1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE

그림문자(GHS)

• 그림문자(GHS)

  

• 신호 어

  Warning

• 유해·위험 문구

  H226：인화성 액체 및 증기

  H315：피부에 자극을 일으킴

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  P240：용기와 수용설비를 접지 및 접합시키시오.

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  P264：취급 후에는 손을 철저히 씻으시오.

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  P370+P378：화재 시 불을 끄기 위해 (Section 5. 폭발, 화재시 대처방법의 적절한 소화제)을(를) 사용하시오.

  P403+P235：환기가 잘 되는 곳에 보관하고 저온으로 유지하시오.

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1-METHOXY-1-TRIMETHYLSILYLOXYPROPENE 화학적 특성, 용도, 생산

• 용도

  1-Methoxy-1-(trimethylsilyloxy)propene is used to reactive nucleophile in Mukaiyama-type aldol reactions with aldehydes, imines, acetals, dialkoxycarbenium ions, and orthoesters; Michael-type additions to α,β-unsaturated carbonyl compounds; substitution reactions with allylic alcohols and esters; acylations; aminations; hydroxylations; and pericyclic reactions; silylating agent.

• 제조 방법

  since the first preparation of a ketene trialkylsilyl acetal by Petrov in 1959 by the reaction of triethylsilane and methyl acrylate, several alternative pathways have been explored. Ainsworth and coworkers prepared 1-methoxy-1-(trimethylsilyloxy)propene in 90% yield by deprotonation of methyl propionate with Lithium Diisopropylamide at -78 °C followed by addition of Chlorotrimethylsilane. Reaction of the lithium enolate of methyl acetate with TMS-Cl provides 65% O-silylated and 35% C-silylated products (eq 1). Substitution on the alcohol portion of the ester favors C-silylation while substitution on the α-carbon favors O-silylation. An increase in the steric bulk of the silylating agent (e.g. use of t-Butyldimethylchlorosilane) results in significantly more O-silylation.
  

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