42746-87-2

Usage

Physical state

Crystalline powder

Common uses

Reagent in organic synthesis, building block in pharmaceutical research

Structure

Quaternary ammonium salt

Features

Cyclopentanone ring with dimethylamino group attached

Stability

Hydrochloride salt form provides stability and ease of handling in laboratory settings

Applications

Primarily used in the synthesis of pharmaceuticals and other organic compounds

Hazards

Can be hazardous if not properly handled, caution is required.

Upstream product

• 50-00-0 formaldehyd 
• 506-59-2 N,N-dimethylammonium chloride 
• 120-92-3 cyclopentanone 
• 30354-18-8 N,N-dimethyl(methylene)ammonium chloride 

Downstream Products

• 1467081-75-9 2-(4-methoxyphenyl)-5,6-trimethylene-4H-1,3,2-oxathiaphosphorine-2-sulfide 
• 65242-18-4 2-amino-3-cyano-5,6-trimethylenepyridine 

Relevant academic research and scientific papers

Efficient Preparation of Substituted 5,6,7,8-Tetrahydroquinolines and Octahydroacridine Derivatives

The reaction of the enamine 4 with different β-amino ketone hydrochlorides 3a-e affords the diketones 5a-e which can be cyclized to the corresponding mono- and disubstituted tetrahydroquinolines 6a-e. Furthermore the preparation of the octahydroacridines 8f and 8g by using a straightforward multi step sequence is described.

Facile synthesis of polycyclic pyridines, bipyridines, and oligopyridines

The preparation of polycyclic heterocycles with one or more nitrogen atoms and different binding angles by a domino reaction is described, These compounds (4-6, 8a-b) are formed by the reaction of β-amino ketone hydrochlorides 1 or 2 (Mannich bases) with ketones 3. Especially the synthesis of the terpyridines 8a and 8b in a double domino reaction is very useful (yield 70 and 59%) and opens a route to torands. VCH Verlagsgesellschaft mbH, 1996.

Evaluation of some Mannich bases of cycloalkanones and related compounds for cytotoxic activity

A number of Mannich bases of cycloalkanones and related quaternary ammonium compounds were prepared for cytotoxic evaluation in order to examine the theory that sequential release of alkylating agents produces increased bioactivity compared to related compounds containing only 1 potential alkylating site.Many of the compounds had significant activity against murine L1210 cells and various human tumours.Some correlations between structure and activity were noted but the biological data did not support the view that potential sequential liberation of cytotoxic species produced compounds with increased potency.The formation of various oximes and oxime benzoates as candidate prodrugs was achieved but in general these compounds were not cytotoxic at the concentrations utilized.This observation may be due to the fact that the oximes were much more stable in deuterated phosphate buffered saline over a period of 48 h at 37 deg than the Mannich bases, as revealed by 1H-NMR spectroscopy. Mannich bases / cytotoxic evaluations / prodrugs / 1H-NMR spectroscopy / structure-activity relationships