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Method for catalytic synthesis of R-2-bromo-1-aryl alcohol using carrot root whole cells

A technology of R-2-, aryl ethanol is applied in the field of preparing optically active alcohol by biocatalysis method, and the effect of high application value is achieved

Inactive Publication Date: 2012-06-27
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of whole plant cells as biocatalysts in the synthesis of optically active α-bromoaromatic alcohols has not been reported

Method used

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  • Method for catalytic synthesis of R-2-bromo-1-aryl alcohol using carrot root whole cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Embodiment 1: add 0.1mol / L, the phosphate buffer saline solution 50mL of pH=7.0 and the chopped carrot root cell of 10g in an Erlenmeyer flask, vibrate (120r / min ) for 20 min to activate carrot root cells, then add 0.02 g (0.4 g / L) α-bromoacetophenone, and shake and react at the same temperature for 24 h. After the reaction, 40mL of ethyl acetate was added to the reaction solution, centrifuged after shaking and extraction, and the extract was separated. After the extract was concentrated, it was detected by a high-performance liquid chromatograph equipped with a Chiralcel OD-H chiral column. The conversion of α-bromoacetophenone and the enantiomeric excess of product R-2-bromo-1-phenylethanol were 83.6% and 88.5%, respectively.

Embodiment 2

[0013] Embodiment 2: add 50mL of 0.1mol / L, the phosphate buffer saline solution of pH=6.4 and 10g chopped carrot root cells in an Erlenmeyer flask, vibrate (120r / min ) for 20 min to activate the carrot root cells, then add 0.02 g (0.4 g / L) α-bromo-p-methylacetophenone, and shake and react at the same temperature for 28 h. After the reaction, 40mL of ethyl acetate was added to the reaction solution, centrifuged after shaking and extraction, and the extract was separated. After the extract was concentrated, it was detected by a high-performance liquid chromatograph equipped with a Chiralcel OD-H chiral column. The conversion of α-bromo-p-methylacetophenone and the enantiomeric excess of the product R-2-bromo-1-p-methylphenethyl alcohol were 63.1% and 88.9%, respectively.

Embodiment 3

[0014] Example 3: Add 50 mL of 0.1 mol / L, pH=6.4 phosphate buffer solution and 15 g of carrot root cells in an Erlenmeyer flask, shake (120 r / min) in a water bath constant temperature oscillator for 20 min at 30 ° C, Activate the carrot root cells, then add 0.02g (0.4g / L) α-bromo-p-methoxyacetophenone, and shake the reaction at the same temperature for 30h. After the reaction, 40mL of ethyl acetate was added to the reaction solution, centrifuged after shaking and extraction, and the extract was separated. After the extract was concentrated, it was detected by a high-performance liquid chromatograph equipped with a Chiralcel OD-H chiral column. The conversion of α-bromo-p-methoxyacetophenone and the enantiomeric excess of product R-2-bromo-1-p-methoxyphenethyl alcohol were 61.5% and 87.7%, respectively.

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Abstract

The invention discloses a method for catalytic synthesis of R-2-bromo-1-aryl alcohol using carrot root whole cells. As shown in the formula, the method uses carrot root whole cells as a biocatalyst which catalyzes asymmetric reduction of alpha-bromo-aryl ethyl ketone under a proper condition to synthesize the corresponding R-2-bromo-1-aryl alcohol, the enantiomer excess is over 82.5%, and in the formula, R is H, p-CH3, p-OCH3, p-Cl, p-NO2, m-Cl and other different substituent groups. The chiral halogenated alcohol R-2-bromo-1-aryl alcohol synthesized using the method of the invention is an important chiral synthesis building block, and can also be transformed to chiral synthesis building block with alpha site being another group, so that R-2-bromo-1-aryl alcohol has high application value in synthesis of medicines, pesticides, additives and other chiral compounds.

Description

technical field [0001] The invention relates to the technical field of preparing optically active alcohols by a biocatalytic method, in particular to a novel preparation method of optically active R-2-bromo-1-arylethanol. Background technique [0002] In recent decades, the research on asymmetric synthesis has developed rapidly because of the great value of the synthetic products themselves in practical applications. Optically active α-bromo aromatic alcohols are an important class of chiral synthetic building blocks. After some simple chemical transformations, the synthetic building blocks of chiral aromatic alcohols with other groups at the α position can be obtained. Therefore, they are used in medicine, pesticides, It has great application value in the synthesis of chiral compounds such as additives. [0003] In addition to some physical and chemical methods, chiral compounds are obtained by asymmetric synthesis, including asymmetric chemical catalytic synthesis and asy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P7/22
Inventor 刘湘王亿杨芬杨青青
Owner JIANGNAN UNIV
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