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Hexaacyl reductive cercosporin photocatalyst, and preparation method and application thereof

A methyl and ethyl technology, applied in the field of catalyst preparation and organic synthesis, can solve the problem of low photoactivity of cercosporine, and achieve the effect of low cost, simple method and easy availability of raw materials

Active Publication Date: 2020-10-30
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In order to solve the above-mentioned problem of low photoactivity of cercosporin, the present invention provides a hexaacyl-reductive cercosporin photocatalyst, which uses cercosporin as a raw material to directly generate hexaacyl Reducing cercosporin, the reaction system in the present invention has high reaction efficiency, and the prepared catalyst can catalyze and realize photochemical reactions such as the reduction and coupling of halogenated hydrocarbons

Method used

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  • Hexaacyl reductive cercosporin photocatalyst, and preparation method and application thereof
  • Hexaacyl reductive cercosporin photocatalyst, and preparation method and application thereof
  • Hexaacyl reductive cercosporin photocatalyst, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] [Example 1] Preparation of Hexaacetyl Reductive Cercosporine

[0047]

[0048] The reaction formula of this example is as shown above, and the specific reaction method is: cercosporin (20 mg), acetic anhydride (400 μL), magnesium powder (30 mg), N,N-dimethyl-4-aminopyridine ( 50 mg) and a stirring bar were added into the reaction vessel, and reacted for 2 hours under nitrogen protection. After the reaction was completed, acetic anhydride (400 μL) was added again, and the reaction was continued for 2 hours. After the reaction was completed, 20 mL of dichloromethane was added to the reaction liquid, and then filtered, and the obtained filtrate was washed three times with 10 mL of distilled water. Finally, the organic phase was dried by adding anhydrous magnesium sulfate, and the filtrate was obtained by suction filtration, and concentrated using a rotary evaporator. Quickly separate with 200-300 mesh silica gel column chromatography, the eluent used is methanol / dichl...

Embodiment 2

[0051] [Example 2] Preparation of hexaisobutyryl cercosporine

[0052]

[0053]The reaction formula of this example is shown above, and the specific reaction method is: mix cercosporin (20mg), isobutyric anhydride (500μL), magnesium powder (30mg), N,N-dimethyl-4-aminopyridine (50 mg) and a stirring bar were added into the reaction vessel, and reacted under nitrogen protection for 2 hours. After the reaction was completed, isobutyric anhydride (500 μL) was added again, and the reaction was continued for 2 hours. After the reaction was completed, 20 mL of dichloromethane was added to the reaction liquid, and then filtered, and the obtained filtrate was washed three times with 10 mL of distilled water. Finally, the organic phase was dried by adding anhydrous magnesium sulfate, and the filtrate was obtained by suction filtration, and concentrated using a rotary evaporator. Quickly separate by 200-300 mesh silica gel column chromatography, the eluent used is methanol / dichlorom...

Embodiment 3

[0056] [Example 3] Preparation of hexa-n-butyryl cercosporine

[0057]

[0058] The reaction formula of this example is shown above, and the specific reaction method is: cercosporin (20 mg), butyric anhydride (500 μL), magnesium powder (30 mg), N,N-dimethyl-4-aminopyridine ( 50 mg) and a stirring bar were added into the reaction vessel, and reacted for 2 hours under nitrogen protection. After the reaction was completed, butyric anhydride (500 μL) was added again, and the reaction was continued for 2 hours. After the reaction was completed, 20 mL of dichloromethane was added to the reaction liquid, and then filtered, and the obtained filtrate was washed three times with 10 mL of distilled water. Finally, the organic phase was dried by adding anhydrous magnesium sulfate, and the filtrate was obtained by suction filtration, and concentrated using a rotary evaporator. Quickly separate by 200-300 mesh silica gel column chromatography, the eluent used is methanol / dichloromethan...

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Abstract

The invention discloses a hexacyloyl reductive cercosporin photocatalyst and preparation and application thereof, belonging to the technical field of preparation methods and organic synthesis of catalysts. The preparation method comprises the following steps: adding anhydride into a mixture of cercosporin, a reducing agent and alkali, carrying out stirring at room temperature for 1-3 hours, addinganhydride, continuing reacting for 1-3 hours, and carrying out suction filtration, extraction, concentration and column chromatography purification to obtain the catalyst. The catalyst provided by the invention can catalyze reduction, coupling and other photochemical reactions of halogenated hydrocarbons, and has strong reaction activity and industrialization prospects.

Description

technical field [0001] The invention relates to a hexacyl reducing cercosporin photocatalyst and its preparation and application, and belongs to the technical field of catalyst preparation methods and organic synthesis. Background technique [0002] Cercosporine is a naturally occurring perylenequinone compound. Cercosporine absorbs light energy under light and produces active oxygen: singlet oxygen ( 1 o 2 ) and superoxide radicals (O 2 .- ). Therefore, it can be used as a new class of phototherapeutic drugs, has broad application prospects in photodynamic therapy, and can be used as a photocatalyst in photocatalytic reactions. [0003] However, since the light-absorbing ability and redox ability of cercosporin are in the middle, in order to improve the catalytic activity of these compounds, it is necessary to modify the structure of cercosporin, thereby improving its light-absorbing ability and redox ability, and can better Catalyze organic reactions. However, there...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D321/10B01J31/02B01J37/16C07C67/317C07C69/78C07C253/30C07C255/53C07C255/54C07C255/55C07C303/40C07C311/21A61K41/00
CPCC07D321/10B01J31/0209B01J37/16C07C67/317C07C253/30C07C303/40A61K41/0057C07C2531/02B01J2231/64B01J2231/4283B01J2231/4288B01J35/39C07C69/78C07C255/53C07C255/54C07C255/55C07C311/21
Inventor 饶义剑袁振波张艳刘昌梅李敏
Owner JIANGNAN UNIV
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