Method for preparing flavanone compound

A compound and flavanone technology, applied in the field of preparing flavanone compounds, can solve the problems of long reaction time, low yield and the like, and achieve the effects of short reaction time, simple operation, great application value and economic benefit

Inactive Publication Date: 2010-07-14
CHONGQING TECH & BUSINESS UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Aiming at the disadvantages of long reaction time and low yield in the cyclization of 2'-hydroxychalcones under basic catalysts to generate flavanones, the purpose of the present invention is to provide a 2'-hydroxychalcone Method for cyclization of ketones to generate flavanones

Method used

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  • Method for preparing flavanone compound
  • Method for preparing flavanone compound
  • Method for preparing flavanone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of flavanones based on bromo-n-butylpyridine

[0033] In a 50ml beaker, add 2'-hydroxychalcone 10mg, brominated n-butylpyridine (0.015g / ml) 0.05ml, NaOH (8mol / L) 0.05ml and H 2 O 10ml, stirred vigorously, controlled the temperature at 15°C, and reacted for 1.5h; the reacted mixture was extracted with benzene, then concentrated under reduced pressure; The peak area was measured at the peak 251nm, and the flavanone content was calculated, and the yield was 59.1%.

Embodiment 2

[0034] Example 2: Synthesis of flavanones based on bromo-n-butylpyridine

[0035] In a 50ml beaker, add 2'-hydroxychalcone 10mg, brominated n-butylpyridine (0.015g / ml) 0.10ml, NaOH (8mol / L) 0.10ml and H 2 O 10ml, stirred vigorously, the temperature was controlled at 20°C, and reacted for 2h; the reacted mixture was washed with CH 2 Cl 2 Extraction is carried out, and then concentrated under reduced pressure; after the concentrate is chromatographically separated, the peak area is measured at the characteristic peak of flavanones at 251 nm by high performance liquid chromatography, and the content of flavanones is calculated, and the yield is 89.4%.

Embodiment 3

[0036] Example 3: Synthesis of flavanones based on bromo-n-butylpyridine

[0037] In a 50ml beaker, add 2'-hydroxychalcone 10mg, brominated n-butylpyridine (0.015g / ml) 0.15ml, NaOH (8mol / L) 0.15ml and H 2 O 10ml, vigorously stirred, the temperature was controlled at 20°C, and reacted for 1.5h; the reacted mixture was extracted with ethyl acetate, and then concentrated under reduced pressure; The peak area was measured at 251 nm of the characteristic peak of ketone, and the content of flavanone was calculated, and the yield was 73.6%.

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Abstract

The invention relates to the field of the chemical synthesis and particularly discloses a method for preparing a flavanone compound. A 2'-hydroxy chalcone compound carries out a cyclization reaction to generate the flavanone compound under the condition that pyridinium onium salt, NaOH and water exist. The method of the invention has the advantages of short reaction time, higher product yield, no by-product, no toxicity of the catalyst and easy separation and purification of the product, and has wide industrial application prospect.

Description

technical field [0001] The invention relates to the field of chemical synthesis, and specifically discloses a method for preparing flavanone compounds from 2'-hydroxychalcone compounds. Background technique [0002] Flavanones are one of the active ingredients of various medicinal plants. Due to its remarkable biological and pharmacological activities and unique plastic structure, it has attracted strong research interest of chemists for nearly a hundred years. According to relevant literature reports, many flavanone compounds have many biological activities such as antibacterial, anti-inflammatory, anti-HIV virus, anti-tumor, anti-mutagenesis, and anti-oxidation. They are a class of compounds with high research value and broad application prospects. [0003] Flavanone compounds refer to a class of compounds derived from 2-phenyldihydrochromanone as the core. 2-Phenyl dihydrochromone is flavanone, also known as dihydroflavone. Most of the hydroxy derivatives exist in plan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32
Inventor 郑旭煦殷钟意谢晶晶何文香
Owner CHONGQING TECH & BUSINESS UNIV
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