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Fluorinated quinolylamide foldamer, preparation method, chirality recognition method and application

A kind of fluoroquinoline amide, quinoline amide technology, applied in the field of fluoroquinoline amide folded body, can solve the problem of consuming a lot of time and energy and the like

Active Publication Date: 2019-05-03
WUYI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The current methods used to determine the absolute configuration and enantiomeric purity (ee value) of chiral small molecules rely on chromatographic techniques (HPLC, GC), but small changes in analyte structures in chromatographic techniques may be attributable to the choice of chiral stationary phase. Significant differences in properties basically require method screening for each structure, which consumes a lot of time and effort

Method used

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  • Fluorinated quinolylamide foldamer, preparation method, chirality recognition method and application
  • Fluorinated quinolylamide foldamer, preparation method, chirality recognition method and application
  • Fluorinated quinolylamide foldamer, preparation method, chirality recognition method and application

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preparation example Construction

[0057] The preparation method of fluorine-containing quinoline amide folding body shown in above-mentioned formula (1) of the present invention, comprises the steps:

[0058]

[0059] 1) As shown in formula (3), compound Q F Soluble in concentrated H 2 SO 4 and CH 3 In COOH (v / v=1 / 1), heat and stir at 115-125°C for 10-15h; TLC monitors the reaction progress, after the reaction is completely completed, cool to room temperature; pour the above reaction solution into ice water, extract three times with DCM , combine the organic phases and wash with anhydrous Na 2 SO 4 Dry and spin dry to obtain compound Q F COOH;

[0060] 2) Put Q F COOH is dissolved in anhydrous DCM (abbreviation of dichloromethane) under the protection of argon, and 1.8-2.2 equivalents of oxalyl chloride and catalytic amount of DMF (abbreviation of dimethylformamide) are added to it; the above solution is reacted at room temperature 1.8-2.2h, after the reaction is over, drain the above solution and c...

Embodiment 1

[0080] Fluorine-containing quinoline amide fold Q F Q 4 The absolute configuration of chiral phenylethylamine and the determination of ee value comprise the steps:

[0081] 1) Configure 7.5mmol / L of DMF-d of R-phenethylamine and S-phenethylamine 7 Solution. Weigh 4.5 mg each of R-phenethylamine and S-phenethylamine and add them to two 5mL volumetric flasks, add DMF-d 7 to the tick mark;

[0082] 2) Accurately weigh the fluoroquinolinamide folded body Q F Q 4 3.23 mg, K 2 CO 3 0.52mg is placed in an NMR tube, and the DMF-d of R-phenethylamine and S-phenethylamine is extracted separately with a micro-injector 7 Solution 500μL / 0μL, 450μL / 50μL, 400μL / 100μL, 350μL / 150μL, 300μL / 200μL, 250μL / 250μL, 200μL / 300μL, 150μL / 350μL, 100μL / 400μL, 50μL / 450μL, 0μL / 500μL tube, heated to 95 °C. Use 1H NMR to monitor the reaction until complete;

[0083] 3) Use a micro-injector to take 10 μL of the above reaction solution and add it to a 10mm*10mm cuvette, then add 2mL of spectrally pure D...

Embodiment 2

[0086] Fluorine-containing quinoline amide fold Q F Q 4 The determination of the absolute configuration of 1-naphthylethylamine and the ee value comprises the steps:

[0087] 1) Configure 7.5mmol / L of DMF-d of R-1-naphthylethylamine and S-1-naphthylethylamine 7 Solution. Weigh 6.4 mg each of R-1-naphthylethylamine and S-1-naphthylethylamine and add to two 5mL volumetric flasks, add DMF-d 7 to the tick mark;

[0088] 2) Accurately weigh the fluoroquinolinamide folded body Q F Q 4 3.23 mg, K 2 CO 30.52mg is placed in the NMR tube, and the DMF-d of R-1-naphthylethylamine and S-1-naphthylethylamine are respectively extracted with a micro-injector 7 500μL / 0μL, 450μL / 50μL, 400μL / 100μL, 350μL / 150μL, 300μL / 200μL, 250μL / 250μL, 200μL / 300μL, 150μL / 350μL, 100μL / 400μL, 50μL / 450μL, 0μL / 500μL, respectively In an NMR tube, heat to 85°C; use 1H NMR to detect the reaction until complete;

[0089] 3) Take 10 μL of the above reaction solution and add 2 mL of spectroscopically pure DCM fo...

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Abstract

The invention discloses a fluorinated quinolylamide foldamer, a preparation method, a chirality recognition method of the fluorinated quinolylamide foldamer and an application of the fluorinated quinolylamide foldamer. The fluorinated quinolylamide foldamer has a structural formula represented by a formula (1) shown in the description, wherein R1 and R4 represent alkoxy of any length and may be the same or different, X is an O or N atom, R2 is an electron withdrawing group, for example nitro or cyano, R3 is alkyl of any length, and n is a random positive integer. The fluorinated quinolylamidefoldamer disclosed by the invention can be applied to the recognition and ee value determination of absolute configurations such as chiral amines, chiral diamines, chiral amine alcohols and chiral amino-acid esters. According to the fluorinated quinolylamide foldamer, the preparation method, the chirality recognition method and the application, a chiral group is linked to the quinolylamide foldamer in a covalent bond mode in a manner that amino attacks the fluorinated quinolylamide foldamer under alkaline conditions, so that chirality is transferred to the quinolylamide foldamer, and absoluteconfigurations and ee values of chiral guest molecules are detected according to CD signals of corresponding quinolylamide foldamers.

Description

technical field [0001] The invention relates to the field of chiral recognition, in particular to a fluoroquinoline amide folded body, a preparation method and a chiral recognition method and application thereof. Background technique [0002] Different enantiomers of the same compound not only have different physical and chemical properties, but also often have great differences in physiological activity, toxicity and catalytic activity. Therefore, it is important to analyze the absolute configuration and enantiomeric purity of chiral molecules. meaning. The current methods used to determine the absolute configuration and enantiomeric purity (ee value) of chiral small molecules rely on chromatographic techniques (HPLC, GC), but small changes in analyte structures in chromatographic techniques may be attributable to the choice of chiral stationary phase. Significant differences in properties basically require method screening for each structure, which consumes a lot of time ...

Claims

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Application Information

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IPC IPC(8): C07D215/48G01N21/19G01N21/25G01N21/75G01N24/08
Inventor 郑璐江华张焜
Owner WUYI UNIV
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