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Preparation of 3-(3,4-dihydroxyphenyl)-acrylic acid 2-(3,4-dihydroxyphenyl)-ethyl ester and derivative phenyl acrylic acid phenyl alkyl ester compound

A technology of phenylalkenyl phenylacrylate and compounds, which is applied in the field of caffeic acid 3, phenylalkenyl phenylacrylate compounds, and can solve the problems of difficult separation of target compounds, many reaction by-products, and low yield

Inactive Publication Date: 2009-08-05
张治针
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Chinese patent application (publication number CN1879672A) also discloses the method for preparing caffeic acid 3,4-dihydroxyphenethyl ester under the catalysis of coupling reagent dicyclohexylcarbodiimide (DDC), but this reaction by-product is many, The target compound is difficult to separate and the yield is low
In addition, the research on CADPE derivatives has not been reported

Method used

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  • Preparation of 3-(3,4-dihydroxyphenyl)-acrylic acid 2-(3,4-dihydroxyphenyl)-ethyl ester and derivative phenyl acrylic acid phenyl alkyl ester compound
  • Preparation of 3-(3,4-dihydroxyphenyl)-acrylic acid 2-(3,4-dihydroxyphenyl)-ethyl ester and derivative phenyl acrylic acid phenyl alkyl ester compound
  • Preparation of 3-(3,4-dihydroxyphenyl)-acrylic acid 2-(3,4-dihydroxyphenyl)-ethyl ester and derivative phenyl acrylic acid phenyl alkyl ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0162] Preparation of Meldrum's acid

[0163] Slowly add concentrated sulfuric acid to the mixture of malonic acid and acetic anhydride and keep stirring until most of the malonic acid is dissolved, then add acetone and keep the temperature at 20-25°C. The reactant was placed in a refrigerator at 4°C overnight until crystals were precipitated, and the filtered crystals were washed three times with ice water to obtain Meldrum's acid. The ratio of malonic acid, acetic anhydride, acetone and concentrated sulfuric acid used in the reaction is 1.0(mol):1.2~1.5(mol):1.1~1.3(mol):5~8(ml).

[0164] 1 H-NMR (MeOH-d 4 , 600MHz) δ 1.77 (6H, s, -CH 3 ), 3.85 (2H, s, -CH 2 -);

[0165] 13 C-NMR (MeOH-d 4 , 150MHz) δ 27.7 (q, -CH 3 ), 37.0(t, -CH 2 -), 107.6 (s, O-C-O), 165.7 (s, -C=O).

Embodiment 2

[0167] Preparation of CADPE: the synthetic route is shown in the appendix figure 1

[0168] 1) Preparation of 3,4-dihydroxyphenylacetic acid methyl ester: 3,4-dihydroxyphenylacetic acid (336.3 grams, 2.0mol) was dissolved in 4000mL of anhydrous methanol, and gradually added thionyl chloride ( 174.0 mL, 2.4 mol) and stirred for 15 minutes, then left at room temperature for 7-8 hours without constant stirring. The reactant was concentrated under reduced pressure to obtain a residue, and the residue was eluted with a mixed solvent of cyclohexane and ethyl acetate (4:1) through silica gel column chromatography. (TLC) detects each component under the ultraviolet light, will contain 3, after the eluent of 4-dihydroxyphenylacetic acid methyl ester is combined, reclaim solvent and obtain 3, 4-dihydroxyphenylacetic acid methyl ester (332.2 grams, yield 91.2%).

[0169] 1 H-NMR (MeOH-d 4 , 600MHz) δ 3.45 (2H, s, H-7), 3.64 (3H, s, OCH 3 ), 6.55 (1H, dd, J=2.0 / 8.0Hz, H-6), 6.69 (1...

Embodiment 3

[0184] Preparation of 2-(3,4-diacetoxyphenyl)ethyl 3-(3,4-diacetoxyphenyl)-allylic acid ester

[0185] Dissolve 3,4-dihydroxyphenethyl caffeic acid (prepared in Example 2, 1.0 g) in a mixed solvent (50 mL) of pyridine and acetic anhydride (2:1), leave it at room temperature overnight, add a small amount of distilled water, and wait for the reaction The residue was naturally cooled and concentrated under reduced pressure to obtain a residue. The residue was separated and purified by silica gel column chromatography (eluted with a mixed solvent of cyclohexane and ethyl acetate) to obtain the target compound (1.39 g).

[0186] The molecular formula of this compound is C 25 h 24 o 10 , Colorless powder, soluble in methanol, ethyl acetate and chloroform.

[0187] 1 H-NMR data (MeOH-d 4 , 600MHz) δ 2.19, 2.20, 2.21, 2.22 (each 3H, s, OAc-3, 4, 3′, 4′), 2.96 (2H, t, J=6.8Hz, H-7′), 4.36 (2H , t, J=6.8Hz, H-8'), 6.42(1H, d, J=15.9Hz, H-8), 7.03(1H, d, J=8.0Hz, H-5), 7.12(1H, d,...

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Abstract

The invention discloses a method for preparing a benzolene propionic acid benzene alkyl ester compound, particularly a method for preparing a caffeic acid 3,4-dihydroxyl phenethyl ester. The preparation method has the advantages of single reaction product obtained in each step, less byproducts, easy separation and purification, high yield of target products and suitability for the industrialized production.

Description

technical field [0001] The invention belongs to the field of pharmacy, and relates to a preparation method of phenylalkane phenylpropionate compounds, in particular 3,4-dihydroxyphenethyl caffeic acid. Background technique [0002] Amani MD et al.Phytochemistry, 2000; 55: 927-931 disclosed for the first time that a new phenylalkenyl phenylacrylate compound, caffeic acid 3,4-dihydroxyphenethyl ester (chemical name: 3-(3,4-dihydroxyphenyl)-allylic acid 2-(3,4-dihydroxyphenyl)ethyl ester, referred to as CADPE), and its chemical structure, but its biological activity is not disclosed. [0003] Chinese patent application (publication number CN1879672A) discloses that caffeic acid 3,4-dihydroxyphenethyl ester has antitumor activity, and when used in combination with traditional chemotherapeutic drugs, caffeic acid 3,4-dihydroxyphenethyl ester can also significantly increase the effect of chemotherapy. The efficacy of drugs and reduce the toxicity of chemotherapy drugs. [0004] ...

Claims

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Application Information

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IPC IPC(8): C07C67/03C07C67/08C07C67/14C07C69/732C07C69/734C07C69/73A61P35/00
Inventor 张治针
Owner 张治针
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