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Asymmetric synthesis method for chiral dihydrofuran compound

A technology of dihydrofuran and synthesis method, applied in the direction of organic chemistry, etc., can solve problems such as unsatisfactory ee value

Active Publication Date: 2017-09-29
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the less satisfactory range of ee values ​​is 66% to 92%

Method used

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  • Asymmetric synthesis method for chiral dihydrofuran compound
  • Asymmetric synthesis method for chiral dihydrofuran compound
  • Asymmetric synthesis method for chiral dihydrofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Synthesis of (2R,3R)-6,6-dimethyl-2-nitro-3-phenyl-3,5,6,7-tetrahydrofuran-4(2H)-one;

[0052]

[0053] (A) Take a 10mL clean small test tube, add 5,5-dimethyl-1,3-cyclohexanedione (0.3mmol, 0.042g), (E)-nitroalkene (0.3mmol, 0.045g), and Squaric acid catalyst V (0.05mmol, 0.00254g), solvent chloroform (2mL). After reacting at 25° C. for 0.5 h, after the complete reaction of the raw materials was detected by TLC, the solvent was distilled off under reduced pressure to obtain a mixture (0.0887 g) containing intermediate compound 1-A.

[0054] (B) In the mixture containing intermediate compound 1-A obtained in the previous step (wherein the amount of 1-A theoretical substance containing 0.3mmol, total mass 0.0887g), add cuprous iodide (0.076g, 0.4mmol), Potassium carbonate (0.6mmol, 0.0682g), solvent acetonitrile (2mL). After reacting at 25°C for 8h, extract with ethyl acetate (3×10mL), and desolvate the organic phase under reduced pressure, use ethyl acet...

Embodiment 2

[0055] Example 2: (2R,3R)-3-(2-anisole)-6,6-dimethyl-2-nitro-3,5,6,7-tetrahydrofuran-4(2H)-one ;

[0056]

[0057] (A) Take a 10mL clean small test tube, add 5,5-dimethyl-1,3-cyclohexanedione (0.3mmol, 0.042g), (E)-2-methoxynitroalkene (0.3mmol, 0.054g), chiral squaraine catalyst VII (0.05mmol, 0.00315g), solvent chloroform (2mL). After reacting at 25°C for 0.5h, after the complete reaction of the raw materials was detected by TLC, the solvent was distilled off under reduced pressure to obtain a mixture containing intermediate compound 2-A (0.094g)

[0058] (B) in the mixture containing intermediate compound 2-A obtained in the previous step (wherein the amount of 2-A theoretical substance containing 0.3mmol, total mass 0.094g), then add iodobenzene acetate (0.4mmol, 0.1288g), Triethylenediamine (0.6mmol, 0.0606g), solvent tetrahydrofuran (3mL), after reacting at 25°C for 6h, extracted with ethyl acetate (3×10mL), the organic phase was desolvated under reduced pressure, a...

Embodiment 3

[0059] Example 3: (2R,3R)-3-(3-anisole)-6,6-dimethyl-2-nitro-3,5,6,7-tetrahydrofuran-4(2H)-one ;

[0060]

[0061] (A) Take a 10mL clean small test tube, add 5,5-dimethyl-1,3-cyclohexanedione (0.3mmol, 0.042g), (E)-3-methoxynitroalkene (0.3mmol, 0.054g), chiral squaraine catalyst IX (0.05mmol, 0.0024g), solvent chloroform (2mL). After reacting at 25° C. for 0.5 h, the raw material was completely reacted by TLC, and the solvent was distilled off under reduced pressure to obtain a mixture (0.094 g) containing intermediate compound 3-A.

[0062] (B) In the mixture containing the intermediate compound 3-A obtained in the previous step (wherein the amount of 3-A theoretical substance is 0.3mmol, and the total mass is 0.094g), add tetrabutylammonium iodide (0.5mmol, 0.1845 g), sodium hydroxide (0.0672g, 0.8mmol), solvent methanol (0.5mL), after 25 ℃ of reaction 4h, extract with ethyl acetate (3 * 10mL), organic phase decompression precipitation, with ethyl acetate: Petroleum e...

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Abstract

The invention provides an asymmetric synthesis method for a chiral dihydrofuran compound shown as formula (I). The synthesis method is carried out according to the following steps: 1,3-cyclohexanedione compound shown as formula (II), nitroolefin compound shown as formula (III), chiral squaric acid catalyst and organic solvent A are mixed and thoroughly react under negative 20 DEG C to negative 60 DEG C, so that a compound shown as formula (IV) is obtained; iodine source additive, an alkaline substance and organic solvent B are added into the compound shown as formula (IV) and thoroughly react under negative 20 DEG C to negative 60 DEG C, and after reaction solution is post-treated, the chiral dihydrofuran compound shown as formula (I) is obtained. the asymmetric synthesis method has the advantages of mild reaction conditions, high product yield and excellent selectivity; the prepared chiral dihydrofuran compound is chiral, and the core framework structure is novel. (img file='DDA00012852165300000II.TIF' wi='1549' he='406' / ).

Description

technical field [0001] The invention relates to an asymmetric synthesis method of chiral dihydrofuran compounds. Background technique [0002] Furan is one of the most important skeletons in oxygen-containing heterocyclic compounds. A large number of furan derivatives have been widely used as starting materials to produce pharmaceutically and industrially important compounds. The dihydrofuran skeleton is also a common structural unit present in natural products and bioactive compounds. The preparation of dihydrofuran derivatives has attracted considerable attention over the past few decades due to their wide application in the field of drug discovery and agricultural research. In recent years, some hydrogenated furan derivatives have been found to have antiviral, antitumor, antibacterial, and antiviral effects. Benzodihydrofurans have attracted attention because of their important pharmacological activities and their widespread occurrence in nature. Some of them have sig...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/82
CPCC07D307/82
Inventor 夏爱宝封凯祥张晓龙
Owner ZHEJIANG UNIV OF TECH
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