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Synthesis method of coenzyme Q kind compound

A synthesis method and technology of amine compounds, which are applied in the field of synthesis of coenzyme Q compounds, can solve the problems of harsh reaction conditions, low yield, and difficult synthesis of coenzyme Q compounds, and achieve mild reaction conditions, high yield, excellent The effect of stereoselectivity

Inactive Publication Date: 2007-05-09
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0029] (3) In 2003, Jae-Hong Min et al. (J.Org.Chem.2003, 68, 7925-7927) used the Friedel-Crafts reaction to directly introduce a terminal functionalized isoprene unit to the protected mother ring, Short reaction routes and high yields in critical steps, but use of expensive and hazardous reagents
[0034] Where n=2m+2, in the stage of chain growth, the productive rate of each step coupling reaction ranges from 80 to 90%, slightly decreases with the growth of chain length, and has good stereoselectivity, but the reaction steps more cumbersome
[0035] The synthesis of coenzyme Q compounds is relatively difficult, and various synthetic routes have disadvantages such as numerous steps, harsh reaction conditions, low yield and poor stereoselectivity to varying degrees, and there are no mature synthetic reports in China.

Method used

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  • Synthesis method of coenzyme Q kind compound
  • Synthesis method of coenzyme Q kind compound
  • Synthesis method of coenzyme Q kind compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] 1mol 6-(3-methyl-(E)-4-sulfonyl-2-butenyl)-2,3,4,5-tetramethoxytoluene dissolved in (V:V) 1:1 THF : mixed solvent of DMF, add 1.0mol of potassium tert-butoxide, then condense with 1mol of the halide having the following general formula (wherein m=1):

[0066]

[0067] Where X is chlorine, at a low temperature of -20°C, react with a reducing agent of 2 mol lithium dissolved in 10 mol methylamine and 20 mol dimethylamine to remove sulfone, use 1.0 mol 2,4,6-tricarboxypyridine catalyst, and use cerium nitrate Ammonium (CAN) is oxidized to obtain the product coenzyme Q 2 .

Embodiment 2

[0069] 1mol 6-(3-methyl-(E)-4-sulfonyl-2-butenyl)-2,3,4,5-tetramethoxytoluene is dissolved in the reaction solvent (V:V) 10:1 THF: DMF mixed solvent, add 1.25mol potassium tert-butoxide, then condense with 1mol halide having the following general formula (wherein m=2):

[0070]

[0071] Wherein X is chlorine, at a low temperature of -70°C, react with a reducing agent that dissolves 8 mol lithium in 20 mol dimethylamine and 20 mol ethylamine to remove sulfone, use 0.75 mol 2,6-dicarboxypyridine catalyst, and use cerium ammonium nitrate ( CAN) is oxidized to obtain the product coenzyme Q 3 .

Embodiment 3

[0073] 1mol 6-(3-methyl-(E)-4-sulfonyl-2-butenyl)-2,3,4,5-tetramethoxytoluene dissolved in (V:V) 10:1 THF : mixed solvent of HMPA, add 1.5mol of potassium tert-butoxide, then condense with 1mol of the halide having the following general formula (wherein m=3):

[0074]

[0075] Wherein X is bromine, at a low temperature of -90 ° C, react with a reducing agent of 5 mol lithium dissolved in 16 mol ethylamine to remove sulfone, use 0.5 mol 2,4,6-tricarboxypyridine catalyst, and use cerium ammonium nitrate (CAN) to carry out Oxidation, the product coenzyme Q 4 .

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Abstract

An improved process for synthesizing coenzyme Qn includes dissolving 6-(3-methyl-(E)-4-sulfonyl-2-butenyl)-2,3,4,5-tetramethoxy toluent in reaction solvent, adding tert-butanol potassium, condensating on the halide, low-temp reacting on the reducer prepared by dissolving Li in amine compound for desulfonilating, and oxidizing by cerium ammonium nitrate under the action of catalyst. Its advantaegs are low cost and gentle reaction condition.

Description

technical field [0001] The invention relates to a method for synthesizing coenzyme Q compounds. Background technique [0002] coenzyme Q n (Coenzyme Q n , referred to as CoQ n ), also known as ubiquinone (Ubiquinone), has the following general formula: [0003] [0004] where n=1~10 [0005] Coenzyme Q compounds are combined with the inner membrane of mitochondria in the cells of animals, plants, microorganisms, etc., and are important hydrogen transporters in the respiratory chain. They are natural antioxidants produced by cells themselves, activators of cell metabolism, and can improve the body's immunity. force. especially coenzyme Q 10 , is a class of drugs with high application value, and has been found to be effective in preventing diseases such as heart failure, arrhythmia, stroke, high blood pressure, heart attack, arteriosclerosis, muscle atrophy, gingival recession and AIDS. [0006] Coenzyme Q compounds have broad application prospects, and their synthes...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/26C07C46/00
Inventor 唐飞宇陈志荣
Owner ZHEJIANG UNIV