199. Akuammicine
Nomenclature
CAS number: 639-43-0
2,16,19-20-Tetradehydrocuran-17-oic acid methyl ester. C20H22N2O2; mol wt 322.40.
C 74.51%, H 6.88%, N 8.69%, O 9.93%.
Description and references
From the seeds of Picralima klaineana, Pierre, Apocynaceae found in the Gold Coast: Henry, Sharp, J. Chem. Soc. 1927, 1950; Henry, ibid. 1932, 2759. Structure: Aghoramurthy, Robinson, Tetrahedron 1, 172 (1957); Bernauer et al., Helv. Chim. Acta 43, 717 (1960); Edwards, Smith, J. Chem. Soc. 1961 152. Derivs: Robinson, Thomas, ibid. 1955, 2049. Total synthesis: Kutney, Fuller, Heterocycles 3, 197 (1975).
Properties
Plates from ethanol+ water, mp 182°. [α]D16 745° (c = 0.994 in ethanol). pKa 7.45. uv max (ethanol): 227, 300, 330 nm (log ε 4.09, 4.07, 4.24).Derivative
Hydrochloride dihydrate.C20H22N2O2.HCl.2H2O; mol wt 394.89.
C 60.83%, H 6.89%, N 7.09%, O 16.21%, Cl 8.98%.
Properties
Leaflets from alcohol or water, mp 171°. [α]D21 610° (c = 1.430 in ethanol).Derivative
Perchlorate monohydrate.C20H22N2O2.HClO4.H2O; mol wt 440.87.
C 54.49%, H 5.72%, N 6.35%, O 25.40%, Cl 8.04%.
Properties
Needles from ethanol + water, mp 134-136°.Derivative
Hydriodide monohydrate.C20H22N2O2.HI.H2O; mol wt 468.33.
C 51.29%, H 5.38%, N 5.98%, O 10.25%, I 27.10%.