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Method for resolving curcumenol epoxy chirality isomer by ionic liquid

A technology of ionic liquid and curcumitol, which is applied in the separation of epoxy chiral isomers of curcumitol, the new resolution of organic chiral compounds, and the separation of other chiral epoxy compounds to achieve high resolution efficiency. , low consumption, simple processing effect

Inactive Publication Date: 2010-10-06
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the method of using ionic liquid as a resolving agent to obtain optically pure curcumol epoxidized enantiomers E1 and E2 has not been reported in the literature

Method used

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  • Method for resolving curcumenol epoxy chirality isomer by ionic liquid
  • Method for resolving curcumenol epoxy chirality isomer by ionic liquid
  • Method for resolving curcumenol epoxy chirality isomer by ionic liquid

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Dissolve 0.45 g of curcumol epoxidized racemate E (containing about 30% of E1 and about 70% of E2) prepared in the laboratory in 2 mL of dichloromethane, and add 5 mL of [Bmim] BF 4 , heated and concentrated to remove dichloromethane, cooled and placed for 24 hours, 0.19 grams of white solid complexes were precipitated, filtered, and the solid was filtered with fresh [Bmim] BF 4 washing. The solid was dissolved in ether, washed 3 times with 10% ethanol, and the ether layer was concentrated to obtain 0.10 g of optically pure curcumol epoxidized enantiomer E1, a white solid with a yield of 22%; 10% was added to the remaining ionic liquid filtrate. % ethanol aqueous solution 10mL, boiled for 30 minutes, extracted 5 times with ether, and combined the extracts. The extract was washed twice with 5% ethanol aqueous solution, and the ether layer was concentrated to obtain a white solid, which was recrystallized with dioxane: water=1:15 to obtain 0.22 g of optically pure curcum...

Embodiment 2

[0034] Dissolve 0.45 g of curcumol epoxidized racemate E (containing about 30% of E1 and about 70% of E2) prepared in the laboratory in 2 mL of dichloromethane, and add 5 mL of [Bmim] PF 6 , heating and concentrating to remove dichloromethane, cooling and standing for 24 hours, 0.23 grams of white solid complexes were precipitated, filtered, and the solid was filtered with fresh [Bmim]PF 6 washing. The solid was dissolved in 2 mL of ethanol, and after boiling for 30 minutes, it was poured into 50 mL of water while it was hot. Slowly, solids were precipitated. After filtration, 0.12 g of white solid optically pure curcumol epoxidized enantiomer E1 was obtained, with a yield of 26.7%. α] 25 D =-37.8 (c=0.54, MeOH), 99% ee;

[0035] Add 10 mL of 10% ethanol aqueous solution to the remaining ionic liquid filtrate, boil for 30 minutes, extract with ether three times, and combine the extracts. The extract was washed twice with 5% ethanol aqueous solution, and the ether layer was...

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Abstract

The invention relates to a method for resolving curcumenol epoxy chirality isomer by ionic liquid. Quaternary ammonium salt type ionic liquid containing boron tetrafluoride or phosphorus hexafluoride anion is taken as resolving agent, the principle that complexes formed by two optically pure curcumenol epoxidation enantiomers with ionic liquid has obviously different solubility properties in the ionic liquid is utilized, the two complexes are conveniently separated, decomposition and purification are respectively carried out on the complexes, so as to respectively obtain two high quality and high enantiomeric excess (e. e%) optically pure curcumenol epoxidation enantiomers. The invention has simple post treatment, requires no conventional optically pure chirality compound to be taken as resolving agent, has low ionic liquid consumption, can recycle the ionic liquid and is applicable to mass production.

Description

technical field [0001] The invention belongs to the technical field of chemical separation of chiral compounds, and relates to a new resolution method for organic chiral compounds, that is, a method for resolving curcumol epoxy chiral isomers, which is also applicable to other chiral rings. Resolution of oxygen compounds. Background technique [0002] The optically active curcumol epoxidized racemate E is a white crystalline powder, odorless, insoluble in water, easily soluble in organic solvents such as ethanol and chloroform, with a melting point of 147-150°C, and its structural formula is as follows: figure 1 , the racemic form E is a mixture of two enantiomers E1 and E2. [0003] Curcumol epoxy compounds are epoxy derivatives of curcumol, an active ingredient in traditional Chinese medicine Curcuma. In recent years, with the in-depth study of curcumol anti-tumor and antiviral drugs, the research on optically pure curcumol derivatives has been promoted and the demand fo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20C07B57/00
Inventor 郭平姚其正杨树林李校堃叶发青刘剑敏
Owner WENZHOU MEDICAL UNIV
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