145586-78-3

Basic information

• Product Name: phenacyl tert-butyl carbonate
• Synonyms: phenacyl tert-butyl carbonate
• CAS NO: 145586-78-3
• Molecular Weight: 236.268
• Mol File: 145586-78-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: phenacyl tert-butyl carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: phenacyl tert-butyl carbonate(145586-78-3)
• EPA Substance Registry System: phenacyl tert-butyl carbonate(145586-78-3)

Safety Data

• Hazardous Substances Data: 145586-78-3(Hazardous Substances Data)

Upstream product

• 582-24-1 1-phenyl-2-hydroxyethanone 
• 49761-82-2 tert-butyl 1H-imidazole-1-carboxylate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 75-65-0 tert-butyl alcohol 
• 1421353-71-0 (2S,3R)-2-tert-butoxycarbonyloxy-1,3-diphenyl-3-(tosylamino)propan-1-one 
• 1421353-72-1 (2S,3R)-3-(4-bromophenyl)-2-tert-butoxycarbonyloxy-1-phenyl-3-(tosylamino)propan-1-one 
• 125289-60-3 tert-butyl 2-phenyl-2-propen-1-yl carbonate 
• 98-86-2 acetophenone 

Relevant articles and documents

Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes

Enantioenriched, polycyclic compounds were obtained from a simple acylphloroglucinol scaffold. Highly enantioselective dearomatization was accomplished using a Trost ligand–palladium(0) complex. A computational DFT model was developed to rationalize observed enantioselectivities and revealed a key reactant-ligand hydrogen bonding interaction. Dearomatized products were used in visible light-mediated photocycloadditions and oxidative free radical cyclizations to obtain novel polycyclic chemotypes including tricyclo[4.3.1.01,4]decan-10-ones, bicyclo[3.2.1]octan-8-ones and highly substituted cycloheptanones.

Photoreleasable protecting groups based on electron transfer chemistry. Donor sensitized release of phenacyl groups from alcohols, phosphates and diacids

The electron transfer mediated photochemical release of alcohols, phosphates and diacids is examined. The alcohols can be protected as mixed phenacyl carbonate esters. Irradiation of mixtures containing electron donating sensitizers and phenacyl alkyl carbonate ester initiates a series of bond scission reactions that result in clean release of the corresponding alcohols. This was demonstrated for a variety of primary, secondary and tertiary hydroxyl groups, including the 5'-hydroxy group of thymidine. Sensitizers that were effective in promoting photolytic release include 9,10- dimethylanthracene and 9-methylcarbazole. GC/MS and NMR analysis of the by- products formed in these release reactions implicates the intermediacy of radical ion intermediates in these reactions. It is further demonstrated that the electron transfer sensitized release method can be extended to phosphate esters and di-functional acids.