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Preparation method of phenanthrenequinone and derivatives of phenanthrenequinone

A derivative, the technology of phenanthrenequinone, which is applied in the field of synthesis of phenanthrenequinone and its derivatives, can solve the problems of harsh reaction conditions, harmful oxidants, complicated operation, etc., and achieve the effects of mild reaction temperature, simple operation and simple reaction

Inactive Publication Date: 2018-02-06
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are not easy to prepare, which greatly limits its development, and some oxidants used are harmful; (2) the intramolecular oxidative coupling method of dibenzoyl and 1,1'-diformylbiphenyl (for example: Tamarkin, D .; Benny, D.; Rabinovitz, M. Angew. Chem. 1984, 96, 594-5; Enders, D.; Niemeier, O. Synlett 2004, 2111-2114)
The main disadvantage of this method is that its raw materials limit the popularity of the substrate, which is not conducive to its development; (3) other methods (for example: Somai M.; Krishna B.; Xia, L.; et al Chem.Commun.2015, 51, 8592-8595; Togashi, D.M.; Nicodem, D.E. Synth. Commun. 1998, 28, 1051-1063)
This method has harsh reaction conditions, complicated operation and unfriendly environment.

Method used

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  • Preparation method of phenanthrenequinone and derivatives of phenanthrenequinone
  • Preparation method of phenanthrenequinone and derivatives of phenanthrenequinone
  • Preparation method of phenanthrenequinone and derivatives of phenanthrenequinone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Embodiment 1: take o-phenylacetophenone as raw material, prepare phenanthrenequinone

[0026]

[0027] Add 58.8mg (0.30mmol) of o-phenylacetophenone, 2.4mg (0.03mmol) of selenium powder, and 318.6mg (0.9mmol) of Selectfluor into a 25mL pressure-resistant sealed container in sequence, and then add 3mL of acetonitrile. The mixture was stirred and reacted at 80°C, followed by TLC detection, and the reaction was completed after 24 hours. The reaction solution was diluted with 10 mL of dichloromethane, and the clear liquid was obtained by filtration. After the organic solvent was evaporated, it was purified with a silica gel column, and then column chromatography (Eluant ratio: volume ratio of petroleum ether to ethyl acetate 10:1) Separation, collecting the eluate and evaporating the solvent to obtain 48 mg of reddish-brown solid phenanthrenequinone (76% yield).

[0028] Reddish-brown solid; m.p.218–220°C; IR(neat):1673(C=O)cm -1 ; 1 H NMR (400MHz, CDCl 3 ):δ8.16(dd,J...

Embodiment 2

[0029] Embodiment 2: take o-phenylacetophenone as raw material, prepare phenanthrenequinone

[0030]

[0031] Add 58.8mg (0.30mmol) of o-phenylacetophenone, 4.8mg (0.06mmol) of selenium powder, and 159.3mg (0.45mmol) of Selectfluor into a 25mL pressure-resistant sealed container in sequence, and then add 1.5mL of nitromethane. The mixture was stirred and reacted at 100°C, followed by TLC detection, and the reaction was completed after 24 hours. The reaction liquid was diluted with 10 mL of dichloromethane, and the clear liquid was obtained by filtration. After the organic solvent was evaporated, it was purified with a silica gel column, and then column chromatography (Eluant ratio: volume ratio of petroleum ether to ethyl acetate 10:1) Separation, collecting the eluate and evaporating the solvent to obtain 40 mg of reddish-brown solid phenanthrenequinone (65% yield).

[0032] Reddish-brown solid; m.p.218–220°C; IR(neat):1673(C=O)cm -1 ; 1 H NMR (400MHz, CDCl 3 ):δ8.16(dd...

Embodiment 3

[0033] Embodiment 3: take o-phenylacetophenone as raw material, prepare phenanthrenequinone

[0034]

[0035]Add 58.8mg (0.30mmol) of o-phenylacetophenone, 1.2mg (0.015mmol) of selenium powder, and 371.7mg (1.05mmol) of Selectfluor into a 25mL pressure-resistant sealed container, and then add 4.5mL of acetonitrile. The mixture was stirred and reacted at 100°C, followed by TLC detection, and the reaction was completed after 12 hours. The reaction solution was diluted with 10 mL of dichloromethane, and the clear liquid was obtained by filtration. After the organic solvent was evaporated, it was purified with a silica gel column, and then column chromatography (Eluant ratio: volume ratio of petroleum ether to ethyl acetate 10:1) separation, collecting the eluate and evaporating the solvent to obtain 44 mg of reddish-brown solid phenanthrenequinone (70% yield).

[0036] Reddish-brown solid; m.p.218–220°C; IR(neat):1673(C=O)cm -1 ; 1 H NMR (400MHz, CDCl 3 ):δ8.16(dd,J 1 =8.0...

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Abstract

The invention provides a preparation method of phenanthrenequinone and derivatives of the phenanthrenequinone. O-aryl acetophenone compounds shown as the formula (I) are used as raw materials; in an organic solvent, reaction is performed for 12 to 36h at 60 to 100 DEG C in a pressure-proof sealing tube under the effects of catalysts and oxidizing agents; obtained reaction liquid is separated and purified to prepare the phenanthrenequinone and derivatives of the derivatives shown as the formula (II); the catalysts are selenium and selenium oxide. The preparation method has the advantages that the raw materials are simple and can be easily obtained; the reaction conditions are mild; the functional group tolerance is good; the operation is simple and achieves an environment-friendly effect; anovel method for synthetizing the phenanthrenequinone containing various substituent groups is provided.

Description

technical field [0001] The invention relates to a synthesis method of phenanthrenequinone and its derivatives. Background technique [0002] Phenanthrenequinone and its derivatives are an important class of compounds, which are widely used in organic synthesis, such as the production of benzoantrone or multifunctional plant growth regulator plasticin. Phenanthrenequinone itself also has antibacterial ability. The method for industrially preparing phenanthrenequinone is to utilize the oxidation method of phenanthrene, but the oxidizing agent used in this method is potassium dichromate or concentrated sulfuric acid, which is not friendly to the environment, and the substrate popularity of this method is narrow. In recent years, many new methods for the synthesis of phenanthrenequinone have also been developed, mainly containing the following three types: (1) the oxidation method of hydrogenated phenanthrene and phenanthrene phenol (for example: Uyanik, M; Mutsuga, T.; Ishihar...

Claims

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Application Information

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IPC IPC(8): C07C46/02C07C50/16C07C50/24C07C50/34
CPCC07C46/02C07C50/16C07C50/24C07C50/34
Inventor 刘运奎张剑鲍汉扬
Owner ZHEJIANG UNIV OF TECH
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