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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 high production cost and complex process, and achieve the effects of low production cost, simple process and high purity

Inactive Publication Date: 2010-06-23
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

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1: Synthesis of tri-substituted benzopyran cyclic ether

[0023] Add 1.0g (7.94mmol) of phloroglucinol, 2.2g (31.75mmol) of butenone, 2.0g of anhydrous magnesium sulfate to a 50ml round bottom flask, then add 30ml of anhydrous methanol, stir at 0℃ to dissolve, Then slowly add 2.56g (15.88mmol) of p-toluenesulfonic acid, continue to stir the reaction, let it slowly rise to room temperature, and react for 8h. After the reaction is tracked by TLC, 10ml of saturated NH4Cl is added at 0℃ to stop the reaction. 100ml EtOAc, saturated NH 4 Wash with Cl (1×10ml), saturated brine (2×10ml), anhydrous MgSO 4 Drying, concentration under reduced pressure. Column chromatography to obtain 2.85g of white solid, yield 95%. mp 134-135℃; 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] Add 1.0g (7.94mmol) of phloroglucinol, 1.3g (18.26mmol) of butenone, 1.5g of anhydrous magnesium sulfate to a 50ml round bottom flask, then add 30ml of anhydrous methanol, stir at 0℃ to dissolve, Then slowly add 1.43 g (7.94 mmol) of p-toluenesulfonic acid, continue to stir the reaction, let it slowly rise to room temperature, and react for 8 hours. After the reaction is tracked by TLC, saturated NH is added at 0°C. 4 Cl 10ml, stop the reaction, add 100ml EtOAc, saturated NH 4 Wash with Cl (1×10ml), saturated brine (2×10ml), anhydrous MgSO 4 Drying, concentration under reduced pressure, column chromatography to obtain 1.68 g of white solid, yield 72%. mp 170-171℃, 1 H NMR(CDCl 3 , 400MHz) δ: 5.997 (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 disubstituted...

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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 a synthesis technology of a class of marine fungal metabolites Xyloketals compounds. Background technique [0002] Xyloketals compounds are a series of ketal compounds with new skeletons and rare structures isolated from the South China Sea marine fungus Xylarias sp. (#2508) in 2001 by our research team. The structural formula is: [0003] [0004] The initial activity study showed that Xyloketals series compounds showed strong L-calcium ion channel inhibitory activity (0.2μg / ml, inhibition rate 60%), and had a certain structure-activity relationship. And also showed good acetylcholinesterase inhibitory activity. In view of their unique structure and good biological activity, they have attracted widespread attention at home and abroad, and these compounds have been listed in the Hot off the press in Nat. Prod. Res. 2001. It is particularly important that research groups such as Germany and Canada have obtained their national funding...

Claims

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Application Information

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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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