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Method for synthesizing 1,2-naphthoquinone and derivatives thereof

A synthesis method and derivative technology, applied in the preparation of oxidized quinone, organic chemistry, etc., can solve problems such as complex processes, and achieve the effects of short reaction time, high reaction efficiency, and mild reaction conditions

Inactive Publication Date: 2019-03-05
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of method needs to prepare 1-amino-2-naphthol in advance, and the process is relatively complicated

Method used

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  • Method for synthesizing 1,2-naphthoquinone and derivatives thereof
  • Method for synthesizing 1,2-naphthoquinone and derivatives thereof
  • Method for synthesizing 1,2-naphthoquinone and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Add 0.3mmol (E)-3-phenyl-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one, 0.03mmol ferric chloride, 0.6mmol diiodine pentoxide to In a 15mL thick-walled pressure-resistant reaction tube, add 3mL of 1,4-dioxane as a solvent. Next, magnetic stirring was performed at 100° C. for 0.5 hours. After cooling to room temperature, add two tablespoons of column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure, and then separate the product 3-phenyl-1,2-naphthoquinone by column chromatography Pure product (petroleum ether / ethyl acetate = 10:1 as eluent). The material was a red solid in 57% yield.

[0032] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ7.31–7.47(m,8H),7.58(m,1H,),8.03(d,J=7.6Hz,1H).. 13 C NMR (125MHz, CDCl 3 ) : δ180.0, 179.1, 141.9, 138.8, 136.0, 135.3, 134.1, 130.8, 30.4, 130.1, 130.0, 128.9, 128.5, 128.4.

Embodiment 2

[0034]

[0035] Add 0.3mmol (E)-3-phenyl-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one, 0.03mmol ferric nitrate, 0.6mmol diiodine pentoxide to 15mL In the thick-walled pressure-resistant reaction tube, add 3 mL of 1,4-dioxane as a solvent. Next, magnetic stirring was performed at 100° C. for 0.5 hours. After cooling to room temperature, add two tablespoons of column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure, and then separate the product 3-phenyl-1,2-naphthoquinone by column chromatography Pure product (petroleum ether / ethyl acetate = 10:1 as eluent). The material was a red solid, 53% yield.

[0036] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ7.31–7.47(m,8H),7.58(m,1H,),8.03(d,J=7.6Hz,1H).. 13 C NMR (125MHz, CDCl 3 ) : δ180.0, 179.1, 141.9, 138.8, 136.0, 135.3, 134.1, 130.8, 30.4, 130.1, 130.0, 128.9, 128.5, 128.4.

Embodiment 3

[0038]

[0039] Add 0.3mmol (E)-3-phenyl-1-(2-(phenylethynyl)phenyl)prop-2-en-1-one, 0.015mmol ferric chloride, 0.6mmol diiodine pentoxide to In a 15mL thick-walled pressure-resistant reaction tube, add 3mL of 1,4-dioxane as a solvent. Next, magnetic stirring was performed at 100° C. for 0.5 hours. After cooling to room temperature, add two tablespoons of column chromatography silica gel (100-200 mesh) to the reaction solution, and remove the solvent by distillation under reduced pressure, and then separate the product 3-phenyl-1,2-naphthoquinone by column chromatography Pure product (petroleum ether / ethyl acetate = 10:1 as eluent). The material was a red solid, 43% yield.

[0040] Characterization data: 1 H NMR (500MHz, CDCl 3 ):δ7.31–7.47(m,8H),7.58(m,1H,),8.03(d,J=7.6Hz,1H).. 13 C NMR (125MHz, CDCl 3 ): δ180.0,179.1,141.9,138.8,136.0,135.3,134.1,130.8,30.4,130.1,130.0,128.9,128.5,128.4.

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Abstract

The present invention provides a method of synthesizing 1,2-naphthoquinone and derivatives thereof. The synthesis method takes an o-alkynyl chalcone compound represented by a formula (I) as an initialsubstance, ferric chloride or ferric nitrate as a catalyst, and iodine pentoxide as an oxidant, in an organic solvent, a reaction is carried out at a temperature of 70 DEG C to 120 DEG C for 0.1 to 2hours, and separation and purification are carried out, so that a corresponding target product is obtained. The synthesis method of the invention has the characteristics of small environmental hazard, mild reaction conditions, simple operation and the like.

Description

technical field [0001] The present invention relates to a synthesis method of organic compounds, in particular to a preparation method of 1,2-naphthoquinone and its derivatives. Background technique [0002] Molecules with quinone structures occupy a unique position in organic chemistry and have a wide range of applications. Quinone compounds are a class of compounds that include quinones or are easily transformed into compounds with quinone properties, and are closely related to quinones in biosynthesis. They often exist in nature as pigments in animals, plants, and microorganisms. Many important Chinese medicines such as rhubarb, cassia, senna, comfrey, knotweed, fleece-flower root, aloe, etc. have quinone compounds in their main active ingredients. According to different chemical structures, quinone compounds can be divided into benzoquinones, naphthoquinones, anthraquinones and phenanthrenequinones. Among them, naphthoquinone has been widely used in dyes and organic in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/02C07C50/10C07C50/32C07C50/24
CPCC07C46/02C07C50/10C07C50/32C07C50/24
Inventor 刘运奎郑立孟杨欢
Owner ZHEJIANG UNIV OF TECH
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