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A kind of synthetic method of 1,1-diarylethene derivatives

A diarylethene and synthesis method technology, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of halogenated hydrocarbons, etc., can solve problems such as increased reaction cost, many by-products, harsh reaction conditions, etc., and achieve production cost Low impact on the environment, easy preparation

Active Publication Date: 2021-03-19
郑州德瑞医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are two main synthesis methods, one is the reaction of phenylmagnesium bromide and 1,1-diphenylethanol, but the reaction conditions are harsh and needs to be reacted at minus 78°C; the other is the reaction of bromobenzene and phenylethyl alcohol. Ketone reaction, the disadvantage is that there are more by-products of the reaction
The recently reported synthetic method reacts iodobenzene and N-toluenesulfonylhydrazone, which uses expensive tamoxifen, which increases the cost of the reaction

Method used

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  • A kind of synthetic method of 1,1-diarylethene derivatives
  • A kind of synthetic method of 1,1-diarylethene derivatives
  • A kind of synthetic method of 1,1-diarylethene derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1-4

[0038] The structural formula of the target compound is:

[0039]

[0040] The reaction equation is:

[0041]

[0042] Synthesized by:

[0043] In the 5mL reactor, first replace it with argon three times, then add 1mm magneton, p-methoxycinnamic acid (0.4mmol), palladium catalyst (0.08mmol), 2 times the equivalent of cuprous oxide (0.8mmol), (0.08mmol), 2 times the equivalent of cesium fluoride (0.8mmol), 2 times the equivalent of p-benzoquinone (BQ, 0.8mmol), 75mg molecular sieves (water removal), the reactor is evacuated, replaced three times with argon, and then Phenyltriethoxysilane (0.8mmol) and dimethylsulfoxide (DMSO, 2mL) were mixed and added to the reactor, then an argon balloon was inserted, and then the reactor was placed in an oil bath preheated to 120°C , reacted for 24 hours. After the reaction, the reaction solution was filtered with diatomaceous earth, the filtrate was extracted three times with ethyl acetate or dichloromethane, the aqueous phase was ...

Embodiment 5-7

[0051] The structural formula of the target compound is:

[0052] The reaction equation is:

[0053]

[0054]

[0055] Synthesized by:

[0056] In the 5mL reactor, it was replaced with argon three times, and then 1mm magneton, p-methoxycinnamic acid (0.4mmol), and different amounts of Pd(OAc) were added in sequence. 2 Catalyst, 2 times equivalent cuprous oxide (0.8mmol), (0.08mmol), 2 times the equivalent of cesium fluoride (0.8mmol), 2 times the equivalent of p-benzoquinone (BQ, 0.8mmol), 75mg molecular sieves (water removal), the reactor is evacuated, replaced three times with argon, and then Phenyltriethoxysilane (0.8mmol) and dimethylsulfoxide (DMSO, 2mL) were mixed and added to the reactor, then an argon balloon was inserted, and then the reactor was placed in an oil bath preheated to 120°C , reacted for 24 hours. After the reaction, the reaction solution was filtered with diatomaceous earth, the filtrate was extracted three times with ethyl acetate or dichlorome...

Embodiment 8-16

[0063] The structural formula of the target compound is:

[0064]

[0065] The reaction equation is:

[0066]

[0067] Synthesized by:

[0068] In the 5mL reactor, replace with argon three times first, then add 1mm magneton, p-methoxycinnamic acid (0.4mmol), catalyst Pd(OAc) 2 (0.04mmol), 2 times equivalent oxidant (0.8mmol), (0.08mmol), 2 times the equivalent of cesium fluoride (0.8mmol), 2 times the equivalent of p-benzoquinone (BQ, 0.8mmol), 75mg molecular sieves (water removal), the reactor is evacuated, replaced three times with argon, and then Phenyltriethoxysilane (0.8mmol) and dimethylsulfoxide (DMSO, 2mL) were mixed and added to the reactor, then an argon balloon was inserted, and then the reactor was placed in an oil bath preheated to 120°C , reacted for 24 hours. After the reaction, the reaction solution was filtered with diatomaceous earth, the filtrate was extracted three times with ethyl acetate or dichloromethane, the aqueous phase was back-extracted ...

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PUM

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Abstract

The invention discloses a synthetic method of a 1,1-diarylethenes derivative. The synthetic method comprises the following steps: with cinnamic acid derivatives and aryltriethoxysilane as raw materials, mixing the raw materials with a catalyst, an oxidizing agent, a ligand, an additive and alkali; carrying out reaction for 2 to 24 hours at 100 to 160 DEG C under argon protection in a reaction solvent so as to prepare a target compound. Because cinnamic acid is common unsaturated carboxylic acid, the preparation is convenient, cinnamic acid is cheap and easy to obtain; because aryltriethoxysilane is common organosilane in organic chemistry, aryltriethoxysilane is cheap and easy to obtain, is higher in stability and has little impact on an environment; therefore, the 1,1-diarylethenes derivative is synthesized by carrying out coupled reaction between the selected aryltriethoxysilane and the cinnamic acid derivatives. The synthetic method has the advantages of cheap and easy availabilityof the raw materials and low production cost; meanwhile, an experiment is easy to operate, and the synthetic method can be developed as an industrialized production method. According to the syntheticmethod disclosed by the invention, synthetic conditions are also screened and optimized, so that the reaction yield is further improved.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing 1,1-diarylethene derivatives. Background technique [0002] Stilbene derivatives are common and important intermediates in organic synthesis, which have important application value in pesticides, medicines and materials. In medicine, 1,1-stilbene derivatives have anti-estrogen activity, so 1,1-stilbene derivatives have the potential to be developed into anti-estrogen drugs, and anti-estrogen drugs are Drugs commonly used to treat breast cancer. In terms of pesticides, 1,1-stilbene derivatives are important intermediates for the synthesis of isoxadifen, which is a widely used antidote in pesticides. In terms of materials, 1,1-stilbene derivatives have important applications in hole injection, hole transport and other materials. [0003] Since the application of stilbene compounds is becoming more and more extensive, the synthesis and applicat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/215C07C41/30C07C25/24C07C22/08C07C17/26C07C255/50C07C253/30C07D333/08
CPCC07C17/26C07C41/30C07C253/30C07D333/08C07C43/215C07C25/24C07C255/50C07C22/08
Inventor 吴豫生
Owner 郑州德瑞医药科技有限公司