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Preparation method of 4-selenomethoxynaphthalene

A technology of selenomethoxynaphthalene and methoxynaphthalene, which is applied in the direction of organic chemistry to achieve the effects of low reaction cost, high yield and short reaction time

Pending Publication Date: 2021-12-14
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

To the best of our knowledge, there are no other reports on the synthesis of 4-selenomethoxynaphthalene

Method used

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  • Preparation method of 4-selenomethoxynaphthalene
  • Preparation method of 4-selenomethoxynaphthalene
  • Preparation method of 4-selenomethoxynaphthalene

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Add 1-methoxynaphthalene (0.2mmol), 1,2-diphenyldiselenide (0.4mmol), PIFA (0.2mmol) and DCM (2.0mL) respectively into a 4mL reaction flask, and stir at room temperature. TLC tracking detection reaction. After 10 minutes, the reaction was complete. Water and dichloromethane were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with dichloromethane, all organic layers were combined and washed twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (5% ethyl acetate petroleum ether solution) to obtain 50.1 mg of product with a yield of 80%. The reaction process is shown in the following formula:

[0026]

[0027] Carry out nuclear magnetic resonance analysis to the product that present embodiment prepares: 1 H NMR (400MHz, CDCl 3 )δ8.36–8.31(m,2H),7.90(d,J=8.0Hz,1H),7.55–7.49(m,2H),7.23–7.21(m,2H),7.17–7.12(m,3H) ,6.80(d,J=8.0Hz,1H),4.04(s...

Embodiment 2

[0029] Add 1-methoxynaphthalene (0.2mmol), 1,2-diphenyldiselenide (0.4mmol), PIFA (0.4mmol) and DCM (2.0mL) respectively into a 4mL reaction flask, and stir at room temperature. TLC tracking detection reaction. After 5 hours, the reaction was complete. Water and dichloromethane were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with dichloromethane, all organic layers were combined and washed twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (5% ethyl acetate petroleum ether solution) to obtain 50.1 mg of product with a yield of 80%. The reaction process is shown in the following formula:

[0030]

Embodiment 3

[0032] Add 1-methoxynaphthalene (0.2mmol), 1,2-diphenyldiselenide (0.24mmol), PIFA (0.4mmol) and DCM (2.0mL) respectively into a 4mL reaction flask, and stir at room temperature. TLC tracking detection reaction. After 1.5 hours, the reaction was complete. Water and dichloromethane were added to the reaction system, and the organic layer was separated. The aqueous layer was washed twice with dichloromethane, all organic layers were combined and washed twice with water. The organic layer was dried over anhydrous sodium sulfate, concentrated, and separated by column chromatography (5% ethyl acetate petroleum ether solution) to obtain 32.6 mg of product with a yield of 52%. The reaction process is shown in the following formula:

[0033]

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Abstract

The invention discloses a preparation method of a 4-selenomethoxynaphthalene compound, which comprises the following step: in a DCM solvent, synthesizing the 4-selenomethoxynaphthalene at room temperature by using PIFA as an oxidizing agent and 1-methoxynaphthalene and a diselenide compound as substrates. The reaction raw materials are cheap and easy to obtain, the preparation method is simple, the PIFA serves as the oxidizing agent, the reaction cost is low, the reaction time is short, the yield is high, operation is easy, and the method is suitable for synthesis of different types of 4-selenomethoxynaphthalene compounds. The method disclosed by the invention can be used for synthesizing a series of 4-selenomethoxynaphthalene, and the synthesized product not only can be used as an intermediate compound, but also can be used for further constructing a complex active compound; and meanwhile, the compound has great pharmaceutical activity potential.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for preparing 4-selenomethoxynaphthalene through regioselective selenization. Background technique [0002] Naphthalene and its derivatives are distributed as core skeletons in a large number of natural products and pharmaceutically active molecules, which are widely used in synthetic chemistry, medicinal chemistry, agricultural chemistry and materials science. Selenium is a very important element in the human body, and selenium-containing compounds are widely distributed in biologically active compounds, pharmaceutical compounds, natural products and functional materials. Due to the important applications of naphthalene derivatives and selenium-containing compounds in different fields, the synthesis of novel selenonaphthalene derivatives has attracted the interest of synthetic chemists. Direct carbon-hydrogen bond functionalization is considered to be a direct, atom-ec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C391/02C07D213/60
CPCC07C391/02C07D213/60
Inventor 宋增强陈瑶吕梦霞高怡
Owner WENZHOU MEDICAL UNIV
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