2959. Diaboline
Nomenclature
CAS number: 509-40-0
1-Acetyl-19,20-didehydro-17,18-epoxycuran-17-ol; N-acetyl-Wieland-Gumlich aldehyde. C21H24N2O3; mol wt 352.43.
C 71.57%, H 6.86%, N 7.95%, O 13.62%.
Description and references
From Strychnos diaboli Sandw., Loganiaceae: King, J. Chem. Soc. 1949, 955; Bader et al., Helv. Chim. Acta 36, 1256 (1953); Casinovi et al., Nature 193, 1178 (1962). Structure: Battersby, Hodson, Proc. Chem. Soc. London 1959, 123. Synthesis: Deyrup et al., Helv. Chim. Acta 45, 2266 (1962). 13C-NMR study: E. Wenkert et al., J. Org. Chem. 43, 1099 (1978).
Properties
Needles from ether, mp 187°. [α]D22 +37.8° (c = 1.72 in chloroform). uv max (ethanol): 249 nm (log ε 4.06).Derivative
Hydrochloride monohydrate.C21H24N2O3.HCl.H2O; mol wt 406.90.
C 61.99%, H 6.69%, N 6.88%, O 15.73%, Cl 8.71%.