Diaboline

Title: Diaboline
CAS Registry Number: 509-40-0
CAS Name: 1-Acetyl-19,20-didehydro-17,18-epoxycuran-17-ol
Additional Names: N-acetyl-Wieland-Gumlich aldehyde
Molecular Formula: C21H24N2O3
Molecular Weight: 352.43
Percent Composition: C 71.57%, H 6.86%, N 7.95%, O 13.62%
Literature 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°. [a]D22 +37.8° (c = 1.72 in chloroform). uv max (ethanol): 249 nm (log e 4.06).
Melting point: mp 187°
Optical Rotation: [a]D22 +37.8° (c = 1.72 in chloroform)
Absorption maximum: uv max (ethanol): 249 nm (log e 4.06)
Derivative Type: Hydrochloride monohydrate
Molecular Formula: C21H24N2O3.HCl.H2O
Molecular Weight: 406.90
Percent Composition: C 61.99%, H 6.69%, N 6.88%, O 15.73%, Cl 8.71%
Properties: Needles from alcohol + ethyl acetate, mp 300°. For anhydr, [a]205461 +184° (c = 0.57 in water).
Melting point: mp 300°
Optical Rotation: [a]205461 +184° (c = 0.57 in water)
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