272. 3,20-Allopregnanedione

Nomenclature

CAS number: 566-65-4
(5α)-Pregnane-3,20-dione; 3,20-dioxo-5α-pregnane.
C21H32O2; mol wt 316.48.
C 79.70%, H 10.19%, O 10.11%.

Description and references

From pregnancy urine: Hartmann, Locher, Helv. Chim. Acta 18, 160 (1935); Lieberman et al., J. Biol. Chem. 172, 263 (1948). Prepn from pregna-4,11-diene-3,20-dione: Shoppee, Reichstein, Helv. Chim. Acta 24, 356 (1941); by oxidation of allopregnan-3β-ol-20-one with chromium trioxide: Billeter, Miescher, ibid. 30, 1409 (1947); by hydrogenation of pregnenolone: Pappas, Nace, J. Am. Chem. Soc. 81, 4556 (1959); from funtumine: Janot et al., Bull. Soc. Chim. Fr. 1960, 1669.

Properties

Crystals from methylene chloride + hexane, mp 200°. [α]D +125° (c = 1.2 in chloroform).

Use

In the synthesis of progesterone, FR 845034 C.A. 34, 81842 (1940).