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Imine compound as well as synthesis method and application thereof

A technology of amine compounds and synthesis methods, which is applied in the direction of preparation of imino compounds, preparation of amino compounds from amines, organic chemical methods, etc., and can solve problems such as high reaction temperature and complicated waste post-treatment

Active Publication Date: 2021-09-10
SHANGHAI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In view of the above-mentioned shortcomings of the prior art, the purpose of the present invention is to provide a new imine compound and its synthesis method and use, which are used to solve the problems in the prior art, which are highly efficient, high stereoselective, and at the same time Avoid problems such as the use of a large amount of solvents, high reaction temperature, waste and complicated post-processing

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  • Imine compound as well as synthesis method and application thereof
  • Imine compound as well as synthesis method and application thereof
  • Imine compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0053] In the present embodiment, a specific compound shown in formula (III) and compound shown in formula (IV) are as follows:

[0054]

[0055] The preparation method of the compound shown in formula (Ⅲ) is: add 64mg p-dimethylaminobenzaldehyde and 50mg (R,R)-1,2-bis(2-hydroxyphenyl)ethylenediamine in a 15mL ball mill jar , and then add stainless steel grinding beads with a diameter of 12mm, operate and close the grinding chamber, and set the grinding parameters: frequency 40Hz, duration 4 hours. Samples can be taken during the reaction, and the reaction progress can be monitored by TLC (petroleum ether: ethyl acetate = 6:1).

[0056] The reaction product of the above reaction is tested by HPLC, and the test parameters are: CHIRALPAK IC column, 5% isopropanol in hexane, 1.0ml / min; (R, R)-t R =10.0min, (S,S)-t R = 14.0 min. After testing, the purity of the chiral S, S molecule is >99%. It shows that the imine compound represented by the formula (III) formed by grinding...

Embodiment 2

[0061] In the present embodiment, a specific compound shown in formula (III) and compound shown in formula (IV) are as follows:

[0062]

[0063] The preparation method of the compound shown in formula (Ⅲ) is: add 67mg 2-naphthaldehyde and 50mg (R,R)-1,2-bis(2-hydroxyphenyl)ethylenediamine to a 15mL ball mill jar, and then add The grinding beads are 12mm stainless steel, the operation closes the grinding chamber, and the grinding parameters are set: the frequency is 40Hz, and the duration is 3.5 hours. Samples can be taken during the reaction, and the reaction progress can be monitored by TLC (petroleum ether: ethyl acetate = 12:1).

[0064] The reaction product of the above reaction is analyzed by HPLC, and the test parameters are: CHIRALPAK IC column, 20% isopropanol in hexane, 0.8ml / min; (R, R)t R =8.5min, (S,S)t R = 9.8 min. After testing, the purity of the chiral S, S molecule is >99%. It shows that the imine compound represented by the formula (III) formed by grin...

Embodiment 3

[0068] In the present embodiment, a specific compound shown in formula (III) and compound shown in formula (IV) are as follows:

[0069]

[0070] The preparation method of the compound shown in formula (Ⅲ) is: add 46mg benzaldehyde and 50mg (R,R)-1,2-bis(2-hydroxyphenyl)ethylenediamine in a 15mL ball mill jar, and then add 12mm stainless steel grinding beads, operate to close the grinding chamber, set the grinding parameters: frequency 40Hz, duration 3 hours. Samples can be taken during the reaction, and the reaction progress can be monitored by TLC (petroleum ether: ethyl acetate = 12:1).

[0071] The reaction product of above-mentioned reaction adopts HPLC to test, and test parameter is (CHIRALPAK IC column, 1% isopropanol in hexane, 0.5ml / min); (R, R)-t R =12.4min, (S,S)-t R = 17.1 min. After testing, the purity of the chiral S, S molecule is >99%. It shows that the imine compound represented by the formula (III) formed by grinding and reacting in the present applica...

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Abstract

The invention provides an imine compound as well as a preparation method and application thereof, the imine compound is shown as a formula (III), and the imine compound is a traditional Chinese medicine intermediate. The method is realized in a grinding mode, heat supply of a heat source is not needed, a solvent is not needed, the grinding method saves time and cost, aftertreatment is simple, and industrial production is easy.

Description

technical field [0001] The invention relates to the technical field of organic intermediate synthesis, in particular to an imine compound and its synthesis method and application. Background technique [0002] Chiral diamine compounds are an important part of the construction of stereoselective catalysts, including organic catalysts that facilitate oxidation, reduction, hydrolysis, and carbon-carbon bond formation reactions. Chiral diamines are also key components in drug synthesis, including anti- Viral drugs, such as Tamiflu and Ralenza, and cancer drugs, such as oxaliplatin and nutlin-3. The diaza-Cope rearrangement reaction is one of the most general methods to obtain various chiral diamines (J. Am. Chem. Soc., 2008, 130, 12184). This rearrangement reaction can be completed under the leadership of various driving forces, such as hydrogen bonding, electronic effects, steric hindrance effects, conjugation effects, etc. However, the imine compound obtained by the diaza-Co...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/24C07C255/58C07C249/02C07C253/30C07D307/52C07D333/20C07C209/52C07C211/27C07C211/30C07C211/29C07C209/68C07C211/48C07C213/02C07C215/50C07C227/18C07C229/38C07C229/26C07C217/58
CPCC07C251/24C07C255/58C07C249/02C07C253/30C07D307/52C07D333/20C07C209/52C07C211/27C07C211/30C07C211/29C07C209/68C07C211/48C07C213/02C07C215/50C07C227/18C07C229/38C07C229/26C07C217/58C07B2200/07C07C2603/50C07C2603/26
Inventor 甄家劲马文献
Owner SHANGHAI TECH UNIV