729. Aphylline

Nomenclature

CAS number: 577-37-7
(7R,7aS,14S,14aR)-Dodecahydro-7,14-methano-2H,6H-dipyrido[1,2-a:1′,2′-e][1,5]diazocin-6-one.
C15H24N2O; mol wt 248.36.
C 72.54%, H 9.74%, N 11.28%, O 6.44%.

Description and references

From Anabasis aphylla L., Chenopodiaceae. Extraction procedure and structure: Orechoff, Menschikoff, Ber. 64, 266 (1931); 65, 234 (1932). Structure: Galinovsky, Jarish, Monatsh. Chem. 84, 199 (1953). Stereochemistry: Edwards et al., Can. J. Chem. 32, 235 (1954); Galinovsky et al., Monatsh. Chem. 86, 1014 (1955). Synthesis: Bohlmann et al., Ber. 90, 653 (1957).

Chemical structure

Properties

Crystals, mp 52-57°. bp4 200°. [α]D20 +10.3° (c = 20 in methanol). Soluble in the usual organic solvents.

Derivative

Hydrochloride.
C15H24N2O.HCl; mol wt 284.82.
C 63.25%, H 8.85%, N 9.84%, O 5.62%, Cl 12.45%.

Properties

Rhombohedra from alc, mp 209°. [α]D20 +14° (c = 25). Freely soluble in water.