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Method for synthesizing phenanthrene and derivatives thereof

A synthetic method and derivative technology, applied in the field of organic compound synthesis, can solve the problems of being unable to achieve environmental protection, unable to ensure sustainable development, and consuming large energy, and achieve good substrate adaptability and high yield , the effect of mild reaction conditions

Active Publication Date: 2019-03-05
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In industry, philippines are generally obtained from direct distillation of petroleum, which not only cannot be environmentally friendly, but also cannot guarantee sustainable development
At the same time, a large amount of energy is consumed in the process of rectification, so it is very important to find a simple and quick method for synthesizing phenanthrene compounds

Method used

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  • Method for synthesizing phenanthrene and derivatives thereof
  • Method for synthesizing phenanthrene and derivatives thereof
  • Method for synthesizing phenanthrene and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033]

[0034] Add 0.3mmol 2-phenylcinnamaldehyde, 0.6mmol sodium trifluoromethanesulfonate, 0.6mmol potassium persulfate and 0.06mmol silver nitrate into a 15mL thick-walled pressure-resistant reaction tube, and then add 3mL acetonitrile (dry) as a solvent. Next, it was magnetically stirred at 90° C. for 24 hours. After being cooled to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then the product phenanthrene was separated by column chromatography to obtain a pure product (petroleum ether / ethyl acetate = 100:1 as eluent). The material was a white solid in 76% yield.

[0035] Characterization data: 1 H NMR (500MHz, CDCl3): δ8.69(d, J=8.0Hz, 2H), 7.90-7.80(d, J=8.0Hz, 2H), 7.74(s, 2H), 7.67-7.63(t, J = 16.0Hz, 2H), 7.61-7.57(t, J=16.0Hz, 2H). 13 CNMR (125M Hz, CDCl3) δ132.08, 130.33, 128.61, 128.06, 126.95, 126.60, 122.69.

Embodiment 2

[0037]

[0038] Add 0.3mmol 2-phenylcinnamaldehyde, 0.3mmol sodium trifluoromethanesulfonate, 0.6mmol potassium persulfate and 0.06mmol silver nitrate into a 15mL thick-walled pressure-resistant reaction tube, and then add 3mL acetonitrile (dry) as a solvent. Next, it was magnetically stirred at 90° C. for 24 hours. After being cooled to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then the product phenanthrene was separated by column chromatography to obtain a pure product (petroleum ether / ethyl acetate = 100:1 as eluent). The material was a white solid in 56% yield.

[0039] Characterization data: 1 H NMR (500MHz, CDCl3): δ8.69(d, J=8.0Hz, 2H), 7.90-7.80(d, J=8.0Hz, 2H), 7.74(s, 2H), 7.67-7.63(t, J = 16.0Hz, 2H), 7.61-7.57(t, J=16.0Hz, 2H). 13 CNMR (125M Hz, CDCl3) δ132.08, 130.33, 128.61, 128.06, 126.95, 126.60, 122.69.

Embodiment 3

[0041]

[0042] Add 0.3mmol 2-phenylcinnamaldehyde, 0.6mmol sodium trifluoromethanesulfonate, 0.6mmol iodobenzene diacetate and 0.06mmol silver nitrate into a 15mL thick-walled pressure-resistant reaction tube, then add 3mL acetonitrile (dry) as solvent . Next, it was magnetically stirred at 90°C for 24 hours. After cooling to room temperature, two spoonfuls of column chromatography silica gel (100-200 mesh) were added to the reaction solution, and the solvent was removed by distillation under reduced pressure, and then the product phenanthrene was separated by column chromatography to obtain a pure product of phenanthrene (with petroleum ether / ethyl acetate Esters = 100:1 as eluent). The material was a white solid, 65% yield.

[0043] Characterization data: 1 H NMR (500MHz, CDCl3): δ8.69(d, J=8.0Hz, 2H), 7.90-7.80(d, J=8.0Hz, 2H), 7.74(s, 2H), 7.67-7.63(t, J = 16.0Hz, 2H), 7.61-7.57(t, J=16.0Hz, 2H). 13 CNMR (125M Hz, CDCl3) δ132.08, 130.33, 128.61, 128.06, 126.95, 12...

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Abstract

The present invention provides a method for synthesizing phenanthrene and derivatives thereof represented by a formula (III) or (IV). The method is characterized in that a substituted 2-phenylcinnamaldehyde compound represented by a formula (I) or 2-thiophenylcinnamaldehyde represented by a formula (II) is taken as an initial substance, under the effect of a silver catalyst, an oxidant, a basic substance and a solvent, a reaction is carried out at 60 DEG C-100 DEG C for 12-36 hours, the reaction solution is separated and purification is carried out, so that corresponding phenanthrene and derivatives thereof represented by the formula (III) or (IV) are obtained. The synthesis method of the invention has the characteristics of small environmental hazard, mild reaction conditions, simple operation and the like.

Description

technical field [0001] The invention relates to a method for synthesizing organic compounds, in particular to a method for preparing synthetic phenanthrene and its derivatives. Background technique [0002] Phenanthrene is a very important class of condensed ring compounds. This kind of compound can be oxidized to produce phenanthrene quinone, and the biphenyl acid obtained by oxidation can be used to make polyester resin and alkyd resin; phenanthrene oxidation can obtain phthalic anhydride, cyclohexanone, and phenol; In papermaking, phenanthrene can be used as pulp antifogging agent; in medicine, phenanthrene can synthesize alkaloids; in the dye industry, phenanthrene can be used to produce 2-aminophenanthrenequinone, benzoantrone, sulfur vat dyes, etc.; phenanthrene can be used at high temperature Hydrogenation at high pressure yields hydrophenanthrene, a fuel for advanced jet aircraft. [0003] In industry, Philippine is generally obtained from direct distillation of pet...

Claims

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Application Information

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IPC IPC(8): C07C1/207C07C15/30C07C17/361C07C25/22C07C41/18C07C43/20C07D333/74
CPCC07C1/2076C07C17/361C07C41/18C07C2527/24C07C2527/25C07D333/74C07C15/30C07C25/22C07C43/20
Inventor 刘运奎郑立孟杨欢
Owner ZHEJIANG UNIV OF TECH
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