nuttaline
- CAS No.
- 23360-87-4
- Chemical Name:
- nuttaline
- Synonyms
- nuttaline;Nuttalline;(2S,7α,7aβ,14α,14aα)-Dodecahydro-2-hydroxy-7,14-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one;7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one, dodecahydro-9-hydroxy-, (7S,7aR,9S,14S,14aS)-
- CBNumber:
- CB51318697
- Molecular Formula:
- C15H24N2O2
- Molecular Weight:
- 264.36
- MDL Number:
- MOL File:
- 23360-87-4.mol
nuttaline Chemical Properties,Uses,Production
Description
A major constituent of Lupinus nuttallii, this alkaloid is dextrorotatory with [α] 24 D + 25.3 ± 0.9° (c 2.0, EtOH). It has been characterized as the perchlorate, m.p. l70-2°C. Prolonged treatment with NaBH4 yields (-)-4/3-hydroxysparteine, yielding a perchlorate, m.p. 248-2500 C. Oppenauer oxidation of the alkaloid gives 2:4-dioxosparteine. The structure has been established by treatment of the base with P20 S to give (+)-2-oxo-3:4-didehydrosparteine which, on catalytic hydrogenation is converted into deoxynuttalline, identified as (+ )-lupanine by comparison with an authentic specimen.
References
Goldberg, Balthis., 1. Chern. Soc., D, 660 (1969)
nuttaline Preparation Products And Raw materials
Raw materials
Preparation Products
nuttaline
(2S,7α,7aβ,14α,14aα)-Dodecahydro-2-hydroxy-7,14-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one
Nuttalline
7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one, dodecahydro-9-hydroxy-, (7S,7aR,9S,14S,14aS)-
23360-87-4