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A kind of preparation method of cyanohydrin silicon ether compound
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A technology for cyanohydrin silicon ethers and compounds, which is applied in the field of preparation of cyanohydrin silicon ether compounds, can solve the problems of poor environmental friendliness, high cost and the like, and achieves the effects of simple reaction steps, simple structure and mild reaction conditions
Active Publication Date: 2020-08-04
NANJING FORESTRY UNIV
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[0003] At present, many cyanohydrin silyl ether compounds are catalyzed by transition metal catalysts, such as Ru, Mn, V, Ti, Pt and other metals, which generally have certain toxicity, expensive, and poor environmental friendliness.
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Embodiment 1
[0036] NCN three-tooth pincer-shaped magnesium-lithium compound catalyzes the synthesis of cyanohydrin silicon ether compounds from valeraldehyde and trimethylsiliconitrile:
[0037] Under anhydrous and anaerobic conditions, under nitrogen protection, in a glove box, 0.005 mmol of the catalyst tridentate pincer-shaped magnesium-lithium compound was added to about 0.5 mL of CDCl 3 Then, 0.375 mmol of trimethylsilonitrile was added with a pipette to mix evenly, and finally 0.25 mmol of valeraldehyde was added. After 15 minutes of reaction at room temperature, the NMR was measured. Calculated 1 The H spectrum yield was 99%. NMR data of the main products: 1 H NMR (600MHz, CDCl 3 ):δ0.21(d, 3 J HH =1.2Hz, 9H, Si(CH 3 ) 3 ),0.93(m,3H,CH 3 ),1.36(m,2H,CH 2 ),1.45(m,2H,CH 2 ),1.78(m,2H,CH 2 ),4.40(t, 3 J HH =6.6Hz, 1H, OCHCN).
Embodiment 2
[0039] NCN three-tooth pincer-shaped magnesium-lithium compound catalyzed the synthesis of cyanohydrin silicon ether from 5-chlorovaleraldehyde and trimethylsiliconitrile:
[0040] Under anhydrous and anaerobic conditions, under nitrogen protection, in a glove box, 0.005 mmol of the catalyst tridentate pincer-shaped magnesium-lithium compound was added to about 0.5 mL of CDCl 3 Then, 0.375 mmol of trimethylsilonitrile was added with a pipette to mix evenly, and finally 0.25 mmol of 5-chloropentanal was added. After 15 minutes of reaction at room temperature, the NMR was measured. Calculated 1 The H spectrum yield was 99%. NMR data of the main products: 1 H NMR (600MHz, CDCl 3 ):δ0.22(s,9H,Si(CH 3 ) 3 ),1.64(m,2H,CH 2 ),1.82(m,4H,CH 2 ),3.55(t, 3 J HH =6.6Hz, 2H, CH 2 Cl),4.43(t, 3 J HH =6.6Hz, 1H, OCHCN).
Embodiment 3
[0042] NCN three-tooth pincer-shaped magnesium-lithium compound catalyzes the synthesis of cyanohydrin from cyclohexyl formaldehyde and trimethylsiliconitrile:
[0043] Under anhydrous and anaerobic conditions, under nitrogen protection, in a glove box, 0.005 mmol of the catalyst tridentate pincer-shaped magnesium-lithium compound was added to about 0.5 mL of CDCl 3 Then add 0.375 mmol of trimethylsiliconitrile with a pipette and mix evenly, and finally add 0.25 mmol of cyclohexyl formaldehyde, react at room temperature for 15 minutes, and measure the nuclear magnetic resonance. Calculated 1 The H spectrum yield was 99%. NMR data of the main products: 1 H NMR (600MHz, CDCl 3):δ0.20(s,9H,Si(CH 3 ) 3 ),1.22-1.88(m,11H,CH 2 +CH),4.15(d, 3 J HH = 6Hz, 1H, OCHCN).
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Abstract
The invention discloses a method for preparing a cyanohydrinsiliconether compound, which includes the use of a catalyst, the catalyst being a magnesium-lithium bimetallic compound stabilized by a tridentate pincer ligand. The present invention uses NCN tridentate pincer ligandmagnesium The lithium bimetallic compound catalyzes the reaction of aldehydes and trimethylsilonitrile to synthesize cyanohydrinsiliconether compounds. It has high catalytic activity, simple structure, and is easy to synthesize. The scheme further expands the application of the pincer ligandmagnesium-lithium bimetallic compound, and the amount of the catalyst only needs 2% of the molar amount of the substrate, and the reaction selectivity is high. The present invention is convenient and simple to catalyze the siliconitrile of aldehydeReaction system, and reaction conditions are mild, no matter catalyzed aromatic aldehyde or aliphatic aldehyde can almost achieve 100% conversion rate, the reaction system is non-toxic, high reaction selectivity, mild conditions, simple reaction steps, highly in line with the concept of green chemistry.
Description
technical field [0001] The invention belongs to the technical field of magnesium-lithium bimetallic compound catalytic reaction, in particular to a preparation method of a cyanohydrinsiliconether compound. Background technique [0002] Cyanohydrin compounds are widely used in civil, industrial, decoration, military and other fields, especially in pharmaceutical synthesis, such as α-hydroxy acids, α-hydroxy ketones, α-amino acids and β-hydroxy acids with important medical value. Organic compounds such as amino alcohols can be further hydrolyzed from cyanohydrin silicon ether compounds, and they generally have non-toxic and pollution-free properties, which has always been one of the topics of scientists' research and synthesis. The organic cyanohydrin silyl ether derivatives synthesized by the reduction of different organic group substrates expand the application range of cyanohydrin compounds. Therefore, cyanohydrin silyl ether compounds can not only be widely used in medi...
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