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Chiral compounds containing biphenyl skeleton, and preparation method and applications thereof

A chiral compound and biphenyl technology are applied in the field of chiral compounds containing biphenyl skeleton and their preparation, and can solve the problems of complex structure, many synthesis steps, and complicated preparation process of chiral binaphthalene compounds.

Inactive Publication Date: 2018-09-28
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the complex structure of chiral binaphthyl compounds, many synthetic steps, and cumbersome preparation process, it has great limitations in practical applications.

Method used

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  • Chiral compounds containing biphenyl skeleton, and preparation method and applications thereof
  • Chiral compounds containing biphenyl skeleton, and preparation method and applications thereof
  • Chiral compounds containing biphenyl skeleton, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The preparation method of class A compound is as follows:

[0064]

[0065] (1) Under nitrogen protection conditions, weigh 12g of compound 1, 12.50g of phenylboronic acid, 25g of potassium carbonate, 600mg of [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (100mg, 0.12mmol) in a 500mL two-neck reaction flask, after three times of evacuation and nitrogen supplementation, add 300mL of a mixed solvent of ethylene glycol dimethyl ether and water (V / V, 2:1), heat to 95°C and react under nitrogen protection After 10 hours, cool to room temperature, add dichloromethane to dissolve after removing the solvent, remove the insoluble matter by suction filtration, wash the organic phase with saturated sodium chloride, spin dry, and separate the crude product through a column (petroleum ether: dichloromethane=5 : 1), to obtain 9.88g compound 2, productive rate 83%.

[0066] (2) Add 4.78g of compound 2 into a 250mL two-neck round bottom flask, and then inject 70mL of d...

Embodiment 2

[0073] The preparation method of class B compound is as follows:

[0074]

[0075] Weigh 1.5g of compound 5 and 643mg of phosphorus pentasulfide in 20mL of dry dichloromethane, reflux at 150°C for 5h, remove the solvent under reduced pressure after the reaction, extract the reaction solution with dichloromethane and water, combine the organic phases, spin dry, The crude product was separated by column to obtain 1.38 g of compound B with a yield of 78%.

[0076] The analysis result of compound B is: 1 H NMR (CDCl 3 , 400MHz): δ8.14-8.09 (m, 12H), 7.84-7.55 (d, 4H), 7.47-7.40 (d, 4H), 7.38 (s, 2H), 1.62 (s, 6H).

Embodiment 3

[0078] The preparation method of C compound is as follows:

[0079]

[0080] (1) Weigh 2 g of compound 5 and dissolve in 30 mL of dry dichloromethane, add 1 mL of freshly distilled thionium trichloride at one time, and then slowly add 2 mL of anhydrous triethylamine. After stirring at room temperature for 20 h, the solvent was removed under reduced pressure, and the crude product was separated by column to obtain 1.89 g of compound 7 with a yield of 82%.

[0081] (2) Weigh 1.89g of compound 7 and dissolve it in 30mL of dry mixed solution of dichloromethane and acetonitrile (V / V, 1:2), add 771mg of 4-dimethylaminopyridine, 2mL of triethylamine and 1.18g of Trifluoromethanesulfonamide was refluxed for 10h. After the reaction was completed, water was added to quench, and the reaction liquid was extracted with dichloromethane and water. The organic phases were combined, dried, and the solvent was removed under reduced pressure. The crude product was separated by column to obta...

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Abstract

The invention relates to chiral compounds containing a biphenyl skeleton, and a preparation method and applications thereof. The chemical structure of the chiral compounds is disclosed in the invention, wherein R1, and R2 are used for representing groups independently selected from hydrogen, methyl, tertiary butyl, halogen, phenyl, substituted phenyl, naphthyl, or substituted naphthyl; R3 is usedfor representing a group selected from vinyl, carboxyl, or diphenylphosphine; R4 is selected from sulfur, oxygen, or selenium; R5 is selected from hydroxyl or trifluoromethane sulfonamide group; and R6 is selected from sulfur or oxygen. The chiral compound is prepared from (R)-3, 3'-ditert-butyl-5, 5'-dibromo-6, 6'-dimethyl-1, 1'biphenyl-2,2'-diphenol; the chiral compound can be taken as a catalyst in catalytic of asymmetric reaction. Compared with the prior, that preparation method possesses following advantages: the chiral compounds based on biphenyl skeleton are prepared, and comprise chirial phosphoric acid, diphosphine, phosphamide, thiophosphoric acid, thio phosphamide ester, diene, dicarboxylic acid, and the like; the chiral compounds can be taken as catalysts in asymmetric reaction; the structure is relatively simple; synthetic preparation is convenient; and the application prospect is promising.

Description

technical field [0001] The invention belongs to the technical field of chiral compounds, and relates to a chiral compound containing a biphenyl skeleton and a preparation method and application thereof. Background technique [0002] After years of development, asymmetric catalysis has become the most economical and effective method for the synthesis of chiral substances. Among them, axial chiral compounds play a very important role in the synthesis of asymmetric catalysis, and the design and catalytic performance of new axial chiral catalysts have always been a research hotspot. The most representative ones are chiral binaphthyl compounds, which mainly include the following: [0003] [0004] These compounds and their derivatives have been widely used in asymmetric catalysis, and some of them have achieved better catalytic effects. However, due to the complex structure of chiral binaphthyl compounds, many synthesis steps and cumbersome preparation process, there are gre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/50C07F9/6571C07C15/50C07C1/32C07C63/331C07C27/02C07C63/72B01J31/02B01J31/04C07B53/00
CPCB01J31/02B01J31/0255B01J31/0258B01J31/0264B01J31/0268B01J31/04C07B53/00C07B2200/09C07C15/50C07C63/331C07C63/72C07F9/5022C07F9/6571C07F9/657127C07F9/657154
Inventor 崔勇陈旭刘燕
Owner SHANGHAI JIAO TONG UNIV
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