Zinc nitride and copper nitride compound of chiral alpha-phenylethylamine and use thereof

A technology of copper-nitrogen complexes and phenylethylamine, which is applied in the direction of copper organic compounds, zinc organic compounds, and preparation of amino compounds from amines, etc., which can solve the problems of unstable catalysts, difficult industrialization, and large amount of catalysts

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A technology of copper-nitrogen complexes and phenylethylamine, which is applied in the direction of copper organic compounds, zinc organic compounds, and preparation of amino compounds from amines, etc., which can solve the problems of unstable catalysts, difficult industrialization, and large amount of catalysts

CN101830919BInactive Publication Date: 2012-06-20HEFEI UNIV OF TECH

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[0075] (1) Examples of preparation of chiral complexes

[0076] 1, 1a: Synthesis of chiral (S)-α-phenylethylamine zinc acetate metal-organic complexes

[0077] Weigh 2.191g Zn(CH 3 COO) 2 2H 2 O (0.01mol) was added to a 100mL round-bottomed flask, and then 25mL of tetrahydrofuran was added as a solvent, a stirring bar was added, and 2.7mL (S)-α-phenylethylamine (0.02mol) was measured with a syringe under stirring and added to In the flask, install a condensing tube, connect tap water, place on a magnetic heating stirrer and heat to reflux for 24 hours, remove the solvent with a rotary evaporator, recrystallize with a mixed solvent of petroleum ether and absolute ethanol (mass ratio 1: 1), Colorless crystals were obtained with a yield of 90%. 1 HNMR (500MHz, CDCl 3 )7.22~7.31(m, 10H), 4.06~4.07(d, J=6.5Hz, 1H), 3.06(br, 1H), 1.94(s, 6H), 1.40~1.42(d, J=6.5Hz, 6H ). 13 C NMR (75MHz, CDCl 3 )179.70, 144.04, 128.94, 127.92, 125.92, 51.82, 23.94, 23.10. IR (KBr) cm -1 : 31...

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Abstract

The invention discloses a zinc nitride and copper nitride compound of chiral alpha-phenylethylamine, which comprises a (S) alpha-phenylethylamine zinc nitride and copper nitride compound and a (R) alpha-phenylethylamine zinc nitride and copper nitride compound, which are prepared from the alpha-phenylethylamine, zinc acetate dihydrate, copper acetate monohydrate and copper chloride dihydrate and have the following formulas. In the formulas, ML is Zn(OOCCH3)2, Cu(OOCCH3)2 or CuCl2. The compound serves as a chiral catalyst in a Henry reaction.

Description

1. Technical field [0001] The present invention relates to a chiral compound and its use, specifically a zinc-nitrogen and copper-nitrogen complex of chiral α-phenylethylamine and its use. 2. Background technology [0002] Nitrogen-containing metal-organic complexes have novel structures and potential applications in catalysis, electrochemistry, adsorption, ion exchange, and magnetism. Researchers in chemistry, coordination chemistry, metal-organic chemistry and bioinorganic chemistry have paid extensive attention, and have achieved remarkable research results. [0003] 1. Kantchev, Eric Assen B.; O'Brien, Christopher J.; Organ, Michael G. Aldrichimica Acta, 2006, 39(4), 97-111. [0004] 2. Guillarme, S.; Whiting, A. Synlett (2004), (4), 711-713. [0005] 3. Pickin, Kerry A.; Kindy, Jennifer M.; Day, Cynthia S.; Welker, Mark E. Journal of Organometallic Chemistry (2003), 681(1-2), 120-133. [0006] 4. Bayer, A.; Gautun, Odd R. Tetrahedron: Asymmetry (2001), 12(21), 2937-2...

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Application Information

Patent Timeline

20 Jun 2012

Publication

CN101830919B

IPC: C07F3/06; C07F1/08; C07C211/65; C07C209/68; B01J31/22; C07C201/06; C07C205/16; C07C205/04; C07C205/32; C07C205/26

Inventors: 罗梅