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Preparation method of organic boron-nitrogen fluorescent compound

A fluorescent compound and boron-nitrogen technology, which is applied in the field of preparation of organic boron-nitrogen fluorescent compounds, can solve the problems of inconvenient industrialization, long reaction time and high reaction temperature.

Inactive Publication Date: 2018-06-15
汝城县三鑫电化有限公司
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

[0003] However, its reaction temperature is high and the reaction time is long, so it is not easy to carry out industrialization

Method used

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  • Preparation method of organic boron-nitrogen fluorescent compound
  • Preparation method of organic boron-nitrogen fluorescent compound

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Experimental program
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preparation example 1

[0030] Add 0.1 mmol I (wherein R f = CF 3 ; 3 , R 4 , R 5 =H), 0.1mmol II (wherein R 1 , R 2 , R 6 =H), 0.005mmol copper bromide, 0.1mmol R 7 COOH (R 7 =Ph is benzene) and 1mL toluene solution, under nitrogen atmosphere, the reaction is carried out at 90 ° C. 5. After the reaction is completed, filter, concentrate, and obtain III (wherein R f= CF 3 ; 1 , R 2 , R 3 , R 4 , R 5 , R 6 = H, R 7 =Ph), the yield was 82%. Detection of catalytic activity: 0.5mmol aniline (Ar=Ph), 0.5mmol benzaldehyde (Ar=Ph), 0.6mmol 4-phenylcyclohexanone, 0.002 mmol III (where R f = CF 3 ;R 1 , R 2 , R 3 , R 4 , R 5 , R 6 = H, R 7 =Ph) and 1mL toluene (toluene solution), the reaction was carried out at 80°C for 12h, and TLC tracked the reaction until the reaction was complete. The reaction result was: (E)-2-benzyl-4-phenylcyclohexanone, and the yield was 95%, the selectivity of (E)-2-benzyl-4-phenylcyclohexanone is 100%, and the cis-trans selectivity is 1 / 99.

preparation example 2

[0032] Add 0.1 mmol I (wherein R f = CF 3 ; 3 , R 4 , R 5 =H), 0.1mmol II (wherein R 1 , R 2 , R 6 =H), 0.005mmol sodium bromide, 0.1mmol R 7 COOH (R 7 =Ph) and 1mL touluene, under a nitrogen atmosphere, the reaction was carried out at 70°C for 3h. After the reaction was completed, filtered, concentrated, and separated by chromatography to obtain III (wherein R f = CF 3 ; 1 , R 2 , R 3 , R 4 , R 5 , R 6 = H, R 7 =Ph), the yield was 83%. Detection of catalytic activity: add 0.5mmol aniline (Ar=Ph), 0.5mmol benzaldehyde (Ar=Ph), 0.6mmol 4-methoxycyclohexanone, 0.002mmol III (where R f = CF 3 ; 1 , R 2 , R 3 , R 4 , R 5 , R 6 = H, R 7 =Ph) and 1mL toluene, the reaction was carried out at 80°C for 12h, TLC followed the reaction until the reaction was complete. The reaction result was: (E)-2-benzyl-4-methoxycyclohexanone, the yield was 97%, The selectivity of (E)-2-benzyl-4-methoxycyclohexanone was 100%, and the cis-trans selectivity was 1 / 99.

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Abstract

The invention discloses a preparation method of an organic boron-nitrogen fluorescent compound. The preparation method comprises the following steps of: adopting a quinoline amide compound, cheap sodium-tetraphenylborate type derivatives and carboxylic-acid type derivatives as raw materials, adopting cheap copper bromide or sodium bromide as a catalyst, adopting a common organic solvent as a reaction solvent, reacting for a period of time under a certain temperature, and obtaining a novel chiral organic boron-nitrogen fluorescent compound by high yield and high selectivity. The organic boron-nitrogen fluorescent compound is good in stability, can be recovered, has very good diastereoisomeric selectivity in aldehyde-ketone condensation reaction. The preparation method disclosed by the invention has the advantages of lower cost, high yield, simple operation and no pollution and the like, and has certain feasibility for realizing industrial production.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, in particular to a preparation method of an organic boron nitrogen fluorescent compound. 【Background technique】 [0002] Organic Lewis acid-base bifunctional catalysts have been widely used in the field of organic synthesis due to their high regio- and stereoselectivity due to their synergistic activation of nucleophiles and electrophiles. However, compared with metal catalysts, organic catalysts have lower catalytic activity due to their inherent physical and chemical properties similar to organic synthesis reaction products, so usually the addition amount reaches 5-10mol%, resulting in more catalyst residues, but relative to the product , how to quickly detect this low concentration of catalyst residues (<1mol%) through spectroscopy is a problem, especially for medicinal chemistry, the strict requirement that the mono-heterogeneity should not be greater than 0.1% severely limits ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/02
CPCC07F5/027C09K11/02C09K2211/1007C09K2211/1029
Inventor 张福彪
Owner 汝城县三鑫电化有限公司
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