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Chiral titanium complex as well as preparation and application thereof

A complex and chiral technology, applied in the preparation of carboxylate, analysis by nuclear magnetic resonance, organic chemistry, etc., can solve the problems of difficult synthesis, complex structure, disadvantages, etc., and achieve the effect of simple test operation and easy reagent synthesis

Active Publication Date: 2020-02-14
FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the reagents have a good recognition effect on many types of substrates, the actual structure is complex and the synthesis is difficult, which is not conducive to the application of the method.

Method used

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  • Chiral titanium complex as well as preparation and application thereof
  • Chiral titanium complex as well as preparation and application thereof
  • Chiral titanium complex as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] Synthesis of Example 1 Chiral Titanium Complex

[0023] Dissolve 1g of (S)-2,2'-dihydroxy-3,3'-binaphtalic acid in 40mL of methanol, add 0.5g of titanium isopropoxide dropwise at room temperature, continue to stir for 30min, and then add 0.14 g of sodium hydroxide, stir to completely dissolve, then heat up to 60°C, keep warm for 24 hours, then cool down to room temperature, concentrate the mixture under reduced pressure to remove the solvent, and recrystallize the residue with methanol and chloroform to obtain 0.81 g of the product as red crystals. The melting point is greater than 300°C. 1 H NMR (400MHz, CDCl 3 )δ7.63(s, 6H), 7.37(d, J=8.0Hz, 6H), 7.02(t, J=7.5Hz, 6H), 6.86(t, J=7.7Hz, 6H), 6.25(d, J = 8.6Hz, 6H); 13 C NMR (101MHz, CDCl 3 ) δ 169.54, 159.86, 136.22, 130.96, 129.86, 126.69, 125.74, 125.34, 125.02, 120.83, 116.04. Determination of the optical purity of the α-phenylethylamine sample of example 2 unknown optical purity

[0024] Weigh 1 mg of the α-ph...

example 3

[0025] Determination of optical purity of phenylglycine methyl ester hydrochloride sample of unknown optical purity in example 3

[0026] Weigh 1 mg of phenylglycine methyl ester hydrochloride sample to be tested and dissolve it in deuterated dimethyl sulfoxide, then add 6.6 mg of chiral titanium complex, mix well, put it into a 400 MHz nuclear magnetic resonance instrument and record at room temperature 1 H NMR signal, obtain the chemical shift and integral area of ​​the split two groups of α-H peak signals, which is δ 1 =5.25,S 1 =0.365, δ 2 =5.19,S 2 = 0.635. (S 2 -S 1 ) / (S 1 +S 2 )=27.0% indicates that the optical purity of the sample to be tested is 27.0%.

[0027] A brief list of other implementation cases is as follows:

[0028]

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Abstract

The invention discloses a novel chiral titanium complex, and also provides a synthetic method of the chiral titanium compound and an application of the chiral titanium compound in chiral recognition.The novel compound has a structure shown in the specification. The compound is used as a chiral displacement reagent to detect the optical purity of a plurality of chiral compounds such as chiral monoamine, chiral diamine, chiral amino alcohol and chiral amino acid, has the advantages of simple operation and a large difference value in chemical shift, and is a fast, efficient, convenient and practical detection method.

Description

technical field [0001] The invention belongs to the technical field of synthesis of chiral complexes, specifically relates to a chiral titanium complex, and also relates to a synthesis method of the chiral titanium complex and its application in chiral recognition. Background technique [0002] Chiral titanium complexes are a very important class of chiral catalysts. Titanium ions can coordinate with chiral ligands containing O, S, N and other atoms. The complexes can be designed with strong controllability and rich structures, so they are widely used in asymmetric catalytic reactions. Such as asymmetric alkylation of carbonyl compounds (J.Org.Chem., 2018, 83, 6127; Chem.Rev., 1992, 92, 807.), asymmetric reduction (Asian J.Org.Chem., 2015 , 4, 794.), asymmetric cyanation (Chem.Rev., 2008, 108, 5146.) and many other reactions, chiral titanium complexes show good catalytic activity and high enantioselectivity. However, there are few reports on its use as chiral recognition. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C65/11C07C51/41G01N24/08
CPCC07B2200/07C07C65/11G01N24/08
Inventor 边广岭宋玲孙兆峰
Owner FUJIAN INST OF RES ON THE STRUCTURE OF MATTER CHINESE ACAD OF SCI
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