1313877-58-5

Basic information

• Product Name: 3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one hydrochloride
• Synonyms: 3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one hydrochloride
• CAS NO: 1313877-58-5
• Molecular Weight: 447.808
• Mol File: 1313877-58-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one hydrochloride(1313877-58-5)
• EPA Substance Registry System: 3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one hydrochloride(1313877-58-5)

Safety Data

• Hazardous Substances Data: 1313877-58-5(Hazardous Substances Data)

Upstream product

• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 320589-77-3 4-piperidone hydrate hydrochloride 

Downstream Products

• 1260791-17-0 3,5-bis(4-trifluoromethylbenzylidene)-1-[(1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl]piperidin-4-one 

Relevant articles and documents

Synthesis, crystal structures and anti-inflammatory activity of four 3,5-bis(Arylidene)-N-benzene-sulfonyl-4-piperidone derivatives

3,5-Bis(arylidene)-4-piperidone (BAP) derivatives display good antitumour and anti-inflammatory activities because of their double α,β-unsaturated ketone structural characteristics. If N-benzenesulfonyl substituents are introduced into BAPs, the configuration of the BAPs would change significantly and their anti-inflammatory activities should improve. Four N-benzenesulfonyl BAPs, namely (3E,5E)-1-(4-methylbenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C28H21F6NO3S·CH2Cl2, (4), (3E,5E)-1-(4-fluorobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C27H18F7NO3S, (5), (3E,5E)-1-(4-nitrobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one, C27H18F6N2O5S, (6), and (3E,5E)-1-(4-cyanobenzenesulfonyl)-3,5-bis[4-(trifluoromethyl)benzylidene]piperidin-4-one dichloromethane monosolvate, C28H18F6N2O3S·CH2Cl2, (7), were prepared by Claisen-Schmidt condensation and N-sulfonylation. They were characterized by NMR, FT-IR and HRMS (high resolution mass spectrometry). Single-crystal structure analysis reveals that the two 4-(trifluoromethyl)phenyl rings on both sides of the piperidone ring in (4)-(7) adopt an E stereochemistry of the olefinic double bonds. Molecules of both (4) and (6) are connected by hydrogen bonds into one-dimensional chains. In (5) and (7), pairs of adjacent molecules embrace through intermolecular hydrogen bonds to form a bimolecular combination, which are further extended into a two-dimensional sheet. The anti-inflammatory activity data reveal that (4)-(7) significantly inhibit LPS-induced interleukin (IL-6) and tumour necrosis factor (TNF-α) secretion. Most importantly, (6) and (7), with strong electron-withdrawing substituents, display more potential inhibitory effects than (4) and (5).