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Method for optically and selectively epoxidizing alkenone compound

A technology for epoxidizing ketene and compounds, which is applied in the fields of chemical recovery and organic chemistry, and can solve problems such as low yield and optical selectivity, difficulties in transportation and storage, and difficult reaction operations, and achieves less three wastes and easy operation , post-processing operation simple effect

Inactive Publication Date: 2005-06-29
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, optically active α, β-epoxyketene compounds are prepared under the condition of phase transfer catalysis, although there are hydrogen peroxide [Tertahedron Lett., 1998, 39, 7563], sodium hypochlorite [Tertahedron Lett., 1998, 39, 1599] , sodium perborate [Tetrahedron Lett.1995, 36, 663], alkyl hydroperoxide [J.Org.Chem.2002, 67, 259] and other oxidants, but there are yield and optical selection in the process of use Low sensitivity, difficult reaction operation, high risk, high cost, difficult transportation and storage, etc.

Method used

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  • Method for optically and selectively epoxidizing alkenone compound
  • Method for optically and selectively epoxidizing alkenone compound
  • Method for optically and selectively epoxidizing alkenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] In a 100-mL three-necked flask (including a stirrer, thermometer and dropping funnel), add 2.08 g (10 mmol) of chalcone (5, R 1-6 =H), 0.67 g O-benzyl-N-(9-anthracenemethyl)cinchonidine bromide (1a, R 1 =9-anthracene methyl, R 2 = vinyl, R 3 =benzyl) (1 mmol), 1.56 g (6.7 mmol) of TCCA and 30 mL of toluene. The temperature was lowered to 0° C., 3.36 g (30 mmol) of 50% potassium hydroxide aqueous solution was added dropwise with stirring, and the stirring was continued until the disappearance of chalcone was detected by thin layer chromatography. The temperature was raised to room temperature, diluted with 50 ml of ether, filtered, the filtrate was washed with 50 ml of water and saturated brine successively, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the product was recrystallized from n-hexane to obtain a white flake solid product with a yield of 90%, an e.e. value of 82%, and 96% after recrystallization.

Embodiment 2

[0029] The solvent is shown in Table 1 below, and other experimental methods and conditions are the same as in Example 1.

[0030] serial number

Embodiment 3

[0032] Inorganic bases are shown in Table 2 below, and other experimental methods and conditions are the same as in Example 1.

[0033] serial number

[0034] a: Aqueous solution concentration.

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Abstract

The invention relates preparation of optical pure epoxies by insymmetric phase transition catalyzing, concretely, a method for optical selective olefin epoxies and ketene epoxies compound, which uses TCCA as oxidantand optical phase transition catalyze, with the existence of inorganic base, V the epoxidates olefin and ketene compound to be the corresponding epoxies in the solvent. It has high productivity and optical selectivity friendly condition and simple operation..

Description

technical field [0001] The invention relates to a method for preparing optically pure epoxides through asymmetric phase transfer catalysis, in particular to a method for optically selecting epoxidized alkene ketone compounds. Background technique [0002] Optically active epoxides are a class of important physiologically active compounds. These compounds have two chiral carbon atoms in the ring. Through selective ring opening and functional group transformation, many valuable chiral compounds can be synthesized. Therefore, The research on the synthesis of optically active epoxides is of great significance [Organic Chemistry, 2001, 21(12), 1102]. Optically active α, β-epoxy ketene compounds are one of the most important types of optically active epoxides. [0003] At present, the main methods reported in the literature for the preparation of optically active α, β-epoxy ketenes mainly include organometallic complex catalysis [J.Am.Chem.Soc., 1997, 119, 2329], chiral Polyamin...

Claims

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Application Information

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IPC IPC(8): C07C49/794C07C49/80C07C49/84C07C205/45C07D307/46
CPCY02P20/582
Inventor 王永灿叶金星张国富梁鑫淼陈吉平
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI