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Synthesis method of Lupinus luteus wighteone

A synthetic method, the technology of genistein, which is applied in the field of chemical synthesis, can solve the problem of high cost, and achieve the effects of convenient post-processing, cost reduction, and cost reduction

Inactive Publication Date: 2014-07-23
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The third step of Document 2 used the expensive metal catalyst Eu(fod) 3 ,the cost is too high

Method used

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  • Synthesis method of Lupinus luteus wighteone
  • Synthesis method of Lupinus luteus wighteone
  • Synthesis method of Lupinus luteus wighteone

Examples

Experimental program
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Effect test

Embodiment 1

[0031] (1) Dissolve 8 grams of genistein in 150 milliliters of DMF, add 7 milliliters of acetic anhydride, reflux for 2-3 hours, and then detect with TLC. After the reaction, filter with suction to obtain a white solid, wash the solid with water, and then dry it get the product a;

[0032] (2) Dissolve 1 gram of product a in 50 ml of dry DMF, then add 3.5 g of potassium carbonate and 1.6 ml of bromoisoprene, react at room temperature for 1 h, then detect with TLC, evaporate under reduced pressure after the reaction Remove the solvent, wash with petroleum ether, then recrystallize 2-3 times with acetone, and obtain product b after drying;

[0033] (3) 0.5 g of product b was dissolved in 40 ml of N,N-diethylaniline, refluxed for 0.5-1 h, and then detected by TLC. After the reaction, the reaction solution was extracted with ethyl acetate, and then washed with saturated ammonium chloride solution To neutrality, wash with water, dry, pour out the solution, evaporate the solvent un...

Embodiment 2

[0041] (1) Dissolve 12 grams of genistein in 150 ml of DMF, add 7 ml of acetic anhydride, reflux for 2-3 hours, and then detect with TLC. After the reaction, filter the white solid, wash the solid with water, and then dry it get the product a;

[0042] (2) Dissolve 5 g of product a in 50 ml of dry DMF, add 3.5 g of potassium carbonate and 1.6 ml of brominated isoprene, react at room temperature for 1 h, then detect with TLC, evaporate under reduced pressure after the reaction Remove the solvent, wash with petroleum ether, then recrystallize 2-3 times with acetone, and obtain product b after drying;

[0043] (3) 1.5 g of product b was dissolved in 40 ml of N,N-diethylaniline, refluxed for 0.5-1 h, and then detected by TLC. After the reaction, the reaction solution was extracted with ethyl acetate, and then washed with saturated ammonium chloride solution To neutrality, wash with water, dry, pour out the solution, evaporate the solvent under reduced pressure to obtain a white s...

Embodiment 3

[0050] (1) Dissolve 10 grams of genistein in 150 milliliters of DMF, add 7 milliliters of acetic anhydride, reflux for 2-3 hours, and then detect with TLC. After the reaction, filter with suction to obtain a white solid, wash the solid with water, and then dry it get the product a;

[0051] (2) Dissolve 3 grams of product a in 50 ml of dry DMF, add 3.5 g of potassium carbonate and 1.6 ml of brominated isoprene, react at room temperature for 1 h, then detect with TLC, evaporate under reduced pressure after the reaction Remove the solvent, wash with petroleum ether, then recrystallize 2-3 times with acetone, and obtain product b after drying;

[0052] (3) 1 g of product b was dissolved in 40 ml of N,N-diethylaniline, refluxed for 0.5-1 h, and then detected by TLC. After the reaction, the reaction solution was extracted with ethyl acetate, and then washed with saturated ammonium chloride solution To neutrality, wash with water, dry, pour out the solution, evaporate the solvent u...

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Abstract

The invention discloses a synthesis method of Lupinus luteus wighteone. The method provided by the invention toakes genistein as a raw material to undergo four-step reaction so as to obtain Lupinus luteus wighteone. In the second-step reaction of the method, isoamylene bromide, potassium carbonate, and a DMF system are employed to replace isopentenyl alcohol, diethyl azodicarboxylate, triphenylphosphine and a THF system, the cost is greatly reduced, the after-treatment is much more convenient, and the yield is enhanced from 83% to 92%. In the third-step reaction, diethyl aniline, dimethylaniline, decahydronaphthalene and other high-boiling point solvents are adopted as the solvents, and under heating reflux conditions, para Claisen rearrangement of isopentenyl is completed to replace Eu(fod)3 catalyzed rearrangement adopted by original methods, thus saving the precious metal catalyst, greatly reducing the cost, and increasing the yield from original 68% to 87%.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing yellow lupine waiterone. Background technique [0002] Prenylflavones, especially prenylisoflavones, exhibit phytoalexin, insect-feeding, and antifungal activities. It also exhibits anti-inflammatory, anti-cancer, and anti-lipid properties in vitro and in vivo. 5,7,4'-Trihydroxy-8-prenyl isoflavone (yellow lupine waiterone) is isolated from the pods and seeds of white lupine, the root of yellow lupine and the leaves of Glycyrrhiza glabra. In order to study the biological activity of yellow lupine waiterone, a simple and efficient chemical synthesis method is needed. [0003] There are two main chemical synthesis methods at present, one is the total synthesis method reported by Japanese scholars, this method has a total of 15 steps, and the total yield is 7% (document 1: J. Chem. Res. Minipr. 1998, 5, 1181). Obviously, this method is difficu...

Claims

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Application Information

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IPC IPC(8): C07D311/36
CPCC07D311/36
Inventor 胡昆任杰祁燕杰
Owner CHANGZHOU UNIV
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