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Synthesis method of trifluoroacetic acid dihydroisoquinoline derivative and device thereof

A technology of dihydroisoquinoline trifluoroacetic acid and dihydroisoquinoline is applied in chemical instruments and methods, preparation of organic compounds, mixers, etc., and can solve the problems of low yield and purity, low safety, and economic benefits. low level issues

Pending Publication Date: 2021-09-10
HUANGHUAI UNIV
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Problems solved by technology

[0005] The object of the present invention is to provide a kind of synthetic method and the device of trifluoroacetic acid dihydroisoquinoline derivative, solve existing ID-IQ in the prior art aspect organic synthesis, its yield and purity are all lower, The price of raw materials is extremely expensive, the economic benefit is not high, the risk of high experimental operation coefficient and extremely low safety

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  • Synthesis method of trifluoroacetic acid dihydroisoquinoline derivative and device thereof
  • Synthesis method of trifluoroacetic acid dihydroisoquinoline derivative and device thereof
  • Synthesis method of trifluoroacetic acid dihydroisoquinoline derivative and device thereof

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Embodiment Construction

[0034] see Figure 1 to Figure 10 , the invention provides a kind of synthetic method of trifluoroacetic acid dihydroisoquinoline derivative, comprises the steps:

[0035] Put tryptamine (1), benzoic acid (1a) and propylphosphoric anhydride (T3P) in a 40ML microwave tube, add ethyl acetate, put it in a microwave instrument, and react at 120°C for 2 hours to generate dihydroisoquinone The first crude product of morphine (compound2);

[0036] The first crude product of dihydroisoquinoline (compound 2) obtained by the reaction is extracted and purified to obtain the finished product of dihydroisoquinoline (compound 2);

[0037] The resulting dihydroisoquinoline (compound 2) finished product, diphenylacetylene (2a), Cu(OAc) 2 、CF 3 COOAg and rhodium catalyst were placed in a three-necked flask, ethyl acetate was added, the temperature of the reaction was raised to 80° C., and the reaction was carried out for 30 minutes to obtain a small molecule fluorescent probe (ID-IQ).

[0...

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Abstract

The invention relates to the technical field of medicine preparation, in particular to a synthesis method of trifluoroacetic acid dihydroisoquinoline derivatives and a device thereof. The preparation method comprises the following steps: firstly, carrying out acid-amine condensation, namely activating benzoic acid firstly and then reacting with tryptamine, wherein propyl phosphoric anhydride is an excellent reagent for forming amide, is a good condensing agent and can convert an oxygen atom on the benzoic acid into a leaving group to react to generate dihydroisoquinoline, and by taking Cu (OAc) 2 as an oxidizing agent, constructing isoquinoline through C-H bond activation, and obtaining a synthesis route for synthesizing the trifluoroacetic acid dihydroisoquinoline derivative small-molecule fluorescent probe. The route has the advantages of simplicity in operation, lower raw material price, safety, high efficiency and higher purity of the final product.

Description

technical field [0001] The invention relates to the technical field of medicine preparation, in particular to a synthesis method and device of trifluoroacetic acid dihydroisoquinoline derivatives. Background technique [0002] The invention of dihydroisoquinoline trifluoroacetate derivatives in small molecule fluorescent probes belongs to the field of biochemistry and chemical biology detection, and specifically relates to small molecule fluorescent probes and their application in chromosome analysis and cytogenetics. [0003] The ID-IQ in the reported small molecule fluorescent probe has aggregation-induced emission characteristics (it has an aggregation-induced luminescence enhancement effect, which greatly overcomes the deficiency of fluorescence quenching caused by traditional luminescent molecules in a solid state), and is used for CP imaging. [0004] However, in terms of organic synthesis, the existing ID-IQ has low yield and purity, extremely expensive raw material ...

Claims

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Application Information

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IPC IPC(8): C07D459/00C07C53/18C07C51/41C07D471/04C09K11/06B01F13/08B01F15/06B01J19/18
CPCC07D459/00C07C53/18C07C51/412C07D471/04C09K11/06B01J19/18C09K2211/1044
Inventor 徐志崔雯雯梁思佳张兰
Owner HUANGHUAI UNIV
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