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Novel racemized chiral organic boron-nitride fluorescent compound and preparation method thereof

A fluorescent compound and a racemic technology, which is applied in the field of novel quinoline chiral organoboron nitrogen compounds and their preparation, can solve the problems of unreported synthesis of chiral quinoline boron nitrogen compounds and the like.

Active Publication Date: 2017-11-10
HUNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

【J.Am.Chem.Soc., 2015, 137(42), 13472–13475; J.Org.Chem., 2016, 81(2), 458–468; Org.Lett., 2003, 5(14) , 2465–2467; Org.Lett., 2017, 19(1), 22–25; J.Org.Chem., 2016, 81(16), 7093–7101; Organometallics, 2013, 32(9), 2513– 2516; Org.Lett., 2009, 11(23), 5486–5489; J.Org.Chem., 2014, 79(10), 4277–4284; Ind.Eng.Chem.Res., 2016, 55(37 ), 9840–9850; J.Am.Chem.Soc., 2016, 138(47), 15315–15318; J.Org.Chem., 2011, 76(7), 2123–2131; J.Am.Chem. Soc.,2017,139(1),91–94] However, the use of fluorescently labeled bifunctional catalysts for synthetic chemistry has never been reported
And the method for synthesizing chiral quinoline boron nitrogen compound also has no report

Method used

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  • Novel racemized chiral organic boron-nitride fluorescent compound and preparation method thereof
  • Novel racemized chiral organic boron-nitride fluorescent compound and preparation method thereof
  • Novel racemized chiral organic boron-nitride fluorescent compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0025] 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), 0.005 mmol CuI, 0.1 mmol R 7 COOH(R 7 =Ph) and 1mL touluene, under nitrogen atmosphere, the reaction was carried out at 150°C for 12h. 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 productive rate is 81%. Detection of catalytic activity: add 0.5mmol aniline (Ar=Ph), 0.5mmol benzaldehyde (Ar=Ph), 0.6mmol4-phenylcyclohexanone, 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, and TLC followed 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

[0027]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), 0.005 mmol KI, 0.1 mmol R 7 COOH(R 7 =Ph) and 1mL touluene, under nitrogen atmosphere, the reaction was carried out at 150°C for 12h. 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 is 83%. Detection of catalytic activity: add 0.5mmol aniline (Ar=Ph), 0.5mmol benzaldehyde (Ar=Ph), 0.6mmol4-methoxycyclohexanone, 0.002 mmol 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.

preparation example 3

[0029] 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), 0.005 mmol LiI, 0.1 mmol R 7 COOH(R 7 =Ph) and 1mL touluene, under nitrogen atmosphere, the reaction was carried out at 150°C for 12h. 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 productive rate is 84%. Detection of catalytic activity: add 0.5mmol aniline (Ar=Ph), 0.5mmol benzaldehyde (Ar=Ph), 0.6mmol4-trifluoromethylcyclohexanone, 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-trifluoromethylcyclohexanone, the yield was 91% , The selectivity of (E)-2-benzyl-4-trifluoromethylcyclohexanone is 100%, and the cis-trans selectivity...

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Abstract

The invention discloses a novel racemized chiral organic boron-nitride fluorescent compound and a preparation method thereof. The compound is characterized in that quinoline amide compounds, cheap sodium tetraphenylborate ramifications and carboxylic ramifications are adopted as raw materials, and molecular iodine which is low in price and easy to obtain serves as a catalyst; common organic solvents are adopted as reaction solvents, the reaction is conducted at a certain temperature for a certain time, and then the novel racemized chiral organic boron-nitride fluorescent compound is obtained in a high production rate and a high selectivity. The catalyst is great in stability and recoverable, and has an excellent non-correspondence isomerism selectivity in condensation reactions of aldehyde ketone. The preparation method has the advantages of being low in cost, high in production rate, simple to operate, free of pollution and the like, and has a certain feasibility in implementation of industrialized production.

Description

【Technical field】 [0001] The invention belongs to the field of catalytic organic synthesis, and in particular relates to a novel quinoline chiral organic boron nitrogen material compound and a preparation method thereof. 【Background technique】 [0002] Organic Lewis acid-base bifunctional catalysts have been widely used in 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...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07F5/02B01J31/02C07C45/74C07C49/683C07C49/753C07C49/697C07C201/12C07C205/45
CPCB01J31/0275B01J2231/4205C07C45/74C07C201/12C07F5/02C09K11/06C09K2211/1055C07C49/683C07C49/753C07C49/697C07C205/45
Inventor 邱仁华阳天宝曹鑫
Owner HUNAN UNIV
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