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CN-122010762-A - Preparation method and application of fluorine-containing imide derivative

CN122010762ACN 122010762 ACN122010762 ACN 122010762ACN-122010762-A

Abstract

The invention discloses a preparation method and application of a fluorine-containing imide derivative, belonging to the technical field of organic synthesis, comprising the following steps of taking carboxylic acid, olefin, halogen substituted ester or halogen substituted alkyl as raw materials, and reacting under the induction of visible light in the presence of a photocatalyst, alkali and a solvent to obtain the fluorine-containing imide derivative; the fluorine-containing imide derivative prepared by the invention depends on the optimization effect of fluorine atoms on molecular physicochemical properties and biological activities, can be applied to the preparation of antibacterial, anti-inflammatory and anticancer drugs and the like, and has very important medicinal value.

Inventors

  • SHEN YONGMIAO
  • LUO JINGYI
  • XI ZIWEI
  • TANG RENHE
  • LI ZHI

Assignees

  • 浙江理工大学
  • 浙江理工大学嵊州创新研究院有限公司

Dates

Publication Date
20260512
Application Date
20260414

Claims (10)

  1. 1. The fluorine-containing imide derivative is characterized by having the following structural formula: ; Wherein R 1 is selected from one of phenyl, p-tolyl, p-methoxyphenyl, phthalimido, phenoxyethyl and cyclohexyl, R 2 is selected from one of phenyl, p-methylphenyl, p-fluorophenyl and benzyloxymethyl, and R 3 is one of halogen substituted ester group and halogen substituted alkyl.
  2. 2. The fluoroimide derivative according to claim 1, wherein R 3 is halogen-substituted ester or halogen-substituted alkyl, and halogen is F or/and Br.
  3. 3. The fluoroimide derivative according to claim 1, wherein the fluoroimide derivative is any one of the following compounds: 。
  4. 4. A process for preparing the fluorine-contained imide derivative as claimed in claim 1, which is characterized by comprising the following steps of taking carboxylic acid, olefin, halogen substituted ester or halogen substituted alkyl as raw materials, and reacting in the presence of photocatalyst, alkali and organic solvent under the induction of visible light to obtain the fluorine-contained imide derivative.
  5. 5. The method for preparing a fluorine-containing imide derivative as claimed in claim 4, wherein the organic solvent is one of 1, 2-dichloroethane, dichloromethane, ethanol, dimethyl sulfoxide, N-dimethylformamide, N-methylpyrrolidone, 1, 4-dioxane, ethyl acetate, tetrahydrofuran and acetonitrile.
  6. 6. The method for preparing a fluorine-containing imide derivative according to claim 4, wherein the catalyst is one of bis [2- (2, 4-difluorophenyl) -5-trifluoromethylpyridine ] iridium (III) hexafluorophosphate, bis [2- (2, 4-difluorophenyl) -5-methylpyridine ] iridium (III) hexafluorophosphate, bis (2-phenylpyridine) -iridium (4, 4' -di-tert-butyl-2, 2' -bipyridine) hexafluorophosphate, bis (2-phenylpyridine) iridium (III) hexafluorophosphate, tris (2-phenylpyridine) iridium (III), tris (2, 2' -bipyridine) ruthenium (II) hexafluorophosphate, 1,2,3, 5-tetrakis (carbazole-9-yl) -4, 6-dicyanobenzene, eosin Y, and the amount of the catalyst is 1-10 mol% of the amount of carboxylic acid based on the amount of the carboxylic acid.
  7. 7. The method for preparing a fluorine-containing imide derivative as claimed in claim 4, wherein the base is one of potassium carbonate, sodium bicarbonate, cesium carbonate, potassium hydroxide, sodium acetate, 1, 8-diazabicyclo [5.4.0] undec-7-ene, N-diisopropylethylamine and triethylamine.
  8. 8. The method for producing a fluorine-containing imide derivative as claimed in claim 4, wherein the reaction temperature is room temperature and the reaction time is 12 to 36 hours.
  9. 9. The method for producing a fluorine-containing imide derivative as claimed in claim 4, wherein the visible light is blue light having a wavelength of 400 to 450 nm.
  10. 10. Use of the fluorine-containing imide derivative of claim 1 in the preparation of antibacterial drugs.

Description

Preparation method and application of fluorine-containing imide derivative Technical Field The invention relates to a preparation method and application of a fluorine-containing imide derivative, and belongs to the technical field of organic synthesis. Background The fluorine-containing imide derivative is an important organic compound containing imide functional groups (-CO-N-CO-) and fluorine substituent groups in the molecular skeleton, and is a functional derivative obtained by fluorine substitution modification of the imide compound. The fluorine atom and the imide structure enable the derivatives to have the advantages of two types of structures, and have irreplaceable application values in the fields of medicine, pesticide, material science and the like. In the technical field of pesticides, the method belongs to branches of agricultural active ingredient precursor research and development technology and efficient pesticide molecular design technology, the structure can adjust the action target selectivity of pesticides, and the method is commonly used for molecular design of pesticides and herbicides, for example, the field duration of the fluorine-containing imide herbicides is prolonged by more than 30 percent compared with non-fluorine similar products. In the technical field of functional materials, the fluorine-containing functional material belongs to the branches of fluorine-containing functional material preparation technology and material surface modification technology, and can be used for synthesizing monomers of fluorine-containing polymers to endow the materials with weather resistance and hydrophobicity. The existing synthesis method of the fluorine-containing imide derivative has the defects of high toxicity, high corrosiveness and high operation difficulty of a part of fluorinated reagent, complicated synthesis route steps, difficult product separation and purification, low yield, and poor suitability for substrates containing sensitive functional groups, and is difficult to meet the synthesis requirement of the fluorine-containing imide derivative with a complex structure, and part of the method relies on a noble metal catalyst, so that the synthesis cost is increased and the problem of heavy metal residue exists. Cai et al (J.am.chem.Soc.2025, 147, 18438-18444) report a novel Kharasch reaction that utilizes various carboxylic acid-derived redox active esters as alkyl sources, can effectively introduce highly functionalized alkyl groups, provides a general method for directly constructing alpha-halocarbonyl compounds from carboxylic acids, but the system is only adaptable to aliphatic carboxylic acids, has a narrow substrate application range, relies on costly reagents, and has a single product structure. Giri et al (chem. Sci.2024,15, 10659-10667) use photooxidation reduction to catalyze and activate chlorodifluoroacetic acid (CDFA) and alpha-halogenated carboxylic acid to realize difunctional solvent control of alkene for synthesizing gamma-lactone, gamma-lactam and alpha, alpha-difluoroester, but the method has strong solvent dependence, and the raw materials cannot be compatible with polycarboxylic acid, fluorine-containing olefin/halogenated compound and the like, has poor compatibility to substrates containing nitrogen and oxygen-containing hetero functional groups, and is difficult to expand the structural types of products. The existing method has the defects of limited substrate, poor functional group tolerance, low reaction condition adaptability, single product structure and the like, and part of the methods have high reagent cost and no industrial amplification feasibility, so that the application expansion of the fluorine-containing imide derivative in the fields of medicines, pesticides and the like is severely limited. Therefore, the preparation method of the fluorine-containing imide derivative which is mild and efficient, has a wide substrate application range and can realize the cooperative construction of the multifunctional groups is developed, and has important practical value and application prospect. Disclosure of Invention In view of the shortcomings in the prior art, a first aspect of the present invention is to provide a fluorine-containing imide derivative. The technical scheme adopted by the invention is as follows: A fluorine-containing imide derivative has the following structural formula: ; Wherein R 1 is selected from one of phenyl, p-tolyl, p-methoxyphenyl, phthalimido, phenoxyethyl and cyclohexyl, R 2 is selected from one of phenyl, p-methylphenyl, p-fluorophenyl and benzyloxymethyl, and R 3 is one of halogen substituted ester group and halogen substituted alkyl. Further, the halogen substituted ester group or halogen substituted alkyl, halogen is F or/and Br. Further, the fluorine-containing imide derivative is any one of the following compounds: 。 The second aspect of the invention aims to provide a simple and efficient preparation method of fluor