33023-01-7

Basic information

• Product Name: (+)-1-[[(8aR)-1,2,3,5,6,8a-Hexahydroindolizine]-8-yl]-1-butanone
• Synonyms: (+)-1-[[(8aR)-1,2,3,5,6,8a-Hexahydroindolizine]-8-yl]-1-butanone;(+)-Eleokanine A;Elaeokanine A;Eleokanine A
• CAS NO: 33023-01-7
• Molecular Formula: C12H19NO
• Molecular Weight: 0
• Mol File: 33023-01-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 311.2°C at 760 mmHg
• Flash Point: 113.7°C
• Appearance: /
• Density: 1.03g/cm³
• Vapor Pressure: 0.000571mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: (+)-1-[[(8aR)-1,2,3,5,6,8a-Hexahydroindolizine]-8-yl]-1-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1-[[(8aR)-1,2,3,5,6,8a-Hexahydroindolizine]-8-yl]-1-butanone(33023-01-7)
• EPA Substance Registry System: (+)-1-[[(8aR)-1,2,3,5,6,8a-Hexahydroindolizine]-8-yl]-1-butanone(33023-01-7)

Safety Data

• Hazardous Substances Data: 33023-01-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 300, 1984 DOI: 10.1021/jo00176a016

InChI:InChI=1/C12H19NO/c1-2-5-12(14)10-6-3-8-13-9-4-7-11(10)13/h6,11H,2-5,7-9H2,1H3/t11-/m1/s1

Upstream product

• 135416-28-3 (+)-elaeokanine C 
• 125517-30-8 (+)-(8aR,1'S)-1,2,3,5,6,8a-hexahydro-8-(1-hydroxybutyl)indolizine 
• 908005-84-5 (R)-8-bromo-1,2,5,6,8a-hexahydroindolizine 
• 5327-51-5 (N-morpholin-4-yl)butan-1-one 
• 908005-83-4 (R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidine 
• 908005-82-3 (1,1-dimethylethyl)-(R)-2-[(Z)-4-bromo-1-(trimethylsilyl)-1-butenyl]-1-pyrrolidinecarboxylate 
• 142009-95-8 (7S,8R,8aR)-(+)-8-butyryl-7-hydroxyindolizidin-3-one 
• 142009-96-9 (7S,8R,8aR)-(+)-7-hydroxy-8-(2-propyl-1,3-dioxolan-2-yl)indolizin-3-one 
• 142009-93-6 (1S,2R,3R,4R,5S,10S,11R)-(+)-4-butyryl-5-hydroxy-8-azatetracyclo<9.2.1.0^2,1.0^3,8>tetradec-12-en-9-one 
• 142009-92-5 (1R,2S,5S,6R,7S)-(+)-4-<2'-(1,3-dioxolan-2-yl)ethyl>-5-(2''-oxopentyl)-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 142009-94-7 (7S,8R,8aR)-(+)-8-butyryl-6,7,8,8a-tetrahydro-7-hydroxyindolizin-3(5H)-one 
• 154634-85-2 (1R,2S,5S,6R,7S)-(+)-4-<2'-(1,3-dioxolan-2-yl)ethyl>-5-methoxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 154634-84-1 (+)-(1R,2S,5S,6R,7S)-4-<2'-(1,3-dioxolan-2-yl)ethyl>-5-hydroxy-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 
• 154634-83-0 (1R,2R,5S,6S,7S)-(+)-4-<2-(1,3-dioxolan-2-yl)ethyl>-5-hydroxy-2-(<(1'S,2'R,4'R,4_S)-2'-hydroxy-7',7'-dimethylbicyclo<2.2.1>heptan-1'-yl>methylsulfinyl)-4-azatricyclo<5.2.1.0^2,6>dec-8-en-3-one 

Relevant articles and documents

Synthesis of (+)-Elaeokanine A and (+)-Elaeokanine C Based upon a Novel Approach Involving Diastereoselective, Nucleophilic Addition to N-Acyliminium Ion and Retro Diels-Alder Reaction

An asymmetric synthesis of Elaeocarpus alkaloids, (+)-elaeokanine A and (+)-elaeokanine C is described.The key steps involve an asymmetric Diels-Alder reaction of a chiral sulfinyl dienophile, diastereoselective nucleophilic addition to the acyliminium ion and retro Diels-Alder reactions.

Enantioselective Synthesis of (+)-Indolizidine, (+)-Laburnine and (+)-Elaeokanines A and C using the Diels-Alder Reaction of α-(2-eyo-Hydroxy-10-bornylsulfinyl)maleimide

The Diels-Alder adduct 5 derived from the N-butynylmaleimide 6 and cyclopentadiene has been transformed into the tetracyclic lactams 12 and 19 via a common precursor 9.The lactams 12 and 19 have been converted into (+)-indolizidine 1 and (+)-laburnine 2, respectively, via retro-Diels-Alder reaction.Similar methodology has bee succesfully applied to the synthesis of (+)-elaeokanine A 3 and (+)-elaeokanine C 4.

Asymmetric Total Syntheses of Elaeokanines A and B via α-Sulfinyl Ketimine

α-Lithiated (+)-(R)-4,5-dihydro-2-methyl>-3H-pyrrole (4) underwent annulation with 1,3-diiodopropane to give (-)-(S,S)-1,2,3,5,6,7-hexahydro-8-indolizine (6), which was converted into (-)-elaeokanine B (three steps) and (+)-elaeokanine A (four steps).