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Preparation method and application of terpenoid 3,7,11-trimethyl-2,4,6,10-dodecatetraene-1-alcohol acetate

A technology of dodecyltetraene and terpenoids, which is applied in the preparation of organic compounds, oxygen-containing compounds, hydroxyl compounds, etc., can solve the problems of complicated process, difficult industrialization, and high cost, and achieve simple and convenient process routes , easy to obtain raw materials and low cost

Inactive Publication Date: 2014-02-05
SHAOXING UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] This method has relatively long route, relatively complicated process, high cost and great difficulty in industrialization

Method used

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  • Preparation method and application of terpenoid 3,7,11-trimethyl-2,4,6,10-dodecatetraene-1-alcohol acetate
  • Preparation method and application of terpenoid 3,7,11-trimethyl-2,4,6,10-dodecatetraene-1-alcohol acetate
  • Preparation method and application of terpenoid 3,7,11-trimethyl-2,4,6,10-dodecatetraene-1-alcohol acetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Preparation of C10 Phosphonate (6)

[0029] In a 1000mL four-necked bottle equipped with a mechanical stirrer and a thermometer, add 250g of triethyl phosphonite, start stirring and heat to 150°C-155°C, add 172.7g of geranyl chloride and 160g of triethylphosphonite dropwise within 1 hour Ethyl mixture. The reaction was tracked by gas chromatography, and the reaction was completed in about 2 hours. After cooling down, excess triethyl phosphonite was recovered under reduced pressure, and the residue was distilled under reduced pressure to collect 272.8 g of 105-109°C / 1mmHg fraction, which was a light yellow transparent liquid with a gas phase content of 98.8% and a yield of 92.1%.

[0030] Product structure confirmation:

[0031] 1 HNMR (400MHz, CDCl 3 )δ (ppm): 1.313 (t, J=7.2Hz, 6H, 2OCH 2 CH* 3 );1.602(s,3H,CH=C(CH* 3 ) 2 );1.656(d,J=3.6Hz,3H,CH=CCH* 3 );1.678(s,3H,CH=C(CH* 3 ) 2 );2.030-2.099(m,4H,CH 2 CH 2 );2.572(dd,J=21.6Hz,7.6Hz,2H,CHCH* 2 P);4.056-4...

Embodiment 2

[0036] Preparation of C15 acetate (1)

[0037] In a nitrogen-protected 500ml three-neck flask, add 12.4 grams of potassium tert-butoxide (0.11mol) and 60 milliliters of a mixture of tetrahydrofuran and dimethyl sulfoxide of 8:1 (volume ratio), keep warm in a cold bath, and stir mechanically. Add 29.2 g of 3,7-dimethyl-2,6-octadiene-phosphonic acid diethyl ester (0.10 mol) dropwise, keep at -30°C for about half an hour to complete the dropwise addition, and continue to keep stirring for about 1 hour to make the carbanion The dissociation reaction is sufficient. Then keep -30°C and add 14.2 grams of C5 aldehyde (7) (0.10mol) dropwise, and the dropwise addition is completed in about 1 hour. Continue to keep warm and stir for about half an hour. After the reaction is completed by gas chromatography, 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 ml eac...

Embodiment 3-8

[0044] Preparation of C15 acetate (1) under different conditions

[0045] 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 types of alkali and solvent), keep warm in a cold bath, and under mechanical stirring, add dropwise 40ml of a certain amount of C10 phosphonate (6) (see the table below for the molar amount) of the solvent (same as the above solvent), keep a certain temperature (see the table below for the temperature) for about half an hour to complete the dropwise addition, and continue to keep warm and stir for about 1 hour to fully dissociate the carbanions.

[0046] Then keep the above temperature and add dropwise the solvent (0.10mol) dissolved with 14.2 grams of C5 aldehyde (7) (same as the above solvent), and the dropwise addition is completed in about 1 hour. Continue to keep warm and stir for about half an hour. After the reaction is completed by gas chromatography, add 50 ml Wate...

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Abstract

The invention relates to the technical field of organic synthesis and discloses a preparation method and an application of a terpenoid 3,7,11-trimethyl-2,4,6,10-dodecatetraene-1-alcohol acetate. The preparation method comprises the following steps: firstly carrying out dissociation reaction on C10 phosphonate at minus 40-30 DEG C in the presence of an organic solvent and an alkali under the protection of inert gases; after dissociation is completed, adding C5 aldehyde and carrying out Wittig-Horner condensation reaction at minus 40-30 DEG C in the presence of the organic solvent and the alkali. The prepared target product 3,7,11-trimethyl-2,4,6,10-dodecatetraene-1-alcohol acetate (1) is concise in process route, accessible in raw materials and low in cost and extremely has industrial value.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of a terpenoid compound 3,7,11-trimethyl-2,4,6,10-dodecanyl tetraen-1-ol acetate and its application. 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. At present, the preparation method of 3,7,11-trimethyl-2,4,6,10-dodedecyltetraen-1-ol acetate (1) is mainly based on linalool (2) React with sodium benzenesulfonate to obtain C10 sulfone (3), then react with Π-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...

Claims

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Application Information

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IPC IPC(8): C07C69/145C07C67/293C07C33/02C07C27/02
CPCC07C67/293C07C29/095C07C69/145C07C33/02
Inventor 沈润溥宋小华吴春雷高晓忠刘伟潭艳於红艳吴毅斌
Owner SHAOXING UNIVERSITY
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