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Phenylacetylene derivatives with ester groups in side groups and preparation, polymerization and application methods

A technology of derivatives and phenylacetylene, which is applied in the field of liquid chromatography chiral stationary phase compounds, can solve problems such as potential safety hazards, and achieve the effects of low cost, good chiral resolution ability, high product purity and yield

Active Publication Date: 2017-10-03
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The use of racemic drugs and pesticides has great safety hazards, so the preparation of enantiomers with high enantiomeric excess values ​​(ee) has received more and more attention

Method used

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  • Phenylacetylene derivatives with ester groups in side groups and preparation, polymerization and application methods
  • Phenylacetylene derivatives with ester groups in side groups and preparation, polymerization and application methods
  • Phenylacetylene derivatives with ester groups in side groups and preparation, polymerization and application methods

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preparation example Construction

[0063] Furthermore, the present invention provides a method for preparing a chiral stationary phase from the above-mentioned helical polyphenylene vinylene derivatives with ester groups in side groups, and the chiral stationary phase prepared therefrom. The preparation method includes: using an organic solvent as a coating solvent, coating the helical polyphenylene vinylene derivative synthesized above on aminopropyl silica gel to prepare a coating-type high performance liquid chromatography chiral stationary phase.

[0064] The coating solvent is one of chloroform, dichloromethane, methanol, acetone, tetrahydrofuran, N,N-dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, or Various.

Embodiment 1

[0067] (1) A novel optically active phenylacetylene derivative with a butyl benzoate group—(S)-2-(4-ethynylphenylcarbonylamino)-3-methylbenzoic acid butyl (PA-A- The synthetic method of Val-Ben) is: under normal temperature and normal pressure, take by weighing 1.0345gN-(4-ethynylbenzoyl)-L-valinol, according to N-(4-ethynylbenzoyl)-L -Valinol, benzoyl chloride, and triethylamine have a molar ratio of 1:1:1 and dissolve benzoyl chloride and triethylamine in 45 mL of tetrahydrofuran for reaction. The reaction is carried out under nitrogen protection, and the reaction temperature is 25°C. The reaction time is 12h. After the reaction, the reaction solution was extracted by rotary evaporation to remove the solvent. The solvent used in the extraction method is dichloromethane / water. It is then purified by column chromatography. The eluent used in column chromatography was chloroform / ethyl acetate (20 / 1, V / V). The product yield was 1.3728 g, and the yield was 91.52%. Molecular ...

Embodiment 2

[0075] (1) A novel optically active phenylacetylene derivative with a butyl propionate group—(S)-2-(4-ethynylphenylcarbonylamino)-3-methylpropionate butyl (PA-A- The synthetic method of Val-Pro) is: under normal temperature and normal pressure, take by weighing 0.80g N-(4-ethynylbenzoyl)-L-valinol, according to N-(4-ethynylbenzoyl)- The molar ratio of L-valinol, L-propionyl chloride, and triethylamine is 1:2:5, and benzoyl chloride and triethylamine are dissolved in 40 mL of tetrahydrofuran for reaction. The reaction is carried out under nitrogen protection, and the reaction temperature is 35 °C, the reaction time is 24h. After the reaction, the reaction solution was extracted by rotary evaporation to remove the solvent. The solvent used in the extraction method is dichloromethane / water. It is then purified by column chromatography. The eluent used in column chromatography was chloroform / ethyl acetate (15 / 1, V / V). The product yield was 0.8187 g, and the yield was 82.36%. ...

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Abstract

The invention provides a phenylacetylene derivative with an ester group on a lateral base band and preparation, polymerization and application methods. The invention provides a phenylacetylene derivative with an ester group, a spiral phenylacetylene derivative with an ester group on a lateral base band prepared from the phenylacetylene derivative, and a method for preparing a coating chiral stationary phase from the spiral phenylacetylene derivative. According to the methods, a series of novel optical activity phenylacetylene derivatives with ester groups are synthesized; homopolymerization is realized by virtue of a rhodium-based catalyst; a series of optical-activity spiral phenylacetylene derivatives with the ester groups on the lateral base bands are synthesized; and corresponding coating high-performance liquid chromatography chiral stationary phases are prepared. The high-performance liquid chromatography chiral stationary phases of the series of polymers have relatively good chiral recognition and resolution properties; and the coating phenylacetylene high-performance liquid chromatography chiral stationary phase has the characteristics of relatively high purity and high yield, short preparation cycle, simple process, low cost, and wide application prospect in the fields of chiral recognition resolution.

Description

technical field [0001] The invention relates to a compound used for liquid chromatography chiral stationary phase, application and preparation method of the compound. Specifically, it is an optically active helical polyphenylene vinylene derivative, and its application method and preparation method as a coating-type high-performance liquid chromatography chiral stationary phase. Background technique [0002] A molecule that cannot be superimposed on its mirror image no matter how it is rotated like a hand is called a chiral molecule, and a chiral molecule and its mirror image are isomers. Chirality is one of the essential attributes of nature that human beings rely on for survival. Chirality exists in everything from planetary rotation to mineral crystals, from inanimate objects to life phenomena. Biological macromolecules such as polysaccharides, proteins, nucleic acids, etc. are chiral molecules, so many drugs, pesticides, etc. have chirality (Chen Liren, Liquid Chromatog...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/69C07C231/12C08F138/00C08F2/38C08F4/52B01J20/29B01J20/30
Inventor 张春红马睿王静莹王仲鹏董彦君伍康华刘立佳冈本佳男
Owner HARBIN ENG UNIV
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