532392-25-9

Basic information

• Product Name: (E)-3-(trimethylsilyl)prop-2-en-1-yl N-(benzoyl)glycinate
• CAS NO: 532392-25-9
• Molecular Weight: 291.422
• Mol File: 532392-25-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (E)-3-(trimethylsilyl)prop-2-en-1-yl N-(benzoyl)glycinate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-(trimethylsilyl)prop-2-en-1-yl N-(benzoyl)glycinate(532392-25-9)
• EPA Substance Registry System: (E)-3-(trimethylsilyl)prop-2-en-1-yl N-(benzoyl)glycinate(532392-25-9)

Safety Data

• Hazardous Substances Data: 532392-25-9(Hazardous Substances Data)

Upstream product

• 495-69-2 Hippuric Acid 
• 59376-64-6 (2E)-3-(trimethylsilyl)prop-2-en-1-ol 
• 5272-36-6 3-trimethylsilyl-2-propyn-1-ol 

Relevant articles and documents

Allylsilane-modified amino acids from the Claisen rearrangement

The Claisen rearrangement of the N-protected, silylated allyl glycinates 11 and 12 led to the formation of allyl/silyl-functionalized amino acids 13 and 14 in yields up to 80%. The diastereoisomer ratio varied from 2:1 to 29:1 for 11mb, and from 2:1 to 46:1 (syn/anti) for 12mb, depending on reaction conditions, as shown by X-ray crystallographic analysis of 14mb. The relationship between the size of the alkyl groups on the chlorosilane reagent (Me2R″SiCl, R″ = Cl, Me, t-Bu, Ph) used as an enolate trap and the observed stereoselectivity was investigated in the case of the Ireland - Claisen variant. Me3SiCl gave the best results. However, the size of the alkyl groups on the silylated ester (Me2R″Si, R = Me, t-Bu, Ph, i-Pr) did not exert a significant effect on the diastereoselectivity or yield of the rearrangement.