Method for synthesizing deca-isoprene alcohol

A technology of decyl isoprenol and synthesis method, which is applied in chemical instruments and methods, preparation of hydroxyl compounds, preparation of organic compounds, etc., can solve problems such as inability to realize industrialized production, limitation of large-scale application, active chemical properties, etc. To achieve the effect of reducing difficulty and workload, stable nature and easy storage

Inactive Publication Date: 2005-11-09
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the difficulty in the synthesis of the key intermediate 4-bromo-3-methyl-2-buten-1-ol acetate, industrial production cannot be realized yet, and its source is limited; and its chemical properties are lively and difficult to preserve. This limits the large-scale application of this method

Method used

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  • Method for synthesizing deca-isoprene alcohol
  • Method for synthesizing deca-isoprene alcohol
  • Method for synthesizing deca-isoprene alcohol

Examples

Experimental program
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Embodiment 1

[0033] Synthesis of 5-Sulfonyl Decaprenol Acetate

[0034]

[0035] Dissolve 0.75g of solanyl sulfone in 10ml of tetrahydrofuran and 2ml of dimethylformamide in a mixed solution, cool in an ice-salt bath to -15°C, add 0.56g of potassium tert-butoxide under vigorous stirring, stir for 10-15 minutes, add 4- 0.20 g of chloro-3-methyl-2-buten-1-ol acetate and 0.20 g of sodium iodide were stirred for 15 hours, during which the temperature of the system rose from -15°C to 10°C. Stop the reaction, add 50ml of ether, wash with 5% phosphoric acid, wash with water, wash with saturated brine, and remove the solvent to obtain 0.74g of light yellow oil, with a yield of 85%. 1 H-NMR analysis confirmed that it was 5-sulfonyl deprenol acetate.

Embodiment 2

[0045] Synthesis of Decaprenol

[0046]

[0047] 0.88g of 5-sulfonyldecaprenol acetate was dissolved in anhydrous ether and added to a 100ml three-neck flask. The system was cooled to -65°C, and 25ml of liquid methylamine was added. 0.14g of lithium ribbon was cut and put into the reaction system, and stirred vigorously for a period of time. The reaction was quenched by adding isoprene, methanol and ammonium chloride. After rising to room temperature, the reaction solution was poured into ice water containing diethyl ether, separated, the aqueous phase was extracted with diethyl ether, and the organic phases were combined. After treatment, 0.60 g of a light yellow oily product was obtained, with a yield of 86%. product by 1 H-NMR confirms that it is deprenol.

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Abstract

The invention provides a process for synthesizing deca-isoprene alcohol comprises, in the mixed solvent of tetrahydrofuran and dimethyl formamide, using tert-butanol potassium as alkaline reagent, and using sodium iodide or sodium bromide as halogen exchanger, condensing nicotine based sulfone with 4-chlorin-3-methyl-2-butylene-1-alcohol acetic acid ester, thus obtaining 5-sulfuryl deca-isoprene alcohol acetic acid ester, removing sulfuryl in methylamine by using lithium, thus preparing destination product deca-isoprene alcohol.

Description

technical field [0001] The invention relates to a method for synthesizing decaprenyl alcohol. Background technique [0002] Decaprenol (all-trans-decaprenol, (2E, 6E, 10E, 14E, 18E, 22E, 26E, 30E, 34E)-3, 7, 11, 15, 19, 23, 27, 31, 35 , 39-decamethyl-2, 6, 10, 14, 18, 22, 26, 30, 34, 38-tetracontadecaen-1-ol) is a straight-chain diterpenoid, and its molecular structure is: [0003] [0004] Decaprenol is a synthetic coenzyme Q 10 important intermediates. [0005] coenzyme Q 10 Existing in the mitochondria of human cells, as a cofactor of several enzyme systems related to energy conversion, it is an essential substance for the human body to maintain life. It is a drug with high application value and can effectively prevent heart failure, arrhythmia, stroke, Diseases such as high blood pressure, heart attack, arteriosclerosis, muscle atrophy, receding gums, and AIDS have the following molecular formula: [0006] [0007] Decaprenol can be ex...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C29/00C07C29/32C07C33/02
Inventor 唐飞宇陈志荣黄栋
Owner ZHEJIANG UNIV
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