Two enantiomers of 2,6-diamido triptycene and detection and separation method thereof

A technology of diaminotriptycene and enantiomers, which is applied in the field of two enantiomers of 2,6-diaminotriptycene and its detection and separation, can solve problems that have not been seen in research reports so far

Active Publication Date: 2017-08-04
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Although there have been many studies on the application of 2,6-diaminotriptycene racemate, the confirmation of the absolute configu

Method used

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  • Two enantiomers of 2,6-diamido triptycene and detection and separation method thereof
  • Two enantiomers of 2,6-diamido triptycene and detection and separation method thereof
  • Two enantiomers of 2,6-diamido triptycene and detection and separation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Analysis and determination of 2,6-diaminotriptycene enantiomers

[0044] Instrument and chromatographic conditions:

[0045] High-performance liquid chromatography, the chromatographic column is Chiralpak IC, 0.46cm I.D.×15cm L, 1.0μL; the mobile phase is absolute ethanol: diethylamine=100:0.1 (V / V); the column temperature is 35°C; The flow rate is 1.0mL / min; the detection wavelength is 254nm.

[0046] Sample preparation: take 2,6-diaminotriptycene racemate, add mobile phase to dissolve and dilute, prepare a solution with a solubility of 1 mg / mL, shake well as the sample to be tested, inject it into a high-performance liquid chromatograph, flow Phase elution, according to the peak time of the chromatogram, record the chromatogram, the separation degree of the two main peak components is greater than 2.0, see the attached figure 1 , the peak data in the figure are shown in Table 1: the main peak No. 4 represents 2,6-diaminotriptycene in (S,S) configuration, ...

Embodiment 2

[0049] Example 2: 2,6-diaminotriptycene enantiomer (9S,10S)-9,10-dihydro-9,10-[1,2]benzanthracene-2,6-diamine (Peak 4 components in embodiment 1 separation chromatography) detection

[0050] Instrument and chromatographic conditions:

[0051] High-performance liquid chromatography, the chromatographic column is Chiralpak IC, 0.46cm I.D. × 15cm L, 1.0 μ L; the mobile phase is ethanol: diethylamine = 100: 0.1 (V / V); the column temperature is 35 ° C; the flow rate is 1.0mL / min; detection wavelength is 254nm.

[0052] The component of peak 4 in the chromatogram is collected from Example 1, and after the solvent is removed by rotary evaporation, the mobile phase is dissolved again, shaken up as the sample to be tested, injected into the high performance liquid chromatograph, and the mobile phase is eluted, and then According to the peak time of the chromatogram, record the chromatogram, see attached figure 2 , the peak data in the figure are shown in Table 2: Peak No. 1 is 2,6-...

Embodiment 3

[0055] Example 3: 2,6-diaminotriptycene enantiomer (9R,10R)-9,10-dihydro-9,10-[1,2]benzanthracene-2,6-diamine (Peak 5 components in the separation chromatography of embodiment 1) detection

[0056] Instrument and chromatographic conditions:

[0057] High-performance liquid chromatography, the chromatographic column is Chiralpak IC, 0.46cm I.D. × 15cm L, 1.0 μ L; the mobile phase is ethanol: diethylamine = 100: 0.1 (V / V); the column temperature is 35 ° C; the flow rate is 1.0mL / min; detection wavelength is 254nm.

[0058] The component of peak 5 in the chromatogram is collected from Example 1, after the solvent is removed by rotary evaporation, the mobile phase is dissolved again, shaken up as the sample to be tested, injected into the high performance liquid chromatograph, and the mobile phase is eluted, according to Chromatogram peak time, record chromatogram, see attached image 3 , the peak data in the figure are shown in Table 3: the No. 2 main peak is 2,6-diaminotripty...

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Abstract

The invention provides a detection and separation method of two enantiomers of 2,6-diamido triptycene with three-dimensional rigid structures and confirmation of absolute configurations thereof. Bridgehead carbons at the ninth sites and the tenth sites of the structures of the two enantiomers of the 2,6-diamido triptycene are chiral carbon atoms. According to the detection and separation method of the two enantiomers of the 2,6-diamido triptycene with the three-dimensional rigid structures and the confirmation of the absolute configurations thereof provided by the invention, high performance liquid chromatography (HPLC) is adopted, a chiral column is utilized for separating the two enantiomers, two optical voidness isomer components with ee percent being larger than 98 percent are obtained, and through X-ray single crystal diffraction analysis, the absolute configurations are confirmed as an (S,S) type and an (R, R) type, i.e., the two enantiomers are sequentially (9S, 10S)-9,10-dihydro-9,10-[1,2]benzanthracene-2,6-diamine and (9R, 10R)-9,10-dihydro-9,10-[1,2]benzanthracene-2,6-diamine. The prepared enantiomers can be used as key constructing units for synthesizing a chiral catalyst.

Description

technical field [0001] The present invention relates to the confirmation of the absolute configurations of two enantiomers (R, R) and (S, S) of 2,6-diaminotriptycene and the detection and separation methods of the two enantiomers. Background technique [0002] The structural formula of 2,6-diaminotriptycene is as follows: [0003] [0004] 2,6-Diaminotriptycene [0005] It is based on the derivatives of triptycene, and triptycene is a three-dimensional rigid three-dimensional molecule formed by connecting three benzene rings. In terms of space, the three benzene rings form a 120°C relationship with each other. This kind of triptycene and its derivatives with three-dimensional rigid skeleton has its unique advantages in forming intrinsic microporous polymers: larger specific surface area, better thermal stability, more internal molecular free volume, With good electrochemical and photochemical properties and potential medicinal properties, this type of intrinsic micropor...

Claims

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Application Information

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IPC IPC(8): C07C211/61G01N30/02G01N30/06G01N23/20
CPCC07B2200/07C07C211/61G01N23/20G01N30/02G01N30/06
Inventor 张春陈静静朱鹏程马辉王震翟天龙
Owner HUAZHONG UNIV OF SCI & TECH
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