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2-nitro-benzoyl-imino-acenaphthylene derivative compound and use thereof

A technology of dinitrobenzoyl imino acenaphthene and compound is applied in the field of new dinitrobenzoyl imino acenaphthene derivative compounds, which can solve the problem that the spatial structure is not good enough, cannot be split, and can be split. Not good and other problems, to achieve the effect of easy control of synthesis conditions, low cost and mature synthesis route

Inactive Publication Date: 2007-08-29
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The main researcher of the present invention once designed and synthesized the π-basic amide class brush-type chiral stationary phase SH-1CSP (ZL02133368.8), see the following formula, but its resolution results show that this CSP is effective for most of the tested drugs The resolution effect of molecules containing basic aromatic groups is not good
The reason is that, in the interaction force between the drug molecule and CSP, the π-π electron interaction between the aromatic rings is still a necessary condition for the selective separation of enantiomers, and the test drug molecule cannot form an effective reaction with CSP. The π-π effect of , resulting in the inability to be split
The second is that the spatial structure around the chiral carbon atom on the SH-1 CSP is not good enough, and the drug is easily adsorbed to the CSP from multiple spatial positions, resulting in the inability to be split

Method used

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  • 2-nitro-benzoyl-imino-acenaphthylene derivative compound and use thereof
  • 2-nitro-benzoyl-imino-acenaphthylene derivative compound and use thereof
  • 2-nitro-benzoyl-imino-acenaphthylene derivative compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] This example is the preparation of 5-[1-(3,5-dinitrobenzoimide)-4-pentenyl]-acenaphthene compound and its chiral substance.

[0035]Synthesis of 5-acetylacenaphthylene (2) Take 12.0g of anhydrous aluminum trichloride and dissolve it in 120ml of dichloromethane, add 4.4g of acetyl chloride while stirring in an ice bath, and finally add 10.4g of acenaphthylene (1). Remove the ice bath, react at room temperature for 25min, that is, pour ice-distilled water prepared in advance into it to terminate the reaction. Wash with saturated sodium carbonate solution and water, dry, and rotary evaporate. Diethyl ether / n-hexane = 1:3 (V:V) was used as the solvent to recrystallize the product to obtain light yellow solid powder (2) with a yield of 58% and a melting point of 67.0-68.5°C.

[0036] Synthesis of 5-(4-ene-valeryl)-acenaphthene (3) Put 30ml of benzene into a flask and heat up to 50°C, add 3.9g of potassium tert-butoxide powder and 4.2g of propylene bromide; take another 35ml...

Embodiment 2

[0044] This example is the preparation of 5-[1-(3,5-dinitrobenzoimide)-10-undecenoyl]acenaphthene compound and its chiral substance.

[0045] The synthesis of 5-acetyl acenaphthylene (2) is exactly the same as in Example 1, omitted.

[0046] Synthesis of 5-(10-undecenoyl)-acenaphthene (3) Put 30ml of benzene into a flask and heat up to 50°C, add 3.9g of potassium tert-butoxide powder and 4.2g of bromodecadecene; another 40ml of benzene Raise the temperature to 40°C, add 6.0g of the product (2) to dissolve, drop this solution into the flask with a sample injector, and stir while adding; heat the mixture to 95°C, reflux for 3h, and stop the reaction. After the reaction solution was cooled, it was washed with water, dried, and rotary evaporated. Toluene was used for column chromatography to remove raw materials and by-products to obtain reddish-brown crystals (3) with a yield of 24%. The melting point is 113.0-115.0°C.

[0047] Synthesis of 5-(1-amino-10-undecenoyl)-acenaphthe...

Embodiment 3

[0054] This example is the preparation of 5-[1-(3,5-dinitrobenzoimide)-4-pentyl]-acenaphthene compound and its chiral substance.

[0055] Synthesis of 5-acetyl acenaphthylene (2) Take 12.0 g of anhydrous aluminum trichloride and dissolve it in 120 ml of dichloromethane, add 4.4 g of acetyl chloride while stirring in an ice bath, and finally add 10.4 g of acenaphthylene (1), remove Ice bath, react at room temperature for 25min, that is, ice distilled water prepared in advance is poured into it to terminate the reaction. Wash with saturated sodium carbonate solution and water, dry, and rotary evaporate. Diethyl ether / n-hexane = 1:3 (V:V) was used as the solvent to recrystallize the product to obtain light yellow solid powder (2) with a yield of 58% and a melting point of 69.0-71.0°C.

[0056] Synthesis of 5-(4-ene-pentyl)-acenaphthene (3) Put 30ml of benzene into a flask and heat up to 50°C, add 3.9g of potassium tert-butoxide powder and 4.2g of bromopropane; take another 35ml ...

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Abstract

The invention relates to a dinitrobenzene formacyl imdo group acenaphthene derivatization compound that has the structure of general expression (I). And R1 represents hydrogen, C1-C3 is alkyl, R2 is alkylidene group, alkenyl, and R3 expresses one-hydrogen or two-hydrogen. After taking acylation reaction of arene, alpha-H replacing reaction of ketone, and reduction amination of ketone carbonyl, and acylation reaction of amine acyl halide, the product would be gained. The invention also relates to the single antipode of the compound, including chiral reagent or chiral additive. It could be used as chiral reagent in film method and chiral stationary phase or chiral mobile phase.

Description

technical field [0001] The invention belongs to the technical field of acenaphthene derivative compounds and their uses, and specifically relates to a new dinitrobenzoyl imino acenaphthene derivative compound and the use of the compound. Background technique [0002] With the further development of life science and medicine, people have gradually discovered that the chiral enantiomers of drugs are quite different in terms of pharmacology, toxicology and clinical efficacy, such as non-steroidal enantiomers, one of the most widely used drugs at present. The anti-inflammatory drug naproxen, its S (left-handed) monochiral substance is 28 times stronger than the R (dextral) monochiral substance. Since most of the new drugs in this century will be chiral drugs, the splitting of chiral enantiomer drugs is not only necessary for the analysis of their purity, but also for the preparation of chiral drugs in the laboratory for pharmacological, toxicological and clinical research. Indu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C233/64C07B57/00B01J20/29
Inventor 宋航兰先秋余荔李程安永祥
Owner SICHUAN UNIV
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