534616-88-1

Basic information

• Product Name: 2-Azetidinecarboxaldehyde, 1-(phenylmethyl)-
• CAS NO: 534616-88-1
• Molecular Formula: C11H13NO
• Molecular Weight: 175.23
• Mol File: 534616-88-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Azetidinecarboxaldehyde, 1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinecarboxaldehyde, 1-(phenylmethyl)-(534616-88-1)
• EPA Substance Registry System: 2-Azetidinecarboxaldehyde, 1-(phenylmethyl)-(534616-88-1)

Safety Data

• Hazardous Substances Data: 534616-88-1(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 54773-11-4 1-benzylazetidine-2-carboxylic acid ethyl ester 
• 18085-37-5 methyl 1-benzyl-2-azetidinecarboxylate 
• 31247-34-4 (1-benzyl-azetidin-2-yl)-methanol 

Downstream Products

• 5291-77-0 1-benzyl-2-pyrrolidone 
• 1353161-12-2 N-benzyl-2-methoxycarbonylethylazetidine 
• 259822-53-2 C₁₈H₁₉N 
• 1393718-07-4 C₁₉H₂₁NO 
• 1393718-08-5 C₂₂H₂₁N 
• 1393718-09-6 C₁₈H₁₈⁽²⁾HN 
• 1198422-96-6 N-benzyl-2-vinylazetidine 

Relevant articles and documents

Targeting Alzheimer's disease by investigating previously unexplored chemical space surrounding the cholinesterase inhibitor donepezil

A series of twenty seven acetylcholinesterase inhibitors, as potential agents for the treatment of Alzheimer's disease, were designed and synthesised based upon previously unexplored chemical space surrounding the molecular skeleton of the drug donepezil, which is currently used for the management of mild to severe Alzheimer's disease. Two series of analogues were prepared, the first looking at the replacement of the piperidine ring in donepezil with different sized saturated N-containing ring systems and the second looking at the introduction of different linkers between the indanone and piperidine rings in donepezil. The most active analogue 5,6-dimethoxy-1-oxo-2,3-dihydro-1H-inden-2-yl 1-benzylpiperidine-4-carboxylate (67) afforded an in vitro IC50value of 0.03 ± 0.07 μM against acetylcholinesterase with no cytotoxicity observed (IC50of >100 μM, SH-SY5Y cell line). In comparison donepezil had an IC50of 0.05 ± 0.06 μM and an observed cytotoxicity IC50of 15.54 ± 1.12 μM. Molecular modelling showed a strong correlation between activity and in silico binding in the active site of acetylcholinesterase.

Cycloaddition reaction of 2-vinylazetidines with benzyne: A facile access to 1-benzazocine derivatives

The cycloaddition reaction of 2-vinylazetidines with benzyne proceeded smoothly without a catalyst, and various benzazocine derivatives were isolated in good to high yields. The scope of the reaction, as well as the reactions of other arynes, has been studied.

NHC-Catalyzed intramolecular redox amidation for the synthesis of functionalized lactams

A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.