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New synthetic method for xanthotoxol and derivatives thereof

A technology of xanthoxylin and its derivatives, which is applied in the field of new synthesis of xanthoxylin and xanthoxylin and its derivatives, can solve the problems of long reaction steps and achieve the effects of reduced reaction steps, high efficiency and simple operation

Active Publication Date: 2015-02-25
浙江凯普化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the overall yield increased to 9%, the reaction steps were longer

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: 9-hydroxyl-2H-furo[3,2-g]benzopyran-3,7-dione (having the structure shown in chemical formula I, wherein R 1 for the preparation of hydrogen)

[0036] In the reaction flask, add 22 grams of 6,7-dihydroxybenzofuran-3(2H)-one (having the chemical formula IV The structure shown, where, R 4 is hydrogen), 28 grams of 3,3-diethoxypropionic acid (with the formula V structure shown), stirred, and added 20 ml of trifluoroacetic acid and 14 ml of concentrated sulfuric acid as solvents. The temperature was raised to 120 degrees Celsius for 4 hours, and after the reaction was complete, the temperature was lowered to room temperature. Add 300 ml of water for destruction, then extract with 500 ml of dichloromethane, and wash the organic layer with saturated brine. The organic layer was concentrated to dryness and recrystallized from ethanol to obtain 20 g of 9-hydroxy-2H-furo[3,2-g]benzopyran-3,7-dione. The yield was 69%. HREIMS m / z 218.0222 (C 11 h 6 o ...

Embodiment 2

[0037] Example 2: 9-Hydroxy-2H-furo[3,2-g]benzopyran-3,7-dione (with the structure shown in chemical formula I, wherein R 1 for the preparation of hydrogen)

[0038] In the reaction flask, add 22 grams of 6,7-dihydroxybenzofuran-3(2H)-one, 25 grams of 3,3-dimethoxypropionic acid methyl ester (having the formula V structure shown), stirred, and added 20 ml of trifluoroacetic acid and 14 ml of concentrated sulfuric acid as solvents. The temperature was raised to 120 degrees Celsius for 4 hours, and after the reaction was complete, the temperature was lowered to room temperature. Add 300 ml of water for destruction, then extract with 500 ml of dichloromethane, and wash the organic layer with saturated brine. The organic layer was concentrated to dryness and recrystallized from ethanol to obtain 19 g of 9-hydroxy-2H-furo[3,2-g]benzopyran-3,7-dione. The yield was 66%. HREIMS m / z 218.0230 (C 11 h 6 o 5 , calculated value: 218.0215).

Embodiment 3

[0039] Example 3: 9-hydroxyl-2H-furo[3,2-g]benzopyran-3,7-dione (having the structure shown in chemical formula I, wherein R 1 for the preparation of hydrogen)

[0040] In the reaction flask, add 22 grams of 6,7-dihydroxybenzofuran-3(2H)-ketone, 21 grams of 3-oxopropionic acid (having the formula VI structure shown), stirred, and added 20 ml of trifluoroacetic acid and 14 ml of concentrated sulfuric acid as solvents. The temperature was raised to 120 degrees Celsius for 4 hours, and after the reaction was complete, the temperature was lowered to room temperature. It was destroyed by adding 300 ml of water, and then extracted with 500 ml of dichloromethane. The organic layer was washed with saturated brine, concentrated to dryness, and recrystallized from ethanol to obtain 20 g of 9-hydroxy-2H-furo[3,2-g]benzopyran-3,7-dione. The yield was 69%. HREIMS m / z 218.0206 (C 11 h 6 o 5 , calculated value: 218.0215).

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PUM

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Abstract

The invention discloses a new synthetic method for xanthotoxol and derivatives thereof. The key step comprises a cyclization reaction, and compounds with structures shown as the chemical formulas (IV), (VII) and (VIII) are cyclized with any one or a mixture of compounds with structures shown as the chemical formulas (V) and (VI) to obtain the xanthotoxol or the derivatives thereof, wherein, the compounds with the structures shown as the chemical formulas (IV), (VII) and (VIII) are benzofuran derivatives which are analogues and mutual derivatives, the benzofuran derivatives are cyclized with the compound with the structure shown as the chemical formula (V) or (VI) to obtain the xanthotoxol or the derivatives thereof by using hydroxy on each benzene ring and hydrogen atom on an adjacent site, and hexahydric unsaturated cyclo-ester by further reaction after the cyclization reaction. Compared with the prior art, the method has the advantages that the reaction steps are reduced, the operation is simple and the efficiency is high.

Description

technical field [0001] The invention relates to a novel synthesis method of xanthoxylin and xanthoxylin and its derivatives, belonging to the fields of organic chemistry and medicinal chemistry. Background technique [0002] Xanthoxylin is golden yellow or beige crystal, with the structure shown in the following chemical formula (III), [0003] [0004] Among them, R 3 represents hydrogen. [0005] Zanthoxylum bungeanum has good anti-inflammatory and analgesic effects, as well as anti-arrhythmia, lowering blood pressure, anti-osteoporosis, eliminating phlegm and relieving asthma. In addition, xanthoxylin showed antioxidant activity in lipid peroxidation test and hemolysis test. [0006] Xanthotoxin, also known as xantholide, or oxidized psoralen, is a derivative of xanthoxylin. Its properties are white or light yellow crystals with the structure shown in the following chemical formula (III), [0007] [0008] Among them, R 3 Represents methyl. [0009] Zanthoxyl...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04
Inventor 黄建罗林风谭翔晖周忱
Owner 浙江凯普化工有限公司