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A kind of 2,3-dibromo-2,3-dihydro-1,4-naphthoquinone compound, its preparation method and application

A compound and naphthol technology, applied in the field of pharmaceutical synthesis, can solve the problems of high cost, high price and high production cost, and achieve the effects of low cost, high total yield and few by-products

Active Publication Date: 2016-08-31
SHANDONG LUKANG SHELILE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But this method also uses AgNO 3 And ammonium persulfate, the production cost is higher, and the impact on the environment is not good
[0014] Both of the above methods use the expensive AgNO 3 , not only the cost is high and the yield is very low, at the same time, the post-processing process will also cause great damage to the environment

Method used

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  • A kind of 2,3-dibromo-2,3-dihydro-1,4-naphthoquinone compound, its preparation method and application
  • A kind of 2,3-dibromo-2,3-dihydro-1,4-naphthoquinone compound, its preparation method and application
  • A kind of 2,3-dibromo-2,3-dihydro-1,4-naphthoquinone compound, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0071] Example 1 Preparation of 2,3-dibromo-2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone, 3-bromo 2-(4-(4-chlorophenyl)cyclo Hexyl)-1,4-naphthoquinone

[0072] The preparation of A, 2-(4-(4-chlorophenyl) cyclohexyl)-1-naphthol (formula IV)

[0073] Under the protection of nitrogen, 2.9g of 4-(4-chlorophenyl)cyclohexanol, 2g of α-naphthol, and 2.63g of p-toluenesulfonic acid were added to 30ml of toluene, and the reaction was refluxed at 140°C for 3h, and the progress of the reaction was monitored by TLC. After the reaction was complete, the organic phase was washed with water, separated to remove water, the organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and crystallized to obtain 2-(4-(4-chlorophenyl)cyclohexyl)-1-naphthol.

[0074] Preparation of B, 2,3-dibromo-2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone (formula Ⅰ)

[0075] (a), the preparation of 2-(4-(4-chlorophenyl) cyclohexyl)-1,4-naphthoquinone (formula Ⅲ)

...

Embodiment 2

[0081] Example 2 Preparation of 2,3-dibromo 2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone, 3-bromo 2-(4-(4-chlorophenyl)cyclohexyl )-1,4-naphthoquinone

[0082] The preparation of A, 2-(4-(4-chlorophenyl) cyclohexyl)-1-naphthol (formula IV)

[0083] Add 30ml of chlorobenzene, 2g of α-naphthol, 4.65g of 4-(4-chlorophenyl) cyclohexanol and 0.8g of p-toluenesulfonic acid in a 100ml three-necked flask, and reflux reaction for 3h. TLC monitors the reaction, and the reaction is complete. Concentrate under reduced pressure, add chloroform for extraction, wash with water, separate the organic layer, and evaporate the solvent to obtain the product 2-(4-(4-chlorophenyl)cyclohexyl)-1-naphthol.

[0084] Preparation of B, 2,3-dibromo 2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone (formula Ⅰ)

[0085] In 30ml carbon tetrachloride, add 2-(4-(4-chlorophenyl) cyclohexyl)-1-naphthol 3.36g, Br 2 1.6g, 1.2ml of 30% hydrogen peroxide solution, 0.6ml of 98% concentrated sulfuric acid,...

Embodiment 3

[0088] Embodiment three prepares atovaquone

[0089] Dissolve 2.145 g of 3-bromo-2-(4-(4-chlorophenyl) cyclohexyl)-1,4-naphthoquinone and 1.6 g of sodium hydroxide in 65 ml of methanol, reflux reaction, TLC detection of reaction progress, reaction Complete, adjust the pH to 2~3, concentrate to remove methanol, extract with ethyl acetate, concentrate in vacuo, and crystallize at low temperature to obtain the target compound atovaquone (3-hydroxyl-2-(4-(4-chlorophenyl)cyclohexyl)- 1,4-Naphthoquinone).

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PUM

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Abstract

The invention discloses a benzoquinones compound, a preparation method and application thereof, and belongs to the drug synthesis field. The method comprises the following steps: condensing alpha-naphthol and 4-(4-chlorophenyl)cyclohexanol under acid catalysis to obtain 2-(4-(4-chlorophenyl)cyclohexyl)-1-naphthol (formula IV), oxidizing the compound represented by formula IV to obtain 2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone (formula III), enabling the compound represented by the formula III to react with bromine in additive reaction to obtain 2,3-dibromo-2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone (formula I), releasing a molecule of hydrogen bromide to obtain 3-bromo-2-(4-(4-chlorophenyl)cyclohexyl)-1,4-naphthoquinone (formula II). The method further discloses a method for preparing atovaquone by using the compound, the synthesis method is simple, the AgNO3 can be prevented from using, and the total yield is high.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a benzoquinone compound, its preparation method and its application. Background technique [0002] Quinone compounds are a class of compounds that are widely distributed in nature, including quinones and compounds that are easily converted into quinones. [0003] Structurally speaking, quinone compounds can be divided into benzoquinone, naphthoquinone and anthraquinone, which have various physiological activities, such as antidiarrheal, antibacterial, diuretic and hemostatic, etc., and some quinone compounds have anticancer, antiviral , antispasmodic and antiasthmatic effects. Although the preparation methods of some quinone compounds, especially benzoquinone compounds, are disclosed in the prior art, expensive catalysts are commonly used in the preparation process, such as AgNO 3 etc., the production cost is higher. [0004] Atovaquone (Atovaquone) is a homologue of coenzyme Q, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/24C07C46/00C07C50/32
CPCC07C37/16C07C46/00C07C46/06C07C50/24C07C2601/14C07C2602/10C07C39/42C07C50/32
Inventor 董咪咪颜丙春郭强董坤彭欣武茂成
Owner SHANDONG LUKANG SHELILE PHARMA
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