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Method for preparing (E)-4-(benzenesulfonyl) butyl-3-olefine acid

A technology of benzenesulfonyl and crotonic acid, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problem of highly toxic organotin reagents, irritating odor of toluenesulfonyl chloride, and selection of regions that need to be regulated. It can reduce the environmental impact and save the production cost.

Pending Publication Date: 2022-08-02
ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because organotin reagents are highly toxic, p-toluenesulfonyl chloride has an irritating stench, and the hydrogen stannation reaction has disadvantages such as the need to control regioselectivity and low product yields.

Method used

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  • Method for preparing (E)-4-(benzenesulfonyl) butyl-3-olefine acid
  • Method for preparing (E)-4-(benzenesulfonyl) butyl-3-olefine acid
  • Method for preparing (E)-4-(benzenesulfonyl) butyl-3-olefine acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]A synthetic method of (E)-4-(benzenesulfonyl) but-3-enoic acid, comprising the following steps:

[0043] (1) 1.44g (10.00mmol) of 8-aminoquinoline (compound 1) was added to a 250mL round bottom flask filled with dichloromethane (30.0mL, DCM), followed by 4.94g (13.00mmol) of HATU (2-(7-azobenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate), 1.12g (13.00mmol) 3-butenoic acid (compound 2) and 2.42 g (20.00 mmol) of 2,4,6-collidine, and stirred at room temperature for 16 h. The reaction was quenched with ethyl acetate (200 mL), the system was transferred to a separatory funnel, the organic phase was washed with 100 mL of saturated sodium bicarbonate solution and 100 mL of saturated brine successively, and then dried over anhydrous sodium sulfate. Filtration and concentration, the obtained mixture was separated by column chromatography (eluent petroleum ether: ethyl acetate (v / v)=25~20:1) to obtain the target product (compound 3) (1.70 g, yield 80.1%) . The H NM...

Embodiment 2

[0051] A synthetic method of (E)-4-(benzenesulfonyl) but-3-enoic acid, comprising the following steps:

[0052] (1) 1.44g (10.00mmol) of 8-aminoquinoline (compound 1) was added to a 250mL round-bottomed flask filled with dichloromethane (30.0mL), followed by 5.32g (14.00mmol) of HATU (2) -(7-Azobenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate), 1.21 g (14.00 mmol) 3-butenoic acid (compound 2) and 2.67 g g (22.00 mmol) 2,4,6-collidine, and stirred at room temperature for 16 h. The reaction was quenched with ethyl acetate (200 mL), the system was transferred to a separatory funnel, the organic phase was washed successively with 100 mL of saturated sodium bicarbonate solution and 100 mL of saturated brine, and then dried over anhydrous sodium sulfate. Filtration and concentration, the obtained mixture was separated by column chromatography (eluent petroleum ether: ethyl acetate (v / v)=25~20:1) to obtain the target product (compound 3) (1.74 g, yield 82.0%) .

[0053...

Embodiment 3

[0057] A synthetic method of (E)-4-(benzenesulfonyl) but-3-enoic acid, comprising the following steps:

[0058] (1) 1.44g (10.00mmol) of 8-aminoquinoline (compound 1) was added to a 250mL round-bottomed flask filled with dichloromethane (30.0mL), followed by 5.70g (15.00mmol) of HATU (2) -(7-Azobenzotriazole)-N,N,N',N'-tetramethylurea hexafluorophosphate), 1.29g (15.00mmol) 3-butenoic acid (compound 2) and 3.03 g g (25.00 mmol) 2,4,6-collidine, stirred at room temperature for 16 h. The reaction was quenched with ethyl acetate (200 mL), the system was transferred to a separatory funnel, the organic phase was washed with 100 mL of saturated sodium bicarbonate solution and 100 mL of saturated brine successively, and then dried over anhydrous sodium sulfate. Filtration and concentration, the obtained mixture was separated by column chromatography (eluent petroleum ether: ethyl acetate (v / v)=25~20:1) to obtain the target product (compound 3) (1.73 g, yield 81.5%) .

[0059] (2) ...

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Abstract

The invention provides a synthesis method of (E)-4-(benzenesulfonyl) butyl-3-olefine acid, which comprises the following steps: 1) taking 8-aminoquinoline and 3-butenoic acid as raw materials, taking dichloromethane as a solvent, and obtaining a compound 3: N-(quinoline-8-yl) butyl-3-enamine under the action of HATU and 2, 4, 6-trimethylpyridine; 2) taking acetonitrile as a solvent, and reacting the compound 3 with sodium benzenesulfinate under the action of palladium acetate, benzoic acid and silver hexafluoroantimonate to obtain a compound 5: (E)-4-(benzenesulfonyl)-N-(quinoline-8-yl) butyl-2-enamine; and 3) hydrolyzing the compound 5 under the action of an HCl aqueous solution. The method comprises the following steps: carrying out dehydration condensation on 3-butenoic acid and 8-aminoquinoline to obtain amide; under the catalysis of palladium, olefinic bonds in the amide react with sodium benzenesulfinate to obtain allyl sulfone; amido bonds in allyl sulfone are hydrolyzed under the acidic condition, meanwhile, double bonds are shifted, and a target product is obtained and has excellent regioselectivity.

Description

technical field [0001] The invention relates to a method for synthesizing (E)-4-(benzenesulfonyl)but-3-enoic acid, and belongs to the field of organic synthesis. Background technique [0002] Alkenyl sulfones have unique chemical properties and biological activities. They are not only widely used in organic synthesis and pharmaceutical synthesis, but also are the structural units of many natural products and biologically active molecules. (E)-4-(Benzenesulfonyl)but-3-enoic acid belongs to alkenyl sulfone compounds, it not only contains active double bond and biologically active sulfone group, but also contains carboxyl functional group, which provides more modification sites , which is beneficial to obtain structurally diverse sulfone compounds. Therefore, it is of great theoretical significance and application value to develop a method for the construction of alkenyl sulfone compounds with high efficiency and wide applicability. [0003] The analog of existing synthesis (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C315/04C07C317/44C07D215/42
CPCC07C315/04C07D215/42C07B2200/09C07C317/44
Inventor 汪洋刘双良赵茹宋瑞杰刘琦王曼李若楠李梦龙黄勤晨
Owner ZHENGZHOU UNIVERSITY OF LIGHT INDUSTRY
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