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Preparation method of 3-aryl-1-indanone derivate

A technology for indanone and derivatives, which is applied in the field of preparation of 3-aryl-1-indanone derivatives, can solve the problems of difficult purification of drugs or materials in the later stage, achieve reaction atom economy, high synthesis yield, The effect of easy access to raw materials

Inactive Publication Date: 2016-02-24
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing methods all use metal salt-promoted or transition metal-catalyzed reactions to varying degrees, which is very difficult for the later purification of drugs or materials

Method used

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  • Preparation method of 3-aryl-1-indanone derivate
  • Preparation method of 3-aryl-1-indanone derivate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, 2,3-diphenyl-2,3-indanone (in the formula III, R 1 is H, Ar is phenyl, R is phenyl)

[0023] Into a 25 mL reactor, add toluene (0.22 mmol, 39 mg), benzaldehyde (0.2 mmol, 20 μL), methyl trifluoromethanesulfonate (0.04 mmol, 4.6 μL) in sequence, and finally add 0.5 mL of 1,2- Dichloroethane was used as solvent, the reactor was sealed, and reacted at 50°C for 24 hours. After the reaction system was cooled, 15 mL of water and 15 mL of dichloromethane were added and stirred for 30 min, and then extracted three times with 15 mL of dichloromethane, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate for 0.5 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product is separated by column chromatography using petroleum ether: ethyl acetate = 25:1 (volume ratio) as the eluent, and 200-300 mesh silica gel as the adsorption phase t...

Embodiment 2

[0028] Example 2, 2-phenyl-3-p-methylphenyl-2,3-indanone (in formula III, R 1 is H, Ar is p-methylphenyl, R is phenyl)

[0029] To a 25mL reactor, add toluene (0.22mmol, 39mg), 4-methylbenzaldehyde (0.2mmol, 22μL), methyl trifluoromethanesulfonate (0.04mmol, 4.6μL), and finally add 0.5 Use mL1,2-dichloroethane as solvent, seal the reactor, and react at 50°C for 24 hours. After the reaction system was cooled, 15 mL of water and 15 mL of dichloromethane were added and stirred for 30 min, and then extracted three times with 15 mL of dichloromethane, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate for 0.5 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product is separated by column chromatography with petroleum ether: ethyl acetate = 25:1 (volume ratio) as the eluent, and 200-300 mesh silica gel as the adsorption phase to obtain a yellow ...

Embodiment 3

[0034] Example 3, 2-phenyl-3-m-methylphenyl-2,3-indanone (in formula III, R 1 is H, Ar is m-methylphenyl, R is phenyl)

[0035]To a 25mL reactor, add toluene (0.22mmol, 39mg), 3-methylbenzaldehyde (0.2mmol, 22μL), methyl trifluoromethanesulfonate (0.04mmol, 4.6μL) in sequence, and finally add 0.5 Use mL1,2-dichloroethane as solvent, seal the reactor, and react at 50°C for 24 hours. After the reaction system was cooled, 15 mL of water and 15 mL of dichloromethane were added and stirred for 30 min, and then extracted three times with 15 mL of dichloromethane, and the organic phases were combined. The organic phase was washed with saturated brine, and finally dried over anhydrous magnesium sulfate for 0.5 h. After filtration, the organic phase was rotary evaporated to obtain a crude product. The crude product is separated by column chromatography with petroleum ether: ethyl acetate = 50:1 (volume ratio) as the eluent, and 200-300 mesh silica gel as the adsorption phase to obtai...

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Abstract

The invention discloses a preparation method of a 3-aryl-1-indanone derivate. The structural formula of the 3-aryl-1-indanone derivate is shown in the formula III. The preparation method comprises the following steps that a compound shown in the formula I reacts with a compound shown in the formula II in the presence of methyl trifluoromethanesulfonate, and therefore the 3-aryl-1-indanone derivate shown in the formula III is obtained. The preparation method of the 3-aryl-1-indanone derivate is scientific and reasonable, 3-aryl-1-indanone derivates with various substituent groups can be obtained, the raw materials are easy to obtain, no metal participates in the reaction, reaction atoms are economical, and meanwhile the preparation method has the advantages that operation is simple and convenient, the synthesis productive rate is high, the product is easy to purify, and environmental protection is achieved.

Description

technical field [0001] The invention relates to a preparation method of 3-aryl-1-indanone derivatives, belonging to the research field of organic synthesis methods. Background technique [0002] Indanone (or dihydroindanone) (indanone) and its derivatives are an important class of organic intermediates, commonly used in drug synthesis, such as indanoxyacetic acid compounds with salt-expelling diuresis and uric acid, which have irindalone with antihypertensive activity, trans,trans-1-phenyl-3-(pyrrol-1-yl)-indan-2-carboxamide with neurokinin receptor antagonistic activity, etc., are derived from indanone It is synthesized as an intermediate, and important compounds such as isocoumarin can also be synthesized from indanone. Metal complexes with indene ring skeletons can also be used as catalysts for styrene polymerization. In addition, indanone compounds with 3-aryl substitution are extremely valuable pharmaceutical intermediates, and can be used as the skeleton of many drug...

Claims

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Application Information

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IPC IPC(8): C07C49/67C07C49/697C07C49/755C07C45/45
CPCC07C45/45C07C49/67C07C49/697C07C49/755
Inventor 席婵娟刘宇
Owner TSINGHUA UNIV
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