851279-14-6

Basic information

• Product Name: 4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol
• Synonyms: 4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol
• CAS NO: 851279-14-6
• Molecular Weight: 484.39
• Mol File: 851279-14-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol(851279-14-6)
• EPA Substance Registry System: 4,5-di-O-benzyl-2-bromo-1O-diethylcarbamoylbenzenetriol(851279-14-6)

Safety Data

• Hazardous Substances Data: 851279-14-6(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 88-10-8 N,N-diethylcarbamyl chloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 27688-86-4 3,4-dibenzyloxyphenol 
• 851279-13-5 1,2-di-O-benzyl-4-O-diethylcarbamoylbenzenetriol 

Downstream Products

• 257288-33-8 8-epi-19,20-di-O-benzyl-puupehenol 
• 851279-17-9 19,20-di-O-benzyl-puupehenol-6-ene 
• 851279-15-7 3,4-di-benzyloxy-6-(7'-drimen-11'-ylidene)-2,4-cyclohexadienone 

Relevant articles and documents

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

First enantiospecific synthesis of the antitumor marine sponge metabolite (-)-15-oxopuupehenol from (-)-sclareol

(Chemical Equation Presented) A new route toward puupehenone-related bioactive metabolites from (-)-sclareol, based on the palladium(II)-mediated diastereoselective cyclization of a drimenylphenol, is described. Utilizing this, the first enantiospecific synthesis of the antitumor and antimalarial (-)-15-oxopuupehenol, together with improved syntheses of (+)-puupehenone, (+)-puupehedione, and (+)-15-cyanopuupehenone, were accomplished.