N-bisphenylsulfonyl-1-phenylselenyltrifluoroethane derivative and its synthesis method and application

A synthesis method and technology of fluorobisbenzenesulfonimide are applied in the field of N-bisphenylsulfonyl-1-phenylselenyl trifluoroethane derivatives and their synthesis, which can solve the problem of many active functional groups and no synthesis found. methods, difficulty in synthesis, etc., to achieve the effects of simple and safe operation, efficient atom economy, and high universality

Active Publication Date: 2021-10-15
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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-bisphenylsulfonyl-1-phenylselenyltrifluoroethane derivative and its synthesis method and application
  • N-bisphenylsulfonyl-1-phenylselenyltrifluoroethane derivative and its synthesis method and application
  • N-bisphenylsulfonyl-1-phenylselenyltrifluoroethane derivative and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051]

[0052] N-fluoro-bisphenylsulfonimide (0.2 mmol), diphenyl di2 (0.12 mmol) is dissolved in dichloromethane (2.0 mL), then diluted in dichloromethane (1 mL) trifluorides The toluene solution (C = 0.85 mmol / ml, 0.4 mmol) of base weight is slowly added dropwise to the reaction system, and the reaction system is at room temperature (25 ° C), and after the dropwise addition, stir for 10 minutes, remove the solvent under reduced pressure, result The crude product is shown in the formula (4-1). The crude product was columnized (ethyl acetate: petroleum ether = 1: 40 ~ 1: 20) obtained a pure product. The yield is 95%. Nuclear magnetic resonance 1 H NMR, 13 C NMR, 19 F NMR map figure 1 Distance 1 H NMR (400MHz, CDCL 3 : Δ8.23 (D, J = 8.2Hz, 2H), 7.87 (D, J = 8.2 Hz, 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 = 8.0 Hz, 1H) PPM; 13 CNMR (100MHz, CDCL 3 : Δ139.9, 138.0, 134.9, 134.6, 134.5, 129.7, 129.6, 129.4, 129.3, 128.9, 128.8,...

Embodiment 2

[0054]

[0055] N-fluoroisodiphenylsulfonimide (0.2 mmol), diphenyl dichlenyl ether (0.12 mmol) is dissolved in dichloromethane (2.0 mL), and then diluted in dichloromethane (1 mL) pentafluoro The toluene solution (C = 0.85 mmol / ml, 0.4 mmol) of base weight is slowly added dropwise to the reaction system, and the reaction system is at room temperature (25 ° C), and after the dropwise addition, stir for 10 minutes, remove the solvent under reduced pressure, result The crude product is shown in the formula (4-2). The crude product was columnized (ethyl acetate: petroleum ether = 1: 40 ~ 1: 20) obtained a pure product. The yield is 88%. Nuclear magnetic resonance 1 H NMR, 13 C NMR, 19 F NMR map figure 2 Distance 1 H NMR (400MHz, CDCL 3 : Δ8.40 (D, J = 7.8 Hz, 2H), 7.90 (D, J = 7.9 Hz, 2H), 7.71 (T, J = 7.4 Hz, 1H), 7.62 (Q, J = 7.8 Hz, 3H ), 7.45 (t, j = 7.8 Hz, 2H), 7.40-7.32 (m, 3H), 7.31-7.25 (m, 2H), 5.96 (DD, J = 20.0, 6.9 Hz, 1H) PPM; 13 C NMR (100MHz, CDCL 3 : δ139.86, 138...

Embodiment 3

[0057]

[0058] N-fluoroisodiphenylsulfonimide (0.2 mmol), diphenyl dichlenyl ether (0.12 mmol) is dissolved in dichloromethane (2.0 mL), then dilute in dichloromethane (1 mL) Difluoride The chloroform solution (C = 0.85 mmol / mL, 0.4 mmol) was slowly added dropwise to the reaction system, and the reaction system was stirred at room temperature (25 ° C), and the mixture was stirred for 10 minutes, and the solvent was removed under reduced pressure. The crude product is shown in the formula (4-3). The crude product was columnized (ethyl acetate: petroleum ether = 1: 40 ~ 1: 20) obtained a pure product. The yield was 85%. Nuclear magnetic resonance 1 H NMR, 13 C NMR, 19 F NMR map image 3 Distance 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 = 7.9 Hz, 3H), 7.20 (T, J = 7.3Hz, 1H), 7.12 (T, J = 7.4 Hz, 2H), 6.44-6.13 (m, 1H), 5.23-5.11 (m, 1H) ppm; 13 C NMR (100MHz, CDCL 3 : δ139.74, 138.72, 137.84, 134.84, 134.46, 129.4...

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Abstract

The invention discloses a method for synthesizing N-bisbenzenesulfonyl-1-phenylselenyl trifluoroethane derivatives, using diazo compounds, diether compounds and N-fluorobisbenzenesulfonimide as raw materials , without any catalyst, using an organic solvent as a solvent, and through a one-step reaction, the N-bisphenylsulfonyl-1-phenylselenyl trifluoroethane derivative is obtained. The method for synthesizing N-bisbenzenesulfonyl-1-phenylselenyl trifluoroethane derivatives of the present invention has efficient atom economy, does not need any organic catalyst or metal catalyst, is simple and safe to operate, and the synthetically obtained N-bisbenzenesulfonic acid Acyl-1-phenylselenyl trifluoroethane derivatives are important organic synthesis and pharmaceutical intermediates.

Description

Technical field [0001] The present invention belongs to the synthesis of pharmaceuticals, chemical industry, mainly involving N- bis-benzenesulfonyl-1-trifluoroethane phenylselenyl derivatives and their synthesis and applications. Background technique [0002] Trifluoromethyl and selenium based compound has good biological activity, in addition, the organic selenium compounds having important physical and pharmacological activity are widely used in material science and drug design. Constructing a compound having both selenium and trifluoromethyl structure may be provided having more or develop special nature of the class structure. Since the product contains more of such reactive functional groups, the synthesis is difficult, therefore, the product of the synthesis of such structure is not found. Inventive content [0003] The present invention fill the gaps in the synthesis method of such compounds, synthetic methods proposed trifluoromethyl-step synthesis of compounds having b...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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 UNIV
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