596797-37-4

Basic information

• Product Name: 3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-propa-1,2-dienyl}-4-phenyl-oxazolidin-2-one
• Synonyms: 3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-propa-1,2-dienyl}-4-phenyl-oxazolidin-2-one
• CAS NO: 596797-37-4
• Molecular Weight: 387.594
• Mol File: 596797-37-4.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-propa-1,2-dienyl}-4-phenyl-oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-propa-1,2-dienyl}-4-phenyl-oxazolidin-2-one(596797-37-4)
• EPA Substance Registry System: 3-{1-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-propa-1,2-dienyl}-4-phenyl-oxazolidin-2-one(596797-37-4)

Safety Data

• Hazardous Substances Data: 596797-37-4(Hazardous Substances Data)

Upstream product

• 92511-12-1 1-{[dimethyl(1,1-dimethylethyl)silyl]oxy}-4-iodobutane 
• 256382-50-0 (4R)-4-phenyl-3-(1,2-propadienyl)-2-oxazolidinone 

Downstream Products

• 404961-99-5 3-[1-(4-hydroxy-butyl)-propa-1,2-dienyl]-4-phenyl-oxazolidin-2-one 

Relevant articles and documents

NMR studies on epoxidations of allenamides. Evidence for formation of nitrogen-substituted allene oxide and spiro-epoxide via trapping experiments

Two epoxidations of chiral allenamides are described here. While treatment with m-CPBA led to highly stereoselective formation of an α-keto aminal that can be useful synthetically, DMDO oxidation led to conclusive evidence for both nitrogen-substituted allene oxide (via mono-epoxidation) and spiro-epoxide (via bis-epoxidation) using intramolecular nucleophilic trapping experiments. NMR studies provide reliable evidence for a 3-oxetanone that can be derived from the spiro-epoxide and also suggest the presence of an allene oxide. Despite a facile second epoxidation as evidenced by the predominant formation of the 3-oxetanone, in the presence of furan, [4 + 3] cycloaddition of the nitrogen-substituted allene oxide or oxyallyl cation with furan occurs faster than the second epoxidation efficiently leading to cycloadducts. This rate difference plays an invaluable role for the success of a stereoselective sequential epoxidation-[4 + 3] cycloaddition reaction via DMDO epoxidations of chiral allenamides.