67217-85-0

Basic information

• Product Name: indolizidine 223AB
• Synonyms: indolizidine 223AB;(-)-223AB;(-)-Gephyrotoxin 223AB;(3R,8aβ)-3-Butyloctahydro-5α-propylindolizine;(8aβ)-Octahydro-3β-butyl-5α-propylindolizine;[8aβ,(-)]-5α-Propyl-3β-butyloctahydroindolizine
• CAS NO: 67217-85-0
• Molecular Formula: C15H29N
• Molecular Weight: 223.39746
• Mol File: 67217-85-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 271.6°C at 760 mmHg
• Flash Point: 107.9°C
• Appearance: /
• Density: 0.9g/cm³
• Vapor Pressure: 0.0064mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: indolizidine 223AB(CAS DataBase Reference)
• NIST Chemistry Reference: indolizidine 223AB(67217-85-0)
• EPA Substance Registry System: indolizidine 223AB(67217-85-0)

Safety Data

• Hazardous Substances Data: 67217-85-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H29N/c1-3-5-8-14-11-12-15-10-6-9-13(7-4-2)16(14)15/h13-15H,3-12H2,1-2H3/t13-,14-,15-/m1/s1

Upstream product

• 72049-65-1 (3R,8aR)-3-Butyl-5-propyl-3,5,6,7,8,8a-hexahydro-indolizine 
• 63603-35-0 1-(methoxycarbonyl)-2-n-butyl-3-pyrroline 
• 72049-64-0 (2R,5R)-2-(4-Bromo-heptyl)-5-butyl-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester 
• 143679-77-0 (2R,6R)-(-)-2-((3S)-3-hydroxy-1-heptyl)-6-(1-propyl)-piperidine 
• 142841-61-0 (2R,5R)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxoheptyl)pyrrolidine 
• 191665-91-5 (3S,5R,8aR)-3-(1-Chloro-butyl)-5-propyl-octahydro-indolizine 
• 692730-61-3 (-)-(3'R,5'R,8'aS)-3'-butylhexahydro-5-propylspiro[1,3-dithiane-2,7'-(1'H)indolizine] 
• 15681-48-8 dimethyllithium cuprate 
• 292615-27-1 Toluene-4-sulfonic acid 2-((3R,5S,8aR)-3-butyl-octahydro-indolizin-5-yl)-ethyl ester 
• 1034498-78-6 (2R)-(-)-2-n-butyl-5-oxopyrrolidine-1-carboxylic acid benzyl ester 
• 902172-06-9 (R)-2-Butyl-5-ethoxy-pyrrolidine-1-carboxylic acid benzyl ester 
• 136092-38-1 (R)-5-n-Butyl-2-pyrrolidinone 
• 98-79-3 L-Pyroglutamic acid 
• 344749-95-7 3-triethylsilylhept-1-ene-4-ol 

Relevant articles and documents

Cross-coupling of cyclopropanols: Concise syntheses of indolizidine 223AB and congeners

A new synthetic method for indolizidine or pyrrolizidine alkaloids based on readily available and attractively functionalized cyclopropanols, as exemplified in concise syntheses of indolizidine (-)-223AB, its 3-epimer, (-)-indolizidine 239AB, and (-)-indolizidine 239CD, is reported. This work highlights the applications of SN2′ alkylation and C-acylation of cyclopropanols to meet stereochemical challenges in natural product synthesis. Also included is diastereoselective cyclization of the resulting aminoallene adduct for bicyclic ring formation.

Enantiopure 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent: Preparation and application to total syntheses of indolizidine-alkaloids

A general and efficient procedure for the preparation of 2,6-disubstituted piperidines bearing one alkene- or alkyne-containing substituent was developed by using non-racemic Betti base as a chiral auxiliary. Many chiral benzylamines are excellent auxiliaries, but they were rarely used for this purpose because of the inefficient removal of the N-benzyl auxiliary residue under non-hydrogenative conditions. We found that N,N-disubstituted Betti base derivative has a typical Mannich structure of o-naphthol. When it carried out a base-catalyzed formation of o-quinone methide, an efficient non-hydrogenative N-debenzylation was achieved, and the alkene and alkyne groups survived. To demonstrate the efficiency of the method and the versatility of the products, asymmetric total syntheses of indolizidine-alkaloids (-)-167B, (-)-195H, (-)-209D and (-)-223AB were accomplished.

Asymmetric synthesis of 3,5-disubstituted indolizidines by intermolecular addition of an allylsilane on an N-acyliminium ion

A diastereoselective synthesis of 3,5-disubstituted indolizidines based on an intermolecular addition of an allylsilane on an acyliminium ion derived from (S)-pyroglutamic acid is described. The synthetic potential of this methodology is demonstrated by t