A kind of synthetic method of 2-phenyl-3-methylbenzofuran compound

A synthesis method and technology of methylbenzene, applied in the direction of organic chemistry, etc., can solve problems such as expensive catalysts and serious environmental pollution, and achieve the effects of wide application range, high reaction yield, and simple and convenient reaction operation

Active Publication Date: 2021-07-23
SHENYANG PHARMA UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0016] The technical problem solved by the present invention is to overcome the shortcomings of expensive catalysts and serious environmental pollution in the prior art, and provide a kind of 3-benzofuran methyl phenyl ether compound as the substrate for the first time without the need for catalysts and solvents by adding Silica gel as an additive can reduce the reaction temperature and increase the reaction yield. A new method for the synthesis of 2-phenyl-3-methylbenzofuran compounds through rearrangement reaction

Method used

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  • A kind of synthetic method of 2-phenyl-3-methylbenzofuran compound
  • A kind of synthetic method of 2-phenyl-3-methylbenzofuran compound
  • A kind of synthetic method of 2-phenyl-3-methylbenzofuran compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Substrate 1 (1 mmol) was dissolved in mesitylene (2 mL), the reaction mixture was heated to 180 ° C, and stirred for 4 hours. After the reaction was completed, the target product a was separated by flash column chromatography with a yield of 35 %. Its reaction equation is:

[0031]

[0032] The spectral data of product a is: 1 H NMR (600MHz, CDCl 3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [M+H] + 543.2166, Found 543.2173.

Embodiment 2

[0034] Substrate 1 (1 mmol) was dissolved in toluene (2 mL), ZnCl was added 2 (0.2mmol, 27mg), the reaction mixture was heated to 140°C and stirred for 4 hours. After the reaction was completed, the target product a was separated by flash column chromatography with a yield of 40%. Its reaction equation is:

[0035]

[0036] The spectral data of product a is: 1 H NMR (600MHz, CDCl3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [M+H] + 543.2166, Found 543.2173.

Embodiment 3

[0038] Substrate 1 (1 mmol) was dissolved in dichloromethane (2 mL), silica gel (1 g) was added, dichloromethane was evaporated to dryness by distillation under reduced pressure, the reaction mixture was heated to 140° C., and the reaction was stirred for 4 hours. After the reaction was completed, The target product a was separated by flash column chromatography with a yield of 75%. Its reaction equation is:

[0039]

[0040] The spectral data of product a is: 1 H NMR (600MHz, CDCl 3 )δ7.46(d, J=7.4Hz, 2H), 7.42(d, J=7.1Hz, 2H), 7.39(t, J=8.4Hz, 5H), 7.33(m, 2H), 7.25(m, 5H), 7.08(d, J=2.2Hz, 1H), 6.97(dd, J=8.5, 2.2Hz, 1H), 6.32(d, J=2.2Hz, 1H), 6.29(d, J=2.2Hz, 1H), 5.93(s,1H), 5.12(s,2H), 5.04(s,2H), 5.02(s,2H), 2.09(s,3H); 13 C NMR (150MHz, CDCl 3 )δ161.7,158.6,157.3,156.7,155.6,143.9,137.1,136.8,136.7,128.8,128.7,128.6,128.3,128.1,127.8,127.7,127.6,127.1,124.1,119.7,115.8,112.2,100.4,97.3,94.7 ,94.2,70.8,70.6,70.30,9.26; HRMS(ESI):m / z:Calcd.for C 36 h 30 o 5 [...

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Abstract

The invention belongs to the technical field of medicinal chemistry and provides a method for synthesizing 2-phenyl-3-methylbenzofuran compound. The general reaction formula is as follows. The reaction substrates of this method are 3-benzofuran methyl phenyl ethers with different substitutions, and the reaction is promoted by stirring and heating under catalyst-free and solvent-free conditions. This reaction can be rearranged to generate a series of 2-phenyl-3-methylbenzofuran compounds, and has the characteristics of simple operation, wide application range, few by-products, high yield and green reaction.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and relates to a synthesis method of 2-phenyl-3-methylbenzofuran compounds. It specifically relates to a method for generating 2-phenyl-3-methylbenzofuran compounds through rearrangement of 3-benzofuran methyl phenyl ether with specific substitution under the condition of no catalyst and no solvent. Background technique [0002] 2-Phenyl-3-methylbenzofuran is a class of natural products isolated from plants with diverse structures and various activities. Due to its wide range of biological activities, it has attracted the attention of many scientists and can be used as a drug A class of lead compounds developed. A variety of natural products with 2-phenyl-3-methylbenzofuran as the backbone have various biological activities and pharmacological effects, such as antibacterial activity (J.Nat.Prod.2006,69,121-124.), antioxidant activity (Biosci.Biotechnol.Biochem.2001,65,1402-1405.), an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/80
CPCC07D307/80
Inventor 刘永祥程卯生汤迎湛江崇国肖建勇林斌
Owner SHENYANG PHARMA UNIVERSITY
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