Benzene ring-containing compound as well as preparation method and application thereof

A compound and benzene ring technology, applied in the preparation of organic compounds, amino hydroxyl compounds, cyanide reaction preparation, etc., can solve the problem of increasing the production cost and operation difficulty of carbo-rhodamine compounds, unsatisfactory yield and long reaction route and other issues, to achieve the effect of facilitating large-scale production, simple product post-processing, and reducing the difficulty of reaction

Pending Publication Date: 2022-07-19
SHENZHEN HUADA GENE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These unfavorable conditions increase the production cost and operational difficulty of carborhodamine compounds
Simultaneously, above-mentioned reaction route is longer, and there are many steps, because the existence of a large amount of side reactions, after multi-step reaction, productive rate is unsatisfactory
This is one of the reasons why commercial carborhodamine reagents are expensive

Method used

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  • Benzene ring-containing compound as well as preparation method and application thereof
  • Benzene ring-containing compound as well as preparation method and application thereof
  • Benzene ring-containing compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0104]

[0105] 10 g (100 mmol) of compound 3-1 was added to 100 mL of THF and dissolved under stirring, and the temperature was lowered to -20°C under nitrogen protection. About 100 mmol of Grignard reagent 3-2 was slowly added dropwise to the solution of compound 3-1, during which the temperature was maintained not higher than -20°C, and the dropwise addition was completed in 30 min. The Grignard reaction was carried out for about 5 h under the condition of maintaining the temperature and stirring, quenched with about 100 mL of saturated ammonium chloride solution, and the pH value was adjusted to around 7. The mixture was extracted with ethyl acetate, and the organic phases were combined and dried over anhydrous sodium sulfate. After being concentrated under reduced pressure by rotary evaporation, use column chromatography (the stationary phase is 200-300 mesh silica gel powder, the eluent is n-hexane / ethyl acetate mixture, and the volume ratio is 10:1 to 2:1 according t...

Embodiment 2

[0115] 2-(3,6-bis(dimethylamino)-10,10-dimethyl-9,10-dihydroanthracene-9-yl)benzoic acid (2-(3,6-bis(dimethylamino)- Synthesis of 10,10-dimethyl-9,10-dihydroanthracen-9-yl)benzoic acid, compound 1-6)

[0116]

[0117] Under nitrogen protection, 20 g (100 mmol) of p-bromodimethylaniline was slowly added dropwise to 200 mL of THF containing 2.4 g (100 mmol) of magnesium chips, and a small grain of iodine (10 mg) was added, and the reaction was initiated by heating to 40-50 °C. , the dropwise addition time of p-bromodimethylaniline is about 30min. After the dropwise addition was completed, the temperature was kept at 40°C and the stirring was continued for about 2 hours until the magnesium chips basically disappeared. So far, the Grignard reagent shown in formula 1-2 is prepared.

[0118] 16.4 g (100 mmol) of methyl o-aldehyde benzoate was added to 100 mL of THF and stirred to dissolve, and the temperature was lowered to -20° C. under nitrogen protection. About 100 mmol of ...

Embodiment 3

[0121] Synthesis of Compounds 2-6

[0122]

[0123]Under nitrogen protection, 20g (100mmol) of p-bromodimethylaniline was slowly added dropwise to 100mL of THF containing 2.4g (100mmol) of magnesium chips, and a small particle of iodine (about 10mg) was added. Reaction, the dropwise time of p-bromodimethylaniline is about 30min. After the dropwise addition was completed, the temperature was kept at 40°C and the stirring was continued for about 4 hours until the magnesium chips basically disappeared. So far, the Grignard reagent shown in formula 2-2 is prepared.

[0124] 10 g (100 mmol) of benzaldehyde was added to 100 mL of THF and stirred to dissolve, and the temperature was lowered to -20°C under nitrogen protection. About 100 mmol of the prepared Grignard reagent was slowly added dropwise to the methyl o-aldehyde benzoate solution, and the temperature was maintained at no more than -20° C., and the dropwise addition was completed in 30 min. The grating reaction was ca...

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Abstract

The invention discloses a benzene ring-containing compound as well as a preparation method and application thereof. The structure of the benzene ring-containing compound provided by the invention is shown as a formula I; wherein R1, R2, R3 and R4 are independently a C1-6 alkyl group, a C3-6 cycloalkyl group or a C6-20 aryl group; and R5 is hydrogen, halogen, C1-C4 alkyl,-COOMe,-COOEt or carboxyl. According to the compound containing the benzene ring, the carbon rhodamine compound can be obtained under the mild condition, strong oxidants such as potassium permanganate and perchlorate do not need to be used, and the use and storage problems of dangerous chemicals such as tert-butyllithium are not involved.

Description

technical field [0001] The present invention relates to a compound containing a benzene ring and its preparation method and application. Background technique [0002] Carborhodamine dyes are widely used organic fluorescent dyes whose structures are a series of related fluorescent ketone compounds. Carborhodamine dye itself is a synthetic industrial dye, which can be used for tracer labeling, etc., and can also emit strong fluorescence after being excited by laser or other means. Due to this fluorescent feature, carborhodamine-based dyes are widely used in biotechnologies such as fluorescence microscopy, cell labeling, fluorescence correlation spectroscopy, pathogen detection, etc. Carborhodamine dyes can also be used for intracellular structure labeling, drug molecule labeling, protein, nucleotide, antibody and other biological macromolecules labeling. [0003] The current method for synthesizing carborhodamine dyes is to first synthesize the carbocyclic skeleton through F...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/61C07C209/68C07C229/52C07C227/10C07C227/16C07C211/50C07C213/00C07C215/68C07F3/02
CPCC07C211/61C07C209/68C07C229/52C07C227/10C07C227/16C07C211/50C07C213/00C07C215/68C07F3/02C07C2603/24
Inventor 徐讯张泳辉滕波沈亮卓世添章文蔚李汉东
Owner SHENZHEN HUADA GENE INST
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