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Method for preparing aurones compound

A technology for compound and orange ketone, which is applied in the field of preparation of orange ketone compounds, can solve the problems of large amount of catalyst, harsh preparation conditions, serious environmental pollution, etc., and achieves the effects of low equipment requirements, simple operation and improved economic benefits.

Active Publication Date: 2014-07-23
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Advantages of this method: easy preparation of raw materials, simple catalytic system, and easy operation; disadvantages: too much catalyst (≥ 1 equiv) and serious environmental pollution, substrates have certain structural restrictions such as thallium (III) nitrate in the catalytic system 2' - The para-position of the hydroxyl group in the hydroxychalcone derivative needs to be substituted with a methoxy group
However, some reaction products have the generation of by-product flavones; some raw materials are prepared under harsher conditions; some raw materials are easy to get, the yield is high and no by-products are produced, but expensive Au or Ag complexes are used as catalysts

Method used

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  • Method for preparing aurones compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of (Z)-2-phenylmethylene-3(2H)-benzofuranone

[0030] Add (2-bromophenyl)(3-phenyl-2-epoxy)ketone (1.52 g, 5.0 mmol) into a two-necked flask, dissolve it completely with DMF (25 ml), then add cesium carbonate (2.44 g, 7.5 mmol), CuI (0.10 g, 0.5 mmol), 1,10-phenanthroline.Monohydrate (0.2 g, 1.0 mmol), heated at 105°C under nitrogen protection, TLC monitored the end of the reaction, and the reaction was complete in about 4.5 hours . After the reaction was complete, cool down to room temperature, add 50 ml of water and 50 ml of ethyl acetate to it, separate the layers, extract the water layer with 20 ml of ethyl acetate, combine the ethyl acetate layer; wash the ethyl acetate layer with water, wash with saturated NaHCO3, Washed with saturated brine, dried over anhydrous sodium sulfate; spin-dried, concentrated, and separated by column chromatography to obtain the product orange (Z)-2-phenylmethylene-3(2H)-benzofuranone, light yellow powder 0.98g,...

Embodiment 2

[0033] Example 2: Preparation of (Z)-2-phenylmethylene-3(2H)-benzofuranone

[0034] Dissolve (2-bromophenyl)(3-phenyl-2-epoxy)ketone (1.52 g, 5.0 mmol) in a two-necked flask with toluene (25 ml), add cesium carbonate (2.44 g, 7.5 mmol ), CuI (0.10 g, 0.5 mmol), 1,10-phenanthroline (0.18 g, 1.0 mmol), nitrogen protection, 105 ℃ heating TLC to monitor the end of the reaction, the reaction was complete in about 4.5 hours. After the reaction was complete, cool down to room temperature, add 50 ml of water and 50 ml of ethyl acetate to it, separate the layers, extract the water layer with 20 ml of ethyl acetate, combine the ethyl acetate layer; wash the ethyl acetate layer with water, wash with saturated NaHCO3, Washed with saturated brine, dried over anhydrous sodium sulfate; spin-dried, concentrated, and separated by column chromatography to obtain the product orange (Z)-2-phenylmethylene-3(2H)-benzofuranone, light yellow powder , 0.935 g, 84%.

Embodiment 3

[0035] Example 3: Preparation of (Z)-2-phenylmethylene-3(2H)-benzofuranone

[0036] Dissolve (2-bromophenyl)(3-phenyl-2-epoxy)ketone (1.52 g, 5.0 mmol) in a two-necked flask with DMF (25 ml), add cesium carbonate (0.82 g, 2.5 mmol ), CuI (0.01 g, 0.05 mmol), 2,2-bipyridine (0.015 g, 0.1 mmol). Nitrogen protection, 105 ° C heating TLC to monitor the end of the reaction, the reaction was complete in about 4.5 hours. After the reaction was complete, the temperature was lowered to room temperature, and 50 ml of water and 50 ml of ethyl acetate were added thereto. Separate the layers, extract the aqueous layer with 20 ml of ethyl acetate, combine the ethyl acetate layers; wash the ethyl acetate layer with water, wash with saturated NaHCO3, wash with saturated brine, and dry over anhydrous sodium sulfate; spin dry, concentrate, and separate by column chromatography The product arurone (Z)-2-phenylmethylene-3(2H)-benzofuranone was obtained as light yellow powder, 0.72g, 65%.

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Abstract

The invention discloses a method for preparing an aurones compound, and belongs to the technical field of chemical synthesis. The preparation method comprises the following steps of: in an organic solvent, performing reaction on halogenated epoxy chalcone ketone serving as a raw material at 80-140 DEG C for 2.5-5.5 hours in the presence of a copper catalyst, a ligand and an alkaline substance; performing aftertreatment after the end of reaction to obtain the aurones compound. According to the method, halogenated epoxy chalcone ketone is used as the raw material and is reacted to obtain a series of aurones in the presence of the copper catalyst, the ligand and the alkaline substance; epoxy during reaction is subjected to ring opening and cyclization so as to obtain five-membered rings or Z type structures. The compound is high in regioselectivity and stereoselectivity, and has easily-available raw materials for reaction; the catalyst is low in cost so as to avoid using the catalyst which is high in cost and is serious in environment pollution; according to the method, raw materials can be easily obtained, the operation is easy, the reaction condition is mild, the yield is high, the catalyst is low in cost, and the yield is up to more than 80 percent; the method has high application value and social economic benefit and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a preparation method of orange ketone compounds. Background technique [0002] Flavonoids are a class of natural products that exist in almost all green plants, and are one of the main active ingredients of many Chinese herbal medicines. Orange ketone is an isomer of flavone, which is a kind of rare flavonoid compound. Orange ketones are relatively less distributed in nature, and mostly exist in colored flowers and fruits, especially some golden yellow flowers. Orange ketones have a wide range of biological activities, such as analgesic, anti-inflammatory, anti-tumor, anti-cancer, cardiovascular system diseases, anti-aging and other activities in medicine; and anti-feedant and weeding activities in agriculture. [0003] Compared with the research on flavonoids, there are fewer reports on the research on aurone. This type of compound is mainly isolated fr...

Claims

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Application Information

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IPC IPC(8): C07D307/83
CPCC07D307/83
Inventor 翁意意苏为科陈启绪
Owner ZHEJIANG UNIV OF TECH
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