Lamprolobine
Lamprolobine · (+)-Lamprolobine · 2,6-Piperidinedione, 1-[[(1R,9aR)-octahydro-2H-quinolizin-1-yl]methyl]- · 1-[[(1R,9aβ)-Octahydro-2H-quinolizine-1β-yl]methyl]piperidine-2,6-dione · (+)-1-[[(1R,9aβ)-Octahydro-2H-quinolizine-1-yl]methyl]-2,6-piperidinedione · 1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione
Identifikatoren & physikalische Daten
| CAS No. | 18688-40-9 |
|---|---|
| Summenformel | C15H24N2O2 |
| Durchschnittliche Molmasse | 264,36 g/mol |
| Monoisotopische Masse | 264,18377801 g/mol |
| SMILES | O=C1CCCC(=O)N1C[C@H]1CCCN2CCCC[C@H]12 |
| InChIKey | IFGFYNRAHYENJQ-CHWSQXEVSA-N |
| PubChem CID | 87752 |
| ChEBI | CHEBI:6369 |
| DTXSID | DTXSID00171946 |
Chemische & physikalische Eigenschaften
| XLogP | 1,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 40,6 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 353 |
| Siedepunkt | 418.1±18.0 °C(Predicted) |
| Dichte | 1.15±0.1 g/cm3(Predicted) |
| pKa (Säurekonstante) | 10.15±0.40(Predicted) |
Anwendungen & Verwendung
Beschreibung
The leaves of Lamprolobium fruticosum yields this alkaloid as a colourless oil, [α]20Do + 29° (EtOH) and furnishing a crystalline picrate, m.p. 153-4°C. Acid hydrolysis of the alkaloid yields glutaric acid and (+ )-l-aminoethylquinolizidine. The stereochemistry of the latter has been established by demonstrating the identity of the N-acetyl derivative, m.p. l44-5°C; [α]20Do + 46° (EtOH) with that prepared from epilupinine. The structure has been confirmed from the infrared, NMR and mass spectra. The total synthesis of the optically inactive alkaloid and its epimer has been carried out.