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Synthesis method of poly-substituted oxacycloheptatriene-3(2H) ketone compounds

A technology for oxepatriene and ketone compounds, which is applied in the field of synthesis of multi-substituted oxepatriene-3-one compounds, and can solve the problems of difficult preparation of starting materials, harsh reaction conditions, troublesome operation, etc. problems, to achieve the effect of convenient preparation, simple reaction conditions, and easy separation and purification

Inactive Publication Date: 2013-05-08
HENAN NORMAL UNIV
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0004] The technical problem solved by the present invention is to provide a kind of multi-substituted oxepatriene-3(2 H )-The synthetic method of ketone compound, this method has overcome current oxepin-3(2 H )-ketones need expensive catalysts and reagents in the synthesis, the preparation of starting materials is not easy, the reaction conditions are harsh, and the problems such as troublesome operation are a kind of synthetic multi-substituted oxepatriene-3(2 H )-A new method for ketone compounds, the method does not need expensive catalysts and reagents, the starting materials are simple and easy to prepare, the reaction conditions are mild and the operation is simple

Method used

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  • Synthesis method of poly-substituted oxacycloheptatriene-3(2H) ketone compounds
  • Synthesis method of poly-substituted oxacycloheptatriene-3(2H) ketone compounds
  • Synthesis method of poly-substituted oxacycloheptatriene-3(2H) ketone compounds

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Embodiment 1

[0016]

[0017] In a 10 mL round bottom flask was charged 1a (1 mmol, 144 mg), ethyl 4-chloroacetoacetate (1.2 mmol, 197.5 mg) and 3 mL of acetonitrile, followed by potassium carbonate (1 mmol, 138 mg). After stirring at room temperature for 1 hour, the reaction was quenched by adding 2 mL of saturated ammonium chloride solution, extracted with ethyl acetate (5 mL×3), washed with saturated brine, and dried over anhydrous sodium sulfate. Filter, spin dry, and separate through silica gel column (petroleum ether / ethyl acetate = 10 / 1) to obtain the yellow solid product 5-methyl-3-oxo-7-phenyl-2,3-dihydrocycloheptatriene - Ethyl 4-carboxylate 2a (185mg, 68%). The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ: 1.35 (t, J = 7.6 Hz, 3H), 2.21 (s, 3H), 4.34 (q, J = 7.6 Hz, 2H), 4.69 (s, 2H), 6.02 (s, 1H), 7.40-7.46 (m, 3H), 7.71 (d, J = 8.0 Hz, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ: 14.15, 24.82, 61.46, 77.46, 106.94, 127.11, 128.72, 131....

Embodiment 2

[0019] According to the method described in Example 1, add 1a (1 mmol, 144 mg), ethyl 4-chloroacetoacetate (1.2 mmol, 197.5 mg) and 3 mL of acetone into a 10 mL round bottom flask, and then add potassium carbonate (1 mmol, 138 mg). After stirring at room temperature for 1 hour, the product ethyl 5-methyl-3-oxo-7-phenyl-2,3-dihydrocycloheptatriene-4-carboxylate 2a (163 mg, 60%) was obtained.

Embodiment 3

[0021] According to the method described in Example 1, 1a (1 mmol, 144 mg), ethyl 4-chloroacetoacetate (1.2 mmol, 197.5 mg) and 3 mL of dimethyl sulfoxide were added to a 10 mL round bottom flask, and then Potassium carbonate (1 mmol, 138 mg) was added. After stirring at room temperature for 1 hour, the product ethyl 5-methyl-3-oxo-7-phenyl-2,3-dihydrocycloheptatriene-4-carboxylate 2a (201 mg, 74%) was obtained.

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Abstract

The invention discloses a synthesis method of poly-substituted oxacycloheptatriene-3(2H) ketone compounds. According to the technical scheme, the synthesis method comprises the following steps of: dissolving 4-chloracetyl-ethyl acetoacetate and a 1,2-allenyl ketone compound into an organic solvent; subsequently adding alkali; reacting at room temperature so as to obtain the poly-substituted oxacycloheptatriene-3(2H) ketone compound. The synthesis method is a novel method for synthesizing poly-substituted oxacycloheptatriene-3(2H) ketone compounds, needs no expensive catalysts and reagents, and is simple and easy to prepare starting materials, temperate in reaction condition and simple and convenient to operate.

Description

[0001] technical field [0002] The invention belongs to the technical field of organic synthesis, in particular to a multi-substituted oxepatriene-3(2 H )-The synthetic method of ketone compound. Background technique [0003] Oxepatriene-3(2 H )-ketone skeleton widely exists in marine organisms and has broad-spectrum physiological and biological activities. At the same time, it is also an important unit structure for the construction of other complex natural products, and has important development and application values ​​in the fields of biotechnology and medicine. The methods reported in the related literature are mainly prepared by transition metal-catalyzed C–O or C–C bond coupling. These traditional synthetic methods often require expensive catalysts or reagents, strict operation requirements, high cost, and more importantly, the starting materials containing specific functional groups must be prepared first, so they are greatly limited in actual production. Conten...

Claims

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Application Information

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IPC IPC(8): C07D313/04
Inventor 王强范学森徐周庆郭胜海张新迎
Owner HENAN NORMAL UNIV
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