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Silicon-based rhodamine derivative and preparation method thereof

An alkyl and alkenyl technology, applied in the field of silyl-based rhodamine derivatives and their preparation, can solve the problems of harsh reaction conditions, many steps, narrow substrate range, etc.

Inactive Publication Date: 2020-03-27
SHENZHEN HUADA GENE INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, so far, there are not many synthetic routes of silyl-rhodamine compounds.
Currently known synthetic routes have a narrow range of substrates, many steps, harsh reaction conditions, and low yields, so they cannot be used for large-scale synthesis.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109]

[0110] In a 500 mL round bottom flask equipped with a magnetic stirring bar, 7-bromoquinoline (Aldrich, 2.07 g, 10.0 mmol) and paraformaldehyde (Aldrich, 6.0 g, 200 mmol) were added. Under the protection of argon, anhydrous N,N-dimethylformamide (Aldrich, 20 mL) was added, and magnetically stirred at 0° C. for 10 min. At the same temperature, formic acid (Aldrich, 9.2 g, 200 mmol) was slowly added into the reaction flask. Sodium cyanoborohydride (Aldrich, 6.28 g, 100.0 mmol) was slowly added to the reaction flask in batches. The reaction was slowly warmed to 60°C and stirred overnight. 50 mL of water was added to the reaction solution to quench the reaction, and at 0° C., 3M aqueous sodium hydroxide solution was added to the reaction solution to adjust the reaction solution to alkalinity. Add 100mL of dichloromethane to the reaction solution, separate the organic layer with a separatory funnel, extract the aqueous layer with dichloromethane, combine the organic l...

Embodiment 2

[0112]

[0113] Under argon protection, methylene bridging intermediate (3, 0.31 g, 1 mmol) and anhydrous diethyl ether (aldrich, 10 mL) were added to a 100 mL round bottom flask equipped with a magnetic stirring bar. Stirring for 30 minutes at -78°C, n-BuLi (Aldrich, 1.87mL, 1.6M in n-hexane, 3mmol) was slowly added dropwise to the reaction solution. After the dropwise addition, the reaction was continued at the same temperature for 2 hours. Dimethyldichlorosilane (Aldrich, 0.19 g, 1.5 mmol) was dissolved in 5.0 mL of anhydrous ether, and slowly added dropwise to the above reaction solution. After the dropwise addition was completed, the reaction was slowly raised to room temperature, and the reaction was stirred overnight at room temperature. Add 20 mL of water to the reaction bottle to quench the reaction, add 25 mL of dichloromethane, separate the organic layer, extract the water layer with dichloromethane three times, combine the organic layers, wash once with 20 mL of...

Embodiment 3

[0116] The bromooxazoline reacts with n-butyllithium to generate a lithium reagent, which then undergoes an addition reaction with the key silicone intermediate prepared above. After the addition reaction is completed, hydrochloric acid is added to obtain a silicon-based rhodamine derivative. Its reaction process can be expressed as:

[0117]

[0118] Under argon protection, bromooxazoline derivatives (7, 0.253 g, 1 mmol) and anhydrous diethyl ether (aldrich, 10 mL) were added to a 100 mL round bottom flask equipped with a magnetic stirrer. Stirring for 30 minutes at -78°C, n-BuLi (Aldrich, 1.25mL, 1.6M in n-hexane, 2mmol) was slowly added dropwise to the reaction solution. After the dropwise addition, the reaction was continued at the same temperature for 2 hours. The ketone intermediate (6, 0.376 g, 1 mmol) was dissolved in anhydrous ether (Aldrich, 10 mL), and slowly added dropwise to the aforementioned reaction system at -78°C. After the dropwise addition was complete...

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Abstract

The invention provides a silicon-based rhodamine derivative and a preparation method thereof. The method comprises the following steps: (1) carrying out a reductive amination / methylene bridging reaction on a compound represented by a formula (I') to obtain a compound represented by a formula (II'); (2) carrying out a silylation / oxidation reaction on the compound represented by the formula (II') toobtain a compound represented by a formula (III'); and (3) carrying out a metal reagent addition / hydrolysis protection group removing reaction on the compound represented by the formula (III') so asto obtain a silicon-based rhodamine derivative. The method according to the embodiments of the invention is high in synthesis efficiency, simple in reaction condition and convenient to operate, can achieve the large-scale preparation of silicon-based rhodamine derivatives, substantially enriches the substrate selection range, can synthesize silicon-based rhodamine derivatives difficultly synthesized by adopting the previous methods, and easily achieves the further modification and application of silicon-based rhodamine derivatives.

Description

technical field [0001] The invention relates to the field of biotechnology, in particular, the invention relates to a silicon-based rhodamine derivative and a preparation method thereof. Background technique [0002] Rhodamine is a typical class of xanthene compounds. Rhodamine dyes refer to a series of dye derivatives obtained by modifying functional groups based on rhodamine. This type of dye has the advantages of good photostability, high fluorescence quantum yield, and simple chemical synthesis and modification. It is an important fluorescent small molecule dye probe and is widely used in the staining and fluorescent labeling of biological samples. However, rhodamine also has some shortcomings in the application process as a fluorescent probe, especially when it is applied to biological samples. The absorption and emission wavelengths of traditional rhodamine dyes are generally below 600nm. For example, the excitation wavelength of rhodamine B dyes is in the ultraviole...

Claims

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Application Information

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IPC IPC(8): C09B57/00C09K11/06
CPCC09B57/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1096
Inventor 沈亮滕波朱兴利李汉东章文蔚
Owner SHENZHEN HUADA GENE INST
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