Beta-diimine univalence magnesium compound, preparation method and application thereof in aldosterone silicon cyanide

A magnesium compound, magnesium diimide technology, applied in the preparation of amino compounds, organic compounds, organic compounds/hydrides/coordination complex catalysts, etc., to achieve low toxicity of items, simple and easy operation of the reaction process, high yield high effect

Inactive Publication Date: 2018-01-09
NANJING FORESTRY UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the prior art, the application of the monovalent magnesium compound is stoichiometric, and the application of the catalytic amount of the monovalent magnesium compound has not been reported yet.

Method used

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  • Beta-diimine univalence magnesium compound, preparation method and application thereof in aldosterone silicon cyanide
  • Beta-diimine univalence magnesium compound, preparation method and application thereof in aldosterone silicon cyanide
  • Beta-diimine univalence magnesium compound, preparation method and application thereof in aldosterone silicon cyanide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The preparation of the bromide of β-diimine magnesium, the process is as follows:

[0024] In the absence of water and oxygen, 3.27 mmol of β-diimine ligand was dissolved in 30 mL of ether solution in a single-port reaction tube, and 3.27 mmol of methylmagnesium iodide was added dropwise to the above solution at -80°C, and reacted at room temperature for 24 hours. After filtration, the solid was sucked dry, and the filtrate was concentrated to 5 mL to obtain colorless crystals. The mass of solid and crystals was 1.60 g, and the yield was 92%. M.p. 236-238°C. NMR spectrum: 1 HNMR (600MHz, C 6 D. 6 ): δ6.96(s, 6H, Ar-H), 4.75(s, 1H, =CH), 3.26(s, 4H, OCH 2 CH 3 ),2.08(s,12H,CH 3 ),1.45(s,6H,NCCH 3 ),1.11(s,6H,OCH 2 CH 3 ) ppm. 13 C{ 1 H}NMR (151MHz, C 6 D. 6 ): δ169.36 (NCCH 3 ), 146.42, 131.84, 128.99, 124.76 (Ar-C), 95.23 (=CH), 65.90 (OCH 2 CH 3 ), 23.23 (NCCH 3 ), 18.82 (CH 3 ), 15.58 (OCH 2 CH 3 ) ppm.

Embodiment 2

[0026] The preparation of the bromide of β-diimine magnesium, the process is as follows:

[0027] In the absence of water and oxygen, 3.27 mmol of β-diimine ligand was dissolved in 30 mL of ether solution in a single-port reaction tube, and 3.40 mmol of methylmagnesium iodide was added dropwise to the above solution at -60°C, and reacted at room temperature for 15 h. After filtration, the solid was sucked dry, and the filtrate was concentrated to 5 mL to obtain colorless crystals. The mass of solid and crystals was 1.62 g, and the yield was 93%. M.p. 236-238°C. NMR spectrum: 1 HNMR (600MHz, C 6 D. 6 ): δ6.96(s, 6H, Ar-H), 4.75(s, 1H, =CH), 3.26(s, 4H, OCH 2 CH 3 ),2.08(s,12H,CH 3 ),1.45(s,6H,NCCH3 ),1.11(s,6H,OCH 2 CH 3 ) ppm. 13 C{ 1 H}NMR (151MHz,C 6 D. 6 ): δ169.36 (NCCH 3 ), 146.42, 131.84, 128.99, 124.76 (Ar-C), 95.23 (=CH), 65.90 (OCH 2 CH 3 ), 23.23 (NCCH 3 ), 18.82 (CH 3 ), 15.58 (OCH 2 CH 3 ) ppm.

Embodiment 3

[0029] The preparation of the bromide of β-diimine magnesium, the process is as follows:

[0030] In the absence of water and oxygen, 3.27 mmol of β-diimine ligand was dissolved in 25 mL of ether solution in a single-port reaction tube, and 3.51 mmol of methylmagnesium iodide was added dropwise to the above solution at -40°C, and reacted at room temperature for 8 hours. After filtration, the solid was sucked dry, and the filtrate was concentrated to 5 mL to obtain colorless crystals. The mass of solid and crystals was 1.59 g, and the yield was 91%. M.p. 236-238°C. NMR spectrum: 1 H NMR (600MHz, C 6 D. 6 ): δ6.96(s, 6H, Ar-H), 4.75(s, 1H, =CH), 3.26(s, 4H, OCH 2 CH 3 ),2.08(s,12H,CH 3 ),1.45(s,6H,NCCH 3 ),1.11(s,6H,OCH 2 CH 3 ) ppm. 13 C{ 1 H}NMR (151MHz,C 6 D. 6 ): δ169.36 (NCCH 3 ), 146.42, 131.84, 128.99, 124.76 (Ar-C), 95.23 (=CH), 65.90 (OCH 2 CH 3 ), 23.23 (NCCH 3 ), 18.82 (CH 3 ), 15.58 (OCH 2 CH 3 ) ppm.

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Abstract

The invention discloses a β-diimine monovalent magnesium compound and its preparation and application in silanization of aldehydes and ketones. The preparation method is as follows: under anhydrous and oxygen-free conditions, β-diimine ligand reacts with Grignard reagent to generate magnesium bromide, and then reduces it with sodium to obtain yellow crystal, which is β-diimine monovalent magnesium compound. The β-diimine monovalent magnesium compound of the present invention has simple synthesis, convenient separation and purification, clear structure, and high yield; it has high activity as a catalyst to catalyze the reaction of aldehydes or ketones with trimethylsilyl cyanide, and the substrate is universal wide sex.

Description

technical field [0001] The invention relates to the technical field of preparation of metal-organic compounds, in particular to a β-diimine monovalent magnesium compound, a preparation method thereof and an application in silanization of aldehydes and ketones. Background technique [0002] Since the last century, cyanohydrin has received extensive attention, because cyanohydrin is an important intermediate that plays a significant role in industrial production and can successfully synthesize many organic compounds, such as α-hydroxy acids, α- Amino acids, β-amino alcohols, etc. [BrunelJ.M., Holmes I.P.Angew.Chem.Int.Ed.2004,43,2752; . Chem. Rev. 2008, 108, 5146; Pellissier H. Adv. Synth Catal. 2015, 357, 857.]. At first, Lapworth et al. added hydrogen cyanide to carbonyl compounds to synthesize cyanohydrins. Later, because hydrogen cyanide was toxic and difficult to handle, many low-toxicity and easy-to-handle cyanide reagents appeared in large quantities [North M., Usanov ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/00C07C211/53B01J31/22C07C253/00C07C255/36C07C255/43C07C255/37C07C255/31C07D333/24C07C253/30C07C255/53C07C255/46
Inventor 马猛涛王未凡姚薇薇
Owner NANJING FORESTRY UNIV
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