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Method for preparing coumarin derivative

A technology of coumarin and substances, which is applied in the field of preparation of lactone compounds, can solve the problems of low content, complicated extraction, separation and purification process, etc.

Inactive Publication Date: 2014-07-02
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Although naturally occurring coumarin has a wide range of activities, its content in plants is low, and the extraction, separation and purification process is complicated. The total synthesis of coumarin can save production costs and improve production efficiency

Method used

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  • Method for preparing coumarin derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Preparation of 7-hydroxy-6,8-dimethoxycoumarin (isozapyridine)

[0039] (1) Preparation of 4-formyl-2,6-dimethoxyphenyl-2,2-dimethylpropionate:

[0040] Add 3,5-dimethoxy-4-hydroxybenzaldehyde (Ⅱ) (546mg, 3mmol) and anhydrous dichloromethane (3ml) into a 25ml round bottom flask, stir to dissolve at 20°C, then add 4-dimethylamino Pyridine (15mg, 0.12mmol), stirred at 20°C for 0.5h, added dropwise pivaloyl chloride (732µl, 6mmol), triethylamine (940µl, 6mmol), stirred at 20°C for 2h, added 100 times the volume of the reactant (i.e. 100ml ) dichloromethane, washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate after removing the washing liquid, filtered with suction, concentrated the filtrate under reduced pressure to dryness, and obtained 790 mg of a light yellow solid crude product, namely 4-formyl-2,6-dimethoxyphenyl-2,2-dimethylpropionate (IV), yield 99%....

Embodiment 2

[0051] Example 2: Preparation of 7-hydroxy-6,8-dimethoxycoumarin (isozapyridine)

[0052] (1) Preparation of 4-formyl-2,6-dimethoxyphenyl-2,2-dimethylpropionate:

[0053] Add 3,5-dimethoxy-4-hydroxybenzaldehyde (Ⅱ) (546mg, 3mmol) and anhydrous dichloromethane (3ml) into a 25ml round bottom flask, stir to dissolve at 20°C, then add 4-dimethylamino Pyridine (15mg, 0.12mmol), stirred at 20°C for 0.5h, added dropwise pivaloyl chloride (549µl, 4.5mmol), triethylamine (705µl, 4.5mmol), stirred at 20°C for 2h, added 100 times the volume of the reactant ( (i.e. 100ml) dichloromethane, washed successively with saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate after removing the washing liquid, filtered with suction, concentrated the filtrate to dryness under reduced pressure, and obtained 790 mg of crude product of light yellow solid , namely 4-formyl-2,6-dimethoxyphenyl-2,2-dimethylpropionate (Ⅳ), with...

Embodiment 3

[0065] Example 3: Preparation of 7-hydroxy-6-methoxycoumarin (scopolamine)

[0066] (1) Preparation of 4-formyl-22-methoxyphenyl-1,2-dimethylpropionate:

[0067] Add 3-methoxy-4-hydroxybenzaldehyde (456mg, 3mmol) and anhydrous dichloromethane (5ml) into a 25ml round bottom flask, stir and dissolve at 20°C, then add 4-dimethylaminopyridine (15mg, 0.12mmol ), stirred at 20°C for 0.5h, added dropwise pivaloyl chloride (732μl, 6mmol), triethylamine (940μl, 6mmol) successively, stirred at 20°C for 2h, added 100ml of dichloromethane to the reactant, followed by saturated sodium bicarbonate aqueous solution, washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate after removing the washing liquid, filtered with suction, concentrated the filtrate to dryness by rotary evaporation, and dried at 50°C for 5 minutes to obtain 700 mg of a light yellow solid crude product with a purity of 99% and a melting point of 83.8 -95.2°C.

[0068] 1 H NMR (500...

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Abstract

The invention discloses a method for preparing a coumarin derivative. According to the method, the coumarin derivative shown by formula (I) is prepared by using a compound shown by formula (II) as a raw material; the synthetic process route of the coumarin derivative is simple, feasible and safe, the method is suitable for industrial production, the raw materials are low-toxicity and economic, and the yield is universally high. The total yield of isofraxidin is 57.6% and is greater than 47.5% of the existing other synthetic route, the synthetic process step is shortened, and the process route is low-toxicity, environment-friendly and safe; 6,7,8-triethoxycoumarin is synthesized for the first time, the yield is up to 67%, and the synthetic method is simple, convenient, mild in conditions and low in pollution; the yield of scoparone is 77.4%, few byproducts are produced, the conditions are mild, and the experiment is easy in operation; by using the compound with relatively low toxicity, the pollution is low, and the cost is relatively low, so the method is suitable for industrialized production.

Description

(1) Technical field [0001] The invention relates to a preparation method of lactone compounds, in particular to a preparation method of coumarin derivatives. (2) Background technology [0002] Coumarin is a lactone compound that widely exists in nature and has physiological activities such as anti-AIDS, anti-tumor, and immune enhancement. [0003] The chemical name of isofraxidin is 7-hydroxy-6,8-dimethoxybenzopyran-2-one, which mainly exists in Herba Sarcandrae, Radix et Caulis Acanthopanacis Senticosi), grass coral (Sarcandra glabra) and other Chinese medicinal materials. It has been found through research that isoxapyridine is an active ingredient for regulating neurotransmitters, has the therapeutic effect of nourishing the mind and calming the nerves, and can be used clinically to treat palpitations, insomnia, loss of appetite, fatigue, neurasthenia and other diseases. It also has significant antibacterial and anticancer effects, can also improve the body's immunity, ...

Claims

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Application Information

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IPC IPC(8): C07D311/16
CPCC07D311/16
Inventor 李庆勇颜继忠程冬萍楚楚李行诺童胜强
Owner ZHEJIANG UNIV OF TECH
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