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A kind of multi-substituted 10-hydroxyphenanthrene and its derivatives and its synthesis method

A synthesis method and technology of hydroxyphenanthrene are applied in pharmaceutical chemical intermediates and related chemical fields, and can solve the problems of difficult preparation of substrates, many reaction steps, environmental pollution, etc., and achieve easy products, short synthesis routes, and wide substrates. Effect

Inactive Publication Date: 2021-06-29
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many reaction steps in the above method, the substrate is difficult to obtain, and there are defects in the scope of the substrate and selectivity, and most of them need to use transition metals as catalysts, and there are many defects such as environmental pollution.
In the last few steps of drug synthesis, the use of transition metals is often avoided to prevent the impact on product activity testing, so its application is limited

Method used

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  • A kind of multi-substituted 10-hydroxyphenanthrene and its derivatives and its synthesis method
  • A kind of multi-substituted 10-hydroxyphenanthrene and its derivatives and its synthesis method
  • A kind of multi-substituted 10-hydroxyphenanthrene and its derivatives and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1: Synthesis of ethyl 10-hydroxyphenanthrene-9-carboxylate (1a)

[0051]

[0052] The method for synthetic formula (1) compound comprises the steps:

[0053] Step 1: Add tetrakis(triphenylphosphine)palladium (0.3mmol, 346.7mg) and anhydrous potassium carbonate (9mmol, 1.24g) into the three-necked flask. After sealing, exhaust the air in the bottle and fill it with nitrogen. Repeat once. Then add 2'-bromoacetophenone (3 mmol, 405 μL), a mixture of phenylboronic acid (3.6 mmol, 435 mg) dissolved in 3 mL of ethanol, and 12 mL of toluene saturated with nitrogen into the three-necked flask. The reaction mixture was refluxed at 110° C. for 11 hours to obtain the intermediate product biphenylphenone. almost completely converted. Separation and purification by silica gel column (petroleum ether: ethyl acetate = 100:1).

[0054] Step 2: Add 10 mL of anhydrous tetrahydrofuran to a three-necked flask, then add sodium hydride (dispersed in kerosene, content: 60%, 8.4...

Embodiment 2

[0060] Example 2: Synthesis of ethyl 10-hydroxyphenanthrene-9-carboxylate (1a)

[0061]

[0062] The method for synthesizing the compound of formula (1) is as described in Example 1.

[0063] The method for synthetic formula (2) compound comprises the steps:

[0064] Add formula (1) compound ethyl 3-([1,1'-biphenyl]-2-yl)-3-oxopropanoate (0.25mmol, 67mg), N-bromosuccinimide (0.1mmol , 17.8mg), tert-butyl hydroperoxide (0.875mmol, 78.86mg), sodium dihydrogen phosphate dihydrate (0.25mmol, 39mg), tetrahydrofuran 2mL, sealed, and stirred at 90°C for 15 hours. After cooling to room temperature and removing the solvent under reduced pressure, 57.2 mg of the compound ethyl 10-hydroxyphenanthrene-9-carboxylate (1a) of formula (2) was obtained by separation and purification by column chromatography (petroleum ether as the eluent), with a yield of 86%.

Embodiment 3

[0065] Example 3: Synthesis of ethyl 10-hydroxyphenanthrene-9-carboxylate (1a)

[0066]

[0067] The method for synthesizing the compound of formula (1) is as described in Example 1.

[0068] The method for synthetic formula (2) compound comprises the steps:

[0069] Add formula (1) compound ethyl 3-([1,1'-biphenyl]-2-yl)-3-oxopropanoate (0.25mmol, 67mg), N-bromosuccinimide (0.1mmol , 17.8mg), bromoethylamine hydrobromide (0.1mmol, 20.5mg), tert-butyl hydroperoxide (0.875mmol, 78.86mg), sodium dihydrogen phosphate dihydrate (0.25mmol, 39mg), tetrahydrofuran 2mL , sealed, and stirred at 80°C for 15 hours. After cooling to room temperature and removing the solvent under reduced pressure, separation and purification by column chromatography (petroleum ether as the eluent) gave 61.9 mg of the compound ethyl 10-hydroxyphenanthrene-9-carboxylate (1a) of formula (2), with a yield of 93%.

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Abstract

The invention provides a kind of multi-substituted 10-hydroxy phenanthrene and its derivatives and synthetic method thereof, the method comprises: the compound of formula (1) is prepared under the effect of bromine catalyst, additive, peroxide and organic solvent of formula ( 2) compound, its general reaction formula is as follows: wherein, R 1 is hydrogen, halogen, aryl, alkyl or alkoxy, and its binding position is 3 or 4 or 5 or 6; R 2 It is hydrogen, halogen, aryl, alkyl, alkoxy or ester group, and its binding position is 2' or 3' or 4' or 5' or 6'; EWG is cyano, methoxy Formyl, ethoxyformyl or N-phenylformamido. The method of the invention has the advantages of short synthesis route, simple starting material, mild reaction condition, cheap catalyst and no pollution, wide range of substrates and easy separation of products.

Description

technical field [0001] The invention belongs to the field of pharmaceutical and chemical intermediates and related chemical technologies, and specifically relates to a multi-substituted 10-hydroxyphenanthrene and its derivatives and a green synthesis method thereof. Background technique [0002] Polycyclic aromatic hydrocarbons are the basic skeleton of organic molecules and are widely used in the field of chemistry. Organic optoelectronic materials containing polycyclic aromatic hydrocarbons have received extensive attention. Materials containing phenanthrene or phenanthrene derivatives have attracted much attention due to their high photothermal stability, and are widely used in the fields of pigments and optoelectronic materials. At the same time, due to the π-π stacking effect, the skeleton of the polycyclic system can make the overall structure more stable and can also be used to synthesize ligands, which can be used in medicine by combining with biological macromolecu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/333C07C69/94C07D471/04
CPCC07C45/68C07C67/00C07C67/333C07C69/94C07D471/04C07C69/738C07C49/784
Inventor 王彬江雅婷
Owner NANKAI UNIV
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