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Method for synthesizing aryl substituted cyclo-ketene compound

A synthesis method and compound technology are applied in the synthesis of ketene compounds and the synthesis field of aryl-substituted cyclic ketene compounds, which can solve the problem of high electron cloud density of aryl groups, achieve high yield, good application prospects and research potential effect

Inactive Publication Date: 2015-10-28
张琳苹
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] As mentioned above, the prior art discloses a variety of methods for synthesizing unsaturated cyclic ketone compounds, but for the synthesis method of aryl-substituted cyclopentenone compounds, due to the high electron cloud density of aryl, it is difficult to bond to On the specific position of cyclopentenone compound, therefore the synthetic method of aryl substituted cyclopentenone compound is still not reported at present

Method used

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  • Method for synthesizing aryl substituted cyclo-ketene compound
  • Method for synthesizing aryl substituted cyclo-ketene compound
  • Method for synthesizing aryl substituted cyclo-ketene compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]

[0041] At room temperature and under a nitrogen atmosphere, add 100 mmol of the above formula (I) compound, 150 mmol of the above formula (II) compound, 4 mmol of the catalyst Pd (dpbpf)Cl 2 , 50mmol trifluoroacetic acid, 4mmol phosphine ligand L1 and 10mmol of the above additives, then warming up to 50°C, and stirring and reacting at this temperature for 8 hours;

[0042] After the reaction was completed, the reaction system was naturally cooled to room temperature, filtered, and the pH value of the filtrate was adjusted to 6-7 with a 10% NaOH aqueous solution with a mass percentage concentration, then deionized water was added, fully oscillated, and then extracted with ethyl acetate for 2 -3 times, the organic phases were combined, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was separated by 300-400 mesh silica gel column chromatography, and the mixture of petroleum ether and acetone with a volume ratio of 1:2 was ...

Embodiment 2

[0046]

[0047] At room temperature and under a nitrogen atmosphere, add 100 mmol of the above formula (I) compound, 200 mmol of the above formula (II) compound, 6 mmol of the catalyst Pd (dpbpf)Cl 2 , 75mmol trifluoroacetic acid, 6mmol phosphine ligand L1 and 15mmol of the above additives, then warming up to 60°C, and stirring and reacting at this temperature for 6 hours;

[0048] After the reaction was completed, the reaction system was naturally cooled to room temperature, filtered, and the pH value of the filtrate was adjusted to 6-7 with a 10% NaOH aqueous solution with a mass percentage concentration, then deionized water was added, fully oscillated, and then extracted with ethyl acetate for 2 -3 times, the organic phases were combined, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was separated by 300-400 mesh silica gel column chromatography, and the mixture of petroleum ether and acetone with a volume ratio of 1:2 was ...

Embodiment 3

[0052] The reaction formula is the same as in Example 1, and the specific operations are as follows: at room temperature and under a nitrogen atmosphere, add 100 mmol of the above formula (I) compound, 250mmol formula (II) compound, 8mmol catalyst Pd(dpbpf)Cl 2 , 100mmol trifluoroacetic acid, 8mmol phosphine ligand L1 and 20mmol of the above additives, then warming up to 70°C, and stirring and reacting at this temperature for 4 hours;

[0053] After the reaction was completed, the reaction system was naturally cooled to room temperature, filtered, and the pH value of the filtrate was adjusted to 6-7 with a 10% NaOH aqueous solution with a mass percentage concentration, then deionized water was added, fully oscillated, and then extracted with ethyl acetate for 2 -3 times, the organic phases were combined, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was separated by 300-400 mesh silica gel column chromatography, and the mixture of...

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Abstract

The invention relates to a method for synthesizing aryl substituted cyclo-ketene compound represented by a formula (III) shown in the description. The method comprises the step: a compound represented by a formula (I) shown in the description reacts with a compound represented by a formula (II) shown in the description to produce the compound represented by the formula (III) shown in the description in an organic solvent in the presence of a catalyst, acid, a phosphine ligand and adjuvants in a nitrogen atmosphere, wherein R is C1-C6 alkyl or C1-C6 alkoxy. According to the method, through the combination and synergy of the catalyst, the acid, the phosphine ligand, the adjuvants and the organic solvent, the target product can be obtained in a high-yield manner, so that the method has good application prospect and research potential in the technical field of organic synthesis.

Description

technical field [0001] The invention relates to a method for synthesizing ketene compounds, more particularly to a method for synthesizing aryl-substituted cycloalkene compounds, and belongs to the field of organic intermediate synthesis. Background technique [0002] In the technical field of organic chemical synthesis, the Heck reaction is an important way and method to construct C-C bonds. However, the Heck reaction methods of α,β-unsaturated ketones, especially cycloenones, are rarely reported due to stereochemical selectivity and side reactions of elimination reactions. [0003] On the other hand, aryl-substituted cyclopentenone compounds play an important role in organic chemical synthesis due to the presence of unsaturated bonds and carbonyl groups, and are often used as intermediates to further react unsaturated bonds or carbonyl groups. Thereby a variety of non-subsequent yields are obtained. [0004] Therefore, the development of new synthetic reaction methods su...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/68C07C49/753
CPCC07C45/68C07C2601/10C07C49/753
Inventor 张琳苹
Owner 张琳苹
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