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Polysubstitution hydrogenated naphthalene compounds, producing method and uses of the same

A compound, hydrogenated naphthalene technology, applied in the direction of organic chemistry, etc., can solve the problem of quality can not be guaranteed

Inactive Publication Date: 2011-05-11
CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some lactone compounds containing decahydronaphthalene structure (Ger.1057108 (1959)) have a good civet fragrance, but these compounds are mainly prepared by cycloaddition of terpene compounds (such as myrcene, etc.) and dienophiles. Stereo and regioselective problems, often a mixture of several compounds, the quality cannot be guaranteed

Method used

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  • Polysubstitution hydrogenated naphthalene compounds, producing method and uses of the same
  • Polysubstitution hydrogenated naphthalene compounds, producing method and uses of the same
  • Polysubstitution hydrogenated naphthalene compounds, producing method and uses of the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1 Using oleanolic acid as raw material to synthesize compounds 1 and 2

[0046] 1) Preparation of Compound 4:

[0047]

[0048] Dissolve 5 g of compound 3 in 20 mL of dry chloroform, add 10 mL of anhydrous methanol and 1 mL of concentrated sulfuric acid, and then heat it to slowly reflux for 6 h. After cooling, the reaction mixture was successively washed with water, saturated sodium bicarbonate and saturated brine, and dried over anhydrous magnesium sulfate. The desiccant was filtered off and distilled under reduced pressure, and the obtained solid was dried in vacuo. Then it was dissolved in 20 mL of dry chloroform, 5 mL of dry pyridine and 3 mL of acetic anhydride were added, and stirred at room temperature for 12 h. The reaction mixture was washed successively with water, saturated aqueous sodium bicarbonate solution, water and saturated brine. After drying over anhydrous magnesium sulfate and distilling under reduced pressure, a white solid was obtain...

Embodiment 2

[0073] Example 2 Using maslinic acid as raw material to synthesize compounds 1 and 2

[0074] Using the operation steps described in implementation 1, using maslinic acid as raw material, the compounds 1 and 2 obtained are as follows:

[0075]

Embodiment 3

[0076] Example 3 Using ursolic acid as raw material to synthesize compounds 1 and 2

[0077] Adopt as implementing the described operating steps of 1, take ursolic acid as raw material, the compound 1 and 2 that obtain are as follows:

[0078]

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Abstract

The present invention belongs to the field of organic chemistry and relates to a multi-substituted hydrogenated naphthalene compound, a synthesis method and use thereof. In particular, the present invention relates to a chiral multi-substituted ten-hydrogen and / or eight-hydrogen naphthalene compound, the synthetic method and uses. The present invention aims to provide a chiral multi-substituted ten-hydrogen and / or eight-hydrogen naphthalene compound; the oleanane-type or usu-type five-ring triterpenoid compound is used as a raw material for preparing the compound. The multi-substituted ten-hydrogen and / or eight-hydrogen naphthalene compound of the present invention can be used for synthesis of drugs or spices containing multi-hydrogen naphthalene fragments and the analogues. The method of the present invention is simple and easy, low in cost, high in production rate, and can realize industrialization.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to multi-substituted hydrogenated naphthalene compounds, their synthesis method and application, in particular to chiral multi-substituted decahydro or / and octahydronaphthalene compounds and their synthesis method and application. Background technique [0002] Multi-substituted decahydro and / or octahydronaphthalene structural fragments are important structural units of many natural products such as triterpenes, diterpenes, sesquiterpenes and their analogs. Most of these compounds have biological activities such as anti-tumor, herbicidal, anti-fungal, anti-microbial, anti-leukemic and anti-inflammatory. Multi-substituted decahydro and / or octahydronaphthalene itself also has good fragrance and fragrance-fixing properties. [0003] These compounds containing decalin and / or octahydronaphthalene structures are widely distributed in plants, but their content is low and it is difficult to ex...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/91C07C49/637C07C69/757C07C50/02
Inventor 杨海君张国林
Owner CHENGDU INST OF BIOLOGY CHINESE ACAD OF S
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