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A kind of preparation method of spirobenzofuran compound

A technology of compound and furan, which is applied in the field of chemical biomimetic synthesis of natural medicines, achieves the effects of low cost, breakthrough limitations and high production yield

Active Publication Date: 2021-10-26
SOUTHWEST JIAOTONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In recent years, the oxidative [3+2] cycloaddition reaction has developed rapidly, but there are still two points to be improved and resolved: 1. The selective [3+2] cycloaddition reaction of phenols and polyenes to construct spirobenzone There are no related reports on the furan skeleton; 2. The application of oxidative [3+2] cycloaddition reaction to the synthesis of natural products and drug molecules has few related literature reports, and there is still a lot of room for improvement

Method used

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  • A kind of preparation method of spirobenzofuran compound
  • A kind of preparation method of spirobenzofuran compound

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Embodiment

[0027] A 300mL round bottom flask was preheated with an alcohol lamp to remove water for 10 minutes, during which the argon gas was replaced three times. Phlorotriphenol (99%, 12.7 g, 100 mmol) and anhydrous potassium carbonate (99%, 13.8 g, 100 mmol, 1.0 equiv) were added rapidly; the argon was replaced three times again. Add anhydrous acetone (100 mL, commercially purchased acetone needs to be pre-dried with anhydrous calcium chloride, and then distilled at atmospheric pressure for later use). Finally, dimethyl sulfate (99%, 3.2ml, 33mmol, 0.33equiv; protective measures must be taken during the process of adding dimethyl sulfate, and carried out in a fume hood), gradually increased to 55 ° C for ten hours. After the reaction, it was cooled to room temperature, and the acetone was distilled by a rotary evaporator. Extract with ethyl acetate (2×100mL), wash with 1M hydrochloric acid (2×20mL), water (20mL) and saturated brine (20mL) successively, dry over anhydrous sodium sulf...

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Abstract

The invention discloses a preparation method of a spirobenzofuran compound. It discloses that commercially available phloroglucinol and 4‑isopropylcyclohexanone are used as raw materials to synthesize dihydrogenate through Friedel-Crafts reaction and Wittig reaction Chalcone and β-phellandrene with an extracyclic double bond, after obtaining two fragment compounds of hydrochalcone and β-phellandrene, the two fragment compounds are connected by oxidative cycloaddition reaction to construct spirobenzene Furan core skeleton is combined to prepare the natural products adunctin C and adunctin D. The present invention develops a new method for constructing the structural unit by means of synthesis of organic chemistry and guided by the synthesis of the target natural products adunctin C and adunctin D. The method is applied to the synthesis and preparation of natural products adunctin C and D with important physiological and pharmacological activities. The preparation yield is high and the cost is low, which greatly breaks through the limitation of the natural product source.

Description

technical field [0001] The invention relates to the technical field of chemical biomimetic synthesis of natural medicines, in particular to developing a regioselective chemical synthesis method for constructing a spirobenzofuran skeleton structure, and applying the method to the synthesis of natural products or medicines. Background technique [0002] Medicinal chemistry is based on chemistry and biology, and studies the structure and activity of related drugs. The research content includes discovering, modifying and optimizing lead compounds, revealing the mechanism of action of drugs and physiologically active substances at the molecular level, and studying the metabolic process of drugs and physiologically active substances in the body. Study the relationship between the chemical structure and activity of drugs, and create new drugs by obtaining new chemical entities through drug molecule design or chemical modification of lead compounds. This direction is also a compreh...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/94
CPCC07D307/94
Inventor 彭羽肖检王雅雯
Owner SOUTHWEST JIAOTONG UNIV
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