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Difluoromethyl selenate compound and synthesis method thereof

A synthesis method and compound technology, which are applied in the production of steroids, organic chemistry, bulk chemicals, etc., can solve problems such as unreported synthesis methods of difluoromethylselenoate compounds, and achieve environmental friendliness, mild conditions, and simple operation. Effect

Active Publication Date: 2021-01-29
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the literature is limited to the synthesis of difluoromethyl selenide, and no difluoromethyl selenide compound and its synthesis method have been reported.

Method used

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  • Difluoromethyl selenate compound and synthesis method thereof
  • Difluoromethyl selenate compound and synthesis method thereof
  • Difluoromethyl selenate compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Operation steps: add 0.75 mmol p-tolualdehyde 1a, 0.5 mmol benzylselenide difluoromethyl compound 2a and 1.0 mmol AIBN in a 10 mL single-necked flask, seal the rubber stopper and evacuate, and replace the air in the bottle with an argon balloon , so that the bottle is filled with argon. Then, 1,2-dichloroethane (2.5 mL) was added to the flask through a syringe under an argon atmosphere, and reacted at 50°C for 24 h. After the reaction, the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by flash silica gel column to obtain the corresponding difluoromethylselenide compound 3a with a yield of 90%.

[0028]

[0029] Se Yellow solid; Melting point: 46-47 o C; Eluant: ethyl acetate / petroleum ether (1:100,R f = 0.30). 1 H NMR (400 MHz, CDCl 3 ) δ 7.71 (d, J = 8.2 Hz, 2H), 7.61 (t, J =53.6 Hz, 1H), 7.30 (d, J = 8.1 Hz, 2H), 2.43 (s, 3H); 19 F NMR (376 MHz, CDCl 3 ) δ -96.08 (d, J = 53.6 Hz, 2F); 13 C NMR (101 M...

Embodiment 2

[0031] Operation steps: Add 0.75 mmol 4-methoxybenzaldehyde 1b, 0.5 mmol benzyldifluoromethylselenium compound 2a and 1.0 mmol AIBN to a 10 mL single-necked flask, seal it with a rubber stopper, and replace the bottle with an argon balloon The air, so that the bottle is filled with argon. Then, 1,2-dichloroethane (2.5 mL) was added to the flask through a syringe under an argon atmosphere, and reacted at 50°C for 24 h. After the reaction, the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by flash silica gel column to obtain the corresponding difluoromethylselenide compound 3b with a yield of 75%.

[0032]

[0033] Se Yellow solid; Melting point: 38-39 o C. Eluant: ethyl acetate / petroleum ether (1:30,R f = 0.30). 1 H NMR (400 MHz, CDCl 3 ) δ 7.77 (d, J = 8.9 Hz, 2H), 7.60 (t, J =53.6 Hz, 1H), 6.95 (d, J = 8.9 Hz, 2H), 3.88 (s, 3H); 19 F NMR (376 MHz, CDCl 3 ) δ -95.95 (d, J = 53.6 Hz, 2F); 13 C NMR (101 MHz, CD...

Embodiment 3

[0035] Operation steps: add 0.75 mmol 3-methylbenzaldehyde 1b, 0.5 mmol benzyldifluoromethylselenide 2a and 1.0 mmol ADVN to a 10 mL single-necked flask, seal the rubber stopper and evacuate it, and replace the Air, so that the bottle is filled with argon. Then, 1,2-dichloroethane (2.5 mL) was added to the flask through a syringe under an argon atmosphere, and reacted at 50°C for 24 h. After the reaction, the solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by a flash silica gel column to obtain the corresponding difluoromethylselenide compound 3b with a yield of 63%.

[0036]

[0037] Se Yellow liquid; Eluant: ethyl acetate / petroleum ether (1:100, R f = 0.30). 1 HNMR (400 MHz, CDCl 3 ) δ 7.61 (t, J = 53.6 Hz, 1H), 7.61 – 7.60 (m, 2H), 7.48 –7.45 (m, 1H), 7.38 (t, J = 7.9 Hz, 1H), 2.43 (s, 3H); 19 F NMR (376 MHz, CDCl 3 ) δ -96.14 (d, J = 53.6 Hz, 2F); 13 C NMR (101 MHz, CDCl 3 ) δ 191.2 (t, J =2.7 Hz), 139.5, 1...

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Abstract

The invention discloses a difluoromethyl selenate compound and a synthesis method thereof. The synthesis method comprises the following step of: by taking a selenium difluoromethylation reagent and cheap and readily available aldehyde or aldehyde group-containing bioactive molecules as initial raw materials, taking an azo compound as a free radical initiator and taking 1, 2-dichloroethane as a solvent, synthesizing the difluoromethyl selenate compound through free radical reactionin an argon atmosphere. The synthesis method is mild in condition, wide in substrate application range and good infunctional group tolerance, particularly has no metal participation, and has the advantages of being easy to operate, environmentally friendly, complete in regioselectivity and the like.

Description

technical field [0001] The invention relates to a difluoromethyl selenide compound and a synthesis method thereof, belonging to the technical field of organic synthesis. Background technique [0002] Selenium is an essential trace element for humans and other mammals. Organoselenium molecules have a rich history, not only as constituents of selenoproteins, involved in DNA repair, reproduction, and metabolism, but also with potential biological activities, and have shown wide applications in organic synthetic chemistry and materials science. Selenides are another class of organoselenium compounds that have been shown to be useful intermediates in synthetic organic chemistry, serving as precursors of acyl radicals and anions, mild acyl transfer agents and intermediates in the synthesis of ketones, and as A key intermediate for the incorporation of selenocysteine ​​(and other selenoamino acids) into peptides based on natural chemical ligation (NCL) methods. In addition, selen...

Claims

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Application Information

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IPC IPC(8): C07C391/00C07D207/48C07D209/42C07D307/68C07D307/84C07D333/38C07D333/68C07J51/00
CPCC07C391/00C07D333/38C07D333/68C07D307/68C07D307/84C07D207/48C07D209/42C07J51/00C07C2601/14C07C2602/42Y02P20/55
Inventor 王永强郭蕊丽
Owner NORTHWEST UNIV
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