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Synthesis method of (1S, 5R)-lactone

A synthesis method and technology of lactone, applied in the field of synthesis of (1S,5R)-lactone, can solve the problems of limited industrial application prospects, insufficient catalytic efficiency, low enantioselectivity, etc., and achieve high enantioselectivity Catalytic effect, low cost, high chemical yield and high optical purity

Active Publication Date: 2018-05-29
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above methods all have the disadvantages of expensive catalysts, insufficient catalytic efficiency, and low enantioselectivity, and their practical industrial application prospects are limited.

Method used

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  • Synthesis method of (1S, 5R)-lactone
  • Synthesis method of (1S, 5R)-lactone
  • Synthesis method of (1S, 5R)-lactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (1.77g, 0.01 mol), (11aR)-10,11,12,13-tetrahydro-5 -Hydroxy-3,7-bis[2,4,6-triisopropylphenyl]-5-oxo-diindene[7,1-de:1',7'-fg][1,3,2 ] Phosphonic acid dioxide (0.35 g, 0.005 mmol), 30% aqueous hydrogen peroxide solution (2.5 mL, 0.03 mol) and chloroform (20 mL) were placed in a dry reaction flask, and stirred at -20°C~0°C for 36~72 hours. After the reaction was completed, the solvent was recovered under reduced pressure, cooled to room temperature, diethyl ether (50 mL) was added to the residue and stirred for 15 min, then 10% hydrochloric acid (50 mL) was added and stirred for 30 min, left to stand, the organic layer was separated, and dried over anhydrous sodium sulfate . Filtration, the filtrate was recovered under reduced pressure, and a solid was precipitated, dried to obtain a white powder, and recrystallized from ether to obtain the product II (R=Cl, 46%, ee value 96.9%). 1 H NMR (CDCl 3 ): = 5.99 (s, 1H), ...

Embodiment 2

[0024] Example 2: 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (1.77g, 0.01 mol), (11aR)-10,11,12,13-tetrahydro-5 -Hydroxy-3,7-bis[2,4,6-triisopropylphenyl]-5-oxo-diindene[7,1-de:1',7'-fg][1,3,2 ] Dioxyphosphonic acid (0.35 g, 0.005 mmol), 30% hydrogen peroxide solution (2.5 mL, 0.03 mmol) and chloroform (20 mL) were placed in a dry reaction flask, and stirred at -40°C~-20°C for 48~72 hours . After the reaction was completed, the solvent was recovered under reduced pressure, cooled to room temperature, diethyl ether (50 mL) was added to the residue and stirred for 15 min, then 10% hydrochloric acid (50 mL) was added and stirred for 30 min, left to stand, the organic layer was separated, and dried over anhydrous sodium sulfate . Filtration, the filtrate was recovered under reduced pressure, and a solid was precipitated, dried to obtain a white powder, and recrystallized from ether to obtain the product II (R=Cl, 46%, ee value 96.9%). 1 H NMR (CDCl 3 ): = 5.99 (s, 1H), 5.74 (s,...

Embodiment 3

[0025] Example 3: 7,7-dichlorobicyclo[3.2.0]hept-2-en-6-one (1.77g, 0.01 mol), (11aR)-10,11,12,13-tetrahydro-5 -Hydroxy-3,7-bis[2,4,6-triisopropylphenyl]-5-oxo-diindene[7,1-de:1',7'-fg][1,3,2 ] Phosphonic acid dioxide (0.35 g, 0.005 mmol), 30% aqueous hydrogen peroxide solution (2.5 mL, 0.03 mmol) and chloroform (20 mL) were placed in a dry reaction flask and stirred at -20°C to 20°C for 36 to 72 hours. After the reaction was completed, the solvent was recovered under reduced pressure, cooled to room temperature, diethyl ether (50 mL) was added to the residue and stirred for 15 min, then 10% hydrochloric acid (50 mL) was added and stirred for 30 min, left to stand, the organic layer was separated, and dried over anhydrous sodium sulfate . Filtration, the filtrate was recovered under reduced pressure, and a solid was precipitated, dried to obtain a white powder, and recrystallized from ether to obtain the product II (R=Cl, 46%, ee value 96.9%). 1 H NMR (CDCl 3 ): = 5.99 (s...

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Abstract

The invention belongs to the technical field of organic chemistry and particularly relates to a synthesis method of (1S, 5R)-lactone. The synthesis method comprises the following steps of: substituteddicyclo(3. 2. 0)-heptyl-2-alkenyl-6-ketone (II) as a substrate, carrying out enantioselective Baeyer-Villiger oxidation with hydrogen peroxide under the catalysis of chiral phosphonic acid to preparechiral lactone I. The synthesis method has the advantages that the raw materials are easy to obtain, the reaction condition is mild, the operation is simple, the catalyst can be recovered quantitatively, and the reaction selectivity and the stereoselectivity are high, so that the synthesis method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and specifically relates to a synthesis method of (1S,5R)-lactone. Background technique [0002] The structure of (1S,5R)-lactone is shown in formula (I): [0003] [0004] In the formula, R is hydrogen, chlorine, bromine, iodine and other halogens, C 1 -C 8 Alkyl or cycloalkyl, phenyl, mono- or multi-substituted aryl or aralkyl, thienyl, furyl, naphthyl, etc. [0005] The (1S,5R)-lactone shown in formula I is a key intermediate in the synthesis of prostaglandins. (1S,5R)-Lactone was first synthesized by Tolstikov, G. A. et al. ( Zhurnal Organicheskoi Khimii ,1989, 25 , 208) reported that starting from cyclopentadiene, a racemic substrate was synthesized in three steps, and then combined with ( R )-(+)-alpha-methylbenzylamine for diastereomer crystallization resolution, and then lactonization to obtain the desired (1 S ,5 R )-lactone I; these methods have the common problems ...

Claims

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Application Information

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IPC IPC(8): C07D307/93
CPCC07D307/93C07D307/935Y02P20/584
Inventor 陈芬儿彭海辉胡莎孟歌吴妍程荡
Owner FUDAN UNIV
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