Dibenzo selenophene derivative and preparation method thereof

A technology of dibenzoselenophene derivatives and benzoselenophene derivatives, which is applied in the field of dibenzoselenophene derivatives and its preparation, can solve the problems of small lethal dose, limitation, and high toxicity of inorganic selenium supplements. Achieve broad application prospects and complex and diverse structures

Inactive Publication Date: 2016-04-20
ANHUI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the application of inorganic selenium supplements is lim

Method used

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  • Dibenzo selenophene derivative and preparation method thereof
  • Dibenzo selenophene derivative and preparation method thereof
  • Dibenzo selenophene derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] A dibenzoselenophene derivative, the structural formula of the dibenzoselenophene derivative is:

[0045]

[0046] The preparation method of above-mentioned dibenzoselenophene derivative, comprises the following steps:

[0047] A. Using sodium hydride (820mmol, 19.7g) as a catalyst, dimethyl malonate (200mmol, 26.6g) and propargyl bromide (450mmol, 53.5g) were added to 250mL of anhydrous acetonitrile, stirred in an ice-water bath After reacting for 8 hours, the crude product was extracted with water and ethyl acetate, concentrated under reduced pressure, separated and purified by silica gel column chromatography, and the eluent was ethyl acetate:petroleum ether=1:100 to obtain a white solid product, namely compound 1;

[0048] B. Compound 1 (80mmol, 16.7g) was mixed with phenylbromoacetylene substitute (176mmol, 37.9g), and in 1.3gPd(PPh 3 ) 2 Cl2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3 ) 2 Cl 2 The molar ratio of CuI and CuI was 3:1, with trie...

Embodiment 2

[0055] A dibenzoselenophene derivative, the structural formula of the dibenzoselenophene derivative is:

[0056]

[0057] The preparation method of above-mentioned dibenzoselenophene derivative, comprises the following steps:

[0058] A. Using sodium hydride (700mmol, 16.8g) as a catalyst, dimethyl malonate (200mmol, 26.6g) and propargyl bromide (440mmol, 52.3g) were added to 330mL of anhydrous acetonitrile, stirred in an ice-water bath After reacting for 10 hours, the crude product was extracted with water and ethyl acetate, concentrated under reduced pressure, separated and purified by silica gel column chromatography, and the eluent was ethyl acetate:petroleum ether=1:60 to obtain a white solid product, namely compound 1;

[0059] B. Compound 1 (80mmol, 16.7g) was mixed with phenylbromoacetylene substitute (176mmol, 37.9g), and in 3.0gPd(PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3 ) 2 Cl 2 The molar ratio of CuI and CuI was 3:1, with tr...

Embodiment 3

[0063] A dibenzoselenophene derivative, the dibenzoselenophene derivative structural formula is:

[0064]

[0065] The preparation method of above-mentioned dibenzoselenophene derivative, comprises the following steps:

[0066] A. Using sodium hydride (810mmol, 19.4g) as a catalyst, (200mmol, 37.6g) diisopropyl malonate and propargyl bromide (500mmol, 59.5g) were added to 250ml of anhydrous acetonitrile, placed in an ice-water bath The reaction was stirred for 10 hours, the crude product was extracted with water and ethyl acetate, concentrated under reduced pressure, separated and purified by silica gel column chromatography, the eluent was ethyl acetate:petroleum ether=1:100, and a white solid product was obtained, namely compound 3 ;

[0067] B. Compound 3 (80mmol, 21.1g) and phenylbromoacetylene substitute (200mmol, 39.0g) were mixed in 2.17gPd (PPh 3 ) 2 Cl 2 / CuI anhydrous and oxygen-free catalytic system, Pd(PPh 3 ) 2 Cl 2 Pd(PPh in / CuI 3 ) 2 Cl 2 The molar...

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Abstract

The invention provides a dibenzo selenophene derivative and a preparation method thereof. The preparation method comprises the following steps that sodium hydride is used as a catalyst, malonic ester and propargyl bromide are added into an acetonitrile solvent, and a reaction is performed in an ice-water bath for 8-14 h to obtain a compound a; on the oxygen-free and water-free conditions, the compound a and a substituted complex of phenyl acetylene bromide are subjected to a reaction in an acetonitrile solvent under the effect of a catalyst and alkali at the temperature of 20-30 DEG C for 8-14 h to obtain a compound b; the compound b and diphenyl diselenide are subjected to a reaction at the temperature of 95-105 DEG C, and after separation and purification, the dibenzo selenophene derivative can be obtained. Compared with the prior art, the novel polysubstitution dibenzo selenophene synthesis method is provided, a series of novel selenophene derivatives are generated, multi-loops exist in the obtained dibenzo selenophene derivative compared with a common selenophene derivative, the structure is more complex and diversified, and wider application prospect is represented in chemical production and clinic medicine.

Description

technical field [0001] The invention relates to the field of organic compounds, in particular to a dibenzoselenol derivative and a preparation method thereof. Background technique [0002] In the early 19th century, when the Swedish chemist Bezreilus was studying the composition of lead chamber mud, he first isolated a new element from chalcopyrite, and named it selenium (Seslenuim) the next year. Selenium is one of the essential and beneficial trace elements in living organisms, and has many special functions for human health. A large number of studies have shown that selenium has a wide range of biological effects, especially for cancer (such as lung cancer, intestinal cancer, prostate cancer and liver cancer, etc.). Clinical trials have shown that selenium has a strong protective effect and has a good effect on more than 40 human diseases such as heart disease, senile diseases, liver and pancreas diseases, infertility, hypertension, diabetes, cataracts, Keshan disease an...

Claims

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Application Information

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IPC IPC(8): C07D345/00
CPCC07D345/00
Inventor 马杰胡益民
Owner ANHUI NORMAL UNIV
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