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Preparation method of terpenoid 3,7,11-trimethyl-2,4,6,10-docectetraen-1-olacetate

A technology of dodecyltetraene and terpenoids, which is applied to the terpenoid 3,7,11-trimethyl-2,4,6,10-dodecanyltetraen-1-ol acetic acid In the field of ester preparation, it can solve the problems of complex process, difficult industrialization, and high cost, and achieve the effect of simple process route, easy access to raw materials, and low cost

Inactive Publication Date: 2015-11-25
ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] This method has relatively long route, relatively complicated process, high cost and great difficulty in industrialization

Method used

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  • Preparation method of terpenoid 3,7,11-trimethyl-2,4,6,10-docectetraen-1-olacetate

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Embodiment 1

[0023] Embodiment 1: the preparation of C15 acetate (1)

[0024] In a nitrogen-protected 500ml three-necked flask, add 7.5 grams of sodium ethoxide (0.11mol) and 60 milliliters of dimethyl sulfoxide, keep warm in a cold bath, and under mechanical stirring, dropwise add 26.4 grams of 2-methyl-4-acetoxy- 2-butene-phosphonic acid diethyl ester (6) (0.10mol), kept at -30°C for about half an hour to complete the dropwise addition, and continued to keep warm and stir for about 1 hour to make the carbanion dissociation reaction fully. Then keep -30 DEG C and add 15.2 grams of citral (7) (0.10mol) dropwise, about 1 hour dropwise, continue to insulate and stir for about half an hour, gas chromatography traces the end of the reaction, add 50 milliliters of water and 100 milliliters of toluene and stir for 10 minutes , layered, the toluene layer was washed 3 times with 5% aqueous sodium chloride solution (25 milliliters each), the organic layer was dried with magnesium sulfate and filter...

Embodiment 2-7

[0030] Embodiment 2-7: the preparation of C15 acetate (1) under different conditions

[0031] In a 250ml three-necked flask protected by nitrogen, add a certain amount of alkali and 60ml of solvent (see the table below for the type of alkali and solvent), keep it warm in a cold bath, and under mechanical stirring, add dropwise a certain amount of C5 phosphonate (6) dissolved in 40ml. (see the table below for the molar weight) of the solvent (same as the above-mentioned solvent), keep a certain temperature (see the table below for temperature) and drop it in about half an hour, and continue to insulate and stir for about 1 hour to make the carbanion dissociation reaction fully.

[0032] Then keep above-mentioned temperature and add dropwise the solvent (0.10mol) that is dissolved with 15.2 grams of citral (7) (same as above-mentioned solvent), dropwise in about 1 hour, continue to insulate and stir for about half an hour, gas chromatographic tracking reaction ends, add 50 millil...

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Abstract

The invention relates to a preparation method of a terpenoid 3,7,11-trimethyl-2,4,6,10-docectetraen-1-olacetate and its application. An existing synthetic method has disadvantages of long route, complex technology, high cost and great industrialization difficulty. Under inert gas shielding, 2-methyl-4-acetoxyl-2-butylene-diethyl phosphonate is subjected to a dissociation reaction in the presence of an organic solvent and organic alkali; and after the dissociation reaction, citral is added to carry out a Wittig-Horner condensation reaction. The process route is simple, raw materials are easily available, and costs are low. The preparation method has industrial value.

Description

technical field [0001] The invention relates to a preparation method of a terpenoid compound 3,7,11-trimethyl-2,4,6,10-dodecyltetraen-1-ol acetate. Background technique [0002] 3,7,11-trimethyl-2,4,6,10-dodedecyltetraen-1-ol acetate (1) (hereinafter referred to as C15 acetate) has a special terpene structure, as Carotenoid precursors have good application prospects, and their hydrolysis can be used to prepare the important intermediate 3,7,11-trimethyl-2,4,6,10-dodecyltetraene-1- alcohol. [0003] At present, the preparation method of 3,7,11-trimethyl-2,4,6,10-dodecyltetraen-1-ol acetate (1) is mainly based on linalool (2) as raw material. React with sodium benzenesulfonate to obtain C10 sulfone (3), then react with ∏-allyl palladium complex (4) to obtain C15 sulfone (5), and finally remove the benzenesulfonyl group to obtain the target product 3,7,11- Trimethyl-2,4,6,10-dodedecyltetraen-1-ol acetate (1) (Journal of Organic Chemistry, 1978, 43(25):4769-4774). The reacti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/293C07C69/145
Inventor 宋小华叶伟东劳学军曹瑞伟虞国棋陈朝辉
Owner ZHEJIANG MEDICINE CO LTD XINCHANG PHAMACEUTICAL FACTORY