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Synthetic method of diselenide compound

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of harsh conditions, low yield, poor functional group tolerance, etc., and achieve the effects of good tolerance, high yield and mild reaction conditions

Pending Publication Date: 2021-03-12
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, the current synthesis methods of diselenide compounds have the following disadvantages: 1. Most of the synthesis methods require metal catalysis, and the by-products are not environmentally friendly; 2. Most of the synthesis methods use Grignard reagents, which require harsh conditions and functional groups Poor tolerance; 3. Most of the synthetic methods use aryl selenol compounds, which are not environmentally friendly; 4. Most of the synthetic methods have low yields

Method used

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  • Synthetic method of diselenide compound
  • Synthetic method of diselenide compound
  • Synthetic method of diselenide compound

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specific Embodiment 1

[0030] A synthetic method of diselenide compounds, the synthetic method comprising:

[0031] Arylboronic acid derivatives, elemental selenium, trimethylnitrile silane, and an organic solvent are placed in a reaction vessel to obtain a mixed solution, and then the mixed solution is heated to 120°C, and stirred at this temperature for 24 hours to obtain a reaction solution, and then carried out After treatment, the diselenide compound is obtained,

[0032] Arylboronic acid derivatives, elemental selenium, trimethylnitrile silane = 8:9.6:1;

[0033] The consumption of organic solvent is based on the molar weight of arylboronic acid derivative, 5ml / mmol, wherein:

[0034] Arylboronic acid derivatives are shown in formula (1a):

[0035]

[0036] Diselenide compounds are phenylboronic acid derivatives shown in formula (2a):

[0037]

[0038] Wherein: in formula (1a) and formula (2a), R is F.

[0039] Further, the organic solvent is dimethylsulfoxide.

[0040] Further, the...

specific Embodiment 2

[0048] A synthetic method of diselenide compounds, the synthetic method comprising:

[0049] Arylboronic acid derivatives, elemental selenium, trimethylnitrile silane, and organic solvent are placed in a reaction vessel to obtain a mixed solution, and then the mixed solution is heated to 110°C, and stirred at this temperature for 30 hours to obtain a reaction solution, and then carried out After treatment, the diselenide compound is obtained,

[0050] Arylboronic acid derivatives, elemental selenium, trimethylnitrile silane=6:9:1;

[0051] The consumption of organic solvent is based on the molar weight of arylboronic acid or its derivatives, 4ml / mmol, wherein:

[0052] Arylboronic acid derivatives are shown in formula (1a):

[0053]

[0054] Diselenide compounds are phenylboronic acid derivatives shown in formula (2a):

[0055]

[0056] Wherein: in formula (1a) and formula (2a), R is a methyl group.

[0057] Further, the organic solvent is dimethylsulfoxide.

[0058...

specific Embodiment 3

[0065] A synthetic method of diselenide compounds, the synthetic method comprising:

[0066] Put arylboronic acid, elemental selenium, trimethylnitrile silane, and organic solvent in a reaction vessel to obtain a mixed solution, then raise the temperature of the mixed solution to 140°C, and stir the reaction at this temperature for 18 hours to obtain a reaction solution, and then perform post-treatment , to obtain diselenide compounds,

[0067] Arylboronic acid, elemental selenium, trimethylnitrile silane = 10:11:1;

[0068] The consumption of organic solvent is based on the molar weight of arylboronic acid, 6ml / mmol, wherein:

[0069] Arylboronic acid is naphthaleneboronic acid shown in formula (1b):

[0070]

[0071] Diselenide compounds are naphthalene boronic acid shown in formula (2b):

[0072]

[0073] Further, the organic solvent is dimethylsulfoxide.

[0074] Further, the post-processing includes the following steps:

[0075] (1) water is added in the reaction...

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Abstract

The invention relates to a synthetic method of a diselenide compound, which comprises the following steps: putting arylboronic acid or derivatives thereof, elemental selenium, trimethylsilyl cyanide and an organic solvent into a reaction container to obtain a mixed solution, heating the mixed solution to 110-140 DEG C, stirring and reacting at the temperature for 18-30 hours to obtain a reaction solution, and carrying out aftertreatment to obtain a diselenide compound, wherein the ratio of the arylboronic acid or the derivative of the arylboronic acid to the elemental selenium to the trimethylsilyl cyanide is (6-10): (9-11): 1, wherein the dosage of the organic solvent is 4-6ml / mmol based on the molar weight of the arylboronic acid or the derivative thereof. The method has the following beneficial effects: 1, elemental selenium is adopted to replace a metal catalyst, metal is not needed for catalytic reaction, and the product is relatively environment-friendly; 2, the reaction conditions are mild, and the functional group tolerance is good; 3, a non-aryl phenol compound is used, so that the method is relatively environment-friendly; and 4, the yield is high.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing diselenide compounds. Background technique [0002] Organic diselenide compounds have great application value. These compounds can be used as a class of very useful intermediates in synthesis, and can be used to synthesize a series of products with very application value such as monoselenides. It is widely used in the synthesis of biomolecules, the preparation of new materials, and the synthesis of drug molecules. Especially in animal model systems, this type of compound acts as a chemical protective agent as a whole to fight against various chemical carcinogens. thing. [0003] However, the current synthesis methods of diselenide compounds have the following disadvantages: 1. Most of the synthesis methods require metal catalysis, and the by-products are not environmentally friendly; 2. Most of the synthesis methods use Grignard reagents, wh...

Claims

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Application Information

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IPC IPC(8): C07C391/02C07D317/62C07C391/00
CPCC07C391/02C07D317/62C07C391/00
Inventor 吴华悦李金承夏文欣周云兵刘妙昌
Owner WENZHOU UNIVERSITY