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Method for synthesizing polysubstituted dihydrofuran

A technology of dihydrofuran and synthesis method, which is applied in the field of preparation of multi-substituted dihydrofuran, can solve problems such as low utilization rate of atoms, complex operation conditions, expensive metal catalysts, etc., and achieve cheap and environmentally friendly reagents, high atom economy, Good substrate adaptability

Inactive Publication Date: 2019-05-28
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are some reports on the synthetic methods of this class of compounds, the synthetic methods of the reported documents either use expensive metal catalysts, or have complex conditions and operations, or have shortcomings such as low atom utilization, so the development is novel and in line with Synthetic methods of green chemistry are of great significance to scientific research

Method used

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  • Method for synthesizing polysubstituted dihydrofuran
  • Method for synthesizing polysubstituted dihydrofuran
  • Method for synthesizing polysubstituted dihydrofuran

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029]

[0030] 2-allyl-1,3-diphenyl-1,3-propanedione (52.8mg, 0.2mmol), elemental iodine (25.4mg, 0.1mmol) and tert-butyl hydroperoxide (51.4mg, 0.4mmol, 70% aqueous solution) was added to the reaction flask, and finally 2ml of acetonitrile was added, and then reacted at room temperature for 12h. After the reaction, the compound 1 (56.7 mg) was separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 50:1), and the yield was 72.7%.

[0031] Product characterization: white solid; m.p.104-106°C; 1 H NMR (500MHz, CDCl 3 )δ / ppm=7.46-7.44(dd, J=1.2Hz, 8.4Hz, 2H), 7.24-7.16(m, 4H), 7.09-7.04(dd, J=7.5Hz, 15Hz, 2H), 4.90-4.85 (m,1H),3.53-3.46(m,3H),3.10-3.05(dd,J=7Hz,15.4Hz,1H).

Embodiment 2

[0033]

[0034] 2-allyl-1,3-bis(4-methoxyphenyl)-1,3-propanedione (64.8mg, 0.2mmol), elemental iodine (25.4mg, 0.1mmol) and tert-butyl Hydrogen peroxide (51.4mg, 0.4mmol, 70% aqueous solution) was added to the reaction flask, and finally 2ml of acetonitrile was added, and then reacted at room temperature for 12h. After the reaction, the compound 2 (65.9 mg) was separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 20:1), and the yield was 73.2%.

[0035] Product characterization: colorless oily liquid; 1 H NMR (500MHz, CDCl 3 )δ=7.53-7.51(dt, J=2Hz, 8.9Hz, 2H), 7.23-7.21(dt, J=2Hz, 8.9Hz, 2H), 6.65-6.61(m, 4H), 4.87-4.81(m, 1H),3.74(s,3H),3.72(s,3H),3.48-3.46(d,J=5.8Hz,2H),3.45-3.43(t,J=5.3Hz,10Hz,1H),3.06-3.01 (dd,J=7Hz,15.4Hz,1H).

Embodiment 3

[0037]

[0038] 2-allyl-1,3-bis(4-methylphenyl)-1,3-propanedione (58.4mg, 0.2mmol), elemental iodine (25.4mg, 0.1mmol) and tert-butyl per Hydrogen oxide (51.4mg, 0.4mmol, 70% aqueous solution) was added to the reaction flask, and finally 2ml of acetonitrile was added, and then reacted at room temperature for 12h. After the reaction, the compound 3 (58.6 mg) was separated by column chromatography (eluent: petroleum ether / ethyl acetate volume ratio 20:1), and the yield was 70.1%.

[0039] Product characterization: colorless oily liquid; 1 H NMR (500MHz, CDCl3 )δ=7.41-7.39(d, J=8.2Hz, 2H), 7.14-7.12(d, J=8.2Hz, 2H), 6.92-6.88(m, 4H), 4.88-4.82(m, 1H), 3.48 -3.47(d, J=5.8Hz, 2H), 3.46-3.43(t, J=5.3Hz, 10Hz, 1H), 3.07-3.03(dd, J=7Hz, 15.4Hz, 1H), 2.24(s, 3H ),2.23(s,3H).

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Abstract

The invention discloses a novel method for synthesizing a polysubstituted dihydrofuran compound. The method for synthesizing the polysubstituted dihydrofuran compound comprises the following steps that an olefinic dicarbonyl compound shown in the formula (I), an iodine source and an oxidizing agent are mixed in a solvent, after reacting is performed at the room temperature for 8-12 h, a reaction solution is subjected to post-treatment to obtain a dihydrofuran compound shown in the formula (II); the ratio of the amount of feeding materials of the olefinic dicarbonyl compound shown in the formula (I) to the iodine source to the oxidizing agent is 1 to 0.5-1.1-2.5; and the oxidizing agent is tert-butyl hydroperoxide or hydrogen peroxide. The method for synthesizing the polysubstituted dihydrofuran compound directly uses the olefinic dicarbonyl compound as a raw material to carry out an intramolecular cyclization reaction; the whole process does not require a metal catalyst, the metal residue is avoided, the reaction operation is simple, the reaction can be carried out under mild conditions, a good yield is obtained, and the application of the polysubstituted dihydrofuran compound in pharmaceutical synthesis is further facilitated. (Please see the specification for the formulae).

Description

(1) Technical field [0001] The present invention relates to a kind of I 2 / TBHP-mediated preparation of polysubstituted dihydrofurans. (2) Background technology [0002] Dihydrofuran compound is a very important biological structural unit, which widely exists in natural products and drug molecules, and the multi-substituted 2,3-dihydrofuran compound can be used as a synthetic building block of many complex heterocyclic compounds. [0003] For example, the dihydrofuran derivative Clerodin is a chemical component extracted from the natural neem growing in India. They have insect repellent activity and can effectively kill a variety of pests. Another example is the compound nepetaefolin extracted from the lip plant Leonotis nepetaefolia in the Caribbean. , it has strong anti-cancer and anti-tumor activity. Although there are some reports on the synthetic methods of this class of compounds, the synthetic methods of the reported documents either use expensive metal catalysts, o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/28C07D307/79C07D307/30
Inventor 李小青全积宁许响生
Owner ZHEJIANG UNIV OF TECH
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