588699-52-9

Basic information

• Product Name: Morpholine, 4-[5-[(4-nitrophenyl)methylene]-1-cyclopenten-1-yl]-
• CAS NO: 588699-52-9
• Molecular Formula: C16H18N2O3
• Molecular Weight: 286.331
• Mol File: 588699-52-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Morpholine, 4-[5-[(4-nitrophenyl)methylene]-1-cyclopenten-1-yl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Morpholine, 4-[5-[(4-nitrophenyl)methylene]-1-cyclopenten-1-yl]-(588699-52-9)
• EPA Substance Registry System: Morpholine, 4-[5-[(4-nitrophenyl)methylene]-1-cyclopenten-1-yl]-(588699-52-9)

Safety Data

• Hazardous Substances Data: 588699-52-9(Hazardous Substances Data)

Upstream product

• 936-52-7 1-(N-morpholino)cyclopent-1-ene 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 71496-93-0 2-(4-nitrobenzylidene)cyclopentanone 
• 588699-39-2 ethyl 1-(4-fluorophenyl)-6-(4-nitrobenzyliden)-1,4,5,6-tetrahydrocyclopenta[c]pyrazole-3-carboxylate 

Relevant articles and documents

Quinoline synthesis: Scope and regiochemistry of photocyclisation of substituted benzylidenecyclopentanone O-alkyl and O-acetyloximes

Irradiation of substituted 2-benzylidenecyclopentanone O-alkyl and O-acetyloximes in methanol provides a convenient synthesis of alkyl, alkoxy, hydroxy, acetoxy, amino, dimethylamino and benzo substituted annulated quinolines. para-Substituents yield 6-substituted-2,3-dihydro-1H-cyclopenta[b] quinolines with 8-substituted products being obtained from ortho-substituted starting materials. Reactions of meta-substituted precursors are highly regioselective, with alkyl substituents leading to 5-substituted 2,3-dihydro-1H-cyclopenta[b]quinolines and more strongly electron-donating substituents generally resulting in 7-substituted products. 2-Furylmethylene and 2-thienylmethylene analogues yield annulated furo- and thieno-[2,3e]pyridines respectively. Sequential E- to Z-benzylidene group isomerisation and six π-electron cyclisation steps result in formation of a short-lived dihydroquinoline intermediate which spontaneously aromatises by elimination of an alcohol or acetic acid. For 2-benzylidenecyclopentanone O-allyloxime, singlet excited states are involved in both steps. The Royal Society of Chemistry 2007.