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Water-soluble pillararene chiral amplification agent, and preparation method and application thereof

A technology of water-soluble column aromatic hydrocarbons and magnifying agent, which is applied in the field of chiral compound detection, can solve the problems of increasing the test cost, long duration and the like, and achieves the effects of simple operation, low synthesis cost and convenient access.

Active Publication Date: 2019-11-05
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in order to detect the chiral signal of ochratoxin A by circular dichroism detection, ochratoxin A needs to go through the modification and assembly process of gold nanoparticles and silver nanoparticles, which lasts for 32 hours
This method not only takes a long time, but also the gold nanoparticles and silver nanoparticles used are precious metals, which increases the cost of testing

Method used

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  • Water-soluble pillararene chiral amplification agent, and preparation method and application thereof
  • Water-soluble pillararene chiral amplification agent, and preparation method and application thereof
  • Water-soluble pillararene chiral amplification agent, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Synthesis of percarboxylammonium salt pillar[5]arene WP5:

[0043]

[0044] (1) Weigh 2.40g of perhydroxy column [5]arene P5-1 in a 250mL round bottom flask, add 10mL of ethyl chloroacetate, 30g of anhydrous potassium carbonate, 100mL of acetonitrile, under the protection of argon atmosphere, at 85 The reaction was stirred at ℃ for 48h. After the reaction, filter, spin dry the solvent, dissolve the resulting solid in 200 mL of dichloromethane, wash with 300 mL of distilled water, dry over anhydrous sodium sulfate, filter, and separate by silica gel column chromatography, eluents are petroleum ether and acetic acid The mixed solution with ethyl ester volume ratio of 3:1 was concentrated to obtain 0.62 g of full ester group column[5]arene P5-2.

[0045](2) Weigh 0.15 g of the full ester group [5] arene obtained in step (1) into a 100 mL round bottom flask, add 0.30 g of NaOH solid, 20 mL of ethanol, and 20 mL of distilled water in sequence, and react at 90 to 95 ° C f...

Embodiment 2

[0051] Synthesis of full carboxyl sodium salt column [5] arene WP5-1:

[0052]

[0053] (1) Weigh 0.56 g of the percarboxylate sodium salt column [5] arene WP5-OH obtained in step (2) of Example 1 into a 50 mL round bottom flask, add 0.3 g of NaOH solid, 30 mL of distilled water, and stir at room temperature for 13 h. The pH was adjusted to about 6.5 with hydrochloric acid solution, and the distilled water in the system was spin-dried under reduced pressure to obtain 0.62 g of percarboxylate sodium salt column[5]arene WP5-1.

[0054] The characterization data of the product full carboxyl sodium salt column [5] aromatic hydrocarbon WP5-1 prepared in this embodiment is as follows:

[0055] 1 H NMR (400MHz,D 2 O,298K,ppm):δ6.61(s,10H),4.21(s,20H),3.72(br,10H); 13 CNMR (100MHz,D 2 O, 298K, ppm): δ177.8, 151.2, 130.9, 117.7, 69.1, 30.9.

Embodiment 3

[0057] Synthesis of percarboxyammonium salt pillar[6]arene WP6:

[0058]

[0059] (1) Weigh 1.50g of perhydroxy column [6]arene P6-1 in a 250mL round bottom flask, add 10mL of ethyl chloroacetate, 30g of anhydrous potassium carbonate, 100mL of acetonitrile, under the protection of argon atmosphere, in The reaction was stirred at 90°C for 50h. After the reaction, filter and spin dry the solvent, dissolve the resulting solid in 200mL of dichloromethane, dry with 300mL of distilled water and anhydrous sodium sulfate, filter, and separate by silica gel column chromatography, the eluent is petroleum ether and ethyl acetate The mixed solution with a volume ratio of 3:1 was concentrated to obtain 0.33 g of full-ester-based column[6]arene P6-2.

[0060] (2) Weigh 0.16g of the full-ester-based columnar[6]arene P6-2 obtained in step (1) into a 100mL round bottom flask, add 0.35g of NaOH solid, 20mL of ethanol, and 20mL of distilled water in sequence, and react at 95°C for 13h , coo...

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Abstract

The invention discloses a water-soluble pillararene chiral amplification agent, and a preparation method and an application thereof, and belongs to the technical field of chiral compound detection. The water-soluble pillararene chiral amplification agent is a percarboxy ammonium salt pillararene or percarboxyl sodium salt pillararene having a structure represented by formula (I) shown in the description. The water-soluble pillararene chiral amplification agent is prepared by synthesizing a perester pillararene from a perhydroxyl pillararene and reacting the perester pillararene with an alkali.The water-soluble pillararene chiral amplification agent and a chiral small molecule are mixed, and the circular dichroism spectrum signal of the chiral small molecule can be enhanced by complexation, so that the circular dichroism spectrum signal can be detected. A circular dichroism spectrum chiral signal amplification method based on the water-soluble pillararene chiral amplification agent issimple, easy, convenient and fast. In the formula (I), n is 1 or 2, and M is NH4 or Na.

Description

technical field [0001] The invention belongs to the technical field of detection of chiral compounds, and in particular relates to a water-soluble chiral amplification agent for chiral aromatic hydrocarbons and a preparation method and application thereof. Background technique [0002] In many compounds, the molecular formulas of enantiomers are exactly the same, but the configuration of atoms or atomic groups in space is different, and they are mirror images of each other. We call such molecules that cannot overlap with their mirror image structures as chiral molecules. All chiral molecules are optically active, and all molecules of optically active compounds are chiral molecules. Chiral molecules include asymmetric molecules without any element of symmetry and asymmetric molecules with a simple axis of symmetry and no other elements of symmetry. [0003] Chiral molecules have many of the same physical and chemical properties, such as melting point, solubility, and the sam...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/712C07C27/02C07C51/41C07C59/72G01N21/19
CPCC07C51/09C07C51/412C07C67/31C07C2602/42C07C2603/92G01N21/19C07C69/712C07C59/72
Inventor 黄飞鹤朱黄天之李琪
Owner ZHEJIANG UNIV
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