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A kind of synthetic method of 9,10-disubstituted phenanthrene compounds

A synthetic method and compound technology, applied in 9 fields, can solve the problems of rare raw materials, complicated operation, cumbersome and complicated preparation process, etc., and achieve the effect of low raw material cost, simple operation, and easy-to-obtain raw materials

Active Publication Date: 2021-07-02
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In view of this, the main purpose of the present invention is to provide a synthetic method for 9,10-disubstituted phenanthrene compounds, which solves the problems of rare raw materials, tedious and complicated preparation process, complicated operation, poor substrate compatibility and high yield in the prior art. low problem

Method used

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  • A kind of synthetic method of 9,10-disubstituted phenanthrene compounds
  • A kind of synthetic method of 9,10-disubstituted phenanthrene compounds
  • A kind of synthetic method of 9,10-disubstituted phenanthrene compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Synthesis of 9,10-Dimethylphenanthrene

[0023] Using 2-methyl-2-phenyl-propionaldehyde as a raw material and under the joint action of iodobenzene, glycine, silver trifluoroacetate and palladium acetate catalysts to prepare 9,10-dimethylphenanthrene, its chemical reaction formula is:

[0024]

[0025] The specific steps of the method are as follows:

[0026] In air, 2-methyl-2-phenyl-propanal (0.20mmol), iodobenzene (0.5mmol), palladium acetate (0.024mmol), glycine (0.064mmol), silver trifluoroacetate (0.36mmol) Add it into a 35mL pressure tube, then add 1mL of hexafluoroisopropanol, stir at room temperature for 30min, then raise the temperature to 105°C and react for 16h. The reaction is complete as monitored by a TLC plate. The solvent is evaporated under reduced pressure and separated by column chromatography (petroleum ether: Ethyl acetate=50:1) to obtain 9,10-dimethylphenanthrene (white solid, yield 91%).

[0027] 9,10-Dimethylphenanthrene was detected by nuc...

Embodiment 2

[0032] Synthesis of 9,10-Dibutylphenanthrene

[0033] Using 2-butyl-2-phenyl-hexanal as raw material and under the joint action of iodobenzene, glycine, silver trifluoroacetate and palladium acetate catalyst, 9,10-dibutylphenanthrene was prepared, and its chemical reaction formula is :

[0034]

[0035] The specific steps of the method are as follows:

[0036] Under the condition of oxygen, 2-butyl-2-phenyl-hexanal (0.20mmol), iodobenzene (0.6mmol), palladium acetate (0.03mmol), glycine (0.12mmol), silver trifluoroacetate (0.36 mmol) into a 35mL pressure-resistant tube, then 1mL of hexafluoroisopropanol was added, stirred at room temperature for 30min, then heated to 110°C for 16h, the reaction was complete as monitored by TLC, the solvent was distilled off under reduced pressure, and separated by column chromatography (petroleum Ether: ethyl acetate = 50:1) to obtain 9,10-dibutylphenanthrene (55% yield.).

[0037] 9,10-Dibutylphenanthrene was detected by nuclear magneti...

Embodiment 3

[0042] Synthesis of 9-Ethyl-10-Methylphenanthrene

[0043] Using 2-methyl-2-phenyl-butyraldehyde as raw material and under the joint action of iodobenzene, glycine, silver trifluoroacetate and palladium acetate catalyst, 9-ethyl-10-methylphenanthrene was prepared, and its chemical reaction The formula is:

[0044]

[0045] The specific steps of the method are as follows:

[0046] In air, 2-methyl-2-phenyl-butyraldehyde (0.20mmol), iodobenzene (0.4mmol), palladium acetate (0.01mmol), glycine (0.04mmol), silver trifluoroacetate (0.2mmol) Add 1mL of hexafluoroisopropanol into a 35mL pressure-resistant tube, stir at room temperature for 40min, then raise the temperature to 90°C for 20h, monitor the completion of the reaction with a TLC plate, distill off the solvent under reduced pressure, and separate by column chromatography (petroleum ether: Ethyl acetate=50:1) to obtain 9-ethyl-10-methylphenanthrene (yield 56%).

[0047] 9-Ethyl-10-methylphenanthrene was detected by nucl...

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Abstract

The invention discloses a method for synthesizing 9,10-disubstituted phenanthrene compounds. The method is specifically as follows: the method uses the compound of molecular formula 9,10-disubstituted phenanthrene compounds with a molecular weight of 9,10-disubstituted phenanthrene compounds are obtained under the joint action of palladium catalysts; the present invention uses divalent palladium as a catalyst, and uses amino acids as the C(sp 2 )-H arylation and series reaction, one-step construction of 9,10-disubstituted phenanthrene compounds, and high yield of 9,10-disubstituted phenanthrene derivatives; the invention is simple to operate, easy to obtain raw materials, and low cost of raw materials , The reaction is efficient and the use of C-H arylation strategy effectively reduces the use of halides or pseudohalides, and the use of transient directing groups makes the reaction easier and more economical.

Description

technical field [0001] The invention belongs to the technical field of medicine synthesis, and in particular relates to a synthesis method of 9,10-disubstituted phenanthrene compounds. Background technique [0002] The structure of phenanthrene compounds is one of the most common skeletons of fused-ring aromatic hydrocarbons, which are widely used in materials science and medicinal chemistry due to their unique physical properties and biological activities. In the early days, strategies such as double carbonyl coupling and photochemical reaction had many problems such as pollution and low yield. In recent years, the cyclization reaction of biaryl derivatives has been developed to construct phenanthrene compounds, but the synthesis of biaryl derivatives and the pre-functionalization process require multi-step reactions, and there are incompatibility with some groups in the reaction process, which leads to the reaction applicability is limited. In addition, most of the phena...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C15/30C07C1/00C07C25/22C07C17/32C07C43/20C07C41/30
CPCC07C15/30C07C25/22C07C43/20C07C2531/04C07C2603/26
Inventor 周岭陈洁苟博博
Owner NORTHWEST UNIV