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

A kind of multi-substituted phenanthrene derivative and its preparation method

A derivative and multi-substitution technology, applied in the field of organic compound synthesis, can solve the problems of low content of phenanthrene derivatives, limited number of separation and extraction, etc., and achieve the effects of cheap reagents, high yield, and simple synthesis of substrates

Active Publication Date: 2021-06-08
ANHUI NORMAL UNIV
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, the content of phenanthrene derivatives containing multiple substituents in natural products is relatively small, and the number of separation and extraction is limited, and its output cannot meet people's needs at all.

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
  • A kind of multi-substituted phenanthrene derivative and its preparation method
  • A kind of multi-substituted phenanthrene derivative and its preparation method
  • A kind of multi-substituted phenanthrene derivative and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A multi-substituted phenanthrene derivative, the structural formula of the multi-substituted phenanthrene derivative is:

[0035]

[0036] The preparation method of described multi-substituted phenanthrene derivatives is:

[0037] (1) With 830mmol sodium hydride as a catalyst, 200mmol diisopropyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile, stirred and reacted in an ice-water bath for 8.5 hours, the product was washed with water, washed with ethyl acetate Extraction, spin-dried under reduced pressure, column chromatography with ethyl acetate:petroleum ether=1:90 as the eluent by volume ratio, concentrated and dried under reduced pressure, the white solid product compound a-1 was obtained;

[0038] (2) 80mmol compound a-1 is mixed with 200mmol p-chlorophenylethynyl bromide, and in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(PPh 3 ) 2 Cl 2 :CuI=3:1; Pd(PPh 3 ) 2 Cl 2 , CuI are resp...

Embodiment 2

[0045] A multi-substituted phenanthrene derivative, the structural formula of the multi-substituted phenanthrene derivative is:

[0046]

[0047] The preparation method of described multi-substituted phenanthrene derivatives is:

[0048](1) With 830mmol sodium hydride as a catalyst, 200mmol diisopropyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile, stirred and reacted in an ice-water bath for 8.5 hours, the product was washed with water, washed with ethyl acetate Extraction, spin-dried under reduced pressure, column chromatography with ethyl acetate:petroleum ether=1:90 as the eluent by volume ratio, concentrated and dried under reduced pressure, the white solid product compound a-2 was obtained;

[0049] (2) 80mmol compound a-2 is mixed with 200mmol p-methylphenylethynyl bromide, and in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(PPh 3 ) 2 Cl 2 :CuI=3:1; Pd(PPh 3 ) 2 Cl 2 , CuI are 2.56m...

Embodiment 3

[0056] A multi-substituted phenanthrene derivative, the structural formula of the multi-substituted phenanthrene derivative is:

[0057]

[0058] The preparation method of described multi-substituted phenanthrene derivatives is:

[0059] (1) With 830mmol of sodium hydride as a catalyst, 200mmol of diethyl malonate and 440mmol of propargyl bromide were added to 210mL of anhydrous acetonitrile, stirred and reacted in an ice-water bath for 8.5 hours, the product was washed with water, and extracted with ethyl acetate , spin-dried under reduced pressure, and carried out column chromatography with the volume ratio of ethyl acetate:petroleum ether=1:90 as the eluent, concentrated and dried under reduced pressure, and obtained a white solid product compound a-3;

[0060] (2) 80mmol compound a-3 is mixed with 200mmol p-ethylphenylethynyl bromide, and in Pd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, the molar ratio Pd(PPh 3 ) 2 Cl 2 :CuI=3:1; Pd(PPh 3 ) ...

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 multi-substituted phenanthrene derivative and a preparation method thereof. The multi-substituted phenanthrene derivative is constructed through a series reaction with different substituted phenylacetylene substrates. This reaction overcomes the long route, substrate and reaction conditions in previous reactions. Due to the disadvantages of harsh requirements and limited expansion of substituted functional groups, this reaction not only has simple synthesis of substrates and relatively cheap reagents, but also has high atom economy and environmental protection to obtain target molecules, providing a new method for industrial production of multi-substituted phenanthrene derivatives. Very valuable way.

Description

technical field [0001] The invention belongs to the technical field of organic compound synthesis, and specifically relates to a multi-substituted phenanthrene derivative and a preparation method thereof. Background technique [0002] Phenanthrene can be used in synthetic resins, plant growth hormones, vat dyes, tanning materials, etc. The hydrogenated phenanthrene can be used to produce fuel for jet aircraft. The solution has blue fluorescence. Used in the manufacture of dyes and pesticides, etc., and used as a stabilizer for smokeless gunpowder. Phenanthrene quinone is oxidized to produce phenanthrene quinone, and the biphenyl acid obtained by oxidation can be used to make polyester resin and alkyd resin; In medicine, Phenanthrene can synthesize alkaloids; in the dye industry, Phenanthrene can produce 2-aminophenanthrene quinone, benzoantrone, sulfur vat dyes (blue BO, black BB and brown), etc.; Phenanthrene can be hydrogenated under high temperature and high pressure H...

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 Patents(China)
IPC IPC(8): C07C67/347C07C69/757
CPCC07C67/347C07C2603/40C07C69/757
Inventor 刘葆华胡益民
Owner ANHUI NORMAL 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