355114-83-9

Basic information

• Product Name: Indolizine, 5,6-dihydro-5-methyl- (9CI)
• Synonyms: Indolizine, 5,6-dihydro-5-methyl- (9CI)
• CAS NO: 355114-83-9
• Molecular Formula: C9H11N
• Molecular Weight: 133.19034
• Product Categories: AMINETERTIARY
• Mol File: 355114-83-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Indolizine, 5,6-dihydro-5-methyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Indolizine, 5,6-dihydro-5-methyl- (9CI)(355114-83-9)
• EPA Substance Registry System: Indolizine, 5,6-dihydro-5-methyl- (9CI)(355114-83-9)

Safety Data

• Hazardous Substances Data: 355114-83-9(Hazardous Substances Data)

Upstream product

• 201230-82-2 carbon monoxide 
• 1050522-29-6 (+)-(3S)-3-pyrrol-1-ylbut-1-ene 
• 573984-96-0 ethyl (S)-5,6-dihydroindolizine-5-carboxylate 
• 573984-97-1 (S)-(5,6-dihydroindolizin-5-yl)methanol 
• 874300-07-9 (S)-5,6-dihydroindolizine-5-carbaldehyde 
• 874300-10-4 (S)-(5,6-dihydroindolizin-5-yl)methyl tosylate 
• 618905-90-1 (3R)-3-(pyrrol-1-yl)but-1-ene 
• 35801-86-6 1-(1-methyl-2-propenyl)pyrrole 

Relevant articles and documents

(5R)-5-Alkyl-5,6-dihydroindolizines via stereospecific domino hydroformylation/cyclodehydration of (3R)-3-(pyrrol-1-yl)alk-1-enes

(5R)-5-Alkyl-5,6-dihydroindolizines 3a-c having the same high enantiomeric excess (>92%) as the corresponding starting olefins (3R)-3-(pyrrol-1-yl)alk- 1-enes 1a-c were obtained via a highly regioselective and stereospecific domino hydroformylation/cyclodehydration reaction sequence. The reasons for this configurational stability were also analyzed in the light of the general accepted rhodium catalyzed hydroformylation mechanism.

Crucial role of β-elimination in determining regio- and chemoselectivity of the rhodium-catalyzed hydroformylation of N -allylpyrroles: A new approach to 5,6-dihydroindolizines

Rhodium-catalyzed hydroformylation of the chiral (S)-3-alkyl-3-pyrrol-1- ylprop-1-enes at 100 atmospheres total pressure and 25C led to the preferential formation of the branched 3-alkyl-2-methyl-3-pyrrol-1-ylpropanals. At 30 atmospheres and 125°C, the linear 4-alkyl-4-pyrrol-1-ylbutanals were obtained: these aldehydes are not the final products, but evolve into more stable 5,6-dihydroindolizines, with the same optical purity as the starting olefins, via a domino cyclization-dehydration process. According to the generally accepted mechanism for rhodium-catalyzed hydroformylation, the regioselectivity, and then the final chemoselectivity, can be rationalized by taking into account that while at room temperature no -elimination occurs, at high temperature the -elimination involves the branched rhodium-alkyl intermediate only.

5,6-Dihydroindolizines as convenient precursors of indolizidine 167B and analogues

Starting from 5-carboxyethyl-5,6-dihydroindolizine, the title alkaloid was obtained in 25% overall yield via differently C5-substituted 5,6-dihydroindolizines and final exhaustive hydrogenation. An alternative strategy for the synthesis of optically activ

An original approach to 5,6-dihydroindolizines from 1-allylpyrroles by a tandem hydroformylation/cyclization/dehydration sequence

6-Methyl-5,6-dihydroindolizine and 3- or 2-ethyl derivatives were obtained via a one-pot hydroformylation/cyclization/dehydration sequence starting from 1-(2-methyl-2-propenyl)pyrroles. 7-Phenyl-5,6-dihydroindolizine and 5-methyl-5,6-dihydroindolizine were similarly synthesized. An easily occurring electrophilic aromatic substitution by the carbon atom of the carbonyl group on the α-position of the pyrrole ring with the formation of the six-membered ring is the key-step of the process.