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3,4,5-trisubstituted-5-hydroxy-2(5hydro)-furaldone compound and its synthesis and use

A synthetic method and technology of furanone are applied in 3 fields to achieve the effects of convenient post-processing, simple reaction equipment and high reaction yield

Inactive Publication Date: 2004-09-08
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Application Information

AI Technical Summary

Problems solved by technology

However, the method for obtaining 3,4,5-trisubstituted-5-hydroxyl-2(5-hydrogen)-furanone compounds through ring-closing reaction and γ-hydroxylation reaction from 2,3-alkenic acid has not been reported

Method used

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  • 3,4,5-trisubstituted-5-hydroxy-2(5hydro)-furaldone compound and its synthesis and use
  • 3,4,5-trisubstituted-5-hydroxy-2(5hydro)-furaldone compound and its synthesis and use
  • 3,4,5-trisubstituted-5-hydroxy-2(5hydro)-furaldone compound and its synthesis and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025]

[0026] (1) 3-methyl-4-iodo-5-phenyl-5-hydroxy-2(5hydrogen)-furanone:

[0027] Take a reaction tube, add 2-methyl-4-phenyl-2,3-butadienoic acid (86mg, 0.494mmol) in 2mL THF solution, add LiOAc·2H 2 O (63mg, 0.62mmol) and I 2 (250mg, 0.98mmol), stirred at room temperature for 3 hours, added 1ml of DMF to the reaction system, protected the reaction system with an oxygen balloon at 1 atmosphere, heated the oil bath at 40°C for 36 hours, extracted the reaction solution with ether, and washed it with 5% Na 2 S 2 o 3 washed with brine, anhydrous Na 2 SO 4 Drying, column chromatography (petroleum ether: ethyl ether = 3.5: 1) purified to obtain 136mg of 3-methyl-4-iodo-5-phenyl-5-hydroxyl-2(5hydrogen)-furanone, the yield 87%. Solid, melting point 150-152°C (acetone / n-hexane); 1 H NMR (300MHz, CD 3 COCD 3 )δ7.60-7.38 (m, 5H), 7.25-7.15 (bs, 1H), 1.94 (s, 3H); 13 C NMR (75.4MHz, CD 3 COCD 3 )δ169.9, 137.9, 137.1, 130.2, 129.3, 127.3, 127.2, 107.2, 13.2; MS (m / z) 3...

Embodiment 2

[0029]

[0030] (2) 3-n-propyl-4-iodo-5-phenyl-5-hydroxy-2(5hydrogen)-furanone:

[0031] Take a reaction tube, add 2-n-propyl-4-phenyl-2,3-butadienoic acid (101 mg, 0.50 mmol) in 2 mL THF solution, add LiOAc·2H 2 O (65mg, 0.64mmol) and I 2 (257mg, 1.01mmol), stirred at room temperature for 3 hours, added 1ml of DMF to the reaction system, protected the reaction system with an oxygen balloon at 1 atmosphere, heated the oil bath at 40°C for 34 hours, extracted the reaction solution with ether, and washed it with 5% Na 2 S 2 o 3 washed with brine, anhydrous Na 2 SO 4 Drying, column chromatography (petroleum ether: ether = 3.5: 1) purified to obtain 143mg of 3-n-propyl-4-iodo-5-phenyl-5-hydroxyl-2(5hydrogen)-furanone, producing The rate is 83%. liquid; 1 H NMR (300MHz, CD 3 COCD 3 )δ7.62-7.35(m, 5H), 7.22(s, 1H), 2.34(t, J=7.7Hz, 2H), 1.73-1.52(m, 2H), 0.96(t, J=7.4Hz, 3H ); 13 C NMR (75.4MHz, CD 3 COCD 3 )δ169.0, 139.6, 137.3, 129.5, 128.6, 127.3, 126.5, 106.4, 29...

Embodiment 3

[0033]

[0034] (3) 3-benzyl-4-iodo-5-phenyl-5-hydroxy-2(5hydrogen)-furanone:

[0035] Take a reaction tube, add 2-benzyl-4-phenyl-2,3-butadienoic acid (100mg, 0.40mmol) in 2mL THF solution, add LiOAc·2H 2 O (55mg, 0.54mmol) and I 2 (124mg, 0.49mmol), stirred at room temperature for 3 hours, added 1ml of DMF to the reaction system, protected the reaction system with an oxygen balloon at 1 atmosphere, heated the oil bath at 40°C for 8 hours, extracted the reaction solution with ether, and washed it with 5% Na 2 S 2 o 3 washed with brine, anhydrous Na 2 SO 4 Drying, column chromatography (petroleum ether: ether = 3.5: 1) purified to obtain 113mg of 3-benzyl-4-iodo-5-phenyl-5-hydroxyl-2(5hydrogen)-furanone, yield 72%. Solid, melting point 151-155°C (acetone / n-hexane); 1 H NMR (300MHz, CD 3 COCD 3 )δ7.60-7.18 (m, 10H), 3.72 (s, 2H), 2.86 (s, 1H); 13 C NMR (75.4MHz, CD 3 COCD 3 )δ170.0, 139.9, 138.4, 138.1, 130.7, 130.1, 129.9, 129.7, 129.4, 128.2, 127.6, 107.8, 34.3...

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Abstract

The present invention relates to one kind of 3, 4, 5-trisubstitute-5-hydroxy-2(5 hdryo)-furaldone compound and its synthesis and use. The synthesis process has easy-to-obtain material, simple operation, convenient post-treatment and high yield, and is easy to industrial application. The compound may be used in synthesizing compound with gamma-hydroxyl group and gamma-butenic lactone ring and possessing the effects of resisting variation, killing bacteria, resisting tumor and exciting.

Description

technical field [0001] The invention relates to a novel synthesis method and application of a class of 3,4,5-trisubstituted-5-hydroxyl-2(5hydrogen)-furanone compounds. In the method, 3,4,5-trisubstituted-5-hydroxyl-2(5hydrogen)-furanone compound can be obtained through ring closure reaction and γ-hydroxylation reaction starting from 2,3-alkenic acid. This method is easy to operate, and the γ-hydroxylation reaction mainly uses oxygen as the oxidant. As an important molecular block, this compound is widely present in the framework of natural products. It may have certain physiological activities and can also be used to further synthesize some compounds containing γ-hydroxy γ-butenolide rings. Some compounds, these compounds containing γ-hydroxy-γ-butenolide ring have strong physiological activities, such as anti-mutation, bactericide, anti-tumor, stimulant and so on. Background technique [0002] Since the γ-hydroxy-γ-butenolide ring skeleton unit exists in some important na...

Claims

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Application Information

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IPC IPC(8): C07D307/60
Inventor 麻生明吴滨马志超
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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