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A kind of synthetic method of β-aryl-α-naphthol compound

A synthesis method and compound technology, applied in the field of synthesis of β-aryl-α-naphthol compounds, can solve the problems of rare metal resources, low price of precious metal resources, low atom economy, lengthy synthesis steps, etc., and achieve a wide range of substrates , High atomic utilization rate, environment-friendly effect

Active Publication Date: 2022-03-01
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This current synthetic approach often requires substrate prefunctionalization, which requires lengthy synthetic steps and is not atom-economical.
Some aryl organometallic reagents, halides and halide analogues are unstable or difficult to synthesize or relatively toxic, and the reaction conditions are harsh. Therefore, a simple, environmentally friendly, and efficient synthesis is sought β -Aryl- α -A new method for naphthol compounds, which is of great significance
[0003] At present, noble metal catalysts (especially platinum group metals: ruthenium, rhodium, palladium catalysts, etc.) are widely used in laboratory and industrial production, but precious metal resources are scarce and expensive, and have relatively high toxicity

Method used

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  • A kind of synthetic method of β-aryl-α-naphthol compound
  • A kind of synthetic method of β-aryl-α-naphthol compound
  • A kind of synthetic method of β-aryl-α-naphthol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Add deoxybenzoin compound Ia (1.0 mmol) and ferric oxide (1.0 mmol) into a 10 mL round bottom flask, seal with a rubber stopper and evacuate, then use an argon balloon to replace the gas in the reaction bottle, so that the bottle is filled with argon gas. Finally, the solvent xylene (3.0 mL) and alkyne compound IIa (2.0 mmol) were added to the reaction flask under argon atmosphere, and the reaction mixture was stirred at 135 °C for 24 h (the reaction time and temperature were determined by different bases Material decision), thin-layer chromatographic plate detection reaction, until the raw material reaction is complete. column chromatography β -Aryl- α - Naphthol compound IIIa (82% yield).

[0018]

[0019] White solid; Melting point: 103 – 104°C; 1 H NMR (400 MHz, DMSO) δ 9.44 (s, 1H), 8.42 (d, J = 8.3 Hz, 1H), 7.81 (d, J = 8.3 Hz, 1H), 7.68 (d, J = 7.5 Hz, 2H),7.56 – 7.56 (m, 1H), 7.51 – 7.39 (m, 8H), 7.37 – 7.31 (m, 2H); 13 C NMR (100MHz, DMSO) δ 148.6...

Embodiment 2

[0021] Add deoxybenzoin compound Ib (1.0 mmol) and ferric oxide (1.0 mmol) into a 10 mL round bottom flask, seal with a rubber stopper and evacuate, then use an argon balloon to replace the gas in the reaction bottle, so that the bottle is filled with argon gas. Finally, the solvent xylene (3.0 mL) and alkyne compound IIb (2.0 mmol) were added to the reaction flask under argon atmosphere, and the reaction mixture was stirred at 135 °C for 24 h (the reaction time and temperature were determined by different bases Material decision), thin-layer chromatographic plate detection reaction, until the raw material reaction is complete. column chromatography β -Aryl- α - Naphthols IIIb (72% yield).

[0022]

[0023] 6'-methoxy-4'-phenyl-[1,2'-binaphthalen]-1'-ol (IIIb): white solid; melting point: 83 – 84 o C; 1 H NMR (400 MHz, CDCl 3 ) δ 8.31 (d, J = 9.2 Hz, 1H), 7.94 (d, J = 6.4 Hz, 2H), 7.78 (d, J = 8.3 Hz, 1H), 7.62 – 7.50 (m, 5H), 7.47 – 7.44 (m,3H), 7.40 – 7.30 (m, ...

Embodiment 3

[0025] Add deoxybenzoin compound Ic (1.0 mmol) and ferric oxide (1.0 mmol) into a 10 mL round bottom flask, seal with a rubber stopper and evacuate, then use an argon balloon to replace the gas in the reaction bottle, so that the bottle is filled with argon gas. Finally, the solvent xylene (3.0 mL) and alkyne compound IIc (2.0 mmol) were added to the reaction flask under argon atmosphere, and the reaction mixture was stirred at 135 °C for 24 h (the reaction time and temperature were determined by different bases Material decision), thin-layer chromatographic plate detection reaction, until the raw material reaction is complete. column chromatography β -Aryl- α - Naphthol compound IIIc (77% yield).

[0026]

[0027] White solid; melting point: 117 – 118 o C; 1 H NMR (400 MHz, DMSO) δ 9.33 (s, 1H), 8.38 (d, J = 8.2 Hz, 1H), 7.81 (d, J = 8.2 Hz, 1H), 7.67 (d, J = 7.2 Hz, 2H),7.58 – 7.39 (m, 6H), 7.35 (t, J = 7.4 Hz, 1H), 7.28 (s, 1H), 7.06 (d, J = 8.6Hz, 2H), 3....

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Abstract

The invention discloses a β -Aryl- α A synthetic method for naphthol compounds, which uses simple and easy-to-obtain deoxybenzoin compounds and alkyne compounds as raw materials for one-step synthesis β -Aryl- α ‑Naphthols. The method of the present invention realizes the construction of an aromatic ring through domino dehydrogenation, which is simple and efficient β -Aryl- α ‑Naphthol compounds, compared with traditional synthetic methods, the raw materials used are cheap, the operation is simple, the environment is friendly, the yield is high, the substrate adaptability is wider, the complete regioselectivity, and the atom utilization rate are high.

Description

technical field [0001] The present invention relates to a β -Aryl- α -A method for synthesizing naphthol compounds, belonging to the field of organic synthesis. Background technique [0002] β -Aryl- α -Naphthol compounds are an important class of organic compounds, which widely exist in natural products and biologically active molecules. as extracted from Indian cedar β -Aryl- α - Naphthol natural products, experiments have proved that such natural products have good biological activity against pathogens of tropical malaria, leishmaniasis, Chagas disease and African sleeping sickness. because β -Aryl- α - The unique structural characteristics of naphthol compounds, such compounds show excellent electrochemical and photochemical properties, and are key intermediates for the synthesis of functional materials. β -Aryl- α -Naphthol compounds are often seen in axial chiral ligands, and have been used more and more as chiral ligands in chiral catalytic reactions, and ha...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C39/14C07C37/20C07C43/23C07C41/26C07C67/31C07C69/94C07C39/40C07C39/12
CPCC07C37/20C07C41/26C07C67/31C07C2603/24C07C2523/745C07C39/14C07C43/23C07C69/94C07C39/40C07C39/12
Inventor 王永强朱雪庆
Owner NORTHWEST UNIV
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