A kind of multi-substituted fused aromatic hydrocarbon derivative and its preparation method

Abstract

The invention provides a poly-substituted condensed aromatic derivative and a preparation method thereof. Compared with the prior art, in the preparation method, the poly-substituted condensed aromatic derivative is simply, conveniently and efficiently synthesized under the catalyst-free condition by utilizing transfer of witting reagent related electrons and other reaction processes from a new perspective, the reaction time is short, and the efficiency is high. In addition, a series of novel poly-substituted condensed aromatic derivatives are provided. Compared with common poly-substituted condensed aromatic derivatives, the poly-substituted condensed aromatic derivative is complicate and diversified in structure and also has wide application prospect in chemical production and clinic medicine.

Description

technical field

[0001] The invention belongs to the field of organic compounds, and in particular relates to a multi-substituted condensed aromatic hydrocarbon derivative and a preparation method thereof. Background technique

[0002] Aromatics refer to a class of substances with aromatic odors obtained from plant gums, but most of the currently known aromatic compounds have no fragrance. Their molecules all have closed ring conjugated systems; Π electrons satisfy 4n+2, and are highly delocalized; bond lengths are averaged. Therefore, although this type of compound is highly unsaturated, its properties are relatively stable, such as easy substitution, but difficult addition and oxidation.

[0003] Aromatics are important basic raw materials of organic chemical industry, among which single-ring aromatics are more prominent. Benzene and xylene are raw materials for the manufacture of various synthetic resins, synthetic rubber, and synthetic fibers. Toluene can be converted ...

Examples

Embodiment 1

[0033] A multi-substituted fused aromatic hydrocarbon derivative, its structural formula is:

[0034]

[0035] A method for preparing polysubstituted fused aromatic hydrocarbon derivatives, comprising the following steps:

[0036] (1) With 830mmol sodium hydride as a catalyst, 200mmol dimethyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry to obtain a brownish-yellow solid product, i.e. compound 1

[0037] (2) Mix 80mmol compound 1 with 200mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI(2.56mmol / 0.85mmol) anhydrous and oxygen-free catalytic system, the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150mL anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the product was washed with water, extracted with ethyl aceta...

technical field

[0001] The invention belongs to the field of organic compounds, and in particular relates to a multi-substituted condensed aromatic hydrocarbon derivative and a preparation method thereof. Background technique

[0002] Aromatics refer to a class of substances with aromatic odors obtained from plant gums, but most of the currently known aromatic compounds have no fragrance. Their molecules all have closed ring conjugated systems; Π electrons satisfy 4n+2, and are highly delocalized; bond lengths are averaged. Therefore, although this type of compound is highly unsaturated, its properties are relatively stable, such as easy substitution, but difficult addition and oxidation.

[0003] Aromatics are important basic raw materials of organic chemical industry, among which single-ring aromatics are more prominent. Benzene and xylene are raw materials for the manufacture of various synthetic resins, synthetic rubber, and synthetic fibers. Toluene can be converted ...

Examples

Embodiment 1

[0033] A multi-substituted fused aromatic hydrocarbon derivative, its structural formula is:

[0034]

[0035] A method for preparing polysubstituted fused aromatic hydrocarbon derivatives, comprising the following steps:

[0036] (1) With 830mmol sodium hydride as a catalyst, 200mmol dimethyl malonate and 440mmol propargyl bromide were added to 210mL anhydrous acetonitrile in an ice-water bath, stirred and reacted for 8 hours, the product was washed with water, extracted with ethyl acetate, and Press and spin dry to obtain a brownish-yellow solid product, i.e. compound 1

[0037] (2) Mix 80mmol compound 1 with 200mmol phenylethynyl bromide in Pd(PPh 3 ) 2 Cl 2 / CuI(2.56mmol / 0.85mmol) anhydrous and oxygen-free catalytic system, the molar ratio of Pd(PPh 3 ) 2 Cl 2 : CuI=3:1, with 336mmol triethylamine as base, 150mL anhydrous acetonitrile as solvent, stirring and reacting at room temperature for 12 hours, the product was washed with water, extracted with ethyl aceta...

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