Preparation method for disubstituted styrene derivative
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A technology of styrene derivatives and styrenes, applied in the direction of organic chemistry, etc., can solve the problems of low yield, cumbersome steps of disubstituted styrene derivatives, environmental pollution, etc., and achieves high research value, mild conditions, and methods. simple effect
Active Publication Date: 2019-10-08
HARBIN INST OF TECH
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[0004] The purpose of the present invention is to provide a method for preparing disubstituted styrene derivatives in order to solve the problems of cumbersome steps, low yield and environmental pollution in the existing method for synthesizing disubstituted styrene derivatives
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specific Embodiment approach 1
[0013] Specific embodiment one: the preparation method of a kind of disubstituted styrene derivatives in this embodiment comprises the following steps:
[0014] At room temperature, under a nitrogen or oxygen atmosphere, dissolve styrene derivatives, aniline compounds, diphenyldiselenide compounds and photocatalysts in organic solvents, mix well, and place them under blue LEDs for reaction. After the end, spin the solvent, and then separate and purify through silica gel column chromatography to obtain disubstituted styrene derivatives; wherein the molar ratio of styrene compounds, aniline compounds, diphenyldiselenide compounds and photocatalysts is 1:1.5:0.6:0.1; wherein the chemical structural formula of styrene derivatives is:
[0015] The chemical structural formula of aniline compounds is:
[0016] The chemical structural formula of diphenyl diselenide compound is:
[0017] Among them, R 1 , R 2 and R 3 is halogen, alkoxy or alkyl.
[0018] The structural form...
specific Embodiment approach 2
[0024] Specific embodiment two: the difference between this embodiment and specific embodiment one is: styrene derivatives are styrene, 4-methoxystyrene, 4-bromostyrene, 2-chlorostyrene or 2-methylbenzene vinyl. Others are the same as the first embodiment.
specific Embodiment approach 3
[0025] Specific embodiment three: the difference between this embodiment and specific embodiment one or two is that the aniline compound is 3-methylaniline, 2-tert-butylaniline, 3-nitroaniline, N-methylaniline or Benzotriazole. Others are the same as those in Embodiment 1 or 2.
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Abstract
The invention relates to a preparation method for a disubstituted styrene derivative. The objective of the invention is to solve the problems of complicated steps, low yield and pollution to the environment for a conventional method for synthesizing the disubstituted styrene derivative. The preparation method provided by the invention comprises the following steps: dissolving a styrene derivative,an aniline compound, a diphenyl diselenide compound and a photocatalyst into an organic solvent at room temperature under a nitrogen or oxygen atmosphere, carrying out uniform mixing, placing an obtained mixture under blue LEDs lamps for a reaction, after the reaction is completed, carrying out rotary evaporation to remove a solvent, and carrying out separation and purification so as to obtain the disubstituted styrene derivative. The invention provides a simple one-step synthetic method. The method provided by the invention solves the problems of the need of heating for conventional synthesis, low yield caused by a transition metal catalyst system and poor environmental friendliness of a method, and seeks a synthetic route with greenness, high efficiency, mild conditions, simple method and convenient operation. The preparation method provided by the invention is applied to the field of organic synthesis.
Description
technical field [0001] The invention relates to a preparation method of double-substituted styrene derivatives. Background technique [0002] As an important basic organic chemical raw material, olefins participate in reactions that play an extremely important role in the development of organic synthesis. Olefin compounds are cheap and easy to obtain, and can carry out the functional group transformation of many compounds, so the development of olefin functionalization as a new transformation route is of great significance. For the selenium (Se) atom introduced by difunctionalization of olefins in this research project, and its wide application in medicine, introducing it into drug molecules has become a research hotspot in recent years. Moreover, as an indispensable element for the human body, selenium has a variety of biological and medical properties, and can be used for anti-cancer, anti-bacterial and anti-oxidation. Organoselenium drugs are a new class of compounds, w...
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