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A kind of chiral titanium complex and its preparation and application

A complex and chiral technology, applied in carboxylate preparation, nuclear magnetic resonance analysis, organic chemistry, etc., can solve problems such as unfavorable, complex structure, and difficult synthesis

Active Publication Date: 2021-06-18
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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  • A kind of chiral titanium complex and its preparation and application
  • A kind of chiral titanium complex and its preparation and application
  • A kind of chiral titanium complex and its preparation and application

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'-binaphthic 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 and then raise the temperature to 60°C, keep the temperature for 24 hours and then cool down to room temperature. The mixture is concentrated under reduced pressure to remove the solvent, and the residue is recrystallized 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 p...

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 the 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 new chiral titanium complex, and also provides a synthesis method of the chiral titanium compound and its application in chiral recognition. The structure of the new compound is as follows: The compound is used as a chiral shift reagent to detect the optical purity of chiral monoamines, chiral diamines, chiral amino alcohols, chiral amino acids and other chiral compounds. The operation is simple and the chemical shift difference It 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 Patents(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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