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A kind of aziridine type [iron-iron] hydrogenase active center model substance containing phosphine ligand and its synthesis method

A technology of hydrogenase activity and synthesis method, applied in the field of synthesis, can solve problems such as low catalytic hydrogen release performance, and achieve the effects of simple operation, high yield and mild conditions

Active Publication Date: 2018-11-20
SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The object of the present invention is to provide a kind of azapropylene-based [iron-iron] hydrogenase active center containing phosphine ligands for the problem of low catalytic hydrogen desorption performance of the existing [iron-iron] hydrogenase active center model Model substance and its synthesis method, which have good electron-donating phosphine ligands, can improve catalytic activity and have potential industrial application value

Method used

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  • A kind of aziridine type [iron-iron] hydrogenase active center model substance containing phosphine ligand and its synthesis method
  • A kind of aziridine type [iron-iron] hydrogenase active center model substance containing phosphine ligand and its synthesis method
  • A kind of aziridine type [iron-iron] hydrogenase active center model substance containing phosphine ligand and its synthesis method

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Embodiment 1

[0031]A method for synthesizing the model substance 1 of the active center of azapropylene [iron-iron] hydrogenase containing a phosphine ligand, the chemical formula of the model substance 1 is Fe 2 [(SCH 2 ) 2 NCH 2 CH 2 CH 2 SMe] (CO) 5 [P(C 6 h 5 ) 3 ], its chemical synthesis process is as follows:

[0032]

[0033] Concrete synthetic steps are as follows:

[0034] Under the protection condition of inert gas, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 15mL of tetrahydrofuran solvent to obtain a dark red solution, the resulting solution was cooled to -78°C with a liquid nitrogen bath, and 2mL of lithium triethylborohydride (1M in THF) solution was slowly added under stirring conditions and reacted for 15min Finally, add 0.16mL trifluoroacetic acid (2mmol), continue the reaction for 15min, add 0.17mL aqueous formaldehyde solution (37%), raise the reaction system to room temperature, stir the reaction for 1h, then add 288mg...

Embodiment 2

[0039] A method for synthesizing the model object 2 of the active center of azapropylene [iron-iron] hydrogenase containing a phosphine ligand, the chemical formula of the model object 2 being Fe 2 [(SCH 2 ) 2 NCH 2 CH 2 CH 2 SMe] (CO) 5 (Ph 2 PC 5 h 4 N), its chemical synthesis process is as follows:

[0040]

[0041] Under the protection condition of inert gas, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 15mL of tetrahydrofuran solvent to obtain a dark red solution, the resulting solution was cooled to -78°C with an acetone bath, and 2mL of lithium triethylborohydride (1M in THF) was slowly added under stirring conditions. After reacting for 10min , add 0.18mL trifluoroacetic acid (2mmol), continue to react after 15min, add 0.2mL formaldehyde aqueous solution (37%), raise the reaction system to room temperature, add 263mg Ph 2 PC 5 h 4 N (1mmol), after stirring at room temperature for 5h, add 120mg of NH 2 CH 2 CH 2 CH...

Embodiment 3

[0045] A method for synthesizing the model substance 3 of the active center of azapropylene [iron-iron] hydrogenase containing a phosphine ligand, the chemical formula of the model substance 3 being Fe 2 [(SCH 2 ) 2 NCH 2 CH 2 CH(Me) 2 ](CO) 5 [P(C 6 h 5 ) 3 ], its chemical synthesis process is as follows:

[0046]

[0047] Under the protection condition of inert gas, add 344mg Fe in the flask equipped with stirring magnet 2 S 2 (CO) 6 (1mmol) and 30mL of tetrahydrofuran solvent to obtain a dark red solution, the resulting solution was cooled to -78°C with an acetone bath, and 2mL of lithium triethylborohydride (1M in THF) solution was slowly added under stirring conditions, and after 15min of reaction , add 0.2mL trifluoroacetic acid (2mmol), continue to react after 15min, add 0.2mL formaldehyde aqueous solution (37%), the reaction system is raised to room temperature, add 262mg of Ph 3 P (1mmol), add 105mg of NH after stirring at room temperature for 4h 2 CH ...

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Abstract

Belonging to the field of synthesis technology, the invention provides an ADT[Fe-Fe]hydrogenase active center model compound containing a phosphine ligand. The center model compound is Fe2[(SCH2)2NR1](CO)5(Ph2PR2), and the chemical structural formula is shown as the specification, wherein R1 is CH2CH2CH2SMe, CH2CH2CH(Me)2, and R2 is C6H5, C5H4N. The invention also provides a synthesis method of the ADT[Fe-Fe]hydrogenase active center model compound containing the phosphine ligand. The synthesis method adopts "one-pot synthesis method", has the advantages of simple operation process, mild reaction conditions and high product yield, and is suitable for synthesis of a variety of ADT[Fe-Fe]hydrogenase active center model compounds containing a phosphine ligand. The hydrogenase active center model compound prepared by the method provide by the invention has good catalytic hydrogen production capacity and potential industrial application value.

Description

technical field [0001] The invention belongs to the technical field of synthesis, in particular to an aziridine [iron-iron] hydrogenase active center model substance containing a phosphine ligand and a synthesis method thereof. Background technique [0002] Currently, the world is facing two serious problems related to energy. First, with the intense competition worldwide, the continuous consumption of fossil fuels will lead to high costs. Second, the burning of fossil fuels has led to an increase in the concentration of carbon dioxide in the atmosphere, and further increases will have a huge impact on the world's climate. In order to maintain the rapid growth of my country's economy, the state clearly proposes to further promote the energy revolution, focus on promoting the transformation of energy production and utilization methods, optimize the energy structure, improve energy utilization efficiency, and build a clean, low-carbon, safe and efficient modern energy system....

Claims

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Application Information

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IPC IPC(8): C07F15/02B01J31/24
CPCB01J31/2404C07F15/02
Inventor 李玉龙赵培华邹立科母超吴宇邓成龙谢斌
Owner SICHUAN UNIVERSITY OF SCIENCE AND ENGINEERING