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Method for synthesizing 1,3-diaryl-5-hexene-1-ketone

A synthesis method and a diaryl technology, applied in 1 field, can solve the problems of low coupling agent activity, human and environmental hazards, limited substrate scope, etc., and achieve the effects of mild reaction conditions, simple and convenient operation, and short reaction time.

Inactive Publication Date: 2008-03-05
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When allyl bromide is used as the allylation reagent, an equivalent amount of metal is required as a reducing agent such as: iron, magnesium, zinc, copper, manganese, aluminum, indium, samarium, etc., but the metal cannot be recycled, and allyl bromide Bromine has certain toxicity and is harmful to the human body and the environment; allyl tin itself is relatively unstable and has certain toxicity, and requires equivalent metal catalysts such as: titanium tetrachloride, aluminum trichloride , tin tetrachloride; no matter from an economic point of view or from an environmental point of view, it is more unfavorable to use allyl bromide or allyl tin as an allylation reagent, so allyl silane is allyl Reagent of choice for alkylation
However, allyl chlorosilane is very active, and its participation in the reaction needs to be carried out under anhydrous conditions, and the scope of substrates is also greatly limited; the activity of allyl silane coupling agent is relatively low, and its reactivity to enone is weak
Allylalkylsilane is comparatively stable, moderate in activity, and raw material is easy to get, but traditional method often needs complicated reaction condition, as needs the equivalent Lewis acid catalyst (titanium tetrachloride, aluminum trichloride, boron trifluoride Ether, etc.), anhydrous low temperature and other conditions

Method used

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  • Method for synthesizing 1,3-diaryl-5-hexene-1-ketone
  • Method for synthesizing 1,3-diaryl-5-hexene-1-ketone
  • Method for synthesizing 1,3-diaryl-5-hexene-1-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Put a 10ml glass bottle with a rubber stopper on the 85-2 type constant temperature magnetic stirrer, add 2ml of methylene chloride, 1mmol of 1-(3-nitrophenyl)-3-phenyl-propenone, 0.224g ( 1.1mmol) allyltrimethylsilane, quickly weighed 0.016g (0.1mmol) ferric chloride, 0.163g (1.5mmol) trimethylchlorosilane was added to the reaction bottle, and the rubber stopper was covered. It was then stirred at room temperature for 3 hours. After the reaction was complete, extract with dichloromethane, combine the organic phases, and dry over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure (column separation if necessary, stationary phase: silica gel; mobile phase: 10:1 petroleum ether / ethyl acetate), and the solvent was recovered to obtain 0.22 g of a solid product with a yield of 88%. m / z250(M + )130(58)105(100)77(39) 1 HNMR (400MHz, CDCl 3 ) 7.88 (M 2H) 7.52 (M 1H) 7.42 (M 2H) 7.17-7.30 (M 5H) 5.69 (M 1H) 4.99 (M 2H) 3.48 (M 1H) 3.29 (D J = 8HZ ...

Embodiment 2

[0020] Put a 10ml glass bottle with a rubber stopper on the 85-2 type constant temperature magnetic stirrer, add 2ml of methylene chloride, 0.243g (1mmol) 1-phenyl-3-(1-chlorophenyl)-propenone, 0.224 g (1.1mmol) allyltrimethylsilane, quickly weigh 0.016g (0.1mmol) ferric chloride, 0.163g (1.5mmol) trimethylchlorosilane into the reaction bottle, and cover the rubber stopper. Stir at room temperature for 3 hours to fully react, then extract with dichloromethane, combine organic phases, and dry over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure (column separation if necessary, stationary phase: silica gel; mobile phase: 10:1 petroleum ether / ethyl acetate), and the solvent was recovered to obtain 0.241 g of a solid product with a yield of 85%. m / z284(M + )249(12)164(18)129(32)105(100)77(40) 1 H NMR (400MHz, CDCl 3 )7.93(D J=8HZ 2H)7.53(T J=4HZ 1H)7.44(TJ=8HZ 2H)7.35(D J=8HZ 1H)7.24(M 1H)7.13(T J=4HZ 1H)5.70(M 1H)4.98(M 3H ) 4.04 (M 1H) 3.33 (D ...

Embodiment 3

[0022] Put a 10ml glass bottle with a rubber stopper on the 85-2 type constant temperature magnetic stirrer, add 2ml of methylene chloride, 0.222g (1mmol) 1-phenyl-3-(3-methylphenyl)-propenone, 0.224g (1.1mmol) allyltrimethylsilane, quickly weighed 0.016g (0.1mmol) ferric chloride, 0.163g (1.5mmol) trimethylchlorosilane was added to the reaction bottle, and the rubber stopper was covered. Stir at room temperature for 3 hours. Then it was extracted with dichloromethane, and the organic phases were combined and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure (column separation if necessary, stationary phase: silica gel; mobile phase: 10:1 petroleum ether / ethyl acetate), and the solvent was recovered to obtain 0.241 g of a solid product with a yield of 85%. m / z264(M1)144(31)129(10)105(100)77(27) 1 H NMR (400MHz, CDCl 3 )7.89(D J=12HZ 2H)7.52(T J=4HZ 1H)7.42(T J=8HZ 2H)7.11(M 4H)5.69(M 1H)4.97(M 2H)3.43(M 1H)3.26(M 2H)2.44(M 2H) 2.29 (...

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Abstract

The present invention relates to synthesis of organic material, and is especially process of synthesizing 1, 3-diaryl-5-hexene-1-ketone. Inside solvent of nitromethane, dichloromethane, ethyl cyanide, trichloromethane, toluene, tetrahydrofuran, methanol or ethanol, and in the presence of metal catalyst of ferric chloride, zinc dichloride, copper bromide, ferric perchlorate or magnesium perchlorate and organic catalyst of trimethyl clorosilane, Chalcone and allylalkoxyl silane are reacted to produce 1, 3-diaryl-5-hexene-1-ketone. The present invention has the advantages of cheap catalyst, low consumption of catalyst, normal pressure and normal temperature reaction, simple operation, etc. and the synthesized organic intermediate has wide application.

Description

technical field [0001] The invention relates to a method for synthesizing organic matter, in particular to a method for synthesizing 1,3-diaryl-5-hexen-1-one. technical background [0002] 1,3-Diaryl-5-hexen-1-one is an important class of organic compounds. There are generally three types of allylation reagents for the synthesis of 1,3-diaryl-5-hexen-1-one : Allyl Bromide, Allyl Tin, Allyl Silane. When allyl bromide is used as the allylation reagent, an equivalent amount of metal is required as a reducing agent such as: iron, magnesium, zinc, copper, manganese, aluminum, indium, samarium, etc., but the metal cannot be recycled, and allyl bromide Bromine has certain toxicity and is harmful to the human body and the environment; allyl tin itself is relatively unstable and has certain toxicity, and requires equivalent metal catalysts such as: titanium tetrachloride, aluminum trichloride , tin tetrachloride; no matter from the economic point of view or from the point of view o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/807C07C49/84C07C49/76C07C45/61
Inventor 徐利文杨明松张飞豹来国桥蒋剑雄邱化玉
Owner HANGZHOU NORMAL UNIVERSITY