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Preparation method of sateripol compounds

The technology of a compound and gentisol, which is applied in the field of preparation of gentisol compounds, can solve the problems of high price, unfavorable mass production, and high raw material cost, and achieves the effects of ideal yield, reduced cost and easy implementation.

Inactive Publication Date: 2016-06-15
HARBIN INST OF TECH AT WEIHAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biggest defect of the above method is that the cost of raw materials is relatively high, especially the price of 2,5-dimethylol benzaldehyde is quite expensive, which is not conducive to mass production

Method used

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  • Preparation method of sateripol compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Embodiment 1: 2-hydroxymethyl-4-methoxyphenol ( 3 , see attached picture) for the synthesis of

[0017] Add 5 milliliters of deionized water, 4-methoxyphenol ( 2 , see attached image, follow references Organic & biomolecular chemistry 12.19(2014): 3100. Preparation, 2.0mmol), sodium metaborate tetrahydrate (16.0mmol), 0.75ml formalin solution, stirred and reacted at 40°C for 16 hours, TLC detected the end of the reaction. Add 1 ml of dilute hydrochloric acid to quench the reaction, extract the reaction solution with ethyl acetate (20mLx3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain 2-hydroxymethyl-4-methoxy Base phenol, the yield is 91%.

Embodiment 2

[0018] Example 2: Gentioquinone (2-hydroxymethyl-1,4-p-benzoquinone, 4 , see attached picture) for the synthesis of

[0019] Add 2 milliliters of acetonitrile, 2 milliliters of water, 2-hydroxymethyl-4-methoxyphenol ( 3 , see accompanying drawing, 1.0mmol), cerium ammonium nitrate (2.5mmol), stirred and reacted at 0°C for 2 hours, and TLC detected the end of the reaction. The reaction solution was extracted with dichloromethane (10mLx3), the organic phases were combined, dried over anhydrous sodium sulfate, filtered, concentrated, and purified by column chromatography to obtain gentioquinone with a yield of 87%. H NMR spectrum 1 HNMR (400MHz, CDCl 3 )σ6.79(s,1H),6.72(s,2H),4.51(s,2H); C NMR spectrum 13 CNMR (100MHz, CDCl 3 )σ 187.7, 187.5, 147.4, 136.7, 136.5, 131.1, 59.1.

Embodiment 3

[0020] Embodiment 3: Gentianol (2-hydroxymethyl-1,4-hydroquinone, 1 , see attached picture) for the synthesis of

[0021] Add 0.5 milliliters of dichloromethane, 1.5 milliliters of water, 2-hydroxymethyl-1,4-p-benzoquinone ( 4 , see attached figure, 0.2mmol), sodium dithionite (0.6mmol), stirred and reacted at room temperature for 2 hours, and TLC detected the end of the reaction. Add 1 ml of dilute hydrochloric acid to quench the reaction, separate the liquids after shaking, extract the aqueous phase with an organic solvent (10mLx3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate, and purify by column chromatography to obtain gentianol. The yield is 80%. H NMR spectrum 1 HNMR (400MHz, DMSO-d 6 )σ6.72(s,1H),6.54(d,1H,J=8.4Hz),6.41(d,1H,J=8.4Hz),4.39(s,2H); C NMR spectrum 13 CNMR (100MHz, DMSO-d 6 )σ150.2, 146.8, 129.8, 115.5, 114.4, 113.7, 58.7; high resolution mass spectrometry HRMS (TOFMSES + ) m / z :CalcdforC 7 h 8 o 3 [M + ...

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Abstract

The invention relates to a preparation method of sateripol compounds, and belongs to the field of chemical synthesis. 4-alkoxy saligenol compounds are prepared by carrying out a reaction of 4-alkoxy phenol compounds and aldehyde ketone compounds, the gentian quinone compounds are prepared by carrying out an oxidation reaction of the 4-alkoxy saligenol compounds, and the sateripol compounds (shown in the attached drawing described in the specification) are prepared by carrying out a reduction reaction of the gentian quinone compounds. The preparation method has the advantages of low production cost, simple process conditions, easy control, high total yield and the like, and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a preparation method of gentianol compounds. Background technique [0002] Gentianol is an organic compound extracted from Streptomyces for the first time. It not only has high antioxidant activity, promotes angiogenesis, and inhibits apoptosis ( J. Microbial. Biotechnol. 2016, 16 ,475), but also showed inhibitory activity against influenza virus H1N1 and H3N2, half inhibitory concentration (IC 50 ) values ​​are 5.0 and 5.9 μmol L -1 , the selection index (SI) is 3.7 and 3.0 respectively ( Chin. Pharm. J. 2014, 49 ,632). In addition, chlorgentianol has extremely high antifouling activity, and its EC to a variety of marine fouling organisms 50 reached 0.67μg / mL ( Mar. Biotechnol .2006, 8 ,634), which is far below the antifouling agent standard stipulated by the US Navy (EC 50 ≤25μg / mL). [0003] Many people have done related work on the synthesis of gentianol. Wherein, Ahmadibeni utilizes 2,5-dimethylol benzaldehyd...

Claims

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Application Information

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IPC IPC(8): C07C37/07C07C39/11
CPCC07C41/30C07C37/07C07C46/06C07C43/23C07C50/28C07C39/11
Inventor 王龙飞王洪双张振国程云飞张博淞李惠静吴彦超周培林
Owner HARBIN INST OF TECH AT WEIHAI
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