4419-57-2

Usage

Structure

A ketone derivative containing a pyrrolizine ring and a pentanone chain

Usage

Building block in organic synthesis, used as a precursor in the production of pharmaceuticals and other organic compounds

Physical properties

Colorless liquid, soluble in water, has a distinct odor

Importance

An intermediate in the chemical industry used in the synthesis of drugs and other organic compounds

InChI:InChI=1/C9H17NO/c1-2-3-6-9(11)10-7-4-5-8-10/h2-8H2,1H3

Upstream product

• 1036648-33-5 5-oxo-5-(pyrrolidin-1-yl)pentan-2-yl 4-methylbenzoate 
• 73200-35-8 5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one 
• 13991-18-9 1-(pyrrolidin-1-yl)pent-4-yn-1-one 
• 123-75-1 pyrrolidine 
• 2173-56-0 n-pentyl n-pentanoate 
• 71-41-0 pentan-1-ol 
• 108-29-2 5-methyl-dihydro-furan-2-one 
• 116461-11-1 4-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one 
• 1262219-75-9 1-methyl-4-oxo-4-pyrrolidin-1-ylbutyl diphenylphosphinate 
• 109-99-9 tetrahydrofuran 
• 110-59-8 pentanonitrile 

Downstream Products

• 6797-49-5 2-butylbenzo[d]oxazole 

Relevant academic research and scientific papers

MANGANESE BASED COMPLEXES AND USES THEREOF FOR HOMOGENEOUS CATALYSIS

The present invention relates to novel manganese complexes and their use, inter alia, for homogeneous catalysis in (1) the preparation of imine by dehydrogenative coupling of an alcohol and amine; (2) C-C coupling in Michael addition reaction using nitriles as Michael donors; (3) dehydrogenative coupling of alcohols to give esters and hydrogen gas (4) hydrogenation of esters to form alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di- lactones), or polyesters); (5) hydrogenation of amides (including cyclic dipeptides, lactams, diamide, polypeptides and polyamides) to alcohols and amines (or diamine); (6) hydrogenation of organic carbonates (including polycarbonates) to alcohols or hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (7) dehydrogenation of secondary alcohols to ketones; (8) amidation of esters (i.e., synthesis of amides from esters and amines); (9) acylation of alcohols using esters; (10) coupling of alcohols with water and a base to form carboxylic acids; and (11) preparation of amino acids or their salts by coupling of amino alcohols with water and a base. (12) preparation of amides (including formamides, cyclic dipeptides, diamide, lactams, polypeptides and polyamides) by dehydrogenative coupling of alcohols and amines; (13) preparation of imides from diols.

Catalytic hydrogenation of amides to amines under mild conditions

Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright

Electrochemical deoxygenation of primary alcohols

Direct electrolysis of primary alcohols, in the presence of methyl toluate, leads smoothly to the formation of the corresponding deoxygenated product in high yield. Georg Thieme Verlag Stuttgart · New York.

Novel electrochemical deoxygenation reaction using diphenylphosphinates

The electrochemical reduction of diphenylphosphinate esters leads smoothly and in high yields to the corresponding deoxygenated products. In comparison with the previously developed methodologies, the electrolysis could be performed at lower temperature and with a higher current density, resulting in a shorter reaction time.

Direct synthesis of N-acylpyrrolidines from tetrahydrofuran and nitriles of aliphatic and aromatic acids on zeolite catalysts under supercritical conditions

The tetrahydrofuran-nitrile (CH3CN, n-C4H 9CN, C6H5CN)-zeolite (faujasites, mordenite, beta, pentasils) system and its transformations under supercritical conditions were studied. The feasibility of d

Toluates: unexpectedly versatile reagents

The mechanism of the monoelectronic reduction of aromatic esters has been investigated. The unexpected synthetic utility of the toluate moiety in the deoxygenation of alcohols and the allylation of ketones is also reported. Finally, the use of aromatic esters as robust, though easily removable, protecting groups is depicted.

Organic electrosynthesis using toluates as simple and versatile radical precursors

The electrolysis of toluate esters leads smoothly to the formation of the radical of the alkyl fragment. This property has been used to develop a new electrochemical deoxygenation reaction. The Royal Society of Chemistry.

Using toluates as simple and versatile radical precursors

(Chemical Equation Presented) The viability of the toluate moiety as a radical precursor has been examined by studying deoxygenation and cyclization reactions.