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
식별자 및 물리적 특성
| CAS No. | 18688-40-9 |
|---|---|
| 분자식 | C15H24N2O2 |
| 평균 분자량 | 264.36 g/mol |
| 단동위원소 질량 | 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 |
화학 및 물리적 성질
| XLogP | 1.2 |
|---|---|
| 극성 표면적 | 40.6 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 19 |
| 형식 전하 | 0 |
| 복잡도 | 353 |
| 끓는 점 | 418.1±18.0 °C(Predicted) |
| 밀도 | 1.15±0.1 g/cm3(Predicted) |
| pKa(산도 계수) | 10.15±0.40(Predicted) |
용도
개요
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.