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Oximido dehydroabietic acid compound and synthesis method thereof

A technology of dehydroabietic acid and methyl dehydroabietic acid, applied in oxime preparation, organic chemistry, etc., to achieve simple preparation method, excellent physiological activity, and the effect of improving activity

Inactive Publication Date: 2012-10-03
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are no papers or patents describing the synthesis of 12-oximino dehydroabietic acid and 14-oximino dehydroabietic acid

Method used

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  • Oximido dehydroabietic acid compound and synthesis method thereof
  • Oximido dehydroabietic acid compound and synthesis method thereof
  • Oximido dehydroabietic acid compound and synthesis method thereof

Examples

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Effect test

Embodiment 1

[0025] Embodiment 1: the synthetic steps of (E)-12-oximino dehydroabietic acid:

[0026] A. Compound ( 1 ) (10.5 g, 0.035 mol) was dissolved in methanol (280 mL), and concentrated H 2 SO 4 (24 mL), over ten minutes, 90 ° C oil bath for about 12 hours of continuous stirring, separation and purification to obtain 9.9 g colorless transparent crystals, that is, the compound ( 2 ), yield 90.4%;

[0027] B. Compound ( 2 ) (500 mg, 1.59 mmol) was dissolved in nitrobenzene (8 mL), and aluminum trichloride (1.1 g, 8.25 mmol) and dichloromethyl methyl ether (0.19 mL, 2.07 mmol) were added successively under stirring, at room temperature Under stirring for 10 hours, separation and purification after post-treatment gave 304 mg of slightly yellowish transparent oily substance, i.e. the compound ( 3 ), yield 55.8%;

[0028] C. Compound ( 3 ) (200 mg, 0.58 mmol) was dissolved in ethanol (8 mL), and pyridine (0.13 mL) was added, followed by the dropwise addition of ethanol solution of ...

Embodiment 2

[0039] Embodiment 2: the synthetic steps of (Z)-12-oximino dehydroabietic acid:

[0040] A. Compound ( 1 ) (10.5 g, 0.035 mol) was dissolved in methanol (280 mL), and concentrated H 2 SO 4 (24 mL), over ten minutes, 90 ° C oil bath for about 12 hours of continuous stirring, separation and purification to obtain 9.9 g colorless transparent crystals, that is, the compound ( 2 ), yield 90.4%;

[0041] B. Compound ( 2) (500 mg, 1.59 mmol) was dissolved in nitrobenzene (8 mL), and aluminum trichloride (1.1 g, 8.25 mmol) and dichloromethyl methyl ether (0.19 mL, 2.07 mmol) were added successively under stirring, at room temperature Under stirring for 10 hours, separation and purification after post-treatment gave 304 mg of slightly yellowish transparent oily substance, i.e. the compound ( 3 ), yield 55.8%;

[0042] C. Compound ( 3 ) (200 mg, 0.58 mmol) was dissolved in ethanol (8 mL), and pyridine (0.13 mL) was added, followed by the dropwise addition of ethanol solution of h...

Embodiment 3

[0053] Embodiment 3: the synthetic steps of (E)-14-oximino dehydroabietic acid:

[0054] A. Compound ( 1 ) (10.5 g, 0.035 mol) was dissolved in methanol (280 mL), and concentrated H 2 SO 4 (24 mL), over ten minutes, 90 ° C oil bath for about 12 hours of continuous stirring, separation and purification to obtain 9.9 g colorless transparent crystals, that is, the compound ( 2 ), yield 90.4%;

[0055] B. Compound ( 2 ) (500 mg, 1.59 mmol) was dissolved in nitrobenzene (8 mL), and aluminum trichloride (1.1 g, 8.25 mmol) and dichloromethyl methyl ether (0.19 mL, 2.07 mmol) were added successively under stirring, at room temperature Under stirring for 10 hours, separation and purification after post-treatment gave 98 mg of slightly yellowish transparent oily substance, namely the compound ( 4 ), yield 18.0%;

[0056] C. Compound ( 4 ) (200 mg, 0.58 mmol) was dissolved in ethanol (8 mL), and pyridine (0.13 mL) was added, followed by the dropwise addition of ethanol solution of...

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Abstract

The invention relates to an oximido dehydroabietic acid compound and a synthesis method thereof. The compound has structural formulas which are shown in the specification. The compound provided by the invention has a dehydroabietic acid framework structure; and the synthesis method is an efficient and concise preparation method for preparing 12-oximido dehydroabietic acid and 14-oximido dehydroabietic acid by introducing aldehyde groups at the sites 12 and 14 and oximating the aldehyde groups.

Description

technical field [0001] The invention relates to an oxime dehydroabietic acid compound and a synthesis method thereof. Background technique [0002] Dehydroabietic acid, also known as dehydroabietic acid or dehydroabietic acid, is a natural diterpene resin acid. my country is rich in rosin resources, and the annual output of disproportionated rosin reaches hundreds of thousands of tons, so dehydroabietic acid has great development value and potential. Dehydroabietic acid is an excellent raw material for the synthesis of other derivatives. Dehydroabietic acid contains two reactive groups, carboxyl group and aromatic ring, and various modifications can be carried out through the reaction of these two groups. [0003] Catechol compounds containing tricyclic diterpenes in natural products have been widely used and studied deeply because of their good antioxidant activity and significant physiological activity. Dehydroabietic acid is a tricyclic diterpenoid compound with variou...

Claims

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Application Information

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IPC IPC(8): C07C251/48C07C249/08
Inventor 崔永梅王鹤云吕遐师郝增帅林海霞
Owner SHANGHAI UNIV
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