ChemicalBook >> CAS DataBase List >>1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione

1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione

1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione structure

CAS No.: 18688-40-9

Chemical Name:: 1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione

Synonyms: 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

CBNumber:: CB01255290

Molecular Formula:: C15H24N2O2

Molecular Weight:: 264.36

MDL Number:: MFCD28340157

MOL File:: 18688-40-9.mol

Last updated:2023-07-12 16:39:20

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1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione Properties

Boiling point	418.1±18.0 °C(Predicted)
Density	1.15±0.1 g/cm3(Predicted)
pka	10.15±0.40(Predicted)

1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione Chemical Properties,Uses,Production

Description

The leaves of Lamprolobium fruticosum yields this alkaloid as a colourless oil, [α]²⁰_Do + 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]²⁰_Do + 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.

Definition

ChEBI: Lamprolobine is a member of quinolizines.

References

Hart, Johns, Lamberton., Chem. Commun., 302 (1968)
Hart, Johns, Lamberton., Austral. J. Chem., 21, 1619 (1968)
Synthesis:
Jeffcoat., Diss. Abstr. Int., 30B, 4973 (1970)
Yamada, Hatano, Matsui., Agr. Bioi. Chem., 34, 1536 (1970)

1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione Preparation Products And Raw materials

Raw materials

Preparation Products

1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione Suppliers

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1-[[(1R,8aR)-2,3,4,5,6,7,8,8a-octahydro-1H-quinolizin-1-yl]methyl]pipe ridine-2,6-dione (+)-1-[[(1R,9aβ)-Octahydro-2H-quinolizine-1-yl]methyl]-2,6-piperidinedione (+)-Lamprolobine 1-[[(1R,9aβ)-Octahydro-2H-quinolizine-1β-yl]methyl]piperidine-2,6-dione Lamprolobine 2,6-Piperidinedione, 1-[[(1R,9aR)-octahydro-2H-quinolizin-1-yl]methyl]- 18688-40-9