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Method for oxidation synthesis of stilbenes by hexamethylenetetramine

A technology of hexamethylene tetramine and stilbene, which is applied in the field of synthesizing stilbene compounds by oxidation of hexamethylene tetramine, can solve the problems of difficulty in realizing industrialized production, high toxicity, environmental damage and the like, and achieves the The method is simple and easy to implement, the cost is low, and the yield is high.

Inactive Publication Date: 2009-09-16
HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • 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 by substituted Oxidative synthesis of benzyl alcohol, 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 (chlorodichromate pyridine), 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, and it is difficult to realize industrial production

Method used

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  • Method for oxidation synthesis of stilbenes by hexamethylenetetramine
  • Method for oxidation synthesis of stilbenes by hexamethylenetetramine
  • Method for oxidation synthesis of stilbenes by hexamethylenetetramine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] This example is a method for synthesizing 3,4′,5-trihydroxystilbene, namely resveratrol, by oxidation of hexamethylenetetramine, the reaction route of which is shown in formula (II):

[0051]

[0052] Formula (II)

[0053] The reaction process is a1→b1→c1→d1, and the reaction formula of each step is as follows:

[0054]

[0055]

[0056] This method is carried out according to the following sequence of steps:

[0057] a 1 . Compound A1 3, the preparation of 5-dimethoxybenzyl bromide

[0058] Take 10.60g (63.10mmol) of 3,5-dimethoxybenzyl alcohol and 100mL of diethyl ether into a 250mL four-neck flask, stir, cool down, add 7.10mL (75.72mmol) of phosphorus tribromide dropwise at 0°C, and add dropwise After completion, it was raised to room temperature for reaction and monitored by TLC. After the reaction was completed, the reaction solution was poured into ice water, stirred, and the organic layer was separated, washed with water, dried, suction filtered, and...

Embodiment 2

[0066] This example is a method for the oxidation of hexamethylenetetramine to synthesize 3,5-dimethoxy-4'-hydroxystilbene, that is, pterostylbene, and its reaction route is as shown in formula (III):

[0067]

[0068] Formula (III)

[0069] The reaction process is a2→b2→c2→d2, and the reaction formula of each step is as follows:

[0070]

[0071]

[0072] This method is carried out according to the following sequence of steps:

[0073] a 2 .3, the preparation of 5-dimethoxybenzyl chloride namely A2:

[0074] Add 10.82g (64.40mmol) of 3,5-dimethoxybenzyl alcohol and 110mL of dichloromethane into a 250mL four-neck flask, stir, cool down, and add 5.61mL (77.28mmol) of thionyl chloride dropwise at 0°C, dropwise After the addition was completed, it was raised to room temperature for reaction, and monitored by TLC. After the reaction was completed, water was added, the organic layer was separated, washed with water, dried, filtered with suction, and the solvent was rem...

Embodiment 3

[0082] This example is a method for oxidizing hexamethylenetetramine to synthesize 3,5-dimethoxy-4-isopropyl stilbene, that is, styrene moder. The reaction route is as follows:

[0083]

[0084] Formula (IV)

[0085] The reaction process is a3→b3→c3→d3, and the reaction formula of each step is as follows:

[0086]

[0087] This method is carried out according to the following sequence of steps:

[0088] a 3 .Compound A3 is the preparation of 3,5-dimethoxy-4-isopropylbenzyl chloride:

[0089] Take 10.81g (51.48mmol) of 3,5-dimethoxy-4-isopropylbenzyl alcohol and 110mL of dichloromethane into a 250mL four-neck flask, stir, cool down in an ice bath, and add chlorinated chlorinated dropwise at 0°C. Sulfone 4.50mL (61.77mmol), rise to room temperature reaction after dropwise addition, TLC monitoring. After the reaction was completed, water was added, extracted with dichloromethane, washed with water, and the solvent was removed by rotary evaporation to obtain 10.00 g (43....

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Abstract

The invention discloses a method for oxidation synthesis of stilbenes by hexamethylenetetramine, comprising the following steps: preparing halogenated hydrocarbon by substituted benzyl alcohol, oxidizing the halogenated hydrocarbon by the hexamethylenetetramine to prepare corresponding substituted benzaldehydes, and preparing stilbene derivatives by condensation of Wittig-Horner. The method is simple and easy to implement; the reactants involved in the process of synthesis are safe; the resultants produce no pollution to the environment, have low cost and high yield and are suitable for industrially producing stilbenes having antibacterial action, such as resveratrol, pterostilbene and 3, 5-dimethoxy-4-isopropyl stilbene, etc.

Description

technical field [0001] The invention relates to a method for synthesizing a compound with a stilbene skeleton, in particular to a method for synthesizing a stilbene compound by oxidation of hexamethylenetetramine. Background technique [0002] Compounds with 1,2-stilbene skeleton and their polymers are collectively called stilbene compounds, which have high chemical and pharmaceutical activities. 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 contain formazan Oxygen, hydroxyl or amino groups have obvious drug physiological activity. For example, stilbene (resveratrol) whose 3, 5, and 4′ positions are all substituted by hydroxyl groups has been found to have anti-cancer, anti-bacterial and fungal, and anti-lipidemia properties. It also has physiological activities such...

Claims

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Application Information

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IPC IPC(8): C07C39/21C07C37/055C07C43/23C07C41/26
Inventor 张越张艳艳
Owner HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY
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