Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Catalyzed synthesis method of dehydrogenated alpha-lapachol

A synthesis method and compound technology, applied in the field of catalytic synthesis of dehydroα-lapachone, capable of solving problems such as low reaction yield, unfavorable industrial production, and narrow scope of application of substrates

Inactive Publication Date: 2016-02-03
CHENGDU KECHUANG JIASI TECH
View PDF6 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] However, the above-mentioned process method has inherent disadvantages such as low reaction yield and narrow substrate application range, which are not conducive to large-scale industrial production.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Catalyzed synthesis method of dehydrogenated alpha-lapachol
  • Catalyzed synthesis method of dehydrogenated alpha-lapachol
  • Catalyzed synthesis method of dehydrogenated alpha-lapachol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027]

[0028] In reactor, add 1mmol formula (I) compound, 2.3mmol potassium acetate and 28ml solvent acetic acid, continue to add 0.07mmol catalyst, 2.1mmol oxygenant Cu(OTf) under stirring 2 And 0.11mmol auxiliary agent, then add 4.1mmol formula (II) compound, stir and react at room temperature for 150min, after the reaction is completed, cool to room temperature, filter, wash with cold water successively, extract with ethyl acetate, wash with saturated saline solution, separate The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and then separated through a silica gel column (petroleum ether / ethyl acetate) to obtain the compound of formula (III) with a yield of 98.1%.

[0029] Among them, the catalyst is Pd(acac) with a molar ratio of 3:1 2 with CeCl 3 The mixture; auxiliary agent is 1-hexyl-3-methylimidazolium chloride salt.

Embodiment 2

[0031]

[0032] In reactor, add 1mmol formula (I) compound, 2.4mmol potassium acetate and 30ml solvent acetic acid, continue to add 0.08mmol catalyst, 2.2mmol oxidant Cu(OTf) under stirring 2 And 0.12mmol auxiliary agent, then add 4.2mmol formula (II) compound, stir and react at room temperature for 180min, after the reaction is completed, cool to room temperature, filter, wash with cold water successively, extract with ethyl acetate, wash with saturated saline solution, separate The organic phase was dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and then separated through a silica gel column (petroleum ether / ethyl acetate) to obtain the compound of formula (III) with a yield of 97.6%.

[0033] Among them, the catalyst is Pd(acac) with a molar ratio of 3:1 2 with CeCl 3 The mixture; auxiliary agent is 1-hexyl-3-methylimidazolium chloride salt.

Embodiment 3

[0035]

[0036] In reactor, add 1mmol formula (I) compound, 2.2mmol potassium acetate and 25ml solvent acetic acid, continue to add 0.06mmol catalyst, 2mmol oxidant Cu(OTf) under stirring 2 And 0.1mmol auxiliary agent, then add 4mmol formula (II) compound, stir and react at room temperature for 120min, after the reaction is completed, cool to room temperature, filter, wash with cold water successively, extract with ethyl acetate, wash with saturated saline solution, separate the organic The phase was dried over anhydrous sodium sulfate, filtered, concentrated in vacuo, and then separated through a silica gel column (petroleum ether / ethyl acetate) to obtain the compound of formula (III) with a yield of 97.5%.

[0037] Among them, the catalyst is Pd(acac) with a molar ratio of 3:1 2 with CeCl 3 The mixture; auxiliary agent is 1-hexyl-3-methylimidazolium chloride salt.

[0038] The present invention has confirmed and characterized the structures of the target products of all...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a catalyzed synthesis method of dehydrogenated alpha-lapachol. According to the method, a novel carbonate reaction raw material is adopted, a multiplex catalyst system is creatively used, mild and high-efficiency conversion of materials is realized, and the reaction yield is greatly improved. The process has the advantages of high reaction speed, mild reaction conditions, excellent reaction yield and the like, the production cost is saved, and the method has a great benefit to medicinal synthesis and is wide in industrial application prospects.

Description

technical field [0001] The invention relates to a catalytic synthesis method of dehydroα-lapachone, which belongs to the field of drug synthesis. Background technique [0002] 2H-pyranaphthoquinones are a special class of quinones, which have various biological activities, such as anti-inflammatory, anti-cancer, antibacterial, etc. The most common one is dehydroα-lapachone (α-xyloidone), which, as an important active ingredient of antitumor and anticancer drugs, has shown a very wide application prospect. However, the existing methods for obtaining this compound mainly adopt the method of natural plant isolation, but there are few reports on the chemical synthesis process of dehydroα-lapachone. Therefore, the development of a novel synthetic method for dehydroα-lapachone will be very meaningful for the production and research of medicine. [0003] So far, the known methods for synthesizing dehydroα-lapachone mainly include the following, for example: [0004] ("Environmen...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/92
CPCC07D311/92
Inventor 缪家戌
Owner CHENGDU KECHUANG JIASI TECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com