A compound, preparation method and application thereof

Abstract

The present application relates to the technical fields of compound synthesis, and in particular to a compound, a preparation method and application thereof.The chemical structure of the compound is as follows: R1-(CH2) x -C(=O)-O-(CH2) y -R2 formula (I), wherein R1 is at least one cyano-substituted organic group, R2 is a fluorine-containing substituent group, x is an integer of 0-5, and y is an integer of 1-8.The compound provided by the present application is an ester substance with a cyano side chain and a fluorinated alkyl side chain, wherein the cyano group is located on the carboxylic acid side of the ester group, the fluorinated alkyl group is located on the alcohol side of the ester group, the cyano group and the fluorine atom synergistically act on the ester group, affect the electronic distribution of the compound, and make the ester compound stable, balanced in performance, simple in preparation method, and have good application prospects in multiple fields.

Description

Technical Field

[0001] This invention relates to the field of compound synthesis technology, and in particular to a compound, its preparation method, and its application. Background Technology

[0002] With the rapid development of new energy, biomedicine, and materials science, the demand for multifunctional organic compounds with specific electronic structures and physicochemical properties is constantly increasing. Organic esters containing strong electron-withdrawing substituents have potential applications in electrolyte systems, pharmaceutical intermediates, pesticide adjuvants, and functional materials due to their tunable molecular polarity, reactivity, and solvent compatibility.

[0003] Among them, the cyano group, as a strong electron-withdrawing group, can significantly affect the molecular charge distribution and increase molecular polarity; the fluorine substituent can regulate the electron cloud density of neighboring groups through inductive effects, thereby changing the electronic structure and physicochemical properties of the compound. Although compounds containing cyano or fluorine substituents have been reported in the prior art, when cyano and fluorine substituents are introduced into the molecular structure at the same time, it is often difficult to simultaneously meet the performance requirements such as solubility, chemical / thermal stability, and system compatibility, and problems such as insufficient solubility, decreased stability, or limited application window are likely to occur.

[0004] Therefore, developing a cyano-fluorine substituted ester compound with strong structural designability, a simple synthetic route, and applicability to various application scenarios is of great significance for promoting technological progress in related fields. Summary of the Invention

[0005] The purpose of this invention is to provide a compound, its preparation method, and its application, aiming to provide a bifunctional compound that is stable, has balanced performance, and is simple to prepare.

[0006] According to a first aspect of the present invention, a compound is provided, the general chemical structural formula of which is as follows: R1-(CH2) x -C(=O)-O-(CH2) y -R2 formula (I) In formula (I), R1 is at least one cyano-substituted organic group, R2 is a fluorine-substituted group, x is an integer from 0 to 5, and y is an integer from 1 to 8.

[0007] In one embodiment, the organic group is selected from one or more of aliphatic groups, aromatic groups, and heteroaromatic groups.

[0008] In one embodiment, the organic group of R1 further includes a linker selected from -O-, -S-, -SO2-, and -N-.

[0009] In one embodiment, R2 is a partially fluorinated or perfluorinated alkyl, alkenyl, alkynyl, fluorinated ether, fluorinated aryl, or fluorinated heteroaryl.

[0010] In one embodiment, R2 further includes a linker selected from -O-, -S-, and -SO2-.

[0011] In one embodiment, R2 is selected from CF3, CHF2, CF3, CHF2, CH2F, CF2CF2, CH2CH2F, C6H4F, C6H4CF3, and C6H3F2.

[0012] According to a second aspect of the present invention, a method for preparing a compound is provided, comprising the following steps: (1) replacing a cyano-substituted carboxylic acid R1-(CH2) with a cyano-substituted carboxylic acid. x The -COOH group undergoes an acyl chloride reaction to give the intermediate R1-(CH2). x -COCl; (2) An alcoholic compound HO-(CH2) formed by substituting an intermediate with a fluorine atom under alkaline conditions. y -R2 undergoes esterification, followed by post-treatment to obtain the compound as described in any one of claims 1-5.

[0013] In one embodiment, the chlorinating agent in step (1) is selected from oxalyl chloride, thionyl chloride, phosphorus trichloride or phosphorus pentachloride.

[0014] According to a third aspect of the present invention, a method for preparing a compound is provided, comprising the following steps: The cyano-substituted ester compound R1-(CH2) x -COOR3 alcohols with fluorine atom substitution HO-(CH2) y R2 undergoes transesterification under the action of a catalyst, and after post-treatment, the compound as described in any one of claims 1-5 is obtained, wherein R3 is an alkyl group having 1-4 carbon atoms.

[0015] In one embodiment, the catalyst is selected from organometallic compounds, acid catalysts, solid acid catalysts, or base catalysts.

[0016] According to a fourth aspect of the present invention, the above-described compound or the compound prepared by the above-described method is provided as an electrolyte additive, pharmaceutical intermediate, pesticide intermediate, fine chemical raw material, polymer monomer, or resin modification raw material.

[0017] The beneficial effects of using the embodiments of the present invention are as follows: 1. The compound with general formula (I) provided by this invention, as an ester containing both cyano side chains and fluorinated alkyl side chains, provides a polar center and reaction site; the cyano group (-CN), as a strong electron-withdrawing group, has a high dipole moment and electron-withdrawing ability, and can form a conjugation effect with the carbonyl group, significantly reducing the electron density of adjacent carbonyl groups; the fluorinated substituent regulates the overall electron distribution of the molecule through a strong inductive effect, and at the same time forms a spatial shielding effect, which can improve the thermal and chemical stability of the molecule; the above three functional groups coexist in the compound provided by this invention and play a synergistic role, resulting in an asymmetric distribution of intramolecular dipoles, from The formation of a tunable electronic gradient structure and a designable reactive window within the molecule allows for the regulation of the physicochemical properties of the compound, controlling its dual electrophilic and hydrophobic characteristics. Based on this, the compound of the present invention can serve as a precursor for cyano conversion (amidation, reduction to amine) or ester hydrolysis, making it a high-quality pharmaceutical intermediate. Its lipophilicity and membrane permeability are enhanced, making it suitable as a pesticide intermediate. It can also be used as a highly polar solvent or reaction aid in fine chemical production processes. Furthermore, the cyano group in the compound of the present invention can participate in subsequent modification, and the fluorine group can improve the polymer's chemical resistance and low surface energy characteristics, making it a novel polymer intermediate.

[0018] 2. The preparation method provided by this invention has a clear route and simple steps, which is conducive to improving safety and production efficiency and is suitable for industrial scale-up. Attached Figure Description

[0019] To more clearly illustrate the technical solutions in the embodiments of the present invention or the prior art, the drawings used in the description of the embodiments or the prior art will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present invention. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0020] in: Figure 1 The image shows the 1H NMR spectrum of trifluoroethyl cyanoacetate. Figure 2 This is the mass spectrum of trifluoroethyl cyanoacetate; Figure 3 This is the 1H NMR spectrum of difluoroethyl cyanoacetate. Detailed Implementation

[0021] To more clearly illustrate the overall concept of the present invention, a detailed description is provided below with reference to the accompanying drawings and embodiments. Numerous specific details are set forth in the following description to provide a more thorough understanding of the invention. However, it will be apparent to those skilled in the art that the invention can be practiced without one or more of these details. In other instances, certain technical features well-known in the art have not been described to avoid confusion with the present invention.

[0022] This invention provides a compound with the following general chemical structural formula: R1-(CH2) x -C(=O)-O-(CH2) y -R2 formula (I) In formula (I), R1 is at least one cyano-substituted organic group, R2 is a fluorine-substituted group, x is an integer from 0 to 5, and y is an integer from 1 to 8.

[0023] In this embodiment, the compound having the general formula (I), as an ester containing both a cyano side chain and a fluorinated alkyl side chain cyano group, provides a polar center and reaction site; the cyano group (-CN), as a strong electron-withdrawing group, has a high dipole moment and electron-withdrawing ability, and can form a conjugation effect with the carbonyl group, significantly reducing the electron density of adjacent carbonyl groups; the fluorinated substituent regulates the overall electron distribution of the molecule through a strong inductive effect, and at the same time forms a spatial shielding effect, which can improve the thermal and chemical stability of the molecule; the above three functional groups coexist in the compound provided by the present invention and play a synergistic role, resulting in an asymmetric distribution of intramolecular dipoles, from The formation of a tunable electronic gradient structure and a designable reactive window within the molecule allows for the regulation of the physicochemical properties of the compound, controlling its dual electrophilic and hydrophobic characteristics. Based on this, the compound of the present invention can serve as a precursor for cyano conversion (amidation, reduction to amine) or ester hydrolysis, making it a high-quality pharmaceutical intermediate. Its lipophilicity and membrane permeability are enhanced, making it suitable as a pesticide intermediate. It can also be used as a highly polar solvent or reaction aid in fine chemical production processes. Furthermore, the cyano group in the compound of the present invention can participate in subsequent modification, and the fluorine group can improve the polymer's chemical resistance and low surface energy characteristics, making it a novel polymer intermediate.

[0024] In one embodiment, the organic group is selected from one or more of aliphatic groups, aromatic groups, and heteroaromatic groups.

[0025] Specifically, R1 can be selected from CH2CN, -CH2CH2CN, -CH(CN)CH3, -(CH2)3CN, -CH(CN)2, -CH2CH(CN)2, -(CH2)2(CN)2, -C(CN)3, -C(CH3)2CH2CN, -CH(CH3)CH2CN, -C6H4CN, -C 10 H6CN, -C5H3N-CN, -O-CH2CN, -S-CH2CN, -NH-CH2CN, , , , , or .

[0026] In one embodiment, the organic group of R1 further includes a linker selected from -O-, -S-, -SO2-, and -N-.

[0027] Specifically, R1 can be selected from -O-CH2CN, -S-CH2CN, or -NH-CH2CN.

[0028] In one embodiment, R2 is a partially fluorinated or perfluorinated alkyl, alkenyl, alkynyl, fluorinated ether, fluorinated aryl, or fluorinated heteroaryl.

[0029] Specifically, R2 can be selected from -CH2F, -CHF2, -CF3, -CH2CF3, -CH2CHF2, -CH2CH2F, -C2H3F2, -C2H2F3, -C2F5, -C3F7, -C4F9, and -C6F. 13 , -C(CF3)3, -CH(CF3)2, -CH=CHF, -CF=CH2, -C≡CF, -C≡C-CF3, -CH2OCH2F, -CH2OCHF2, -CH2OCF3, -OCH2CF3, -OCH(CF3)2, -O(CF2CF2)nCF3 (n=1-5), -CF2OCH3, -CF2OCH2CH3, , , , , -C6H4F, -C6H3F2, -C6H2F3, -C6HF4, -C6F5, -C6H4CF3, -C6H3(CF3)2, , .

[0030] In one embodiment, R2 further includes a linker selected from -O-, -S-, and -SO2-.

[0031] Specifically, R2 can be selected from -SO2CF3, -SCF3, or -OCF3.

[0032] This invention provides a composition and a method for preparing a compound, comprising the following steps: (1) replacing a cyano-substituted carboxylic acid R1-(CH2) with a cyano-substituted carboxylic acid. x The -COOH group undergoes an acyl chloride reaction to give the intermediate R1-(CH2). x -COCl; (2) An alcoholic compound HO-(CH2) formed by substituting an intermediate with a fluorine atom under alkaline conditions. y -R2 undergoes esterification, followed by post-treatment to obtain the compound as described in any one of claims 1-5.

[0033] In this embodiment, the intermediate obtained is an acid chloride, which can be directly used in the second step reaction without separation and purification, making it convenient for industrial implementation.

[0034] Specifically, the reaction process is as follows: (1) Acyl chloride reaction: The chlorinating agent and the cyano-substituted carboxylic acid were dissolved in an organic solvent and reacted at 0-40℃ under the catalysis of 0.1-5 mol% DMF for 0.5-8 h to obtain the intermediate product. The reaction formula is: HOC(=O)-CH2R1→ ClC(=O)-CH2R1.

[0035] (2) Esterification reaction: The intermediate obtained in step (1) was reacted with fluorinated alcohol in a ratio of 1:(1.0-1.5) at 0-60℃ for 1-12 h to esterify the product and obtain ester compounds.

[0036] The reaction formula is: ClC(=O)-CH2R1+R2-(CH2) y -OH→R2-(CH2) y -OC(=O)-CH2R1.

[0037] (3) Post-processing: Acidic byproducts are removed by washing with water or alkali, and the target product is obtained by vacuum distillation or column chromatography.

[0038] Specifically, in step (1), the organic solvent can be dichloromethane, toluene, or acetonitrile; in step (2), triethylamine, pyridine, or DIPEA is used to adjust the pH to alkaline.

[0039] In one embodiment, the chlorinating agent in step (1) is selected from oxalyl chloride, thionyl chloride, phosphorus trichloride or phosphorus pentachloride.

[0040] This invention provides a method for preparing a compound, comprising the following steps: The cyano-substituted ester compound R1-(CH2) x -COOR3 alcohols with fluorine atom substitution HO-(CH2) y R2 undergoes transesterification under the action of a catalyst, and after post-treatment, the compound as described in any one of claims 1-5 is obtained, wherein R3 is an alkyl group having 1-4 carbon atoms.

[0041] In this embodiment, the use of acid chlorides is avoided, reducing corrosion and the generation and treatment of by-product gases during the production process, making it suitable for industrial scale-up of continuous production.

[0042] Specifically, the reaction process is as follows: (1) Transesterification reaction: 1.0 equivalent of cyano-substituted ester compounds are transesterified with 1.0-3.0 equivalent of fluorinated alcohols under anhydrous or low-water conditions and with the action of a catalyst to generate the target ester and produce low-boiling alcohols as byproducts. During the reaction, the byproduct small molecule alcohols are continuously removed by means of vacuum distillation (50-300 mbar), inert gas (N2) stripping, molecular sieve (3Å / 4Å) adsorption or continuous carry-out in a distillation column, thus promoting the reaction towards the product.

[0043] Reaction formula: (2) Post-processing: After the reaction is completed, the by-product alcohol and unreacted fluorinated alcohol are distilled off under reduced pressure. The alcohol is neutralized by water washing / alkali washing and dried with anhydrous sodium sulfate. Finally, the target product is obtained by vacuum distillation or thin-film evaporation.

[0045] In one embodiment, the catalyst is selected from organometallic compounds, acid catalysts, solid acid catalysts, or base catalysts.

[0046] Specifically, the amount of the organometallic compound used is 0.05-2.0 mol%, which can be selected as 0.1-0.5 mol%; the organometallic compound catalyst is preferably tetraisopropoxytitanium Ti(OiPr)4, tetrabutoxytitanium Ti(OBu)4, tetraethoxytitanium Ti(OEt)4, triisopropoxyaluminum Al(OiPr)3, or zirconium isopropoxide(IV) Zr(OiPr)4; The amount of acid catalyst used is 0.1-5 mol%, preferably 0.5-2 mol%; the acid catalyst can be p-toluenesulfonic acid (p-TsOH), methanesulfonic acid (MSA), BF3·Et2O, AlCl3, ZnCl2; The amount of the solid acid catalyst is 0.5-20 wt%, preferably 2-10 wt%; the acid catalyst can be selected from sulfonated polystyrene resin (Amberlyst-15, Amberlyst-36, Dowex 50WX), Nafion resin (Nafion NR50, etc.), or phosphotungstic acid supported solid acid (H3PW). 12 O 40 / SiO2), mesoporous / zeolite (H-Beta, H-ZSM-5, HY, HZSM-22), zirconium sulfate (SO4²) - / ZrO2), tungsten / zirconium solid acid; The amount of the alkaline catalyst is 0.01-2.0 mol%, preferably 0.05-0.5 mol%; the alkaline catalyst can be sodium methoxide (NaOMe), sodium ethoxide (NaOEt), potassium tert-butoxide (KOtBu), K2CO3, Cs2CO3, DBU, or TBD.

[0047] Specifically, the reaction conditions for transesterification are: Under the catalysis of organometallic compounds, the reaction temperature is 60-130℃ (preferably 80-110℃) and the reaction time is 1-12h (preferably 2-6h). Under the catalysis of solid acid resin, the reaction temperature is 50-120℃ (preferably 70-100℃) and the reaction time is 2-24 h; Under alkaline catalysis, the reaction temperature is 20-80℃ (preferably 30-60℃) and the reaction time is 0.5-8 h.

[0048] This invention provides an application of the above-mentioned compound or the compound prepared by the above-mentioned method as an electrolyte additive, pharmaceutical intermediate, pesticide intermediate, fine chemical raw material, polymer monomer, and resin modification raw material.

[0049] Unless otherwise specified, the test reagents used in the following examples are all conventional biochemical reagents. Example 1 This embodiment relates to the preparation of trifluoroethyl cyanoacetate (CF3CH2OCOCH2CN).

[0050] (1) Acyl chloride reaction: Add 10.0 g (0.118 mol) of cyanoacetic acid and 80 mL of anhydrous dichloromethane to a dry 250 mL three-necked flask, and stir at room temperature for 20 min to form a homogeneous slurry. Add 0.2 mL of DMF, then cool to 0-5 °C in an ice-salt bath. Slowly add 16.5 g (0.130 mol, 1.10 eq) of oxaloyl chloride dropwise over 60 min, maintaining the temperature no higher than 10 °C. After the addition is complete, continue stirring at 0-5 °C for 30 min, then raise the temperature to room temperature and continue stirring for 3 h until gas release has essentially stopped and the reaction is complete. Remove the solvent and volatiles under reduced pressure to obtain a pale yellow acid chloride intermediate, which can be used directly in the next step.

[0051] (2) Esterification reaction: The above-mentioned acid-chlorine intermediate was dissolved in 80 mL of anhydrous dichloromethane and cooled to 0–5 °C in an ice-salt bath. 11 g (0.110 mol, 1.05 eq) of 2,2,2-trifluoroethanol and 18.0 g (0.178 mol, 1.50 eq) of triethylamine dissolved in a small amount of anhydrous dichloromethane were added dropwise to form a homogeneous solution. Under stirring, the mixture was added dropwise over a period of 30 min, keeping the system temperature below 10 °C. After the addition was complete, stirring was continued at 0–5 °C for 1 h, followed by stirring at room temperature for 4 h to obtain the crude product 2-cyanoacetic acid-2,2,2-trifluoroethyl ester.

[0052] (3) Post-processing: The reaction solution was successively washed with 1.2 times the volume of deionized water to remove triethylamine salt and DMF, 1.2 times the volume of saturated NaHCO3 solution to remove residual acid, and 0.75 times the volume of saturated brine. After washing, the solution was allowed to stand until it separated into layers, and the aqueous phase was discarded. The solution was dried with anhydrous sodium sulfate, filtered, concentrated under reduced pressure at 40℃ and -0.08MPa, and purified by distillation to obtain the target colorless and transparent liquid product.

[0053] The NMR spectrum of trifluoroethyl cyanoacetate is shown below. Figure 1 The mass spectrometry detection spectrum is shown below. Figure 2 : ¹H NMR (400 MHz, CDCl3): δ 4.56–4.62 (q, 2H, OCH2), δ 3.62 (s, 2H, CH2CN).

[0054] The mass spectrometry spectrum of the target product is shown below. Figure 2 .

[0055] Example 2 This embodiment relates to the preparation of difluoroethyl cyanoacetate (CHF2CH2OCOCH2CN).

[0056] (1) Acyl chloride reaction Cyanoacetic acid was subjected to acyl chloride reaction according to step (1) of Example 1 to obtain cyanoacetyl chloride intermediate.

[0057] (2) Esterification reaction The cyanoacetyl chloride intermediate was dissolved in 80 mL of anhydrous dichloromethane and cooled to 0–5 °C. 12.0 g (0.150 mol, 1.10–1.20 eq) of 2,2-difluoroethanol was mixed with 18.0 g (0.178 mol, 1.50 eq) of triethylamine, and the mixture was added dropwise at 0–5 °C over approximately 30 min. After addition, the mixture was stirred at low temperature for 1 h, then heated to room temperature and stirred for another 4 h to obtain the crude product, difluoroethyl cyanoacetate.

[0058] (3) The post-processing process is the same as step (3) in Example 1, and a colorless and transparent liquid product is obtained.

[0059] The 1H NMR spectrum of difluoroethyl cyanoacetate is shown below. Figure 3 .

[0060] ¹H NMR (400 MHz, CDCl3): δ 4.37–4.45 (m, 2H, OCH2), δ 3.59 (s, 2H, CH2CN), δ 5.85–6.14 (m, 1H, CHF2).

[0061] Example 3 This embodiment relates to the preparation of 2,2,2-trifluoroethyl p-cyanobenzoic acid (4-CNC6H4COOCH2CF3).

[0062] (1) Acyl chloride reaction Add 10.0 g (0.068 mol) of p-cyanobenzoic acid and 80 mL of anhydrous dichloromethane to a dry 250 mL three-necked flask. Stir at room temperature for 10–30 min, then add 0.2 mL of DMF. Cool to 0–5 °C in an ice bath, and slowly add 8.6 g (0.068 mol, 1.0 eq) of oxalyl chloride dropwise over a period of 45 min. Stir at 0–5 °C for 45 min, then bring the temperature to room temperature and stir for 3 h. Remove the solvent and volatiles under reduced pressure to obtain the acid-chlorine intermediate, which can be used directly in the next step.

[0063] (2) Esterification reaction The intermediate was dissolved in 80 mL of anhydrous dichloromethane, cooled to 0-5 °C, and a mixed solution of 7.2 g (0.071 mol, 1.05 eq) of 2,2,2-trifluoroethanol and 10.3 g (0.102 mol, 1.50 eq) of triethylamine was added dropwise. The mixture was stirred at 0-5 °C for 1 h and then heated to room temperature for 2 h to obtain the crude product of p-cyanobenzoic acid-2,2,2-trifluoroethyl ester.

[0064] (3) Post-processing The post-processing procedure is the same as step (3) in Example 1, to obtain the target product as a colorless to pale yellow liquid.

[0065] 1 H NMR (400MHz, CDCl3): δ 8.0-8.2 (d, 2H, Ar-H), 7.6-7.8 (d, 2H, Ar-H), 4.5-4.7 (q, 2H, OCH2).

[0066] Example 4 This embodiment relates to the preparation of dicyanoacetic acid-2,2,2-trifluoroethyl ester (CF3CH2OCOCH(CN)2).

[0067] (1) Acyl chloride reaction Dicyanoacetic acid was acylated as in Example 1 to obtain a dicyanoacetyl chloride intermediate.

[0068] (2) Esterification reaction The acid-chlorine intermediate was dissolved in 80 mL of anhydrous dichloromethane, and 2,2,2-trifluoroethanol (1.05 eq) and triethylamine (1.2-2.0 eq) were added dropwise at 0-5 °C. After stirring at 0-5 °C for 1 h, the mixture was raised to room temperature and stirred for 6 h to obtain crude dicyanoacetic acid-2,2,2-trifluoroethyl ester.

[0069] (3) The post-processing process is the same as step (3) in Example 1, and a colorless and transparent liquid product is obtained.

[0070] 1 1H NMR (400MHz, CDCl3): δ 4.4-4.7 (q, 2H, OCH2), 5.0-6.0 (s or weak splitting, 1H, CH(CN)2).

[0071] Example 5 This embodiment relates to the preparation of 2-cyanoacetic acid-2-(2,2,2-trifluoroethoxy)ethyl ester (CF3CH2OCH2CH2OCOCH2CN).

[0072] (1) Acyl chloride reaction Cyanoacetic acid was acylated as in Example 1 to obtain a cyanoacetyl chloride intermediate.

[0073] (2) Esterification reaction The intermediate was dissolved in 80 mL of anhydrous dichloromethane, and 2-(2,2,2-trifluoroethoxy)ethanol (1.05 eq) and triethylamine (1.5 eq) were added dropwise at 0-5 °C. After stirring at 0-5 °C for 1 h, the mixture was raised to room temperature and stirred for 4 h to obtain the crude product of 2-cyanoacetic acid-2-(2,2,2-trifluoroethoxy)ethyl ester.

[0074] (3) The post-processing process is the same as step (3) in Example 1, and a colorless and transparent liquid product is obtained.

[0075] 1 H NMR (400MHz, CDCl3): δ 4.2-4.5 (m, 2H, OCH2CO), 3.42 (s, 2H, CH2CN), 3.4-4.0 (m, 4H, OCH2CH2O), 4.4-4.7 (q, 2H, OCH2CF3).

[0076] Example 6 This embodiment relates to the transesterification method for preparing difluoroethyl cyanoacetate (CHF2CH2OCOCH2CN). (1) Transesterification reaction 20.0 g (0.202 mol) of methyl cyanoacetate, 24.0 g (0.293 mol, 1.2 eq) of 2,2-difluoroethanol, and 40.3 mol% of tetraisopropyl titanate (Ti(OiPr)) were added to the reactor. The mixture was heated to 90 °C and reacted for 8 h, while the generated methanol was continuously removed by micro-purging with nitrogen to promote equilibrium.

[0077] (2) Post-processing After cooling, the volatiles were removed by vacuum distillation, and the crude product was purified by vacuum distillation to obtain the target product.

[0078] 1 H NMR (400MHz, CDCl3): δ 4.1-4.4 (m, 2H, OCH2), 3.42 (s, 2H, CH2CN), 5.7-6.1 (t, 1H, CHF2).

[0079] The yield and purity results of the target products in Examples 1-6 are shown in Table 1.

[0080] Purity was determined by gas chromatography (GC).

[0081] Table 1 Table 1 shows that the methods described in Examples 1-6 can all yield the target product with a yield of 76%-85% and a purity of 97.9%-99.1%. This demonstrates that the synthetic route described in this invention exhibits good reaction efficiency and product purity control under different structural substituent conditions, reflecting good process applicability.

[0082] The above description discloses only preferred embodiments of the present invention and should not be construed as limiting the scope of the present invention. Therefore, equivalent variations made in accordance with the claims of the present invention are still within the scope of the present invention.

Claims

1. A compound, characterized in that, The general chemical structural formula of the compound is as follows: R1-(CH2) x -C(=O)-O-(CH2) y -R2 formula (I) In formula (I), R1 is at least one cyano-substituted organic group, R2 is a fluorine-substituted group, x is an integer from 0 to 5, and y is an integer from 1 to 8.

2. The compound according to claim 1, characterized in that, The organic group of R1 is selected from one or more of aliphatic groups, aromatic groups, and heteroaromatic groups.

3. The compound according to claim 2, characterized in that, The organic groups of R1 also include one of the following linking groups: -O-, -S-, -SO2-, and -N-.

4. The compound according to claim 1, characterized in that, R2 is a partially fluorinated or perfluorinated alkyl, alkenyl, alkynyl, fluorinated ether, fluorinated aryl, or fluorinated heteroaryl.

5. The compound according to claim 4, characterized in that, R2 also includes one of the following connecting groups: -O-, -S-, and -SO2-.

6. A method for preparing a compound, characterized in that, Includes the following steps: (1) Carboxylic acids with cyano groups substituted R1-(CH2) x The -COOH group undergoes an acyl chloride reaction to give the intermediate R1-(CH2). x -COCl; (2) An alcoholic compound HO-(CH2) formed by substituting an intermediate with a fluorine atom under alkaline conditions. y -R2 undergoes esterification, followed by post-treatment to obtain the compound as described in any one of claims 1-5.

7. The preparation method according to claim 6, characterized in that, The chlorinating agent in step (1) is selected from oxalyl chloride, thionyl chloride, phosphorus trichloride or phosphorus pentachloride.

8. A method for preparing a compound, characterized in that, Includes the following steps: The cyano-substituted ester compound R1-(CH2) x -COOR3 alcohols with fluorine atom substitution HO-(CH2) y R2 undergoes transesterification under the action of a catalyst, and after post-treatment, the compound as described in any one of claims 1-5 is obtained, wherein R3 is an alkyl group having 1-4 carbon atoms.

9. The preparation method according to claim 8, characterized in that, The catalyst is selected from organometallic compounds, acid catalysts, solid acid catalysts, or base catalysts.

10. The compound prepared by the method of any one of claims 1-5 or any one of claims 6-9, and its application as an electrolyte additive, pharmaceutical intermediate, pesticide intermediate, fine chemical raw material, polymer monomer, or resin modification raw material.

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