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Phenanthrene compound and preparation technology thereof

A preparation process and compound technology, which is applied in the field of phenanthrene and its derivatives, can solve problems such as complex processes, use of a large amount of raw materials, and difficulty in scaling phenanthrene derivatives, and achieve the effect of simple synthesis steps

Active Publication Date: 2016-12-21
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] It can be seen from the above formula that the synthesis of 3,6-dichlorophenanthrene requires a complex process, and a large amount of raw materials need to be used in the synthesis process, which causes a burden on the environment
Therefore, from an economic point of view, the current method for synthesizing phenanthrene derivatives with specific groups is difficult to scale up

Method used

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  • Phenanthrene compound and preparation technology thereof
  • Phenanthrene compound and preparation technology thereof
  • Phenanthrene compound and preparation technology thereof

Examples

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preparation example Construction

[0040] The present invention also provides a preparation process of a phenanthrene compound, which is obtained by reacting a first raw material with a second raw material in an organic solvent in the presence of an alkali and a palladium source. There is preferably a ligand in the reaction process, the molar ratio of the first raw material and the second raw material is 1-4:1-4, preferably 1:2, and the molar ratio of the first raw material and the base is 1-4:1- 4, preferably 1:2.

[0041] Among them, the first raw material is X is selected from one of halogens, preferably bromine, Y is selected from chlorine, fluorine, cyano or trifluoromethyl, and the second raw material is norbornadiene

[0042] The alkali is potassium acetate KOAC, sodium acetate NaOAC, potassium carbonate K 2 CO 3 , Cesium Carbonate Cs 2 CO 3 , Potassium tert-butoxide t-BuOK, potassium methoxide CH 3 OK, a kind of cesium fluoride CsF.

[0043] Palladium source is palladium acetate Pd (OAC) 2 , Pd(OCH 2 CF 3 )...

Embodiment 1

[0060] This embodiment provides a phenanthrene compound, the phenanthrene compound is 3,6-dichlorophenanthrene, and its structural formula is:

[0061] The reaction equation for preparing 3,6-dichlorophenanthrene is:

[0062]

[0063] The specific preparation process of 3,6-dichlorophenanthrene is:

[0064] Add the first raw material: 191mg (1mmol) p-bromochlorobenzene into a 25ml reaction tube The second raw material: 2ml (2mmol) norbornadiene, palladium source: 11mg (5.0mol%) Pd(OAC) 2 As a catalyst, base: 196mg (2mmol) KOAC, organic solvent: 3ml DMAc, seal the test tube, use N 2 Replace 4 times to obtain the first solution;

[0065] React in the first solution at 110°C for 24 hours, after the reaction is completed, a second solution is obtained;

[0066] Add 15ml water to the second solution and use 20mlCH respectively 2 Cl 2 Extract 3 times, combine the organic phases obtained from each extraction to obtain a third solution;

[0067] The third solution was passed through the column...

Embodiment 2

[0074] In this embodiment, a phenanthrene compound is provided, and the phenanthrene compound is The specific preparation process is:

[0075] Add the first raw material to the 25ml reaction tube: 1mmol The second raw material: 1.5ml (1.5mmol) norbornadiene, palladium source: 11mg (5.0mol%) Pd(OCH) 2 CF 3 ) 2 As a catalyst, base: 1.5mmol) NaOAC, organic solvent: 3ml DMAC, seal the test tube, use N 2 Replace 3 times to obtain the first solution;

[0076] React the first solution at 110°C for 20 hours, after the reaction is completed, the second solution is obtained;

[0077] Add 15ml water to the second solution and use 20mlCH respectively 2 Cl 2 Extract 4 times, combine the organic phases obtained from each extraction to obtain a third solution;

[0078] The third solution was passed through the column with a volume ratio of petroleum ether:ethyl acetate=8:1 to obtain a white solid.

[0079] The NMR detection results of the synthesized product in this example are as follows:

[0080] 1...

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Abstract

The invention discloses a preparation technology of a phenanthrene compound, and relates to the field of phenanthrene and derivatives thereof. The preparation technology comprises the steps that on the condition that an alkali source and an palladium source exist, in an organic solvent, a first raw material shown as the formula (please see the formula in the description) and norbornadiene which are low in price and easy to obtain are adopted, reacting is conducted, a compound with a parent body of norbornadiene is obtained, molecular cyclopentadiene is removed through heating, and the target phenanthrene compound shown as the formula (please see the formula in the description) is obtained. The raw materials of the preparation method are easy to obtain, the synthetic steps are simple, and the preparation method is suitable for producing phenanthrene derivatives with special groups on a large scale. The invention further provides the phenanthrene compound which can be applied to the pharmaceutical field and the industrial field.

Description

Technical field [0001] The invention relates to the field of phenanthrene and its derivatives, and particularly relates to a phenanthrene compound and a preparation process thereof. Background technique [0002] Due to the potential pharmaceutical activity of phenanthrene and its derivatives, and its application in new materials, phenanthrene and its derivatives have attracted much attention. For example, phenanthrene quinone obtained by oxidation of phenanthrene, and bifenic acid obtained by oxidation can be used to make polyester resins and alkyd resins; phenanthrene oxidation can also produce phthalic anhydride, cyclohexanone, and phenol; in the paper industry, phenanthrene can be used as Pulp antifogging agent; in the field of medicine, phenanthrene can synthesize alkaloids; in the dye industry, phenanthrene can produce 2-aminophenanthrenequinone, sulfur vat dyes, etc.; phenanthrene can be hydrogenated under high temperature and pressure to obtain hydrogen phenanthrene, which...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C17/26C07C25/22C07C253/00C07C255/52C07C22/08C07D471/04
CPCC07C17/26C07C253/00C07D471/04C07C25/22C07C255/52C07C22/08
Inventor 付海燕浩涛涛陈华
Owner SICHUAN UNIV
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