B(OR) is a methyl or substituted or unsubstituted aryl group. 3 )2 is an oxo-diol-derived alkoxyboronic acid ester; the substituted substituent is methyl, methoxy, ethyl, tert-butyl or benzyloxy.

2. The functionalized silicon heterocyclohexene compound according to claim 1, characterized in that, B(OR 3 )2 forms one of the following structures: 。 3. The functionalized silicon heterocyclohexene compound according to claim 1, characterized in that, The structural formula of the functionalized silane heterocyclohexene compound is selected from any one of the following B1 to B21: 。 4. A method for preparing the functionalized silane heterocyclohexene compound according to any one of claims 1-3, characterized in that, The preparation method includes the following steps: Under an inert gas atmosphere, the halomethyl allenylsilane compound shown in formula (II), the borate ester shown in formula (III), a copper catalyst, a phosphine ligand, a base, and a solvent were mixed and stirred, and reacted at 0–90 °C for 8–24 h to obtain the functionalized silane heterocyclohexene compound shown in formula (I); wherein the structural formulas of the halomethyl allenylsilane compound and the borate ester are shown below: 。 5. The preparation method according to claim 4, characterized in that, The phosphine ligand is one of the following formulas: 。 6. The preparation method according to claim 4, characterized in that, The copper catalyst is one of cuprous chloride, cuprous bromide, cuprous iodide, cuprous acetate, cuprous cyanide, or cuprous thiophene-2-carboxylate.

7. The preparation method according to claim 4, characterized in that, The alkali is one of lithium tert-butoxide, sodium tert-butoxide, cesium carbonate, or potassium tert-butoxide.

8. The preparation method according to claim 4, characterized in that, The solvent is 1,4-dioxane, tetrahydrofuran, diethyl ether, toluene, dichloromethane, or... N , N One of the dimethylformamides.

9. The preparation method according to claim 4, characterized in that, The molar ratio of the halomethyl allenyl silane compound shown in formula (II) to the borate ester shown in formula (III) is 0.5:1.0~1.0-2.0, and the concentration of the halomethyl allenyl silane compound shown in formula (II) and the borate ester shown in formula (III) is 0.10 mol / L~0.20 mol / L.

10. The use of the functionalized silane heterocyclohexene compound as described in any one of claims 1-3 in organic synthesis, materials science, or the synthesis of bioactive pharmaceuticals.

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