Functionalized cyanosilane, synthesis method and applications thereof

Abstract

The present invention discloses a functionalized cyanosilane and a synthesis method thereof. The method comprises: adding a raw material halogenated silane and a cyanogen source MCN into an organic solvent to synthesize the functionalized cyanosilane in the absence of a catalyst or by adopting a metal salt as a catalyst. According to the present invention, the functionalized cyanosilane can participate in the reactions capable of being participated by classic TMSCN to synthesize cyanhydrin, aminoalcohol, alpha-amino cyanide compounds and other important synthesis intermediates, and can further transfer the functional group carried by the silicon protecting group into the obtained addition product in the addition reaction through the appropriate conversion so as to substantially improve the synthesis efficiency and the atomic economy of the reaction, and synthesize a variety of products impossibly synthesized by the conventional TMSCN reagents.

Description

technical field [0001] The invention belongs to the technical field of organic compound technology application, and in particular relates to functionalized cyanosilane and its synthesis method and application. Background technique [0002] Cyanosilane is an important class of cyanation reagents, which are widely used in the silicocyanation reaction of carbonyl compounds to synthesize amino alcohol compounds, and in the Strecker reaction of imine compounds to synthesize amino acid compounds. These compounds are widely found in natural compounds and drug molecules, so how to efficiently synthesize diverse cyanosilanes has been a hot topic for chemists for a long time. Taking trimethylsilyl cyanide as an example, the common synthesis methods include: [0003] 1) In 1958, Sharkey reported the use of TMSCl and AgCN to prepare TMSCN. On the one hand, the cyanide source AgCN is an expensive raw material; on the other hand, at a high temperature of 120° C. for 12 hours, only a yie...

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Problems solved by technology

[0004] 2) Evans et al. used cheap HCN as a cyanide source to realize the synthesis of TMSCN in 1973. Although the yield of the reaction was high, the HCN gas greatly increased the risk of the reaction operation. The reaction process was as shown in the route in formula (II) 2 shown

[0006] 3) Sukata et al. used NaCN adsorbed by adsorption resin (XAD) in 1987 to synthesize TMSCN as a cyanogen source, and the yield was higher, but the cyanogen source NaCN used for the reaction needed to be prepared in advance, which made the operation of the reaction more cumbersome, and the reaction The atom economy of is low, and the reaction process is shown in scheme 3

[0008] Although there are so many synthetic routes to synthesize cyanosilanes, most of these methods are only used to synthesize simple cyanosilanes. For the synthesis of functionalized cyanosilanes, there is no literature report so far.

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