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Macrocyclic molecule, preparation method and application thereof

A technology for macrocyclic molecules and reactions, applied in the field of macrocyclic molecules and their preparation, can solve the problems of complex preparation methods and inability to use chiral molecular recognition, and achieve simple and easy preparation methods, high yields, and increased recognition efficiency Effect

Active Publication Date: 2019-05-03
SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

CN104496933A discloses a photosensitive chiral macrocyclic molecule and its preparation method and application. The preparation method of the chiral macrocyclic molecule adopts the following steps: oligoethylene glycol, sodium hydroxide and p-toluenesulfonyl chloride are mixed in an inert Under the atmosphere, react in the tetrahydrofuran solvent, then the intermediate product is dissolved in DMF with o-dihydroxyazobenzene, cesium carbonate and dibenzooctadecacrown hexacrown, and then reacted with chiral binaphthol compounds, cesium carbonate and The target product is obtained through the reaction of dibenzooctadecacrown; its preparation method is too complicated, and it is mainly used for the identification of chiral ammonium salts, and cannot be used for the identification of chiral molecules in the aqueous phase

Method used

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  • Macrocyclic molecule, preparation method and application thereof
  • Macrocyclic molecule, preparation method and application thereof
  • Macrocyclic molecule, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] This embodiment provides a macrocyclic molecule with the following structure:

[0086]

[0087]

[0088]The preparation method is as follows:

[0089] (1) Synthetic symmetrical rigid bridged bis-naphthalene, the reaction process is as follows:

[0090]

[0091] Intermediate Compound S 1 Synthesis of: anhydrous NaH (12g, 281.3mmol) was added into a solution of 2,6-dihydroxynaphthalene (50g, 312.5mmol) in DMF (500mL) and stirred for 1 hour, then the bromoacetic acid was added through a constant pressure dropping funnel Ethyl ester (31.5mL, 296.9mmol) was slowly added to the reaction solution; the reaction was stirred at room temperature for 12 hours, after the reaction was completed, the reaction solution was poured into 2L of ice water, and a small amount of dilute hydrochloric acid (to pH=7) was added to stir, and a large amount of insoluble solids Precipitate. Filter and wash the filter residue with a large amount of water, dissolve the filter residue in 2L...

Embodiment 2

[0114] This embodiment provides a chiral macrocyclic molecule with the following structure:

[0115]

[0116] The preparation method is as follows:

[0117] (1) Referring to Example 1, compound A was synthesized.

[0118] (2) Synthesis of chiral macrocyclic molecules rac-6-1 and rac-6-2, the process is as follows:

[0119]

[0120] Perform chiral resolution on compound A:

[0121] A pair of enantiomers R, S-A and S, R-A were obtained by chiral resolution of racemic compound A by high performance liquid chromatography, and the purity ee%>97% was confirmed by HPLC, and the detection spectrum was as follows Figure 4-Figure 6 shown.

[0122] Chromatographic conditions:

[0123] Shimadzu LC-20AD high performance liquid chromatography (Shimadzu, Japan); chiral column: CHIRALPAK IG (ID00CD-UF004, 0.46cm I.D.×25cm L, Daicel Pharmaceutical Chiral Technology (Shanghai) Co., Ltd.); mobile phase : Dichloromethane / methanol / diethanolamine / acetic acid=90 / 10 / 0.1 / 0.3(V / V / V / V); flow...

Embodiment 3

[0127] This embodiment provides a chiral macrocyclic molecule with the following structure:

[0128]

[0129] The preparation method is as follows:

[0130] (1) react using the rac-6-1 and rac-6-2 obtained prepared in Example 1, the method is as follows:

[0131] Synthesis of Compound 1: Sodium hydroxide aqueous solution (3.0mL, 6.0N) was added into a mixed solution of methanol (5mL) and tetrahydrofuran (5mL) dissolved with rac-6-1 (234mg, 0.2mmol), reacted at room temperature overnight, and the reaction After completion, add 10% hydrochloric acid (5mL), filter the precipitate, dissolve the filter residue in aqueous sodium hydroxide solution (20mg / mL, 1.6mL), and stir for a few minutes, spin off the solvent, and dry to obtain compound 1 (white solid ).

[0132] The obtained compound 1 was characterized by proton nuclear magnetic spectrum, carbon nuclear magnetic spectrum and mass spectrometry, and the data results are as follows:

[0133] 1 H NMR (500MHz,D 2 O, 298K) δ...

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Abstract

The invention provides a macrocyclic molecule, a preparation method and an application thereof. A chiral macrocyclic molecule, as the formula I or II, has the function of chiral recognition; an internal compensation macrocyclic molecule, as the formula III, has the function of recognizing a strong-hydrophilic neutral molecule.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry and relates to a macrocyclic molecule and its preparation method and application. Background technique [0002] Chiral recognition in aqueous phase is very common in biological systems and constitutes the basis of life phenomena. Studying chiral recognition in aqueous phase not only helps to understand chiral recognition in complex biological systems, but also provides new means for enantioselective sensing and separation. There are generally two ways to use chiral molecules for chiral recognition. One is to use natural chiral host compounds for molecular recognition, and the other is to use artificially synthesized chiral molecules for chiral recognition. [0003] The main driving force for molecular recognition in water by conventional supramolecular macrocyclic hosts such as cyclodextrins, calixarenes, cucurbiturils, and pillararenes is the hydrophobic effect. However, alt...

Claims

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Application Information

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IPC IPC(8): C07D491/22G01N30/02G01N30/06
Inventor 蒋伟陈昭柴洪新
Owner SOUTH UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA
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