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

Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof

A tetracyclic compound and synthetic method technology, applied in the field of organic compound synthesis, can solve the problems of low yield and cumbersome reaction steps, and achieve the effects of high yield, single stereoselectivity, and simple operation

Active Publication Date: 2022-06-07
NANJING FORESTRY UNIV
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most of the methods for synthesizing benzene ring-fused 6 / 7 / 6 tricyclic skeleton compounds usually require multiple reaction steps, which are cumbersome and have low yields

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
  • Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof
  • Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof
  • Benzene ring fused 5/6/7/6 tetracyclic compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Take a 10mL round-bottomed flask, add o-alkynylbenzaldehyde 2a (0.2mmol), Molecular sieves (100 mg) and platinum dibromide catalyst (0.01 mmol) were added to tetrahydrofuran (2 mL) under an argon atmosphere, and the reaction was carried out at 70° C. for 12 hours. After cooling to room temperature, tetrabutylammonium tribromide (0.01 mmol) was added to the reaction system, and methanol (2 ml) was further reacted for 1 hour. After the reaction, the insolubles were removed by filtration, water and ethyl acetate were added for extraction twice, the organic phases were combined, dried over anhydrous magnesium sulfate, the filtrate was filtered and concentrated by rotary evaporation, and the crude product was separated by silica gel column chromatography with a volume ratio of 25: The 2-25:8 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain 40.2 mg of the target product 1a.

[0035] The reaction equation is:

[0036]...

Embodiment 2

[0044] Take a 10mL round-bottomed flask, add o-alkynylbenzaldehyde 2b (0.2mmol), Molecular sieves (100 mg) and platinum dibromide catalyst (0.01 mmol) were added to tetrahydrofuran (2 mL) under argon atmosphere, and the reaction was carried out at 70° C. for 12 hours. After cooling to room temperature, tetrabutylammonium tribromide (0.01 mmol) was added to the reaction system, and methanol (2 ml) was further reacted for 1 hour. After the reaction, the insolubles were removed by filtration, water and ethyl acetate were added for extraction twice, the organic phases were combined, dried over anhydrous magnesium sulfate, the filtrate was filtered and concentrated by rotary evaporation, and the crude product was separated by silica gel column chromatography with a volume ratio of 25: A mixed solution of petroleum ether and ethyl acetate in a ratio of 1 to 25:6 was used as the eluent for gradient elution to obtain 57.5 mg of the target product 1b.

[0045] The reaction equation i...

Embodiment 3

[0051] Take a 10mL round-bottomed flask, add o-alkynylbenzaldehyde 2c (0.2mmol), Molecular sieves (100 mg) and platinum dibromide catalyst (0.01 mmol) were added to tetrahydrofuran (2 mL) under argon atmosphere, and the reaction was carried out at 70° C. for 12 hours. After cooling to room temperature, tetrabutylammonium tribromide (0.01 mmol) was added to the reaction system, and methanol (2 ml) was further reacted for 1 hour. After the reaction, the insolubles were removed by filtration, water and ethyl acetate were added for extraction twice, the organic phases were combined, dried over anhydrous magnesium sulfate, the filtrate was filtered and concentrated by rotary evaporation, and the crude product was separated by silica gel column chromatography with a volume ratio of 25: A 1-5:1 mixed solution of petroleum ether and ethyl acetate was used as the eluent for gradient elution to obtain 59.7 mg of the target product 1c.

[0052] The reaction equation is:

[0053]

...

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 discloses a benzene ring-fused 5 / 6 / 7 / 6 tetracyclic compound and a synthesis method thereof, and the benzene ring-fused 5 / 6 / 7 / 6 tetracyclic compound is obtained by taking an o-alkynyl benzaldehyde compound connected with cyclohexadienone propargyl ether as a raw material, carrying out heating reaction in a solvent tetrahydrofuran under the catalysis of a platinum catalyst, and carrying out post-treatment. The invention provides a novel synthesis method of a benzene ring fused 5 / 6 / 7 / 6 tetracyclic compound which is not easy to prepare by a conventional method, four continuous chiral centers can be constructed in one step, and the compound has excellent stereoselectivity; the method has the advantages of simplicity in operation, wide substrate range, high yield and the like.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, in particular to a benzene ring-fused 5 / 6 / 7 / 6 tetracyclic compound and a synthesis method thereof. Background technique [0002] The benzene ring-fused 6 / 7 / 6 tricyclic skeleton is an important building block for many natural product molecules, and studies have shown that these compounds have diverse biological activities, such as antibacterial, antifungal, antioxidant and anticancer activities. For example, the natural product (-)-Barbatusol extracted from the root of Coleus serrata can be used to treat high blood pressure, and the natural product Fruticulin A extracted from Salvia has anti-inflammatory and labor pain effects. Pisiferin extracted from leaves has good cytotoxicity to cancer cells, (+)-Rosmaridiphenol is a rosmarinol isolated from rosemary leaves and has strong antioxidant properties. Taxamairin H was the first terpenoid isolated from the stem bark of Taxus chin...

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
IPC IPC(8): C07D307/77C07D493/06C07D493/08
CPCC07D307/77C07D493/06C07D493/08C07B2200/13Y02A50/30
Inventor 饶卫东胡睿王泽梁陈继超
Owner NANJING FORESTRY UNIV
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