Art for synthesizing acetylide of coenzyme Q10 intermediate

A synthesis process and technology of acetylide, which is applied in the field of synthesis process of coenzyme Q10 intermediate acetylide, can solve problems such as high process cost, use safety problems, environmental pollution, etc., and achieve good safety, easy storage, and low process cost Effect

Inactive Publication Date: 2006-04-12
QINGHUA MEDICINAL CHEM SHANTOU CITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the U.S. patent of method 2 requires vinyl bromide with a low boiling point as a raw material, and method 3 also uses vinyl chloride with a low boiling point as a raw material. When a large number of applications are used, there are inconveniences in storage and transportation, and there are difficulties in large-scale industrial application.
Method 1 is an ideal method for introducing an isoprenyl group into solanesol, but

Method used

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  • Art for synthesizing acetylide of coenzyme Q10 intermediate
  • Art for synthesizing acetylide of coenzyme Q10 intermediate
  • Art for synthesizing acetylide of coenzyme Q10 intermediate

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Experimental program
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Effect test

Embodiment 1

[0026] Coenzyme Q 10 The synthesis process of the intermediate acetylide is a semi-synthetic method to prepare coenzyme Q 10 In the process, the synthetic technique of obtaining 3-methyl-solanylbutyn-1-alcohol-3 by introducing ethynyl through ethynylation by solanyl acetone is characterized in that: the synthetic technique is that 40 grams of hydrogen Sodium oxide, 400 milliliters of isobutanol and 530 milliliters of toluene are placed in a 2000 milliliter flask equipped with a water separator and a stirrer, heated to reflux under stirring to make it fully react, and about 18 to 20 milliliters of generated water are separated and removed, and the reaction liquid After cooling, feed acetylene gas to react with it, and absorb about 2.5-3 liters of acetylene to obtain acetylene reaction liquid. Add 100 milliliters of solution containing 40 grams of solanylacetone dropwise to the acetylene reaction liquid under stirring conditions at room temperature and react for 5 hours, then a...

Embodiment 2

[0028] Coenzyme Q 10 The synthesis process of the intermediate acetylide is a semi-synthetic method to prepare coenzyme Q 10 In the process, the synthetic technique that obtains 3-methyl-solanylbutyn-1-alcohol-3 by introducing ethynyl through ethynylation by solanyl acetone is characterized in that: the synthetic technique is that 150 grams of hydrogen Potassium oxide, 1200 milliliters of butanol and 1200 milliliters of toluene are placed in a 3000 milliliter flask equipped with a water separator and a stirrer, heated to reflux under stirring to make it fully react, and about 60-64 milliliters of generated water is separated and removed. Enter acetylene gas to react with it, absorb about 8-10 liters of acetylene to obtain acetylene reaction liquid. Add 250 milliliters of solutions containing 100 grams of solanylacetone dropwise to the acetylene reaction solution under stirring at room temperature for 5 hours, then import into a 5000 milliliter beaker filled with 1000 millilit...

Embodiment 3

[0030] Coenzyme Q 10 The synthesis process of the intermediate acetylide is a semi-synthetic method to prepare coenzyme Q 10 In the process, the synthetic technique of obtaining 3-methyl-solanylbutyn-1-alcohol-3 by introducing ethynyl through ethynylation from solanyl acetone is characterized in that: the synthetic technique is that 2.5 kilograms of hydrogen Potassium oxide, 25 liters of isobutanol and 58 liters of toluene are placed in a reaction kettle equipped with a water separator and agitator, heated to reflux to make it fully react, and about 0.85-0.9 liters of generated water are separated and removed, and the reaction liquid is cooled and passed into acetylene The gas reacts with it and absorbs about 125-150 liters of acetylene to obtain an acetylene reaction liquid. Add 5 liters of solution containing 2 kg of solanyl acetone to the acetylene reaction solution under stirring conditions at room temperature and react for 3 hours, then add 20 liters of ice water to the ...

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Abstract

A synthesis process for ethynyl compounds - an intermediate of a coenzyme Q10. This invention is for improving existing techniques problems of high cost for ethynylation, apparent safety risk and environmental pollution etc. The main points of the technique: during the preparation process of coenzyme Q10 from semi-synthesis method, the solane-acetone through ethynylation from introducing ethynyl to produce 3-methyl-solane-butynyl-1-alcohol-3 synthesis technique. The synthesis technique is characterized by fist adding appropriate sodium hydroxide or potassium hydroxide alcohol solution and toluene into a reaction vessel, heating and refluxing reactants to make the reaction completely, separating water, the reaction liquid cooled down, ethyne going through the solution to get a ethyne reaction solution, adding the solane-acetone solution into the ethyne reaction solution to make the reaction happen, after the reaction, adding appropriate water, cooling and neutralizing with acidic solution, separating water and organic layer, washing the organic layer with water, heated to remove organic solvent, 3-methyl- solane-butynyl-1-alcohol-3 is produced.

Description

technical field [0001] The invention relates to a semi-synthetic method for preparing coenzyme Q 10 Preparation method of intermediate substances in the process, especially coenzyme Q 10 Synthetic process of intermediate acetylides. Background technique [0002] coenzyme Q 10 It is a fat-soluble quinone compound widely present in living organisms, chemical name: 2,3-dimethoxy-5-methyl-6-decyl isoprenyl-1,4-benzoquinone, chemical structural formula : [0003] [0004] Studies have shown that coenzyme Q 10 It plays an important role in proton translocation and electron transfer in the human respiratory chain. It can be used as an activator of cell metabolism and cellular respiration, as well as an important antioxidant and non-specific immune enhancer. It can promote oxidative phosphorylation and protect the integrity of biofilm structure. sex. Clinically, coenzyme Q 10 It can be used as an adjuvant drug for congestive heart failure, coronary heart disease, hypertens...

Claims

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Application Information

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IPC IPC(8): C07C29/143C07C33/048
Inventor 李惠庭潘雪松郑松明
Owner QINGHUA MEDICINAL CHEM SHANTOU CITY
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