Water-phase one-pot synthesis method of 3-flavonol and 3-flavonol derivative

A technology of hydroxyflavone and synthesis method, applied in the direction of organic chemistry, etc., can solve the problems of unknown adaptability of 3-hydroxyflavone, unknown substrate adaptability, unknown reaction mechanism, etc. High, simple and easy-to-control synthesis conditions

Inactive Publication Date: 2019-02-12
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0019] This method has the following limitations: (1) the product yield is low (46.3%, 41.6%); (2) only aldehydes containing electron-donating groups and acetophenones containing electron-withdrawing groups are reported, and other substrates are adaptable Unknown, especially the adaptability of synthesizing 5-substituted 3-hydroxyflavone from 6-position substituted acetophenone is unknown; (3) The reaction mechanism is unknown; (4) In the air environment, the organic solvent is not conducive to the intermediate The iminium ion proceeds in the direction of generating flavonol, and easily produces by-products such as orange ketone and peroxide

Method used

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  • Water-phase one-pot synthesis method of 3-flavonol and 3-flavonol derivative
  • Water-phase one-pot synthesis method of 3-flavonol and 3-flavonol derivative
  • Water-phase one-pot synthesis method of 3-flavonol and 3-flavonol derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] use figure 1 Raw material A in 1 and B 1 react. The reaction system includes: raw material A 1 (1.0mmol), B 1 (1.1mmol), base, reaction medium (10.0mL), and the reaction system was open to the atmosphere. Moore, A 1 :B 1 : Alkali=1:1.1:(2~16).

[0062] The reaction process is: after adding alkali into 10mL reaction medium, slowly add A 1 (1.0mmol), stir vigorously to dissolve and then slowly add B 1 (1.1mmol), then react at room temperature or by heating, the reaction system communicates with the atmosphere or oxygen, keep stirring for 24h, and the reaction ends.

[0063] After the reaction, the reaction system was adjusted to pH≤7.0 with 6.0 mol / L hydrochloric acid aqueous solution, and the insoluble solid was filtered to obtain the crude product. The crude product was subjected to silica gel column chromatography (petroleum ether: ethyl acetate=4:1) to obtain the final product C 1 (Structural formula such as figure 2 shown). Wherein, the specific parame...

Embodiment 2

[0068] In addition to the different reaction raw materials, based on cost and environmental considerations, we chose the specific reaction conditions of Example Group 11 with lower energy consumption, less organic base consumption, and similar yields to carry out the reaction in this example. The structural formulas of raw materials A and B used in this embodiment are specifically as figure 1 Shown, the structural formula of each final product C produced is specifically as follows figure 2 shown. The specific reaction system is: raw material A (1.0 mmol), B (1.1 mmol), pyrrolidine (10.0 mmol), water (20.0 mL).

[0069] The concrete raw material A, B that each group of present embodiment is used, the product C of production and yield are as shown in table 2.

[0070] Table 2 Reaction system and yield comparison table

[0071] group

Embodiment 3

[0073] Except that the reaction raw materials are different, the same conditions as in Example Group 11 were selected to carry out the reaction of this example. The structural formula of each raw material Ch used in this embodiment is specifically as follows figure 1 Shown, the structural formula of each final product C produced is specifically as follows figure 2 shown. The specific reaction system is: raw material Ch (1.0 mmol), pyrrolidine (10.0 mmol), water (20.0 mL).

[0074] The specific raw materials Ch used in each group of the present embodiment, the product C produced and the yield are shown in Table 3.

[0075] Table 3 reaction system and yield comparison table

[0076] group

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Abstract

The invention belongs to the field of chemical synthesis, and particularly relates to a water-phase one-pot synthesis method of 3-flavonol and a 3-flavonol derivative. According to the method, 2-hydroxyacetophenone, 2-hydroxyacetophenone derivatives, benzaldehyde and benzaldehyde derivatives are used as reaction substrates, or 2-hydroxy-chalcone and hydroxy-chalcone derivatives are used as reaction substrates; water or ethanol water solution is used as a solvent; under the aerobic condition at 20 to 100 DEG C, reaction is performed to obtain the 3-flavonol and the 3-flavonol derivative. The invention provides a fire-new reaction mechanism, and develops a novel 3-flavonol synthesis method with the advantages of high efficiency, convenience, high speed and wide substrate adaptability. The invention also provides a fire-new 3-flavonol derivative synthesized by the novel method; important application values are realized in the field of medical care sanitation.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a water-phase one-pot synthesis method of 3-hydroxyflavone and derivatives thereof. Background technique [0002] 3-Hydroxyflavonoids (also known as flavonols) are a class of flavonoids with unique structures, not only complex and diverse in structure, but also numerous in quantity. 3-Hydroxyflavones and their derivatives have a variety of biological activities, such as anti-oxidation, anti-cancer, cardiovascular protection, anti-bacterial, anti-virus, anti-inflammatory, etc., and have huge applications in the field of pharmaceutical research and human health protection. 3-Hydroxyflavones are widely distributed in the plant kingdom, such as ginkgo, myrobalan, seabuckthorn, and vegetables (tomatoes, beans, broccoli, onions, etc.), fruits (grapes, apples, etc.) and tea in daily life. However, the number and types of natural 3-hydroxyflavones are limited, and extractio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30
CPCC07D311/30
Inventor 王淳张国林熊伟
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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