2716. Cyclobuxine D

Nomenclature

CAS number: 2241-90-9
(3β,5α,16α,20S)-14-Methyl-3,20-bis(methylamino)-4-methylene-9,19-cyclopregnan-16-ol; cyclobuxine.
C25H42N2O; mol wt 386.61.
C 77.67%, H 10.95%, N 7.25%, O 4.14%.

Description and references

From Buxus sempervirens L., Buxaceae: E. Schlittler et al., Helv. Chim. Acta 32, 2209 (1949). Probably identical with Alkaloid A: Heusler, Schlittler, ibid. 2226. Structure: Brown, Kupchan, J. Am. Chem. Soc. 84, 4590 (1962). Stereochemistry: eidem, ibid. 86, 4424 (1964).

Chemical structure

Properties

Crystals, dec 245-247°. [α]D23 +98° (chloroform).

Derivative

Dihydrobromide.
C25H42N2O.2HBr; mol wt 548.44.
C 54.75%, H 8.09%, N 5.11%, O 2.92%, Br 29.14%.

Properties

Crystals, dec 288-292°.

Derivative

N,N′-Dimethylcyclobuxine D.

Nomenclature

CAS number: 4282-16-0
C27H46N2O; mol wt 414.67.
C 78.20%, H 11.18%, N 6.76%, O 3.86%.

Properties

Crystals, dec 204-205°. [α]D25 +99° (chloroform).