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A pinoresinol precursor and a synthetic method thereof

A technology of pinoresin and precursors, applied in the field of organic chemical synthesis, to achieve the effects of easy acquisition, reduced reaction cost, and simple and easy-to-obtain raw materials

Inactive Publication Date: 2017-07-14
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The invention discloses a method of directly using samarium metal to promote the one-step reaction of vanillin and maleate in the presence of cuprous iodide and molecular sieves to prepare a dilactone-type pinoresin precursor. This method has not yet been reported in domestic and foreign literature

Method used

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  • A pinoresinol precursor and a synthetic method thereof
  • A pinoresinol precursor and a synthetic method thereof

Examples

Experimental program
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Effect test

example 1

[0016] Add 3 g of freshly prepared samarium metal powder, 3.9 g of cuprous iodide, and 6.8 g of potassium iodide in turn into the reaction vessel, then add 100 mL of tetrahydrofuran that has been dehydrated and dried in advance, and stir magnetically. Add 3 g of vanillin, 5 mL of dimethyl maleate, and 5 g of 4A molecular sieves. The color of the reaction solution became dark within 2h, and the reaction was continued for 8h. Add 50mL dilute hydrochloric acid (2mol L -1 ) to terminate the reaction, the reaction mixture was post-treated to obtain a crude product, and then further purified through a chromatographic column to obtain a dilactone-type pinoresin precursor with a yield of 80%.

[0017] White solid, melting point>250℃. 1 HNMR (500MHz, CDCl 3 )δppm 9.85(s,2H),7.09-6.94(m,2H),6.87-6.75(m,4H),6.03-6.02(m,1H),5.97(m,1H),3.96-3.93(m,6H ),3.77-3.74(m,2H); 13 C NMR (125MHz, CDCl 3 )δppm 177.6, 173.2, 139.4, 137.6, 137.1, 136.5, 133.1, 132.2, 130.0, 126.8, 125.9, 124.0, 1...

example 2

[0019] According to the method of Example 1, using 3A molecular sieve instead of 4A molecular sieve, a dilactone-type pinoresin precursor was obtained with a yield of 73%.

example 3

[0021] According to the method of Example 1, diethyl maleate was used instead of dimethyl maleate to obtain a dilactone-type pinoresin precursor with a yield of 61%.

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Abstract

The invention discloses a method of preparing a dilactone type pinoresinol precursor under the existence of cuprous iodide and a molecular sieve through directly promoting a one-step reaction between vanillin and maleate by utilizing metal samarium. The vanillin and the maleate are mixed and dissolved, under stirring, into tetrahydrofuran dehydrated and dried in advance, and then the metal samarium powder, the cuprous iodide powder and the molecular sieve are added into the mixture in order. A reaction system is performed under a condition of absolutely no water. The mixture is stirred at room temperature until the reaction is finished. The obtained reaction mixed solution is subjected to solvent recovery, and a residue is subjected to after-treatment and chromatographic column separation to obtain a high-purity product of the dilactone type pinoresinol precursor.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a method for conveniently preparing a dilactone-type pinoresin precursor by using vanillin and maleate. Background technique [0002] Pinoresin, a natural product, is widely found in the root of Araliaceae Sessilis Acanthopanax, sesame seeds or seed oil of Flaxaceae, Paulownia tomentosa Xybe of Scrophulariaceae and other plants. One of the active ingredients of various medicinal materials [Document 1: Liu Donglei, Xu Suixu, Wang Weifang. Journal of Chinese Pharmaceutical Sciences 1998, 7, 49-51; Document 2: Leng Guang, Wang Haiou, Ming Dongsheng. Journal of Shanxi Medical University, 2003, 3, 227 -228; Literature 3: Wang Jinmei. Henan University, 2008 master's thesis]. Pinoresin has strong antioxidant activity, and has various physiological activities such as lowering serum cholesterol, regulating lipid metabolism, stabilizing blood pressure and anticancer i...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 齐燕刘永军
Owner QINGDAO UNIV OF SCI & TECH
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