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Seleno morpholine, its derivative and their prepn. and use

A technology of selenomorpholine and its derivatives, applied in application, fertilizer mixture, organic chemistry, etc., can solve the problems of low selenium content in soil, selenium content in grain cannot meet nutritional needs, etc.

Inactive Publication Date: 2002-02-20
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] There are more than 40 countries and regions in the world that belong to the low-selenium zone, and their soil selenium content is far below the normal level, such as Norway, Sweden, Finland, Scotland, France, Switzerland, Germany, Hungary, Canada, Argentina, Australia, New Zealand, Japan , the western and northeastern United States, etc., the selenium content in food in these areas is far from meeting people's nutritional needs

Method used

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  • Seleno morpholine, its derivative and their prepn. and use
  • Seleno morpholine, its derivative and their prepn. and use
  • Seleno morpholine, its derivative and their prepn. and use

Examples

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Comparison scheme
Effect test

Embodiment 1

[0014] Example 1: In a 500ml there-necked flask, add 7.9g (0.10mol) of selenium and 6.0g (0.11mol) of potassium borohydride, add 100ml of absolute ethanol and stir and heat until it is a colorless liquid, cool to room temperature, and add 4.4g (0.11mol) sodium hydroxide, then dropwise add 200ml absolute ethanol solution containing 17.8g (0.10mol) nitrogen mustard hydrochloride, and reflux for 4hr after the dropwise addition. The reaction mixture was cooled and filtered, the solvent was distilled off, the residue was distilled under reduced pressure, and the 61-63°C / 7mmHg fraction was collected to obtain 7.5g of colorless liquid selenomorpholine, with a yield of 50.0%.

Embodiment 2

[0015] Example 2: In a 100ml three-necked flask, add 0.9g (6mmol) of selenomorpholine, 1.6g (6mmol) of 1-bromoundecanoic acid, dissolve in 30ml of dichloromethane, and add 1.25ml in batches under ice-salt bath cooling. g (6.1 mmol) of dicyclohexylcarbodiimide was added in about 10 minutes, stirred in ice bath for 30 minutes, and then stirred at room temperature for 4 hours. After the reaction, filter, wash the solid with a solvent, wash with dilute hydrochloric acid and dilute sodium hydroxide solution until neutral, dry, evaporate the solvent, and recrystallize the crude product from absolute ethanol to obtain 2.08 g of white solid 4-(1- Bromoundecanoyl) selenomorpholine, yield 87.3%. m.p.70-72°C.

Embodiment 3

[0016] Example 3: In a 100ml there-necked flask, add 0.75ml (20mol) of formic acid, 3.0g (20mmol) of selenomorpholine, dissolve in 30ml of dichloromethane, and under ice-salt bath cooling, add 4.1g (20mmol) of dicyclohexyl Carbodiimide was added to the reaction liquid in batches, and the addition was completed in about 10 minutes. After stirring in an ice bath for 30 minutes, continue stirring at room temperature for 4 hours. The resulting white solid dicyclohexyl urea was removed by filtration, washed with a small amount of dichloromethane, and the filtrate was washed with dilute hydrochloric acid and dilute sodium hydroxide solution until neutral, dried, and evaporated to remove the solvent. 3.24 g of colorless liquid 4-formylselenomorpholine was obtained with a yield of 91.0%.

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Abstract

The present invention relates to preparation of seleno morpholine and its derivative, its general formula is disclosed. The preparation process is as follows: selenium and potassium borohydride react to obtain potassium selenium hydride, then react with nitrogen mustard hydro-chloride, collect seleno morpholine from reaction mixture, the seleno morpholine reacts with halohydrocarbon to obtain alkyl seleno morpholine, selenomorpholine reacts with R'COX to obtain acyl seleno morpholine, selenomorpholine reacts with R'CHO, (RO)2POH to obtain phosphonate ester substituted alkyl morpholine. The invented product can be used as selenium enriching agent for plants, especially for garlic, it can raise selenium content in garlic to more than 10 times.

Description

technical field [0001] The present invention relates to selenomorpholine, selenomorpholine derivatives and their preparation method and application. Background technique [0002] As an essential trace element for the human body, selenium has many important physiological functions and is closely related to the health of the human body. Studies have shown that selenium has the functions of anti-cancer, anti-inflammation, maintaining cardiovascular health, improving male reproductive function, enhancing human immunity, and anti-aging. There are more than 40 known human diseases related to selenium deficiency, including cancer, cerebrovascular disease, diabetes, liver disease, and thyroid hormone imbalance. Clinical studies on selenium in the medical circles of the United States and Japan have proved that selenium has a high preventive effect on cancer, hyperlipidemia, arteriosclerosis, cataracts, rheumatism, and allergic constitution. Therefore, in order to maintain human hea...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C05G3/00C07D345/00
Inventor 徐汉生吴军胡利明刘秀芳
Owner WUHAN UNIV
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