Method for calculating and determining absolute configuration of chiral amines according to nuclear magnetic resonance fluorine spectrum theory

A theoretical calculation and absolute configuration technology, applied in molecular entity identification, analysis of two-dimensional or three-dimensional molecular structure, instruments, etc., can solve problems such as inconsistency of facts and deviation of configuration determination results.

Inactive Publication Date: 2019-07-23
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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Problems solved by technology

In the NMR nuclear magnetic resonance method, the use of chiral derivatization reagent method and chiral solvation reagent method to determine the absolute configuration of chiral compounds is a commonly used method in the field of nuclear magnetic recognition technology, but this method is only based on the experience of the mosher model formula method, the obtained configuration judgment results sometimes have deviations and do not conform to the facts

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  • Method for calculating and determining absolute configuration of chiral amines according to nuclear magnetic resonance fluorine spectrum theory
  • Method for calculating and determining absolute configuration of chiral amines according to nuclear magnetic resonance fluorine spectrum theory

Examples

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example 1

[0012] Example 1 Determination of the Absolute Configuration of Optical α-Phenylethylamine

[0013] The specific implementation method of determining the absolute configuration by the nuclear magnetic resonance fluorine spectrum theoretical calculation method is as follows:

[0014] i) The molecular structural formula of the amidation product generated by the reaction of (R)-α-fluorophenylacetate and (S)-α-phenylethylamine was initially simulated by the ball and stick model in the Gaussian 09 system. Optimization, to obtain the lowest Gibbs free energy conformer, obtain the calculated value of the chemical shift of the α-fluorine of the derivative δ α-F R (calcd.) =-192.32ppm.

[0015] ii) The molecular structural formula of the amidation product generated by the reaction of (S)-α-selenofluorophenylacetate and (S)-α-phenylethylamine was initially simulated by the ball-and-stick model in the Gaussian 09 system. Optimization, to obtain the lowest Gibbs free energy conformer,...

example 2

[0019] Example 2 Determination of the Absolute Configuration of Optical Amphetamine

[0020] The specific implementation method of determining the absolute configuration by the nuclear magnetic resonance fluorine spectrum theoretical calculation method is as follows:

[0021] i) The molecular structure of the amidation product produced by the reaction of (R)-α-selenofluorophenylacetate and (R)-2-amino-3-phenyl-1-propanol was performed on the ball-and-stick model in the Gaussian 09 system Preliminary simulation of , through continuous geometric optimization, the lowest Gibbs free energy conformer is obtained, and the calculated value of the chemical shift of the derivative α-fluorine δ α-F R (calcd.) =-191.64ppm.

[0022] ii) The molecular structure of the amidation product produced by the reaction of (S)-α-selenofluorophenylacetate and (R)-2-amino-3-phenyl-1-propanol was performed on a Gaussian 09 system using a ball-and-stick model Preliminary simulation of , through cont...

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Abstract

The invention discloses a method for calculating and determining absolute configuration of chiral amines according to nuclear magnetic resonance fluorine spectrum theory. The main features of the method for determining the absolute configuration of chiral amines are: obtaining theoretically calculating two configurations of a diastereomeric amide compound having the most stable conformation through a theoretical calculation fluorine spectrum method, theoretically calculating the fluorine spectral chemical shift difference DeltadeltaAlpha-FR, S, and then using the nuclear magnetic resonance fluorine spectrum to obtain the chemical shift difference DeltadeltaAlpha-FR, S of the diastereomer amide compound, by comparing the DeltadeltaAlpha-FR, S positive and negative signs obtained by the twomethods, accurately determining the absolute configuration of the sample to be tested. The method is applicable to the determination of the absolute configuration of chiral amines, amino alcohols, amino acid esters and various chiral compounds. The method is simple, easy to operate and high in accuracy. The method is a simple and efficient new method for determining absolute configuration.

Description

technical field [0001] The invention belongs to the technical field of analysis of chiral compounds, and in particular relates to the application of using chiral α-selenofluorophenylacetate as a chiral sensor to determine the absolute configuration of chiral amine compounds using a nuclear magnetic resonance instrument fluorine spectrum theoretical calculation method. Background technique [0002] The determination of the absolute configuration of chiral molecules requires the actual determination of the three-dimensional structure of the molecule, which is of great significance for the study of the physical and chemical properties of chiral compounds and the mechanism of asymmetric catalytic reactions, including toxicological metabolism experiments of drug molecules. At present, the common methods for determining the absolute configuration of chiral amine compounds are as follows: X-ray diffraction method, chiral spectroscopy method, chemical correlation method, and NMR nucl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G16B15/20G16C20/20
CPCG16B15/20G16C20/20
Inventor 杨士伟宋玲边广岭
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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