Optically active indoline cyclopentenone and its derivatives and preparation method

A technology of indole spirocyclopentenone and optical activity, applied in organic chemistry methods, organic chemistry, etc., can solve the problem of rare cyclopentenone and achieve high yield and simple preparation process

Inactive Publication Date: 2017-07-28
CHINA WEST NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Chiral cyclopentenone is an important intermediate in organic synthesis and an important part of many natural products and drug molecules. Therefore, this type of compound has very important biopharmacological activity, and its synthesis method is often obtained through multi-step reactions. At present, the method of obtaining cyclopentenone by one-pot synthesis is still rare

Method used

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  • Optically active indoline cyclopentenone and its derivatives and preparation method
  • Optically active indoline cyclopentenone and its derivatives and preparation method
  • Optically active indoline cyclopentenone and its derivatives and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] The synthesis of optically active indole spirocyclopentenone 3a, its reaction formula is:

[0019]

[0020] Add tetrakis[(S)-(-)-N-(p-dodecylbenzenesulfonyl)proline]dirhodium(II)(Rh 2 (DOSP) 4 (9.48mg, 0.005mmol), 2-trimethylsilyloxy-4-methoxy-1,3-butadiene (1.5mmol), add anhydrous and oxygen-free dichloromethane (1mL), stir at room temperature After 30min, a solution of N-benzyl-2-oxo-3-diazoindole (1a, 0.1mmol) dissolved in dichloromethane (1mL) was slowly added thereto, and after the reaction was completed (detecting the reaction by TLC progress), the reaction mixture was lowered to 0°C, added 0.5mL trifluoroacetic acid and stirred for 15min, the reaction mixture was added 5mL saturated NH 4 Cl aqueous solution, the reaction solution was extracted three times with ethyl acetate, 10 mL each time, the organic phases were combined and dried over anhydrous sodium sulfate. After evaporating the solvent, separation and purification by column chromatography (petroleum...

Embodiment 2

[0022] The synthesis of optically active indole spirocyclopentenone 3a, its reaction formula is:

[0023]

[0024] Add chiral rhodium carboxylate I (1.42mg, 0.001mmol), 2-trimethylsilyloxy-4-methoxy-1,3-butadiene (2mmol) into a dry test tube Oxygen carbon tetrachloride (1mL), after stirring at room temperature for 30min, slowly added N-benzyl-2-oxo-3-diazoindole (1a, 0.1mmol) dissolved in carbon tetrachloride ( 1mL) solution, after the reaction was completed (reaction progress was detected by TLC), the reaction compound was lowered to 0°C, 0.5mL trifluoroacetic acid was added and stirred for 15min, and the reaction mixture was added 5mL saturated NH 4 Cl aqueous solution, the reaction solution was extracted three times with ethyl acetate, 10 mL each time, the organic phases were combined and dried over anhydrous sodium sulfate. After evaporating the solvent, separation and purification by column chromatography (petroleum ether: ethyl acetate = 10:1) gave (S)-2-oxo-indole-3...

Embodiment 3

[0027] The synthesis of optically active indole spirocyclopentenone 3a, its reaction formula is:

[0028]

[0029] Add chiral rhodium carboxylate II (2.67mg, 0.002mmol), 2-triethylsilyloxy-4-methoxy-1,3-butadiene (2mmol) into a dry test tube, add anhydrous Oxygen-free carbon tetrachloride (1mL), after stirring at 0°C for 30min, slowly added N-benzyl-2-oxo-3-diazoindole (1a, 0.1mmol) dissolved in tetrachloride Carbon dioxide (1 mL) solution, after the completion of the reaction (reaction progress detected by TLC), the reaction compound was lowered to 0 ° C, 0.5 mL of trifluoroacetic acid was added and stirred for 15 min, and the reaction mixture was added with 5 mL of saturated NH 4 Cl aqueous solution, the reaction solution was extracted three times with ethyl acetate, 10 mL each time, the organic phases were combined and dried over anhydrous sodium sulfate. After evaporating the solvent, separation and purification by column chromatography (petroleum ether: ethyl acetate ...

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Abstract

The invention relates to optically active indoline cyclopentenone and its derivatives and preparation method, in particular to optically active cyclopentenone-1,3'-indoline-2-ketone and its derivatives. The preparation method is that indole-2-diazocompound and trans-2-trimethylsiloxy-4-methoxy-1, 3-butadiene are taken as raw materials, chiral rhodium carboxylic acid is used as a catalyst, and the raw materials and the catalysts are reacted for 2 to 24 hours to complete synthesis. According to the method, the yield ranges from 65% to 95%, and the optical purity of products reaches 20-99% ee. Compared with the conventional method, the preparation method has the advantages of high yield and simple preparation process.

Description

technical field [0001] The invention relates to a method for synthesizing optically active indole spirocyclopentenone, in particular to optically active cyclopentenone-1,3'-indoline-2-one, derivatives thereof and a preparation method. Background technique [0002] Chiral cyclopentenone is an important intermediate in organic synthesis and an important part of many natural products and drug molecules. Therefore, this type of compound has very important biopharmacological activity, and its synthesis method is often obtained through multi-step reactions. At present, the method of obtaining cyclopentenone by one-pot synthesis is still rare. Contents of the invention [0003] The purpose of the present invention is to overcome the deficiencies of the prior art and provide a method for preparing optically active optically active cyclopentenone-1,3'-indoline-2-one and its derivatives with simple process and high yield . [0004] The specific technical solutions are: [0005] O...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/96
CPCC07B2200/07C07D209/96
Inventor 刘全忠潘婷曹菲何龙
Owner CHINA WEST NORMAL UNIVERSITY
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