Process for preparing diselenide compound

A compound and diselenide technology, applied in the field of preparing diselenide compounds, can solve the problems of intense reaction of sodium borohydride, difficult to mass-produce, harsh reaction conditions, etc., and achieve easy control, suitability for large-scale industrial production, and stable reaction Effect

Active Publication Date: 2020-07-28
SHANGHAI SPARK PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The reaction of sodium borohydride is very intense, difficult to control, requires ice bath cooling, and is not easy for large-scale production
The reaction between sodium diselenide and 4-chloroquinoline also needs to be reacted under anhydrous conditions, and the reaction conditions are harsh

Method used

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  • Process for preparing diselenide compound
  • Process for preparing diselenide compound
  • Process for preparing diselenide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In the present embodiment, the dihydroflavonol compound selects dihydromyricetin, and the structural formula is as follows:

[0026]

[0027] Add 22.5g of dihydromyricetin into a four-necked flask (500mL), add 200mL of water, heat to 80°C, keep for 45 minutes, add 2.81g of sodium hydroxide, control the temperature at 80°C for 10 minutes, then add 7.80 g selenium dioxide, controlled temperature and reacted for 70 minutes at 80° C., and the reaction was completed. Then, turn off the heating, let it cool down to room temperature naturally, adjust the pH value to 3-6.5 with hydrochloric acid, extract with methanol, separate by column chromatography, and freeze-dry to obtain the dimyricetin-based diselenide product with a yield of 8.63%.

Embodiment 2

[0029] In the present embodiment, the dihydroflavonol compound selects dihydromyricetin, and the structural formula is as follows:

[0030]

[0031] Add 15g of dihydromyricetin into a four-necked flask (specification: 500mL), add 200mL of water, heat to 90°C, keep for 45 minutes, add 0.75g of sodium hydroxide, control the temperature at 90°C for 60 minutes, then add 4.16 g of selenium dioxide, controlled temperature and reacted at 90° C. for 70 minutes, and the reaction was completed. Then, the heating was turned off, and after cooling down to room temperature naturally, the pH value was adjusted to 3-6.5 with hydrochloric acid, extracted with methanol, separated by column chromatography, and freeze-dried to obtain the product of dimyricetin-based diselenide with a yield of 10.26%.

Embodiment 3

[0033] In the present embodiment, the dihydroflavonol compound selects dihydromyricetin, and the structural formula is as follows:

[0034]

[0035] Add 22.5g of dihydromyricetin into a four-necked flask (specification: 500mL), add 200mL of water, heat to 100°C, keep for 45 minutes, add 2.53g of sodium hydroxide, control the temperature at 100°C for 40 minutes, then add 9.36g of selenium dioxide was reacted at 100° C. for 30 minutes under temperature control, and the reaction was completed. Then, the heating was turned off, and after cooling down to room temperature naturally, the pH was adjusted to 3-6.5 with hydrochloric acid, extracted with methanol, separated by column chromatography, and freeze-dried to obtain the product of dimyricetin-based diselenide with a yield of 9.86%.

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Abstract

The invention provides a process for preparing a diselenide compound. The method comprises the following steps: adding a polar solvent into a flavanonol compound; heating the solution to 80 DEG C to 100 DEG C, keeping the temperature for 40-50 minutes, then adding alkali of which the amount of substance is 0.4-1.0 time of that of the flavanonol compound, and carrying out a reaction for 5-60 minutes at the temperature of 80-100 DEG C; then adding selenium dioxide of which the amount of substance is 0.6-1.2 times of that of the flavanonol compound; and carrying out a reaction for 30-150 minutesat the temperature of 80-100 DEG C to obtain the diselenide compound of the dihydroflavonol compound. The method disclosed by the invention is mild in reaction, small in pollution and suitable for large-scale industrial production, and does not need an anhydrous oxygen-free environment.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a method for preparing diselenide compounds. Background technique [0002] Selenium is an essential trace element for the human body. It has various biological activities such as anti-oxidation, anti-cancer, anti-cancer, protection of bone marrow hematopoiesis, and anti-aging. It also has detoxification effects on some heavy metal elements (such as mercury, arsenic, silver, etc.). There are two sources of selenium intake by the human body, one is inorganic selenium and the other is organic selenium. Inorganic selenium generally refers to sodium selenite and sodium selenate, including yeast selenium and malt selenium with a large amount of inorganic selenium residues. Inorganic selenium is highly toxic and not easily absorbed, so it is not suitable for human and animal use. Organic selenium includes simple selenides, diselenides and oxides of organic seleni...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32
CPCC07D311/32
Inventor 宋昆元陈伟伟
Owner SHANGHAI SPARK PHARM CO LTD
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