A kind of synthetic method of methylcyclopropene probe

A technique for the synthesis of methylcyclopropene, which is applied in chemical instruments and methods, luminescent materials, organic chemistry, etc., can solve the problems of high price, and achieve the effects of low cost, good application prospects, and easy availability of reaction raw materials

Inactive Publication Date: 2018-08-24
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the expensive problem of the existing cyclopropene synthesis method, and provide a method for the easy-to-get reaction raw materials, low cost and high yield of synthetic methylcyclopropene probes

Method used

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  • A kind of synthetic method of methylcyclopropene probe
  • A kind of synthetic method of methylcyclopropene probe
  • A kind of synthetic method of methylcyclopropene probe

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Embodiment 1

[0020] 1. Add 9.8g (76mmol) trimethylsilylpropynyl alcohol and 10.9mL (38mmol) lithium aluminum hydride into 200mL tetrahydrofuran, stir at 0°C for 16 hours, add 5mL saturated ammonium chloride aqueous solution to quench the reaction, and then extract with ether for 3 Once, the organic phase was washed with a saturated NaCl aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain trimethylsilylpropenol; 12g (92mmol) trimethylsilylpropenol, 30g (110mmol) triphenylchloromethane, 1.1 g (9.2mmol) of 4-dimethylaminopyridine and 14.8mL (18.4mmol) of pyridine were added to 200mL of dichloromethane, stirred at room temperature for 12 hours, and then 50mL of 1mol / L hydrochloric acid was added, followed by washing with saturated NaCl aqueous solution, dichloromethane After extraction, drying over anhydrous sodium sulfate, and concentration under reduced pressure, compound 2 was obtained with a yield of 75%.

[0021] 2. Dissolve 4.3g (11.5m...

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Abstract

The invention discloses a synthesis method of a methylcyclopropene probe, and belongs to the technical field of small organic molecule fluorescent probes. The method includes the steps that 3-(trimethylsilyl)-2-propyn-1-ol serves as the raw material and is subjected to a reduction and hydroxyl protection reaction, a cyclopropane intermediate is constructed through a gem-dibromocarbene cycloaddition reaction, and then the target molecular methylcyclopropene probe can be obtained through methylation, deprotection and trimethylsilyl removal. According to the synthesis method, the mode of synthesizing the methylcyclopropene probe by constructing the cyclopropane intermediate through the gem-dibromocarbene cycloaddition reaction is adopted for the first time, reaction raw materials are easy to obtain, cost is low, the product yield is high, and the method has good application prospects.

Description

technical field [0001] The invention belongs to the technical field of synthesis of small organic molecule probes, and in particular relates to a synthesis method of a methylcyclopropene probe. Background technique [0002] Cells are the basic units that make up living organisms. The main life activities of cells are regulated by nucleic acids (DNA, RNA), so observing the changes of nucleic acids in cells can analyze the status of cell proliferation, differentiation, aging and apoptosis, and further study the metabolism of the whole organism. Bioorthogonal reaction probes are a new research tool developed in recent years, and have been successfully applied to label cellular proteins, polynucleotides, lipids and glycans in living cells and animals. [0003] Compared with the reaction of azide / alkyne, the bioorthogonal reaction of methylcyclopropene and S-tetrazine has the advantage of fast reaction rate, and its second-order reaction kinetic constant k 2 13M -1 the s -1 ,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/56C09K11/06
CPCC07D233/56C09K11/06C09K2211/1007C09K2211/1044
Inventor 杨俊陈蕾杜作灵黄治炎
Owner SHAANXI NORMAL UNIV
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