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Phosphoric acid amide bifunctional catalyst and synthetic method thereof

A dual-functional catalyst and synthesis method technology, applied in chemical instruments and methods, physical/chemical process catalysts, organic compounds/hydrides/coordination complex catalysts, etc., to achieve cheap raw materials, good yields, and high catalytic efficiency Effect

Active Publication Date: 2012-01-11
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, phosphonic acid amide catalysts derived from cinchona base have not been reported [(a) E. M. O. Yeboah, S. O. Yeboah and G. S. Singh, Tetrahedron, 2011, 67, 1725; (b) T. Marcelli and H. Hiemstra, Synthesis, 2010, 1229]

Method used

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  • Phosphoric acid amide bifunctional catalyst and synthetic method thereof
  • Phosphoric acid amide bifunctional catalyst and synthetic method thereof
  • Phosphoric acid amide bifunctional catalyst and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Embodiment 1: preparation catalyst

[0049]

[0050] Under nitrogen protection, into a 50 ml round bottom flask was added cinchonidine-derived primary amine (1.0 mmol, 293 mg) and anhydrous CH 2 Cl 2 , and triethylamine (3.0 mmol, 303 mg) was added after complete dissolution. Diethoxyphosphoryl chloride (1.2 mmol, 206.4 mg) was added dropwise at 0 °C, stirred overnight and post-treated: adding 30 ml of water, extracted with dichloromethane, dried over anhydrous sodium sulfate, and column chromatographed to obtain Pale yellow oily pure product catalyst, its structure is shown in the above reaction formula, and the productive rate is 58%. 1 H NMR (400 MHz, CDCl 3 ): 8.68 (s, 1H), 8.02-7.82 (m, 2H), 7.68-7.28 (m, 3H), 5.72-5.68 (m, 1H), 5.02-4.97 (m, 2H), 4.20-3.82 (m, 1H ), 2.24-2.13 (m, 1H), 1.52-1.11 (m, 7H); 13 C NMR (100 MHz, CDCl 3 ): 150.6, 147.9, 141.7, 129.5, 128.5, 126.9, 125.8, 123.5, 121.3, 114.4, 77.8, 76.8, 63.7, 59.6, 54.5, 42.7, 33.2, 29.3, 14...

Embodiment 2

[0051] Embodiment 2: preparation catalyst

[0052]

[0053] Into a 50-ml round-bottomed flask under nitrogen protection, add a Cinchoni-derived primary amine (1.0 mmol, 323 mg) and anhydrous CH 2 Cl 2 , and triethylamine (3.0 mmol, 303 mg) was added after complete dissolution. Diethoxyphosphoryl chloride (1.2 mmol, 206.4 mg) was added dropwise at 0 °C, stirred overnight and post-treated: add 30 ml of water, extract with dichloromethane, dry over anhydrous sodium sulfate and perform column chromatography to obtain Pure product catalyst, its structure is shown in above reaction formula, productive rate 62%. 1 H NMR (400 MHz, CDCl 3 ): 8.68 (s, 1H), 8.02-7.82 (m, 2H), 7.68-7.28 (m, 3H), 5.72-5.68 (m, 1H), 5.02-4.97 (m, 2H), 4.20-3.82 (m, 1H ), 2.35 (m, 3H), 2.24-2.13 (m, 1H), 1.52-1.11 (m, 7H); 13 C NMR (100 MHz, CDCl 3 ): 150.6, 147.9, 147.7, 129.5, 128.5, 126.9, 125.8, 123.5, 121.3, 114.4, 77.8, 76.8, 63.7, 59.6, 54.5, 42.7, 33.2, 29.3, 21.3, 14.1, 14.0. MS (EI):...

Embodiment 3

[0054] Embodiment 3: preparation catalyst

[0055]

[0056] Under nitrogen protection, add binaphthol (1.0 mmol, 186 mg), anhydrous CH 2 Cl 2 and triethylamine (3.0 mmol, 303 mg), then dropwise added phosphorus oxychloride (1.0 mmol, 151 mg) under ice-cooling, gradually warmed up to room temperature, stirred at room temperature for 3 hours, then added dropwise the prepared Cenco Nidine-derived primary amine (1.0 mmol, 294 mg) and anhydrous CH 2 Cl 2 After stirring the mixed solution overnight, carry out post-treatment: add 30 ml of water, extract with dichloromethane, dry over anhydrous sodium sulfate and perform column chromatography to get the pure product catalyst, its structure is shown in the above reaction formula, and the yield is 55 %. 1 H NMR (400 MHz, CDCl 3 ): 8.66 (s, 1H), 8.02-7.31 (m, 6H), 7.04-6.79 (m, 7H), 5.07-4.97 (m, 2H), 4.15-4.10 (m, 1H), 2.85-2.00 (m, 7H ), 1.42-1.41 (m, 3H); 13 C NMR (100 MHz, CDCl 3 ): 156.3, 156.2, 150.6, 147.9, 141.7, ...

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Abstract

The invention relates to a phosphoric acid amide bifunctional catalyst derived from cinchona alkaloid and a synthetic method thereof. According to the invention, the chiral phosphoric acid amide bifunctional catalyst with high efficiency catalytic activity provided in the invention is prepared in one step by reacting corresponding primary amine produced by ammonification of cinchona alkaloid and derivatives thereof with phosphoric acid acyl chloride. The catalyst provided in the invention has the advantages of a novel structure, stable properties, high catalytic activity, etc., and the synthetic method for the catalyst is simple.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and relates to a phosphoric acid amide bifunctional catalyst and a synthesis method thereof. Background technique [0002] Bifunctional catalysts refer to molecules that contain hydrogen bond donors and acceptors at the same time. It is a new type of highly efficient catalytic system that has been gradually developed during the development of catalysts in the past ten years. Since there are both hydrogen bond donors and acceptors in the molecule, it is possible to better activate the substrate in the reaction, thereby improving the activity and selectivity of the reaction. Cinchona alkaloids, especially cinchonine, quinine, cinchonidine, quinidine and other alkaloids, are a class of very efficient chiral catalysts. Due to their cheap and easy to obtain and easy modification of the molecular skeleton, they can be used in asymmetric nucleophilic It has been widely u...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07F9/6561C07F9/6574C07D209/34
Inventor 周剑丁苗刘运林
Owner EAST CHINA NORMAL UNIVERSITY
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