(8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene
![(8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene Structure](CAS/20200611/GIF/2448-27-3.gif)
- CAS No.
- 2448-27-3
- Chemical Name:
- (8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene
- Synonyms
- Panamine;15H-1,5-Imino-10,15a-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene, tetradecahydro-, (1R,5R,8aS,10S,10aR,15aR,15bR)- (9CI);(8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene
- CBNumber:
- CB62445500
- Molecular Formula:
- C20H33N3
- Molecular Weight:
- 315.5
- MDL Number:
- MOL File:
- 2448-27-3.mol
(8aα,10aα,15bβ)-2,3,4,5,7,8,8a,10,10a,11,12,13,14,15b-Tetradecahydro-15H-1α,5α-imino-10β,15aβ-methano-1H,6H,9H-5a,14a-diazadibenz[b,fg]octalene Chemical Properties,Uses,Production
Description
An oily alkaloid isolated from various species of Ormosia, this hex acyclic base has [α]589 -11°C and [α]436 - 21.3 . It may be characterized as the perchlorate, colourless prisms from MeOH-Et20, m.p. 23S-7°C; the picrate, light yellow needles from Me2CO-Et20, m.p. 237°C (dec.) and the N-methyl derivative, m.p. 103°C which has [α]589 + 5° and [α]436+ 19° and gives a methiodide, m.p. 209-211°C. Two of the nitrogen atoms are tertiary, the third being present as an imino group. The original structure has been revised to make the alkaloid the 11-epimer of ormosinine (q.v.).
References
Lloyd, Horning.,J. Amer. Chem. Soc., 80, 1506 (1958)
Naegeli, Wildman, Lloyd., Tetrahedron Lett., 2069,2075 (1963)
Deslongchamps, Wilson, Valenta., ibid, 3896 (1964)
Revised structure:
Wilson., Chem. Ind., 472 (1965)
Wilson., Tetrahedron, 21, 2561 (1965)
Crystal structure:
Karle, Karle., Tetrahedron Lett., 1659 (1966)