36646-77-2

Basic information

• Product Name: 3-(4-methoxyphenylamino)cyclohex-2-en-1-one
• Synonyms: 3-(4-methoxyphenylamino)cyclohex-2-en-1-one
• CAS NO: 36646-77-2
• Molecular Weight: 217.268
• Mol File: 36646-77-2.mol
• Article Data: 22

Chemical Properties

• CAS DataBase Reference: 3-(4-methoxyphenylamino)cyclohex-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-methoxyphenylamino)cyclohex-2-en-1-one(36646-77-2)
• EPA Substance Registry System: 3-(4-methoxyphenylamino)cyclohex-2-en-1-one(36646-77-2)

Safety Data

• Hazardous Substances Data: 36646-77-2(Hazardous Substances Data)

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 104-94-9 4-methoxy-aniline 
• 108-94-1 cyclohexanone 
• 765-87-7 cyclohexane-1,2-dione 
• 80960-09-4 2-((3-oxocyclohex-1-en-1-yl)amino)acetic acid 

Downstream Products

• 1353896-93-1 6,7-dihydro-7-(4-hydroxy-1-(4-methoxyphenyl)-2-phenyl-1H-indol-3-yl)-1-(4-methoxyphenyl)-2-phenyl-1H-indol-4(5H)-one 

Relevant articles and documents

Fe-Catalyzed enaminone synthesis from ketones and amines

We have developed an iron-catalyzed direct olefination for enaminone synthesis, with saturated ketones as a source of olefins. This direct ketone β-functionalization reaction has readily available starting materials and a wide range of substrates and requires mild reaction conditions.

Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification, Mechanism, and Scope

Upon irradiation at = 366 nm, tertiary N-alkoxycarbonyl-N-aryl-β-enaminones furnished exclusively the trans-hexahydrocarbazol-4-ones by a conrotatory [6π] photocyclization but epimerized on silica to cis-hexahydrocarbazol-4-ones (14 examples, 44-98% yield). The acceptor substitution on the nitrogen atom enhanced the stability of the cyclized products compared to N-alkyl-N-aryl-β-enaminones reported previously. The mechanism of the [6π] photocyclization was investigated by quenching experiments, deuterium-labeling experiments, and DFT calculations, suggesting a triplet pathway for the conrotatory ring closure followed by a suprafacial [1,4] hydrogen migration.

Cyclic enaminone as new chemotype for selective cyclooxygenase-2 inhibitory, anti-inflammatory, and analgesic activities

The cyclic enaminone moiety has been identified as a new scaffold for selective inhibition of cyclooxygenase-2 with anti-inflammatory and analgesic activities. The designed cyclic enaminones have been synthesized conveniently through the development of a new catalyst-free methodology and evaluated for cyclooxygenase (COX-1 and COX-2) inhibitory activities. Three compounds 7d, 8, and 9 predominantly inhibited COX-2 with selectivity index of 74.09, 19.45 and 108.68, respectively, and were assessed for in vivo anti-inflammatory activity in carrageenan induced rat paw edema assay. The anti-inflammatory activity of 7d was comparable to that of celecoxib at a dose of 12.5 mg/kg. However, the compounds 8 and 9 were more/equally effective as anti-inflammatory agent compared to celecoxib at the doses of 12.5 mg/kg and 25 mg/kg and also exhibited anti-inflammatory activity comparable to that of diclofenac. The therapeutic potential of the most active compound 9 was further assessed by performing in vivo thermal and mechanical hyperalgesia tests using various models that revealed its analgesic activity. The in vivo non-ulcerogenicity of 9 revealed the gastrointestinal safety as compared to the non-selective COX inhibitor indomethacin. The in vitro antioxidant activity and in vivo experiments on heart rate and blood pressure provided the cardiovascular safety profile of 9. The molecular docking studies rationalize the COX-2 selectivity of the newly found anti-inflammatory compounds 7d, 8, and 9.