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Synthetic method of Xyloketals compounds

A synthesis method and compound technology, applied in organic chemistry and other directions, can solve the problems of complex process and high production cost, and achieve the effect of simple process, low production cost and product purification.

Inactive Publication Date: 2012-06-06
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These synthetic methods have the problems of complicated process and high production cost.

Method used

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  • Synthetic method of Xyloketals compounds
  • Synthetic method of Xyloketals compounds
  • Synthetic method of Xyloketals compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Embodiment 1: the synthesis of three substituted benzopyran ring ethers

[0023] In a 50ml round bottom flask, add 1.0g (7.94mmol) phloroglucinol and 2.2g (31.75mmol) butenone, 2.0g anhydrous magnesium sulfate, then add 30ml of anhydrous methanol, stir at 0°C to dissolve it, Then slowly add 2.56g (15.88mmol) of p-toluenesulfonic acid, continue to stir the reaction, let it slowly rise to room temperature, react for 8h, TLC after the reaction is completed, add saturated NH4Cl 10ml at 0°C to stop the reaction, add 100ml EtOAc, saturated NH 4 Cl (1×10ml), washed with saturated brine (2×10ml), anhydrous MgSO 4 It was dried and concentrated under reduced pressure. Column chromatography gave 2.85 g of white solid with a yield of 95%. mp 134-135°C; 1 H NMR (CDCl 3 , 400MHz) δ: 3.255(s, 3H), 3.242(s, 3H), 3.237(s, 3H), 2.641(m, 6H), 2.058(m, 3H), 1.746(m, 3H), 1.524(s , 6H), 1.518(s, 3H);

Embodiment 2

[0025] 1. Synthesis of disubstituted benzopyran cyclic ether (2)

[0026] In a 50ml round bottom flask, add 1.0g (7.94mmol) phloroglucinol and 1.3g (18.26mmol) butenone, 1.5g anhydrous magnesium sulfate, then add 30ml anhydrous methanol, stir at 0°C to dissolve it, Then slowly add 1.43g (7.94mmol) of p-toluenesulfonic acid, continue to stir the reaction, let it slowly rise to room temperature, react for 8h, TLC after the completion of the tracking reaction, add saturated NH at 0°C 4 Cl 10ml, stop the reaction, add 100ml EtOAc, saturated NH 4 Cl (1×10ml), washed with saturated brine (2×10ml), anhydrous MgSO 4 It was dried and concentrated under reduced pressure. Column chromatography gave 1.68 g of white solid with a yield of 72%. mp 170-171°C, 1 H NMR (CDCl 3 , 400MHz) δ: 5.977(s, 1H), 5.167(s, 1H), 3.270(s, 3H), 3.260(s, 3H), 2.649(m, 2H), 2.604(m, 2H), 2.101(m , 1H), 2.069(m, 1H), 1.792(m, 1H), 1.730(m, 1H), 1.542(s, 3H), 1.518(s, 3H);

[0027] 2. Protection of disubst...

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Abstract

The invention discloses a synthetic method of Xyloketals compounds, which comprises the steps of: 1, synthesizing chroman; 2, protecting phenolichydroxyl of the chroman; 3, generating chromene; 4, generating ketal; and 5, cyclizing radical. The Xyloketals compounds are generated by using phloroglucinol as raw materials and absolute methanol as a solvent and comprising the steps of adding anhydrous magnesium sulfate, reacting with methyl vinyl ketone under the mediation of lewis acid to generate benzopyran cycloether, separating methanol from the benzopyran cycloether to generate benzocycloenol ether, ketalizing and finally cyclizing the radical. The invention has simple process, easy purification of the Xyloketals compounds, high purity, low production cost and suitability for industrialized production. The synthetic method can realize quantitative conversion, and the Xyloketals compounds can be used for the next reaction without being purified. The invention synthesizes the Xyloketals B with the total yield of 38.68 percent.

Description

technical field [0001] The invention relates to the synthesis technology of a class of marine fungal metabolite Xyloketals compounds. Background technique [0002] Xyloketals are a series of ketal compounds with new skeletons and rare structures isolated by our research team from the marine fungus Xylarias sp. (#2508) in the South China Sea in 2001. The structural formula is: [0003] [0004] Preliminary activity studies have shown that Xyloketals series compounds exhibit strong L-calcium ion channel inhibitory activity (0.2 μg / ml, inhibition rate 60%), and have a certain structure-activity relationship. But also showed good acetylcholinesterase inhibitory activity. In view of its rare structure and good biological activity, it has aroused widespread attention at home and abroad, and these compounds were listed in Nat.Prod.Res.2001 publication hotspot (Hot off the press). What is especially important is that research groups such as Germany and Canada have received thei...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C07D493/22C07D493/04
Inventor 庞冀燕林永成许忠良李艺英卢秉泰
Owner SUN YAT SEN UNIV
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