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Spiral polyphenylacetylene derivatives, preparation method thereof and coating type chiral stationary phase prepared thereby

A technology of polyphenylene vinylene and its derivatives, which is applied in the field of helical polyphenylene vinylene derivatives and their preparation and coated chiral stationary phase prepared therefrom, which can solve the problems of little research and achieve the effect of wide application value

Inactive Publication Date: 2015-01-14
DAICEL CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few related studies on the application of optically active helical polyphenylene vinylene derivatives with chiral functional side groups as chiral stationary phase materials for HPLC.

Method used

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  • Spiral polyphenylacetylene derivatives, preparation method thereof and coating type chiral stationary phase prepared thereby
  • Spiral polyphenylacetylene derivatives, preparation method thereof and coating type chiral stationary phase prepared thereby
  • Spiral polyphenylacetylene derivatives, preparation method thereof and coating type chiral stationary phase prepared thereby

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preparation example Construction

[0078] Furthermore, the present invention provides a method for preparing a chiral stationary phase from the above-mentioned helical polyphenylene vinylene derivatives with chiral amino alcohol side groups or carbamate 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 silica gel (for example, aminopropyl silica gel, aminopropyl macroporous silica gel), to prepare a coating type High performance liquid chromatography chiral stationary phase.

[0079] The coating solvent is preferably one or more selected from tetrahydrofuran, N,N-dimethylformamide and N,N-dimethylacetamide.

Embodiment 1

[0083] (1) The synthesis method of N-(4-ethynylbenzoyl)-L-phenylglycinol (PAA-Phg-OH), a novel optically active phenylacetylene derivative with active hydroxyl groups, is: room temperature, room temperature Press down, weigh 5.00g of 4-ethynylbenzoic acid, according to 4-ethynylbenzoic acid, L-phenylglycinol, 4-(4,6-dimethoxytriazine)-4-methylmorpholine salt The acid salt molar ratio is 1:1:1.1. Weigh L-phenylglycine alcohol and 4-(4,6-dimethoxytriazine)-4-methylmorpholine hydrochloride, add 4-ethynyl Benzoic acid, L-phenylglycinol and 4-(4,6-dimethoxytriazine)-4-methylmorpholine hydrochloride were dissolved in 175mL of methanol for amidation reaction, the reaction temperature was 28°C, and the reaction The time is 18h. After the reaction, the reaction liquid was filtered, rotary evaporated, and purified by column chromatography. The eluent used in column chromatography is n-hexane / acetone (5 / 4, V / V). The product is a white flaky solid named PAA-Phg-OH, with a yield of 6.93...

Embodiment 2

[0091] (1) The synthesis method of N-(4-ethynylbenzoyl)-L-phenylglycinol (PAA-Phg-OH), a novel optically active phenylacetylene derivative with active hydroxyl groups, is the same as in Example 1.

[0092] (2) A novel optically active phenylacetylene derivative with carbamate—(S)-2-(4-ethynylphenylcarbonylamino)-2-phenylethyl 3,5-dichlorophenylamino The synthesis method of formate ester (PAA-Phg-3,5DCPC) is as follows: under normal temperature, normal pressure, under the protection of inert gas, weigh 1.00g of PAA-Phg-OH, according to PAA-Phg-OH, 3,5-di The molar ratio of chlorophenyl isocyanate is 1:2.5. PAA-Phg-OH and 3,5-dichlorophenyl isocyanate are dissolved in 37mL of tetrahydrofuran for reaction. The reaction temperature is 39°C and the reaction time is 14h. After the reaction, the solvent was removed by rotary evaporation, and purified by column chromatography. The eluent used in column chromatography was n-hexane / ethyl acetate (5 / 2, V / V). The product is a white solid...

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Abstract

The invention provides phenylacetylene derivatives with chiral amino alcohol or carbamate, a chiral amino alcohol side group or carbamate side group equipped spiral polyphenylacetylene derivatives prepared therefrom, and a method for preparation of a coating type chiral stationary phase from the spiral polyphenylacetylene derivatives. According to the invention, a series of novel optically active phenylacetylene derivatives with active hydroxyl and carbamate groups are synthesized, then polymerization is realized under the action of a rhodium series catalyst to synthesize a series of spiral polyphenylacetylene derivatives with the chiral amino alcohol side group or carbamate side group and prepare the corresponding coating type high performance liquid chromatography chiral stationary phase. The spiral polyphenylacetylene derivative chiral stationary phase provided by the invention has good chiral resolution performance, and has very broad application prospects in the raceme resolution field.

Description

technical field [0001] The present invention relates to the technical field of preparation of high performance liquid chromatography (HPLC) chiral stationary phase (CSP), and mainly relates to the preparation method of optically active helical polyphenylene vinylene derivatives and the high performance liquid chromatography chiral stationary phase prepared from the derivatives , specifically relates to a preparation method of a helical polyphenylene vinylene derivative with a chiral amino alcohol side group or a carbamate side group, and a coating-type high-performance liquid chromatography chiral stationary phase prepared therefrom. Background technique [0002] Chirality is one of the ubiquitous characteristics of living systems. Polysaccharides, proteins, nucleic acids, etc. in living organisms are all chiral molecules. Many biologically and pharmacologically effective compounds, such as drugs, pesticides, food additives and fragrances are chiral, and the physiological pr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/73C07C233/69C07C231/02C07C269/02C07C271/28C08F38/00B01J20/29B01J20/32
Inventor 张春红王海伦杨涛涛冈本佳男
Owner DAICEL CHEM IND LTD
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