152141-40-7

Basic information

• Product Name: (8aS)-hexahydro-5(1H)-Indolizinone
• Synonyms: (8aS)-hexahydro-5(1H)-Indolizinone
• CAS NO: 152141-40-7
• Molecular Formula: C8H13NO
• Molecular Weight: 139.19492
• Mol File: 152141-40-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (8aS)-hexahydro-5(1H)-Indolizinone(CAS DataBase Reference)
• NIST Chemistry Reference: (8aS)-hexahydro-5(1H)-Indolizinone(152141-40-7)
• EPA Substance Registry System: (8aS)-hexahydro-5(1H)-Indolizinone(152141-40-7)

Safety Data

• Hazardous Substances Data: 152141-40-7(Hazardous Substances Data)

Upstream product

• 151983-41-4 (S)-3,5,8,8a-tetrahydro-5-oxo-indolizine 
• 143771-06-6 (-)-(S)-2-(2-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 1413927-27-1 (S)-tert-butyl 2-(4-ethoxy-4-oxobutyl)-5-oxopyrrolidine-1-carboxylate 
• 1413927-35-1 (S)-ethyl 4-(5-oxopyrrolidin-2-yl)butanoate 
• 1413927-34-0 (S)-ethyl 4-(1-(4-methoxyphenyl)-5-oxopyrrolidin-2-yl)butanoate 
• 1413927-25-9 (R,E)-ethyl 4-(1-(4-methoxyphenyl)-5-oxopyrrolidin-2-yl)but-2-enoate 
• 1413927-28-2 (S)-tert-butyl 2-(4-ethoxy-4-oxobutyl)pyrrolidine-1-carboxylate 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 56633-71-7 2-(S)-(2-diazo-1-oxoethyl)pyrrolidine-1-carboxylic acid benzyl ester 
• 56633-73-9 (S)-2-(1-((benzyloxy)carbonyl)pyrrolidine-2-yl)acetic acid 

Downstream Products

• 586347-03-7 indolizidine 139 
• 18881-13-5 (+)-coniceine 

Relevant articles and documents

A general strategy for the catalytic, highly enantio- and diastereoselective synthesis of indolizidine-based alkaloids

Sixteen indolizidine-based alkaloids (IBAs) that were isolated as poison constituents of the skin of frogs were synthesized in a highly flexible and stereoselective manner. As a key step, a three-component, organocatalytic, highly enantio- and diastereose

A general organocatalytic approach toward the enantioselective total synthesis of indolizidine based alkaloids

Four indolizidine based alkaloids (IBAs) have been synthesized in a highly enantioselective, straightforward, and flexible manner. As a key step our previously developed Bronsted acid catalyzed vinylogous Mannich reaction was employed which easily afforded gram amounts of an optically pure central intermediate which can be converted into a wide range of diversely substituted IBAs.

Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids. Applications in Wittig reactions and heterocycle synthesis

N-Z-γ-amino alcohols derived from nonracemic β-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniine, (S)-(-)-coniceine and a pipecoline precursor is described.

Asymmetric Heck reaction of alkenyl iodides in the presence of silver salts. Catalytic asymmetric synthesis of decalin and functionalized indolizidine derivatives

Decalin derivatives 3 (up to 80% ee) and indolizidine derivative 6 (up to 86% ee) have been synthesized by an asymmetric Heck reaction starting with prochiral alkenyl iodides 1 and 4, respectively. The important role of silver salts in the asymmetric Heck

Catalytic asymmetric synthesis of a functionalized indolizidine derivative. A useful intermediate suitable for the synthesis of various glycosidase inhibitors

Indolizidine derivative 7 has been sythesized in up 86% ee by an asymmetric Heack reaction (Pd(O)-BPPFOH, Ag-exchanged zeolite) starting with prochiral alkenyl iodide 5. Conversion of 7 to δconiceine (9) is also described.