Method for synthesizing stilbene compound by utilizing Kornblum oxidation reaction

A stilbene compound and oxidation reaction technology, applied in the field of synthesizing stilbene compounds by Kornblum oxidation reaction, can solve the problems of low yield, high toxicity, environmental damage and the like

Inactive Publication Date: 2010-09-22
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, the skeletons of stilbene compounds reported in literature at home and abroad are generally realized through Wittig-Horner condensation. The condensation reaction is carried out between substituted benzyl diethyl phosphate and substituted benzaldehyde. Some complex substituted benzaldehydes are generally formed from substituted benzene Oxidative synthesis of methanol, in order to prevent the generation of substituted benzoic acid and ensure that the oxidation stays in the aldehyde stage, special oxidizing reagents are usually used, such as highly toxic and carcinogenic PCC (pyridinium chlorochromate) and PDC (pyridinium chlorodichromate) etc. Although the oxidation yield is high, excessive PCC and PDC and a large amount of chromium-containing waste liquid produced after the reaction will cause serious damage to the environment, making it difficult to realize industrial production
There have also been reports on the method of oxidatively synthesizing stilbene compounds with hexamethylenetetramine, but the yield of this method is low

Method used

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  • Method for synthesizing stilbene compound by utilizing Kornblum oxidation reaction
  • Method for synthesizing stilbene compound by utilizing Kornblum oxidation reaction
  • Method for synthesizing stilbene compound by utilizing Kornblum oxidation reaction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] Example 1 A method for synthesizing 3,5-dimethoxy-4-isopropyl stilbene that is styrene modder by Kornblum oxidation reaction

[0102] The reaction scheme of present embodiment is as formula (II):

[0103]

[0104] Formula (II)

[0105] Its reaction process is a 1 →b 1 → c 1 , the step-by-step reaction is as follows:

[0106]

[0107] Utilize the method of Kornblum oxidation reaction to synthesize phenylene moder to carry out according to the following step sequence:

[0108] a 1 .Compound A 1 That is, the preparation of 3,5-dimethoxy-4-isopropylbenzaldehyde:

[0109] Take 10.0g (43.8mmol) of 3,5-dimethoxy-4-isopropylbenzyl chloride, 62.1mLDMSO, 11.0g NaHCO 3 Add it into a four-neck flask, stir, react at room temperature, and monitor by TLC. After the reaction is completed, add water, extract with ethyl acetate, wash with water, and remove the solvent by rotary evaporation to obtain product A 1 7.83g (37.6mmol). Yield 86%.

[0110] b 1 .Compound B 1 T...

Embodiment 2

[0119] Example 2 The method of synthesizing 3,5-dimethoxy-4'-hydroxystilbene, namely pterostylbene by Kornblum oxidation method

[0120] The reaction scheme of present embodiment is as formula (III):

[0121]

[0122] Formula (III)

[0123] Its reaction process is a 2 →b 2 → c 2 , the step-by-step reaction is as follows:

[0124]

[0125] This method is carried out according to the following sequence of steps:

[0126] a 2 .Compound A 2 That is, the preparation of 3,5-dimethoxybenzaldehyde:

[0127] Take 10.0g (53.6mmol) of 3,5-dimethoxybenzyl chloride, 114.1mLDMSO, 27.0g NaHCO 3 Add it into a four-neck flask, stir, react at room temperature, and monitor by TLC. After the reaction is completed, add water, extract with ethyl acetate, wash with water, and remove the solvent by rotary evaporation to obtain product A 2 7.97 (48.0 mmol). Yield 88.5%.

[0128] b 2 .Compound B 2 That is, the preparation of 3,5-dimethoxy-4'-tert-butyldimethylsiloxy stilbene:

[01...

Embodiment 3

[0137] Example 3 Synthesis method 1 of the method for synthesizing 3,5,4'-trihydroxystilbene, that is, resveratrol by Kornblum oxidation reaction

[0138] The reaction scheme of present embodiment is as formula (IV):

[0139]

[0140]

[0141] Formula (IV)

[0142] Its reaction process is a3 →b 3 → c 3 , the step-by-step reaction is as follows:

[0143]

[0144] This method is carried out according to the following sequence of steps:

[0145] a 3 .Compound A 3 That is, the preparation of 3,5-dimethoxybenzaldehyde

[0146] Take 10.0g (53.6mmol) of 3,5-dimethoxybenzyl chloride, 38.0mLDMSO, 4.5gNaHCO 3 Add it into a four-neck flask, stir, react at room temperature, and monitor by TLC. After the reaction is completed, add water, extract with ethyl acetate, wash with water, and remove the solvent by rotary evaporation to obtain product A 3 7.80 g (47.0 mmol). Yield 87.6%.

[0147] b 3 .Compound B 3 That is, the preparation of 3,5,4'-trimethoxystilbene

[0148...

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Abstract

The invention discloses a method for synthesizing a stilbene compound by utilizing a Kornblum oxidation reaction. In the method, substituted benzyl chloride is taken as a raw material, DMSO, namely dimethyl sulfoxide is adopted to prepare a corresponding substituted benzene formaldehyde compound through Kornblum oxidation and a target product stilbene compound is prepared through Wittig-Horner condensation. The method is simple and practicable, has safe reactant in the synthesizing process, moderate reaction condition and high yield, is suitable for industrialization production of various stilbene compounds, such as benximode, rosewood stilbene, resveratrol, oxidized resveratrol and piceatannol and the like, and is further applied to the pharmaceutical field.

Description

technical field [0001] The invention relates to a method for synthesizing stilbene compounds, that is, compounds with a stilbene skeleton, in particular to a method for synthesizing stilbene compounds by Kornblum oxidation reaction. Background technique [0002] Compounds with 1,2-stilbene skeleton and their polymers are collectively called stilbene compounds, which have high chemical and pharmaceutical activities. The stilbene compounds containing different substituents have different uses due to their different chemical properties. The positions of the substituents are mainly concentrated in the 3, 5, 4, and 4' positions of the stilbene molecule. When the 3, 5, and 4' positions are respectively When it contains methoxy, hydroxyl or amino, it has obvious pharmaceutical physiological activity, as shown by research: stilbene substituted by 3,5-position hydroxy, 4-position isopropyl (styrene moder); 3,5-position A Oxygen-substituted, 4'-hydroxyl-substituted stilbene (Pterosti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B37/00C07C39/21C07C37/055C07C43/23C07C41/01
Inventor 张越赵树春
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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