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N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative, synthesis method and applications thereof

A technology of phenylselenyltrifluoroethane and bisphenylsulfonyl, applied in the field of N-bisphenylsulfonyl-1-phenylselenyltrifluoroethane derivatives and their synthesis, can solve the problem of many active functional groups and difficult synthesis , No synthetic method and other problems were found, achieving the effect of simple and easy-to-obtain raw materials, mild conditions, and high-efficiency atom economy

Active Publication Date: 2020-03-03
EAST CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Because this type of product contains more active functional groups, it is difficult to synthesize, therefore, no synthetic method has been found for the product of this type of structure

Method used

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  • N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative, synthesis method and applications thereof
  • N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative, synthesis method and applications thereof
  • N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative, synthesis method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] N-fluorobisbenzenesulfonimide (0.2mmol), diphenyldiselenide (0.12mmol) were dissolved in dichloromethane (2.0mL), then, diluted in dichloromethane (1mL) of trifluoromethane The toluene solution (c=0.85mmol / mL, 0.4mmol) of diazonium was slowly added dropwise to the reaction system, and the reaction system was at room temperature (25°C). After the dropwise addition was completed, it was stirred for 10 minutes, and the solvent was removed under reduced pressure to obtain The crude product has a structure as shown in formula (4-1). The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:40~1:20) to obtain a pure product. The yield was 95%. nuclear magnetic resonance 1 H NMR, 13 C NMR, 19 F NMR spectrum such as figure 1 as shown, 1 H NMR (400MHz, CDCl 3 ):δ8.23(d,J=8.2Hz,2H),7.87(d,J=8.2Hz,2H),7.71-7.57(m,4H),7.46-7.42(m,2H),7.36-7.32( m,3H),7.27-7.23(m,2H),5.54(q,J=8.0Hz,1H)ppm; 13 CNMR (100MHz, CDCl 3 ): δ139.9, 138.0...

Embodiment 2

[0054]

[0055] N-fluorobisbenzenesulfonylimide (0.2mmol), diphenyldiselenide (0.12mmol) were dissolved in dichloromethane (2.0mL), and then, diluted in dichloromethane (1mL) pentafluoroethyl The toluene solution (c=0.85mmol / mL, 0.4mmol) of diazonium was slowly added dropwise to the reaction system, and the reaction system was at room temperature (25°C). After the dropwise addition was completed, it was stirred for 10 minutes, and the solvent was removed under reduced pressure to obtain The crude product has a structure as shown in formula (4-2). The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:40~1:20) to obtain a pure product. The yield was 88%. nuclear magnetic resonance 1 H NMR, 13 C NMR, 19 F NMR spectrum such as figure 2 as shown, 1 H NMR (400MHz, CDCl 3 ): δ8.40(d, J=7.8Hz, 2H), 7.90(d, J=7.9Hz, 2H), 7.71(t, J=7.4Hz, 1H), 7.62(q, J=7.8Hz, 3H ), 7.45 (t, J = 7.8Hz, 2H), 7.40-7.32 (m, 3H), 7.31-7.25 (m, 2H), 5.96 (dd, J...

Embodiment 3

[0057]

[0058] N-fluorobisbenzenesulfonylimide (0.2mmol), diphenyldiselenide (0.12mmol) were dissolved in dichloromethane (2.0mL), then difluoromethane diluted in dichloromethane (1mL) A chloroform solution of diazo (c=0.85mmol / mL, 0.4mmol) was slowly added dropwise to the reaction system, and the reaction system was at room temperature (25°C). After the dropwise addition was completed, it was stirred for 10 minutes, and the solvent was removed under reduced pressure to obtain The crude product has a structure as shown in formula (4-3). The crude product was subjected to column chromatography (ethyl acetate:petroleum ether=1:40~1:20) to obtain a pure product. The yield was 85%. nuclear magnetic resonance 1 H NMR, 13 C NMR, 19 F NMR spectrum such as image 3 as shown, 1 H NMR (400MHz, CDCl 3 ): δ8.12(d, J=7.6Hz, 2H), 7.70(d, J=7.6Hz, 2H), 7.59-7.41(m, 5H), 7.29(d, J=7.9Hz, 3H), 7.20 (t, J=7.3Hz, 1H), 7.12(t, J=7.4Hz, 2H), 6.44-6.13(m, 1H), 5.23-5.11(m, 1H)ppm; 13 C...

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Abstract

The invention discloses an N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative synthesis method, which comprises: carrying out a one-step reaction by using a diazo compound, a diether compound and N-fluorobisbenzenesulfonyl imide as raw materials and using an organic solvent as a solvent in the absence of a catalyst to obtain the N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative. According to the invention, the synthesis method has efficient atom economy, does not need any organic catalysts or metal catalysts, and is simple and safe to operate, and the synthesized N-bisbenzenesulfonyl-1-phenylseleno trifluoroethane derivative is an important organic synthesis and medical intermediate.

Description

technical field [0001] The invention belongs to the fields of synthetic medicine and chemical industry, and mainly relates to N-bisphenylsulfonyl-1-phenylselenyltrifluoroethane derivatives and their synthesis method and application. Background technique [0002] Selenium-containing and trifluoromethyl compounds have good biological activity. In addition, organic selenium compounds have important physical and pharmaceutical activities, and are widely used in material science and drug design. Constructing compounds with both selenium and trifluoromethyl structures can provide or develop more special properties with such structures. Because this type of product contains more active functional groups, it is difficult to synthesize, therefore, no synthetic method has been found for the product of this type of structure. Contents of the invention [0003] The present invention fills up the gap in the synthesis method of this type of compound, and proposes a synthesis method for...

Claims

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Application Information

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IPC IPC(8): C07C391/02C07F9/48C07C391/00C07C323/49C07C395/00C07D213/60C07D333/30
CPCC07C323/49C07C391/00C07C391/02C07C395/00C07D213/60C07D333/30C07F9/4816
Inventor 胡文浩李玖零马超群
Owner EAST CHINA NORMAL UNIVERSITY
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