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Preparation method of spirobenzofuran compounds

A compound, furan technology, applied in the field of chemical biomimetic synthesis of natural medicines

Active Publication Date: 2020-10-30
SOUTHWEST JIAOTONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Preparation method of spirobenzofuran compounds
  • Preparation method of spirobenzofuran compounds

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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 spirobenzofuran compounds. The method comprises the steps: taking commercially available phloroglucinol and 4-isopropyl cyclohexanone as raw materials;dihydrochalcone and beta-phellandrene with an extracyclic double bond are respectively synthesized through a Friedel-Crafts reaction and a Wittig reaction; after two fragment compounds of the hydrochalcone and the beta-phellandrene are obtained, with oxidized cycloaddition reactions, connecting the two fragment compounds, constructing a spirobenzofuran core skeleton, and thus preparing natural products adunctin C and adunctin D. According to the invention, an organic chemical synthesis means is adopted, synthesis of the target natural products adunctin C and adunctin D is used as guidance, anda new method for constructing the structural units is developed; meanwhile, the method is applied to synthesis and preparation of the natural products adunctin C and D with important physiological and pharmacological activities, the preparation yield is high, the cost is low, and the limitation of sources of the natural products is greatly broken through.

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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IPC IPC(8): C07D307/94
CPCC07D307/94
Inventor 彭羽肖检王雅雯
Owner SOUTHWEST JIAOTONG UNIV
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