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Silicon-based rhodamine derivative, preparation method and applications thereof

A technology of silyl-rhodamine and its derivatives, applied in the field of chemistry, can solve problems such as many steps, inability to synthesize substituted silyl-rhodamine, and limited range of substrate selection

Inactive Publication Date: 2015-01-07
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In these patents, the method of nucleophilic addition of an active metal reagent to a carbonyl group is used to prepare silyl-rhodamine derivatives. On the one hand, this synthesis method has many steps, harsh reaction conditions, and low yield, so it cannot be used for a large amount of Synthesis; on the other hand, the use of active metal reagents greatly limits the range of substrate selection, and some substituted silicon-based rhodamines cannot even be synthesized, which affects its application in biological sample imaging

Method used

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  • Silicon-based rhodamine derivative, preparation method and applications thereof
  • Silicon-based rhodamine derivative, preparation method and applications thereof
  • Silicon-based rhodamine derivative, preparation method and applications thereof

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Effect test

Embodiment 1

[0074]

[0075] In a 500 mL long-necked reaction flask equipped with a magnetic stirrer, 27.376 g (120.0 mmol) of N,N-diethyl-m-bromoaniline was added. Under the protection of argon, 120 mL of anhydrous diethyl ether was added, and magnetically stirred at 0 °C for 5 min. Will n -BuLi 52.5 mL (2.4 M in n- Hexane, 126.0 mmol) was slowly added dropwise to the reaction solution, and after the dropwise addition was completed, the reaction was continued at 0 °C for 2 h. Dissolve 8.8 mL (72.0 mmol) of dimethyldichlorosilane in 30 mL of anhydrous ether, and slowly add it dropwise to the above reaction solution. After the dropwise addition, the reaction was slowly warmed to room temperature and stirred overnight. Add 150 mL of water to the reaction solution, separate the organic layer with a separatory funnel, and extract the aqueous layer with diethyl ether (50 mL 3), combined organic layers, washed once with 150 mL of water, once with 150 mL of saturated NaCl aqueous solution...

Embodiment 2

[0078]

[0079] In a 250 mL long-necked reaction flask equipped with a magnetic stirring bar, add 4.070 g (18.0 mmol) of 1-ethyl-6-bromoindoline. Under the protection of argon, 50 mL of anhydrous diethyl ether was added, and magnetically stirred at 0 °C for 5 min. Will n -BuLi 11.8 mL (1.6 M in n- Hexane, 18.9 mmol) was slowly added dropwise into the reaction solution, and after the dropwise addition was completed, the reaction was continued at 0 °C for 2 h. Dissolve 1.3 mL (10.8 mmol) of dimethyldichlorosilane in 10 mL of anhydrous ether, and slowly add it dropwise to the above reaction solution. After the dropwise addition, the reaction was slowly warmed to room temperature and stirred overnight. 50 mL of water was added to the reaction solution, the organic layer was separated, and the aqueous layer was extracted with ether (30 mL 3), combined organic layers, washed once with 50 mL of water, washed once with 50 mL of saturated NaCl aqueous solution, and washed once...

Embodiment 3

[0082]

[0083] In a 100 mL long-necked reaction flask equipped with a magnetic stirring bar, add 2.738 g (12.0 mmol) of N,N-diethyl-m-bromoaniline. Under the protection of argon, 10 mL of anhydrous diethyl ether was added, and magnetically stirred at 0 °C for 5 min. Will n -BuLi 7.9 mL (1.6 M in n- Hexane, 12.6 mmol) was slowly added dropwise into the reaction solution, and after the dropwise addition was completed, the reaction was continued at 0 °C for 2 h. Dissolve 7.3 mL (60.0 mmol) of dimethyldichlorosilane in 30 mL of anhydrous ether, and slowly introduce it into the above reaction solution. After the dropwise addition, the reaction was slowly raised to room temperature, and reacted at room temperature for 2 hours. The solvent and unreacted dimethyldichlorosilane were removed under reduced pressure to obtain crude SiNCl. ​​Under the protection of argon, 5 mL of anhydrous ether was added to dissolve the crude SiNCl, and the resulting solution was used for future us...

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Abstract

The invention relates to a silicon-based rhodamine derivative, which is represented by a biological structural formula shown in the description. The invention also relates to a preparation method of the silicon-based rhodamine derivative, and applications of the silicon-based rhodamine derivative in preparation of cell dye, biological dye, biological molecule / particle fluorescent marker, and the like. The provided synthesis method of silicon-based rhodamine derivative has the advantages of high yield, simple reaction conditions, convenient operation, capability for massive production, and wide substrate selection range.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to a silicon-based rhodamine derivative and its preparation method and application. Background technique [0002] Rhodamine is one of the xanthene compounds. It has the advantages of good photostability, high fluorescence quantum yield, and simple chemical modification. It is a good fluorescent small molecule dye probe and is widely used in the detection of biological samples. Staining and fluorescent labeling. However, rhodamine also has many shortcomings in the application process as a fluorescent probe, especially when it is applied to biological samples. For example, the excitation wavelength of rhodamine B dye is in the ultraviolet-visible region, and biological samples will produce serious background signal interference in the ultraviolet-visible region. On the other hand, ultraviolet-visible light has poor penetration ability to tissues and is highly phototoxic to biological sample...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/10C09K11/06C09B57/00C12Q1/02G01N21/64
CPCC07F7/10C09K11/06G01N21/33G01N21/64G01N33/58
Inventor 汪亭王保刚柴晓云吴秋业
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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