Measurement method of optical purity of 4-(3H)-quinazolinone compound alkaloid

A determination method and quinazolinone technology are applied in the field of optical purity of 4-quinazolinone alkaloids, and achieve the effects of high basic research value, social and economic benefits, simple operation and high precision

Active Publication Date: 2018-08-24
WENZHOU UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In contrast, identifying and determining the optical purity and steric ...

Method used

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  • Measurement method of optical purity of 4-(3H)-quinazolinone compound alkaloid
  • Measurement method of optical purity of 4-(3H)-quinazolinone compound alkaloid
  • Measurement method of optical purity of 4-(3H)-quinazolinone compound alkaloid

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Experimental program
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Embodiment 1

[0026] R 1 for hydrogen, R 2 for hydrogen, R 3 is a furan group, R 4 The substance ratio of methyl 4-(3H) quinazolinone 1a to chiral phosphoric acid recognition agent is 1.0:1.0, substrate 4-(3H) quinazolinone 3.0mg (0.1mmol), ( S)-3,3'-bis(1-naphthyl)-1,1'-binaphthol phosphate 6.0 mg (0.1 mmol); the deuterated solvent is deuterated chloroform 0.6 mL. At room temperature, add (S)-3,3'-bis(1-naphthyl)-1,1'-binaphthol phosphate and 4-(3H)quinazolinone compounds into the NMR tube, add After deuterated chloroform was dissolved and mixed evenly, the H-NMR spectrum was detected. The optical purity of the 4-(3H)quinazolinone compound is determined by calculating the chemical shift shift and ratio of the characteristic peaks of the diastereoisomers. Here, the H NMR spectrum of the methyl group of the 4-(3H) quinazolinone compound is selected as the characteristic peak for comparison, and the chemical shift shift is ΔΔδ=0.16ppm. The specific structure and NMR characterization of ...

Embodiment 2

[0028] Substrate 4-(3H) quinazolinone 3.0mg (0.1mmol), (S)-3,3'-bis(1-naphthyl)-1,1'-binaphthol phosphate 6.0mg (0.1mmol ); deuterated solvent is deuterated methanol 0.6mL.

[0029] The rest are the same as in Example 1, and the chemical shift shift is ΔΔδ=0.01ppm.

Embodiment 3

[0031] Substrate 4-(3H) quinazolinone 3.0mg (0.1mmol), (S)-3,3'-bis(1-naphthyl)-1,1'-binaphthol phosphate 6.0mg (0.1mmol ); deuterated solvent is deuterated acetone 0.6mL.

[0032] The rest are the same as in Example 1, and the chemical shift shift is ΔΔδ=0.03ppm.

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Abstract

The invention discloses a measurement method of an optical purity of 4-(3H)-quinazolinone compound alkaloid, wherein with chiral phosphoric acid as a chiral recognizer, the optical purity of the quinazolinone alkaloid is measured through nuclear magnetic resonance (1H NMR). The method includes the steps of: directly performing measurement and analysis on 1H NMR spectrum with a 4-(3H)-quinazolinonecompound, which has axial chirality, as a recognition object in a deuteration reagent with chiral phosphoric acid as the recognizer. The method can quickly, easily and accurately detect the optical purity of 4-(3H)-quinazolinone compound alkaloid having axial chirality. The invention, for the first time, provides the method for directly measuring the optical purity of 4-(3H)-quinazolinone compound alkaloid having axial chirality through the 1H NMR with the chiral phosphoric acid ((S)-3,3'-bis(1-naphthyl)-1,1'-binaphthol phosphate) as the recognizer. The method has the following advantages: 1)the method is simple in operations; 2) the method can quickly measure the optical purity of the 4-(3H)-quinazolinone compound alkaloid having axial chirality; 3) the method has excellent effect on compatibility of the recognition issue and is high in accuracy.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a new method for measuring the optical purity of 4-(3H) quinazolinone alkaloids with axial chirality by using chiral phosphoric acid. Background technique [0002] With the continuous deepening of the research on the pharmacological activity of chiral drugs in recent years, the determination of the absolute configuration of chiral drug molecules has attracted much attention. 4-(3H)quinazolinones with axial chirality are an important class of drug backbone molecules, which widely exist in natural products and many types of molecules with important physiological and pharmacological activities. Therefore, how to develop an efficient, fast and simple method to identify and analyze the optical purity of chiral drug molecules has important practical application value. [0003] According to the existing reports, many excellent chiral solvating reagents can efficiently recognize chiral ...

Claims

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Application Information

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IPC IPC(8): G01N24/08
CPCG01N24/082
Inventor 蒋俊刘洪鑫肖洪平李娟吴超飞李新华
Owner WENZHOU UNIVERSITY
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