199192-11-5

Basic information

• Product Name: Ethanone, 1-(5,6,7,8-tetrahydro-1-indolizinyl)- (9CI)
• Synonyms: Ethanone, 1-(5,6,7,8-tetrahydro-1-indolizinyl)- (9CI)
• CAS NO: 199192-11-5
• Molecular Formula: C10H13NO
• Molecular Weight: 163.21632
• Product Categories: ACETYLGROUP
• Mol File: 199192-11-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethanone, 1-(5,6,7,8-tetrahydro-1-indolizinyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(5,6,7,8-tetrahydro-1-indolizinyl)- (9CI)(199192-11-5)
• EPA Substance Registry System: Ethanone, 1-(5,6,7,8-tetrahydro-1-indolizinyl)- (9CI)(199192-11-5)

Safety Data

• Hazardous Substances Data: 199192-11-5(Hazardous Substances Data)

Upstream product

• 852174-82-4 4-(3-acetylpyrrol-1-yl)butanal 
• 1072-82-8 3-acetylpyrrole 
• 852174-78-8 1-allyl-3-acetylpyrrole 
• 917-54-4 methyllithium 
• 67421-69-6 5,6,7,8-tetrahydroindolizine-1-carbonitrile 
• 660-88-8 5-aminopentanoic acid 

Relevant articles and documents

A Route to 2-Substituted 3-Cyanopyrroles: Synthesis of Danaidal and Suffrutine A

The title compounds were prepared in a two-step sequence from 4,4-dimethoxybutyronitrile and the respective esters by Claisen condensation and subsequent Paal-Knorr pyrrole synthesis. The sequence could be performed as a one-pot procedure delivering the pyrroles in yields of 47-72% over two steps (13 examples). Intramolecular variants of the method were applied to the total synthesis of danaidal and suffrutine A from the respective trityl-protected ω-amino alkanoates.

Domino reaction sequences in the rhodium-catalyzed hydroformylation of 3-acetyl-1-allylpyrrole: A short route to 5,6,7,8-tetrahydroindolizines

When 3-acetyl-1-allylpyrrole (1) was subjected under hydroformylation conditions, with Rh4(CO)12 as catalyst precursor, to 30 atm CO/H2 (1:1) total pressure and 140°C, an equimolar mixture of the isomeric 5,6,7,8-tetrahydroindolizines 4′ and 5′ was obtained as the almost exclusive product. In both cases a domino hydroformylation/ cyclization on the α pyrrole positions by the aldehyde 3 carbonyl group occurs which involves different intermediates: while 4′ is generated via the dihydroindolizine 4, 5′ forms via direct reduction of 8-hydroxytetrahydroindolizine 5, a structure that has never been observed before from 1-allylpyrroles under oxo conditions.

Bu3SnH mediated oxidative radical cyclisation onto imidazoles and pyrroles

A new protocol using radical cyclisation has been developed for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles. The intermediate nucleophilic N-alkyl radicals, generated using Bu3SnH from N- (ω-bromoalkyl) or N-[ω-(phenylselanyl)alkyl] imidazoles and pyrroles, undergo regio-selective radical cyclisalion onto the azole rings followed by oxidative re-aromatisation.

Oxidative radical cyclisations onto imidazoles and pyrroles using Bu3SnH

Oxidative radical cyclisation using Bu3SnH has been used for the synthesis of [1,2-c]-fused imidazoles and [1,2-a]-fused pyrroles from imidazolecarbaldehydes and acylpyrroles respectively. The intermediate nucleophilic N-alkyl radicals cyclise onto imidazole and pyrrole rings followed by oxidative re-aromatisation.