92013-50-8

Basic information

• Product Name: Butanoic acid, 4-[[(phenylmethoxy)carbonyl]amino]-, (9,10-dihydro-9,10-dioxo-2-anthracenyl)methyl ester
• CAS NO: 92013-50-8
• Molecular Formula: C27H23NO6
• Molecular Weight: 457.483
• Mol File: 92013-50-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Butanoic acid, 4-[[(phenylmethoxy)carbonyl]amino]-, (9,10-dihydro-9,10-dioxo-2-anthracenyl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Butanoic acid, 4-[[(phenylmethoxy)carbonyl]amino]-, (9,10-dihydro-9,10-dioxo-2-anthracenyl)methyl ester(92013-50-8)
• EPA Substance Registry System: Butanoic acid, 4-[[(phenylmethoxy)carbonyl]amino]-, (9,10-dihydro-9,10-dioxo-2-anthracenyl)methyl ester(92013-50-8)

Safety Data

• Hazardous Substances Data: 92013-50-8(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 
• 5105-78-2 4-(benzyloxycarbonylamino)butyric acid 
• 17241-59-7 2-Hydroxymethylanthraquinone 

Relevant articles and documents

Electroreductive Cleavage of 2-Methylene-9,10-anthraquinone (Maq) Esters of Carboxylic Acids and N-Substituted Carbamic Acids: Protecting Groups for Carboxylic Acids and Primary Amines

The 2-methylene-9,10-anthraquinone (Maq) ester of γ-(benzyloxycarbonylamino)butyric acid (3a) and the Maq ester of N-(3-benzyloxycarbonylpropyl)carbamic acid (4) were synthesized as possible γ-aminobutyric acid (GABA) delivery systems.Electrochemical reduction of these Maq esters at -0.5 V (SCE) in 50percent aqueous THF buffer (pH 7.0) produced their corresponding anthrahydroquinones, which failed to give detectable cleavage products after several hours.In contrast, reduction of 3a and 4 in DMF at -0.9 V (-1.2 V) produced their radical anions (dianions), which formed theMaq cleavage products 2-methyl-9,10-anthraquinone and 2-(hydroxymethyl)-9,10-anthraquinone in combined yields of >80percent.Comparable yields of the other cleavage products, the GABA esters, were also found.This work demonstrates that electrochemical reduction can be used as an alternative method for deprotection of Maq esters of carboxylic acids used in the synthesis of peptides.In addition, the synthesis of 4 and its reductive cleavage shows that Maq esters of carbamates can serve as protecting groups of primary amines.