Polysubstitution phenanthrene derivative and preparation method thereof

A multi-substitution, derivative 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 high atom economy.

Active Publication Date: 2019-04-19
ANHUI NORMAL UNIV
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  • 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 relat

Method used

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  • Polysubstitution phenanthrene derivative and preparation method thereof
  • Polysubstitution phenanthrene derivative and preparation method thereof
  • Polysubstitution phenanthrene derivative and preparation method thereof

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 ) ...

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Abstract

The invention discloses a polysubstitution phenanthrene derivative and a preparation method thereof. With different substitution phenylacetylene substrates, the polysubstitution phenanthrene derivative is constructed through a cascade reaction. The reaction overcomes the defects that in an existing reaction, a path is too long, the demands for substrates and reaction conditions are strict, and substitution functional groups are limited in expansion. During the reaction, substrate synthesis is simple, reagent is cheap, target molecules are obtained with high atom economy and environmental protection, and a quite valued approach is provided for industrialized production of the polysubstitution phenanthrene derivative.

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

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Application Information

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