A dihydropyrrolone derivative, its preparation method and use thereof

Abstract

The application discloses a novel compound, a preparation method and application of a dihydropyrrolone derivative, and a structure formula of the dihydropyrrolone derivative is as follows: the dihydropyrrolone derivative is prepared by reacting a certain amount of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl) azo, methanesulfonic acid and a solvent under certain temperature conditions. After the reaction is completed, part of the solvent is removed under reduced pressure, the reaction is quenched by using saturated sodium bicarbonate aqueous solution, extraction, drying, and then column chromatography purification are carried out to obtain a pure dihydropyrrolone derivative. The dihydropyrrolone derivative can effectively absorb 200-250 nm ultraviolet light. The dihydropyrrolone derivative prepared by the application can be used as an ultraviolet absorber, and is expected to improve the light stability of polymer products.

Description

Technical Field

[0001] This invention relates to a novel compound, a dihydropyrrolidone derivative, its preparation method, and its applications. Background Technology

[0002] Short-wave ultraviolet (UVC) radiation is widely used for disinfection of water, air, and object surfaces, but it can also cause materials to age, discolor, chalk, and even fail. Organic UV absorbers absorb UVC energy through their conjugated structures and convert it into harmless heat. Extremely high UVC blocking rates can be achieved at very low addition levels while maintaining properties such as the substrate's transparency and gloss. Therefore, the development of high-performance UV absorbers, especially leveraging the great flexibility in the synthesis of organic UV absorbers—through fine-tuning of molecular structures and precise design of absorption peak positions—to select organic absorbers with absorption wavelengths that precisely match specific UVC light sources and extend the lifespan of products used in UVC applications, is an urgent problem to be solved. Summary of the Invention

[0003] To address the aforementioned problems, this invention provides a dihydropyrrolidone derivative with a simple preparation method, mild reaction conditions, concise operation steps, and complex product structure, as well as the preparation method and application of the derivative.

[0004] This invention discloses a novel dihydropyrrolidone derivative, the structural formula of which is as follows: .

[0005] This invention patent also discloses a method for preparing the above-mentioned novel compound dihydropyrrolidone derivative, specifically including the following steps: Step 1) Reacting a certain amount of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo, methanesulfonic acid and solvent under certain temperature conditions;

[0006] Step 2) After the reaction is complete, some solvent is removed under reduced pressure, the reaction is quenched with saturated sodium bicarbonate aqueous solution, extracted, dried, and purified by column chromatography to obtain the pure dihydropyrrolidone derivative; wherein the structural formula of the dihydropyrrolidone derivative is as follows: .

[0007] The above-mentioned dihydropyrrolidone derivatives were prepared in anhydrous ethanol to form 10 -5 The solution, at room temperature, exhibits good UV absorption properties when tested for UV absorption at a concentration of mol / L.

[0008] Preferably, the solvent is methanol.

[0009] Preferably, the reaction temperature is 20-40°C. o C.

[0010] Preferably, the molar ratio of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo to methanesulfonic acid is 1:0.05-0.2.

[0011] Preferably, when the amount of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo is 0.2 mmol, the amount of solvent is 2-5 mL.

[0012] This invention patent also discloses the application of the dihydropyrrolidone derivative, which is used as a polymeric ultraviolet absorber.

[0013] The above technical solution has the following beneficial effects: 1. The reaction conditions are mild and the product structure is complex; 2. The synthesis steps are simple, the product yield is high, and the reaction chemical selectivity is high; 3. The product molecule has active groups, which can increase its stability in polymers; 4. The dihydropyrrolidone derivative synthesized in this invention has good ultraviolet absorption performance. Attached Figure Description

[0014] Figure 1 The target compound of the present invention 1 H NMR spectrum.

[0015] Figure 2 The target compound of the present invention 13 C10 NMR spectrum.

[0016] Figure 3 This is the ultraviolet-visible absorption spectrum of the target compound in an embodiment of the present invention. Detailed Implementation

[0017] The following specific embodiments illustrate the implementation of the present invention. Those skilled in the art can easily understand other advantages and effects of the present invention from the content disclosed in this specification.

[0018] Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, these exemplary embodiments can be implemented in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided to make the invention more comprehensive and complete, and to fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics can be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a full understanding of embodiments of the invention. However, those skilled in the art will recognize that the technical solutions of the invention may be practiced with one or more of these specific details omitted, or other methods, components, apparatus, steps, etc., may be employed. In other instances, well-known technical solutions are not shown or described in detail to avoid obscuring various aspects of the invention.

[0019] The present invention will be further described in detail below with reference to the embodiments.

[0020] This invention patent discloses a dihydropyrrolidone derivative, the structural formula of which is as follows: The preparation method of this derivative is described below in the examples.

[0021] Example: Preparation method of 5-methoxy-3-methyl-5-phenyl-1-(4-methylphenylamino)-1,5-dihydropyrrole-2-one.

[0022] Step 1) In a 10 mL reactor, add 0.2 mmol of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo and 2.5 mL of methanol. Then add 0.04 mmol of methanesulfonic acid and stir at room temperature for 6 hours.

[0023] Step 2) After the reaction is complete, some solvent is removed under reduced pressure, the reaction is quenched with saturated sodium bicarbonate aqueous solution, extracted with dichloromethane, and dried to obtain the crude product. The crude product is then purified by column chromatography to obtain pure 5-methoxy-3-methyl-5-phenyl-1-(4-methylphenylamino)-1,5-dihydropyrrole-2-one, with the following structural formula:

[0024]

[0025] Yield: 91%; white solid; as Figures 1 to 2 As shown, its 1H NMR spectrum (Chloroform-d, 400 MHz) is as follows: δ 7.40 (d, J = 4.8 Hz, 2H), 7.34 (d, J = 6.0 Hz, 3H), 6.92 (d, J = 7.6 Hz, 2H), 6.62 (d, J = 6.4 Hz, 3H), 5.26 (s, 1H), 3.29 (s, 3H), 2.21 (s, 3H), 2.08 (s, 3H). Carbon NMR spectrum (Chloroform-d, 101 MHz): δ 170.7, 144.2, 140.8, 136.3, 136.1, 130.7, 129.2, 128.8, 128.6, 126.3, 115.5, 94.7, 77.3, 77.0, 76.7, 51.7, 20.5, 11.3. High-resolution mass spectrometry (ESI) calcd for C 19 H 21 N₂O₂ [M+H] + 309.1598, found309.1613.

[0026] The preparation method employs mild reaction conditions and produces complex products; the synthetic steps are simple and the reaction exhibits high chemical selectivity; the product molecule contains active groups, which can increase its stability in polymers. The dihydropyrrolidone derivatives synthesized in this invention possess excellent ultraviolet absorption properties.

[0027] Experimental example: in 10 -5 The UV-Vis absorption spectrum of 5-methoxy-3-methyl-5-phenyl-1-(4-methylphenylamino)-1,5-dihydropyrrole-2-one was measured at room temperature at a concentration of mol / L; Figure 3 It is known that 5-methoxy-3-methyl-5-phenyl-1-(4-methylphenylamino)-1,5-dihydropyrrole-2-one has strong ultraviolet absorption at 200-250 nm.

[0028] The above embodiments are merely illustrative of the principles and effects of the present invention and are not intended to limit the invention. Any person skilled in the art can modify or alter the above embodiments without departing from the spirit and scope of the present invention. Therefore, all equivalent modifications or alterations made by those skilled in the art without departing from the spirit and technical concept disclosed in the present invention should still be covered by the claims of the present invention.

Claims

1. A dihydropyrrolidone derivative, characterized in that: Its structural formula is as follows: .

2. A method for preparing the dihydropyrrolidone derivative of claim 1, characterized in that, It includes the following steps: Step 1) A certain amount of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo, methanesulfonic acid and solvent are reacted under certain temperature conditions; Step 2) After the reaction is complete, some solvent is removed under reduced pressure, the reaction is quenched with saturated sodium bicarbonate aqueous solution, extracted, dried, and purified by column chromatography to obtain the pure dihydropyrrolidone derivative; wherein the structural formula of the dihydropyrrolidone derivative is as follows: .

3. The method for preparing the dihydropyrrolidone derivative according to claim 2, characterized in that: The solvent is methanol.

4. The method for preparing the dihydropyrrolidone derivative according to claim 2, characterized in that: The reaction temperature is 20-40°C. o C.

5. The method for preparing the dihydropyrrolidone derivative according to claim 2, characterized in that: The molar ratio of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo and methanesulfonic acid is 1:0.05-0.

2.

6. The method for preparing the dihydropyrrolidone derivative according to claim 2, characterized in that: When the amount of 1-(3-methyl-5-phenylfuran-2-yl)-2-(4-methylphenyl)azo is 0.2 mmol, the amount of solvent used is 2-5 mL.

7. An application of the dihydropyrrolidone derivative of claim 1, characterized in that: It is used to prepare polymeric ultraviolet absorbers.

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