Method for inducing asymmetric sulfydryl-alkene click reaction through chiral inorganic liquid crystal carrier

A technology of inorganic liquid crystals and chiral liquid crystals, applied in asymmetric synthesis, organic chemical methods, liquid crystal materials, etc., can solve the problems of poor one-handedness and small excess value of living organisms

Active Publication Date: 2020-07-07
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the enantiomeric excess value (ee%) obtained simply by the asymmetric photochemical reaction induced by circularly polarized light is very small, the highest so far is only 4.19%, which is far worse than the monochirality of living organisms.

Method used

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  • Method for inducing asymmetric sulfydryl-alkene click reaction through chiral inorganic liquid crystal carrier
  • Method for inducing asymmetric sulfydryl-alkene click reaction through chiral inorganic liquid crystal carrier
  • Method for inducing asymmetric sulfydryl-alkene click reaction through chiral inorganic liquid crystal carrier

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Preparation of Silver Nanowires Cholesteric Chiral Liquid Crystal Phase

[0048]Weigh 0.781g of PVP and 25mL of glycerin solution into a round bottom flask with a volume of 100mL, and stir the mixture in an oil bath at 45°C until the PVP is completely dissolved. Add 0.21 g of silver nitrate to the dissolved solution, and then add 1.3 mL of glycerol, 7.8 mg of sodium chloride, and a prefabricated mixed solution composed of 0.66 mL of water. Subsequently, the round-bottomed flask was placed in a sand bath, and the temperature was slowly raised to 210° C., with stirring at a speed of 400 rpm during the heating process. During the entire heating process, as the temperature increased, the color of the mixture gradually changed from colorless and transparent to bright light brownish red, reddish gray, dark gray, and finally grayish green. After the temperature reached 210° C., continue heating for 10 minutes, then stop heating, and place the product at room temperature to co...

Embodiment 2

[0053] Asymmetric mercapto-ene click reaction

[0054] Measure 1mmol of 1-phenylethylmercaptan and 1mmol of 1,4 cyclohexadiene, weigh 1mmol of N-vinylacetamide and dissolve it in 1,4-dioxane, and take 1 μL of the silver prepared in Example 1 Add the nanowires into the solution, move the solution into a quartz cuvette with an optical path of 1 cm, and irradiate the cuvette containing the sample solution with ordinary ultraviolet light with a wavelength of 300-400 nm at room temperature for 24 hours. At this time, the sample solution From colorless and transparent to pale yellow liquid, the final reaction degree was detected by thin-layer chromatography. The final product is purified and separated through a chromatographic column to obtain an oily liquid N-(2-(1-phenylethylthio)ethyl)acetamide molecule.

[0055] The molecular structure is as follows:

[0056]

[0057] Its NMR spectrum is shown in Figure 5 .

[0058] The obtained N-(2-(1-phenylethylthio)ethyl)acetamide mo...

Embodiment 3

[0060] Ethanol solution of silver nanowires as a chiral dopant induces the transformation of nematic liquid crystal E7 into cholesteric chiral liquid crystal

[0061] Take a 4mL reaction bottle, add 1mL silver nanowire ethanol solution prepared in Example 1 and 1mL nematic liquid crystal E7 respectively, oscillate fully to mix evenly, pipette 1 drop of the mixed solution and drop it on the cover glass, and examine it through a polarizing microscope (POM) observation, get a POM map rich in rainbow colors, such as Figure 7 shown. It can be seen that the nematic liquid crystal E7 is transformed into a cholesteric chiral liquid crystal under the induction of the silver nanowire ethanol solution.

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Abstract

The invention provides a method for inducing an asymmetric sulfydryl-alkene click reaction through a chiral inorganic liquid crystal carrier. The method comprises the following step: carrying out click reaction on a sulfhydryl compound with chiral carbon and olefin in a chiral inorganic liquid crystal phase under the irradiation of ultraviolet light with the wavelength of 300-400 nm to obtain thecompound with optical activity. In the invention, the sulfhydryl compounds and alkene small molecules are subjected to a photocatalytic reaction through ultraviolet irradiation in a microenvironment with a chiral inorganic liquid crystal phase to form small molecules with optical activity, so that the chiral catalysis is achieved through chiral inorganic liquid crystals such as a silver nanowire cholesteric chiral liquid crystal phase for the first time, and optically active molecules are prepared. A certain enlightenment effect is achieved on the biological homochirality phenomenon and the life origin.

Description

technical field [0001] The invention relates to the technical field of small molecule reactions, in particular to a method for inducing an asymmetric mercapto-ene click reaction through a chiral inorganic liquid crystal carrier. Background technique [0002] Inorganic liquid crystal materials have extraordinary advantages in physical properties, such as magnetism, conductivity, and high temperature resistance. In addition, inorganic liquid crystals have better dispersion and high tolerance to pH changes. In addition, According to the properties of rod-shaped or disc-shaped inorganic liquid crystals, inorganic liquid crystals usually have special photoelectric and electromagnetic effects. In inorganic liquid crystals, there are electrostatic repulsion and van der Waals forces between particles. Therefore, factors such as pH value, particle size and distribution, temperature, and particle strength have a great influence on the interaction between particles. By adjusting these...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/18C07C323/41C09K19/36C09K19/58C07B53/00
CPCC07B53/00C07B2200/07C07C319/18C09K19/36C09K19/586C07C323/41
Inventor 邹纲谢逸帆何晨露
Owner UNIV OF SCI & TECH OF CHINA
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