391609-26-0

Basic information

• Product Name: Carbamic acid, [2-[3-(acetyloxy)-3-methoxy-4-oxo-1,5-cyclohexadien-1-yl]ethyl]-, methyl ester
• CAS NO: 391609-26-0
• Molecular Formula: C13H17NO6
• Molecular Weight: 283.281
• Mol File: 391609-26-0.mol

Chemical Properties

• CAS DataBase Reference: Carbamic acid, [2-[3-(acetyloxy)-3-methoxy-4-oxo-1,5-cyclohexadien-1-yl]ethyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbamic acid, [2-[3-(acetyloxy)-3-methoxy-4-oxo-1,5-cyclohexadien-1-yl]ethyl]-, methyl ester(391609-26-0)
• EPA Substance Registry System: Carbamic acid, [2-[3-(acetyloxy)-3-methoxy-4-oxo-1,5-cyclohexadien-1-yl]ethyl]-, methyl ester(391609-26-0)

Safety Data

• Hazardous Substances Data: 391609-26-0(Hazardous Substances Data)

Upstream product

• 164228-27-7 2-(4-hydroxy-3-methoxyphenyl)-ethyl-N-methoxycarbonylamine 
• 63909-38-6 3-methoxy-4-benzyloxy-ω-nitrostyrolene 
• 157669-71-1 2-(4-benzyloxy-3-methoxyphenyl)-ethyl-N-methoxycarbonylamine 
• 121-33-5 vanillin 
• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 3240-34-4 [bis(acetoxy)iodo]benzene 

Relevant articles and documents

Iodine (III)-mediated generation of nitrogen-tethered orthoquinol acetates for the construction of oxygenated indole, quinoline, and phenanthridine alkaloid motifs

Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen-tethered 2-methoxyphenols via phenyliodine(III) diacetate mediated oxidative acetoxylation, followed by a fluoride- or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type addition step is further discussed in view of the rearrangement of orthoquinol acetate intermediates into paraquinol acetates that is sometimes observed in situ. Application of this methodology to the synthesis of a functionalized phenanthridine, and its potential for the construction of polyoxygenated lycorine-type alkaloid skeleta are here described.

Hypervalent iodine(III)-mediated oxidative acetoxylation of 2-methoxyphenols for regiocontrolled nitrogen benzannulation

Nitrogen-tethered 2-methoxyphenols are conveniently dearomatized into synthetically useful orthoquinol acetates by treatment with phenyliodine(III) diacetate in methylene chloride at low temperature. Subsequent fluoride- or base-induced intramolecular nucleophilic addition reactions furnish indole and quinoline derivatives. The potential of this methodology for the synthesis of a functionalized lycorine-type alkaloid skeleton is introduced here.