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A method for visible identification of chiral sulfenamides

A sulfenamide and chiral technology, applied in the field of chiral recognition, can solve the problems of complex post-processing and cumbersome testing procedures

Active Publication Date: 2019-02-26
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods require cumbersome testing procedures, and there are problems such as complex post-processing

Method used

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  • A method for visible identification of chiral sulfenamides
  • A method for visible identification of chiral sulfenamides
  • A method for visible identification of chiral sulfenamides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Example 1. Recognition of Chiral tert-Butylsulfinamide by Supramolecular Polymerization of Diacetylene Glutamic Acid Derivatives - Using Vesicle System for Recognition

[0080] Weigh 5 mg of the synthesized diacetylenyl glutamic acid derivative into a 100 ml round flask, and add 50 ml of dichloromethane to dissolve it.

[0081] After being completely dissolved, place it on a rotary evaporator for rotary evaporation until the solvent evaporates completely.

[0082] Add 50ml of ultrapure water, and ultrasonically shake at 70°C for 20 minutes to obtain the vesicle structure.

[0083] Prepare R-type tert-butylsulfinamide aqueous solution and S-type tert-butylsulfinamide aqueous solution with different concentrations. Concentrations are 0M, 0.02M, 0.1M, 0.2M, 0.5M, 1M, 1.5M, 2M

[0084] Take 1ml of the vesicle-containing aqueous solution, add it to a 5ml sample bottle, and irradiate it with 254nm ultraviolet light to turn into a blue solution.

[0085] Add 50ul of differe...

Embodiment 2

[0089] Example 2. Recognition of Chiral tert-Butylsulfinamide by Supramolecular Polymerization of Diacetylene Glutamic Acid Derivatives—Recognition Using Gel System

[0090] Weigh 5 mg of the synthesized diacetylenyl glutamic acid derivative into a 3 ml sample bottle, and add 250 ul of methanol for dissolution.

[0091] After it is completely dissolved, add 250ul of water, some uneven precipitation occurs, heat slightly until it is completely dissolved, and let it stand at room temperature.

[0092] After standing at room temperature for 2 hours, a white translucent gel formed.

[0093] The gel was irradiated with 254nm ultraviolet light to turn into a blue gel.

[0094] Add R-type and S-type tert-butylsulfinamide respectively, shake and mix evenly, and add until the final concentration of R-type tert-butylsulfinamide and S-type tert-butylsulfinamide is 2M.

[0095] By visual observation, it can be seen that the gel added with S-type tert-butyl sulfinamide turns from blue to...

Embodiment 3

[0098] Example 3. Recognition of chiral p-toluenesulfinamide by supramolecular polymerization of diacetylenyl glutamic acid derivatives—recognition by gel system

[0099] The synthesized and good diacetylenic glutamic acid derivatives were prepared as 4mg / ml methanol solution.

[0100] Take 100ul of the prepared methanol solution and add it to a 1mm cuvette.

[0101] Prepare R-type p-toluenesulfinamide methanol solution and S-type p-toluenesulfinamide methanol solution with a concentration of 2.5M.

[0102] Add 25ul of prepared R-type and S-type p-toluenesulfinamide methanol solutions to two cuvettes, shake gently and mix well.

[0103] Then add 275ul of high-purity water to the cuvette, shake gently and let it stand for 2 hours to form a translucent gel.

[0104] Both gels were irradiated with UV light at 254 nm.

[0105] By visual observation, it can be seen that the gel added with S-type p-toluenesulfinamide directly turns purple, while the gel added with R-type p-toluen...

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Abstract

The invention provides a method for visibly identifying chiral sulfenamide. According to the method, sulfenamide with different chirality can be rapidly distinguished by mixing a supermolecular aggregate of a diacetylene glutamic acid derivative with to-be-detected chiral sulfenamide according to color variation, so that the chiral identification efficiency is greatly improved.

Description

technical field [0001] The invention belongs to the field of chiral recognition, in particular to a method for visual recognition of chiral sulfinamides. Background technique [0002] Chirality is one of the most important properties in nature, molecular chiral recognition plays an extremely important role in life activities. The two enantiomers of the same compound not only have different optical properties and physical and chemical properties, but also have different biological activities. Therefore, the design and synthesis of artificial receptors with chiral recognition ability has become a frontier of current supramolecular chemistry research. direction. At present, most of the receptors with good chiral recognition function are based on platforms with good pre-organization, such as chiral crown ethers, binaphthyls, cyclodextrins, porphyrins, chiral macrocycles, and calixarenes. Among them, diacetylene The molecule has become one of the most concerned molecules in rec...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/49C08F2/48C08F138/00G01N21/33
CPCC07C233/49C08F2/48C08F138/00G01N21/33
Inventor 刘鸣华李帅张莉江建
Owner INST OF CHEM CHINESE ACAD OF SCI