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Diaryl diselenide compound synthesis method

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of side reaction functional group compatibility, deterioration, and high reaction temperature

Active Publication Date: 2014-04-23
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] As mentioned above, although a variety of methods for preparing diaryldiselenides have been disclosed in the prior art, there are certain defects in these methods, such as the use of extremely active Grignard reagents, high reaction temperature, and the need for nano-form catalysts etc., these are likely to cause problems such as side reactions and poor compatibility of functional groups

Method used

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  • Diaryl diselenide compound synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: the synthesis of diphenyl diselenide

[0049]

[0050] In a dry and clean reactor, add 50ml of solvent THF, then add 10mmol of compound (II), 10mmol of elemental selenium, 5mmol of N-bromosuccinimide and 15mmol of pyridine in sequence. The reaction was stirred for 16 hours.

[0051] After the reaction was finished, the reaction system was cooled to room temperature, and then the solvent was removed by rotary evaporation with a rotary evaporator to remove the solvent from the mixture obtained after the reaction, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product. The yield was It is 98.7%, and the purity is 99.8% (HPLC).

[0052] NMR: 1 H NMR (CDCl 3 ,500MHz):δ7.64-7.62(m,4H),7.26-7.29(m,6H);

[0053] 13 C NMR (CDCl 3 ,125MHz): δ131.5(2C), 130.9(4C), 129.2(4C), 127.7(2C).

Embodiment 2

[0054] Embodiment 2: the synthesis of two (p-methylphenyl) diselenides

[0055]

[0056] In a dry and clean reactor, add 50ml solvent 1,2-dichloroethane, then add 10mmol (II) compound, 12.5mmol elemental selenium, 10mmol N-bromosuccinimide and 20mmol pyridine successively, and react The system was stirred and reacted at 50° C. for 14 hours under an air atmosphere.

[0057] After the reaction was finished, the reaction system was cooled to room temperature, and then the solvent was removed by rotary evaporation with a rotary evaporator to remove the solvent from the mixture obtained after the reaction, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product. The yield was It is 97.6%, and the purity is 99.2% (HPLC).

[0058] NMR: 1 H NMR (CDCl 3 ,500MHz):δ7.49-7.53(m,4H),7.08-7.11(d,4H),2.37(s,6H);

[0059] 13 C NMR (CDCl 3 ,125MHz): δ137.9(2C), 132.3(4C), 129.9(4C), 127.7(2C), 21.1(2C).

Embodiment 3

[0060] Embodiment 3: the synthesis of two (p-methoxyphenyl) diselenides

[0061]

[0062] In a dry and clean reactor, add 50ml solvent 1,4-dioxane, then add 10mmol (II) compound, 15mmol elemental selenium, 15mmol N-bromosuccinimide and 25mmol pyridine successively, and the reaction system The reaction was stirred at 60°C for 12 hours under air atmosphere.

[0063] After the reaction was finished, the reaction system was cooled to room temperature, and then the solvent was removed by rotary evaporation with a rotary evaporator to remove the solvent from the mixture obtained after the reaction, and the residue was purified by 300-400 mesh silica gel column chromatography to obtain the target product. The yield was It is 84.7%, and the purity is 98.6% (HPLC).

[0064] NMR: 1 H NMR (CDCl 3 ,500MHz):δ7.48-7.51(m,4H),6.81(m,4H),3.81(s,6H);

[0065] 13 C NMR (CDCl 3 ,125MHz): δ160.1(2C), 135.4(4C), 122.0(4C), 114.7(2C), 55.3(2C).

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Abstract

The present invention relates to a diaryl diselenide compound synthesis method, which comprises that: in the presence of an alkali and N-halosuccinimide, aryl boronic acid and elemental selenium (Se) are subjected to a reaction at a temperature of 40-80 DEG C to prepare the diaryl diselenide compound. The synthesis method has advantages of low temperature, easy process control, short reaction time, high product yield, high product purity and the like, and further has good scientific research values and good industrial prospects.

Description

technical field [0001] The invention provides a method for synthesizing selenide compounds, more specifically, a method for synthesizing diaryl diselenides, which belongs to the field of organic chemical synthesis. Background technique [0002] As a trace element, selenium is necessary for a variety of metabolic and physiological activities in organisms. It has a variety of special functions for human health, and is known as "the fire of life" and "the king of anti-cancer". [0003] A large number of scientific studies have shown that many organic selenium compounds not only have anti-virus, anti-tumor and therapeutic effects on nervous system diseases, but also have biochemical and pharmacological effects such as anti-inflammation, anti-aging, prevention and treatment of cardiovascular diseases and liver diseases. . For example, Ebselen (Ebselen) and Selenazofurin (Selenazofurin) are two representative drugs that are undergoing clinical research. In addition, organic sele...

Claims

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Application Information

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IPC IPC(8): C07C391/02
Inventor 陈久喜刘妙昌黄小波高文霞丁金昌吴华悦
Owner WENZHOU UNIVERSITY
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