105553-63-7

Basic information

• Product Name: 2-[(4-methoxyphenyl)amino]cyclohex-2-en-1-one
• Synonyms: 2-[(4-methoxyphenyl)amino]cyclohex-2-en-1-one
• CAS NO: 105553-63-7
• Molecular Weight: 217.268
• Mol File: 105553-63-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-[(4-methoxyphenyl)amino]cyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-methoxyphenyl)amino]cyclohex-2-en-1-one(105553-63-7)
• EPA Substance Registry System: 2-[(4-methoxyphenyl)amino]cyclohex-2-en-1-one(105553-63-7)

Safety Data

• Hazardous Substances Data: 105553-63-7(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 1069130-74-0 1-benzyloxy-3-formyl-6-methoxy-9H-carbazole 
• 58751-07-8 4-methoxy-N-(2-methoxyphenyl)benzenamine 

Relevant articles and documents

Iodine-catalyzed synthesis of N, N ′-diaryl-o-phenylenediamines from cyclohexanones and anilines using DMSO and O2 as oxidants

A novel I2-catalyzed cross-dehydrogenative aromatization of cyclohexanones and anilines to synthesize N,N′-diaryl-o-phenylenediamines has been unprecedentedly developed with dimethyl sulfoxide and oxygen employed as mild terminal oxidants. To prove the rationality of the two separate dehydration steps of the proposed mechanism, a resulting I2-catalyzed cross-dehydrogenative aromatization of cyclohexenones and anilines to synthesize diarylamines has also been reported.

Can Primary Arylamines Form Enamine? Evidence, α-Enaminone, and [3+3] Cycloaddition Reaction

The formation of enamine from primary arylamines was detected and confirmed by nuclear magnetic resonance spectroscopy. The presence of a radical quencher, e.g., (2,2,6,6-tetramethylpiperidin-1-yl)oxidanyl, was found to be essential for the detection of enamine formation. A direct synthesis of α-enaminones from primary arylamines and ketones was also developed. Mechanistic investigation of α-enaminone formation suggests that an amine radical cation generated through O2 singlet energy transfer was involved in initiating α-enaminone formation. The reactivity and utility of α-enaminones were explored with a [3+3] cycloaddition reaction of enones affording dihydropyridines in good yields (58-85%). α-Enaminones displayed a set of reactivities that is different from that of enamines. The knowledge gained in this work advances our basic understanding of organic chemistry, providing insights and new opportunities in enamine catalysis.