Method for synthesizing selenium-containing compound through decarboxylation coupled reaction one-pot method

A decarboxylation coupling and compound technology is applied in the field of synthesizing selenium compounds, which can solve the problems of limited sources of organic selenium and the like

Inactive Publication Date: 2017-03-15
GUANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the source of organic selenium is limited, so it is an important research topic to develop more new methods to synthesize organic selenium compounds

Method used

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  • Method for synthesizing selenium-containing compound through decarboxylation coupled reaction one-pot method
  • Method for synthesizing selenium-containing compound through decarboxylation coupled reaction one-pot method
  • Method for synthesizing selenium-containing compound through decarboxylation coupled reaction one-pot method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Synthesis of (2-phenylethylene-1,1,2-triyl) tris(phenyl selenide), its chemical reaction formula is:

[0018]

[0019] The synthesis method is as follows: add 0.5 mmol of phenylpropylic acid, 1.5 equivalents of diphenyl diselenide, 5% copper acetate, 1.2 equivalents of sodium carbonate and 10 mL of N-methyl pyrrolidone, at 90 o The reaction was carried out at C for 6 h, followed by TLC;

[0020] After the reaction is complete, cool to room temperature, pour the reactant into 15 mL of water, and extract 3 times with 20-30 mL of ethyl acetate, then wash once with saturated brine, and finally wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent under reduced pressure, and purify by flash silica gel column chromatography, using petroleum ether as the eluent, and evaporate the eluent to dryness to obtain a yellow oily liquid 1a with a yield of 81%.

[0021] 1 H NMR (400 MHz, CDCl 3 ) δ 7.78 (dd, J = 7.3, 1.8 Hz, 1H), 7.64 – 7.58(m, 2H), 7.44 (dd, J = 6.6...

Embodiment 2

[0023] Synthesis of (2-(p-tolyl)ethylene-1,1,2-triyl)tri(phenylselenide), the chemical reaction formula is:

[0024]

[0025] The synthesis method is as follows: in a 25 mL round bottom flask, add 0.5 mmol p-tolylpropiolic acid, 1.5 equivalents of diphenyl diselenide, 5% copper chloride, 1.2 equivalents of sodium bicarbonate and 10 mL N-Methylpyrrolidone, at 90 o The reaction was carried out at C for 6 h, followed by TLC;

[0026] After the reaction is complete, cool to room temperature, pour the reactant into 15 mL of water, and extract 3 times with 20-30 mL of ethyl acetate, then wash once with saturated brine, and finally wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent under reduced pressure, and purify by flash silica gel column chromatography, using petroleum ether as the eluent, and evaporate the eluent to dryness to obtain yellow oily liquid 2a with a yield of 83%.

[0027] 1 H NMR (400 MHz, CDCl 3 ) δ 7.40 (dd, J = 7.3, 2.0 Hz, 2H), 7.28 – 7.21(...

Embodiment 3

[0029] Synthesis of (2-(m-tolyl)ethylene-1,1,2-triyl)tri(phenylselenide), the chemical reaction formula is:

[0030]

[0031] The synthesis method is as follows: in a 25 mL round bottom flask, add 0.5 mmol m-tolylpropylic acid, 1.5 equivalents of diphenyl diselenide, 5% cuprous chloride, 1.2 equivalents of potassium carbonate and 10 mL N-Methylpyrrolidone, at 90 o The reaction was carried out at C for 6 h, followed by TLC;

[0032] After the reaction is complete, cool to room temperature, pour the reactant into 15 mL of water, and extract 3 times with 20-30 mL of ethyl acetate, then wash once with saturated brine, and finally wash with anhydrous Na 2 SO 4 Dry, filter, remove the solvent under reduced pressure, purify by flash silica gel column chromatography, use petroleum ether as the eluent, and evaporate the eluent to dryness to obtain yellow oily liquid 3a with a yield of 79%.

[0033] 1 H NMR (400 MHz, CDCl 3 ) δ 7.33 (s, 2H), 7.18 – 7.04 (m, 8H), 7.03 –6.95 (m, 3...

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Abstract

The invention discloses a method for synthesizing a selenium-containing compound through a decarboxylation coupled reaction one-pot method. The general synthesizing method comprises the following steps that 0.5 mmol of carboxylic acid, 1.5 equivalent amount of selenide, 5% of Cu catalyst, 1.2 equivalent amount of alkali and 10 mL of N-methyl pyrrolidone solvent are added into a 25 ml round-bottom flask, reaction is performed under 90 DEG C for 6 hours, and TLC tracking reaction is performed; after reaction is completed, cooling is performed to reach room temperature, a reactant is poured into 15 mL of water, extraction is performed by using 20-30 mL of ethyl acetate for 3 times, then washing is performed with saturated salt water for one time, finally drying is performed with anhydrous Na2SO4, filtration is performed, pressure reduction is performed to remove the solvent, quick silica gel column chromatography and purification are performed, petroleum ether is used as eluent, and the solvent is dried with the eluent through evaporation to obtain the product. The method is a novel method for synthesizing an organic selenium compound. Specifically, the organic selenium compound containing two or three carbon-selenium bonds is synthesized through the decarboxylation coupled reaction one-pot method, and the preparation method is simple in operation and wide in application prospect and includes few reaction steps, the raw materials are easy to obtain, and the yield is high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing selenium compounds through a one-pot method of decarboxylation coupling reaction. Background technique [0002] In literature reports, Guo Li et al. reported that phenylaminoethyl selenium (PAESe) has antihypertensive effects ("Chinese Journal of New Drugs", 2000, 9, 155-158). Song Xiaoyu et al. reported that the combination of selenium compounds and vincristine (VCR) can enhance the anti-tumor effect, and selenium compounds can also reduce the cytotoxicity of VCR ("Journal of China Agricultural University", 2007, 12, 14-18). Shi Changjin and others found that a new selenium-containing compound BBSKE (1,2-[bis(1,2-benzisoselazol-3(2H)-one)]ethane) can inhibit the proliferation of PC-3 prostate cancer cells in vitro And induce its apoptosis, and animal experiments have also proved its anti-tumor activity in vivo ("Chinese Medical Journal", 2003, 83, 1984...

Claims

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Application Information

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IPC IPC(8): C07C391/02
CPCC07C391/02
Inventor 潘英明苏世霞崔飞虎
Owner GUANGXI NORMAL UNIV
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