Diselenide oxalate compound and its synthesis method and application

A technology of ester compound and synthesis method, which is applied in the direction of organic chemistry, organic chemistry, etc., can solve the problem of limited selenium alkylation reagents, and achieve the effects of high atom utilization, simple operation, and easy post-processing

Active Publication Date: 2022-05-17
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To date, very limited selenoalkylating reagents have been reported in the literature

Method used

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  • Diselenide oxalate compound and its synthesis method and application
  • Diselenide oxalate compound and its synthesis method and application
  • Diselenide oxalate compound and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] In a round bottom flask add 1.2 mmol dimethyldiselenide, 1.2 mmol N-methylimidazolium salt, 3 mL CH 3 CN, placed in a 100°C oil bath and stirred for 12 h to stop the reaction. The reaction solution was cooled to room temperature, and 1 mmol oxalyl chloride was added quickly, and the reaction was stopped after 2 h of reaction. The solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by flash silica gel column to obtain methyl diselenide oxalate with a yield of 75%.

[0027]

[0028] Compound 3a: yellow solid; melting point: 85-86 o C; Eluant: ethyl acetate / petroleumether (1:100, R f = 0.30). 1 H NMR (400 MHz, CDCl 3 ) δ 2.33 – 2.30 (m, 6H); 13 CNMR (101 MHz, CDCl 3 ) δ 193.9 (2C), 4.7 (2C). IR (KBr): ν = 2954, 2920, 2850, 1671, 1461, 1377, 927 cm -1 . HRMS (ESI) for C 4 h 6 o 2 Se 2 Na (M+Na) + : Calcd: 268.8590, Found: 268.8579.

[0029] Using N,N-dimethylformamide instead of acetonitrile, and other conditions u...

Embodiment 2

[0031] Add 1.2 mmol diethyldiselenide, 1.2 mmol N-methylimidazolium salt, 3 mL CH 3 CN, placed in a 90°C oil bath and stirred for 12 h to stop the reaction. The reaction solution was cooled to room temperature, and 1 mmol oxalyl chloride was added quickly, and the reaction was stopped after 2 h of reaction. The solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by flash silica gel column to obtain ethyl diselenide oxalate with a yield of 78%.

[0032]

[0033] Compound 3b: yellow liquid; Eluant: ethyl acetate / petroleum ether (1:100, R f = 0.30). 1 H NMR (400 MHz, CDCl 3 ) δ 3.00 (q, J = 7.5 Hz, 4H), 1.46 (t, J = 7.5Hz, 6H); 13 C NMR (101 MHz, CDCl 3 ) δ 194.3 (2C), 19.2 (2C), 15.3 (2C). IR(KBr): ν = 2955, 2919, 2849, 1693, 1647, 1468, 1377, 1275, 1261, 1018, 764,750 cm -1 . HRMS (ESI) for C 6 h 10 o 2 Se 2 Na (M+Na) + : Calcd: 296.8903, Found: 296.8916.

[0034] Using 1,2-dichloroethane instead of acetonitrile, and...

Embodiment 3

[0036] In a round bottom flask add 1.2 mmol dipentyl diselenide, 1.2 mmol N-methylimidazolium salt, 3 mL CH 3 CN, placed in an 80°C oil bath and stirred for 15 h to stop the reaction. The reaction solution was cooled to room temperature, and 1 mmol oxalyl chloride was added quickly, and the reaction was stopped after 3 h of reaction. The solvent was removed by rotary evaporation under reduced pressure, and the residue was purified by flash silica gel column to obtain diselenyl oxalate with a yield of 74%.

[0037]

[0038] Compound 3c: yellow liquid; Eluant: ethyl acetate / petroleum ether (1:100, R f = 0.30). 1 H NMR (400 MHz, CDCl 3 ) δ 3.00 (t, J = 7.4 Hz, 4H), 1.75 – 1.67 (m,4H), 1.41 – 1.31 (m, 8H), 0.90 (t, J = 6.9 Hz, 6H); 13 C NMR (101 MHz, CDCl 3) δ194.1 (2C), 32.1 (2C), 29.6 (2C), 25.3 (2C), 22.2 (2C), 14.0 (2C). IR (KBr):ν = 2956, 2920, 2850, 1691, 1647, 1468, 1378, 1275, 764, 750, 721, 700 cm -1 .HRMS (ESI) for C 12 h 22 o 2 Se 2 Na (M+Na) + : Calc...

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Abstract

The invention discloses a new type of diselenide oxalate compound and its synthesis method and application. The preparation method uses oxalyl chloride as an oxalylating reagent, dialkyl diselenide as a selenyl source, and N-methylimidazolium salt As an additive, acetonitrile is used as a solvent, and diselenide oxalate is synthesized under heating conditions. The preparation method has the advantages of simple operation, short steps, mild conditions, easy post-processing and no metal participation. The synthesized diselenide oxalate is a new class of selenide compounds, which can realize the selenoalkylation of indole compounds under photocatalysis.

Description

technical field [0001] The invention relates to diselenide oxalate compounds and their synthesis method and application, belonging to the technical field of organic synthesis. Background technique [0002] Selenium (Se) is an essential micronutrient for plants, microorganisms, animals and humans. Selenium-containing compounds have strong biological activities, such as anti-oxidation, anti-fatigue, immunity, and activities to prevent liver damage and gastric mucosal damage. In addition, from the perspective of functional organic materials, organoselenium compounds can also be used in conductive polymers, Synthesis of organic semiconductors and liquid crystals. [0003] Selenides are an important class of organoselenium compounds that exhibit a wide range of pharmaceutical activities, such as antiproliferative, antitumor and chemopreventive. However, diselenide oxalate is a brand-new selenide compound, which has not been reported yet, and its chemical structure is novel. In...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C391/00C07D209/30
CPCC07C391/00C07D209/30C07B2200/13
Inventor 王永强郭蕊丽
Owner NORTHWEST UNIV
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