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Synthesis method of Acrylodan and analogues thereof

A technology of acryloyl dan and a synthesis method, which is applied in the field of fluorescent probe synthesis in biochemistry, can solve the problems of expensive raw materials, many synthesis steps, complicated operations, etc., and achieves simple and easy operation, unique application prospect, and cheap and easy-to-obtain raw materials. Effect

Pending Publication Date: 2021-04-13
LANZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] These synthetic methods use perodane, which is expensive and difficult to synthesize, as the main intermediate for the synthesis of acryloyldane. There are many synthetic steps for the required reaction, complex operations, low yield, expensive raw materials, and harsh process conditions. Greatly limit the application of acryloyl dan and its analogues

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  • Synthesis method of Acrylodan and analogues thereof
  • Synthesis method of Acrylodan and analogues thereof
  • Synthesis method of Acrylodan and analogues thereof

Examples

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Effect test

Embodiment 1

[0043] (1) Compound 3-2 was synthesized by using 6-methoxy-2-acetylnaphthalene as a raw material to undergo substitution reaction with lithium dimethylamide.

[0044] Operation method: Dissolve 6-methoxy-2-acetylnaphthalene (1.0g, 5mmol) into 5mL of anhydrous N,N-dimethylformamide, add 5mL of N,N-dimethylpropenylurea, LiN(CH 3 ) 2 solution (30mmol), the reaction was reacted at room temperature for 24 hours, after the reaction was completed, the reaction solution was added to ice water, concentrated hydrochloric acid was added to adjust the reaction solution to pH 1-2 range, extracted with ethyl acetate, the aqueous phase was collected, and then added to the solution. Solid sodium hydroxide was added to the aqueous phase to make it basic, extracted with ethyl acetate, the organic phase was collected, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to obtain compound 3-2 in a yield of 81%. 1 H NMR (400MHz, CDCl 3 )δ: 8.31(s, 1H), 7.93...

Embodiment 2

[0050] (1) Compound 3-2 was synthesized by using 6-methoxy-2-acetylnaphthalene as a raw material to undergo substitution reaction with lithium dimethylamide.

[0051] Operation method: 6-methoxy-2-acetylnaphthalene (1.0 g, 5 mmol) was dissolved in 5 mL of anhydrous tetrahydrofuran, 5 mL of acetamide was added, and LiN (CH) was added under the protection of argon. 3 ) 2 solution (30mmol), the reaction was reacted at room temperature for 24 hours, after the reaction finished, the reaction solution was added to ice water, concentrated hydrochloric acid was added to adjust the reaction solution to pH 1-2 range, extracted with ethyl acetate, the water phase was collected, and then added to the solution. Solid sodium hydroxide was added to the aqueous phase to make it basic, extracted with ethyl acetate, the organic phase was collected, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to obtain compound 3-2 in a yield of 81%.

[0052] (2) Co...

Embodiment 3

[0057] (1) Compound 3-2 was synthesized by using 6-methoxy-2-acetylnaphthalene as a raw material to undergo substitution reaction with lithium dimethylamide.

[0058] Operation method: Dissolve 6-methoxy-2-acetylnaphthalene (1.0 g, 5 mmol) into 5 mL of anhydrous tetrahydrofuran, add 5 mL of N,N-dimethylpropenyl urea, and add LiN (CH) under argon protection 3 ) 2 Solution (30mmol), the reaction was reacted at room temperature for 24 hours, after the reaction, the reaction solution was added to ice water, concentrated hydrochloric acid was added to adjust the reaction solution to pH 1-2, extracted with ethyl acetate, the water phase was collected, and then added to the solution. Solid sodium hydroxide was added to the aqueous phase to make it basic, extracted with ethyl acetate, the organic phase was collected, dried over anhydrous sodium sulfate, concentrated, and subjected to column chromatography to obtain compound 3-2 in a yield of 81%.

[0059] (2) Compound 3-3 is synthesi...

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Abstract

The invention belongs to the technical field of synthesis of fluorescent probes in biochemistry, and particularly relates to an environment-sensitive fluorescent probe and a synthesis process route of Acrylodan and analogues thereof. A method comprises the following steps: taking 6-methoxy-2-acetyl naphthalene as a raw material, carrying out substitution reaction on the 6-methoxy-2-acetyl naphthalene and a lithium amide salt, carrying out addition elimination reaction on an obtained amino-substituted acetyl naphthalene product and trifluoroacetic acid, and then carrying out addition elimination reaction on the obtained amino-substituted acetyl naphthalene product and aldehydes to finally obtain the high-purity Acrylodan compound and analogues. The method has the advantages of simple synthesis steps, short reaction time, high yield, low production cost and the like, and solves the problems of complex synthesis steps, harsh synthesis conditions and expensive synthesis raw materials in original synthesis methods. The optimization and improvement of the synthetic process route of Acrylodan and analogues can greatly promote the application of the environment-sensitive probe in the field of biochemistry.

Description

Technical field: [0001] The invention relates to the technical field of fluorescent probe synthesis in biochemistry, in particular to a new method for synthesizing an environment-sensitive naphthalene fluorescent probe-acryloyl dan and its analogs (general formula I). Its general structure is as follows: [0002] [0003] where, where R 1 and R 2 Represents any combination of hydrogen, alkyl chains of 1-10 carbon atoms, alkyl chains (containing 1-10 carbon atoms) containing amine, carboxylic acid, hydroxyl functional groups at the end. [0004] Acrylodan (Formula Ia), chemical name is 6-acryloyl-2-dimethylaminonaphthalene, molecular formula C 15 H 15 NO, molecular weight 225.29, CAS registration number 86636-92-2, its structural formula is as follows: [0005] Background technique: [0006] Environmentally sensitive fluorescent probes are a class of optical probe molecules that can change their fluorescence signals with changes in the physicochemical properties ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C221/00C07C225/22
CPCC07C221/00C07C225/22
Inventor 房建国赵澜宁马迪
Owner LANZHOU UNIVERSITY
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