4-α,5-α-EPOXY-17-β-HYDROXY-4,17-DIMETH-YL-3-OXOANDROSTANE-2-α-CARBO-NITRILE

Systematic Name: (2alpha,4alpha,17beta)-17-Hydroxy-4,17-dimethyl-3-oxo-4,5-epoxyandrostane-2-carbonitrile
Synonyms of 4,17-Dimethyltrilostane (CAS NO.71507-79-4): (2alpha,4alpha,5alpha,17beta)-4,5-Epoxy-17-hydroxy-4,17-dimethyl-3-oxoandrosta-2-carbonitrile ; Androstane-2-alpha-carbonitrile, 4-alpha,5-alpha-epoxy-17-beta-hydroxy-4,17-dimethyl-3-oxo-
CAS NO: 71507-79-4
Molecular Formula: C₂₂H₃₁NO₃
Molecular Weight: 357.4864
Molecular Structure:
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 1
Polar Surface Area: 62.62 Å²
Index of Refraction: 1.572
Molar Refractivity: 96.98 cm³
Molar Volume: 294.5 cm³
Surface Tension: 51.5 dyne/cm
Density: 1.21 g/cm³
Flash Point: 263.1 °C
Enthalpy of Vaporization: 90.08 kJ/mol
Boiling Point: 511.5 °C at 760 mmHg
Vapour Pressure: 1.33E-12 mmHg at 25°
InChI: InChI=1/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h13-16,25H,5-11H2,1-4H3/t13-,14-,15-,16-,18-,19+,20-,21+,22?/m0/s1
InChIKey: VOPNDTFUMCWVME-WSEXDDBFBW
Std. InChI: InChI=1S/C22H31NO3/c1-18-8-6-16-14(15(18)7-9-20(18,3)25)5-10-22-19(16,2)11-13(12-23)17(24)21(22,4)26-22/h13-16,25H,5-11H2,1-4H3/t13-,14-,15-,16-,18-,19+,20-,21+,22?/m0/s1
Std. InChIKey: VOPNDTFUMCWVME-WSEXDDBFSA-N

The reaction of 17beta-hydroxy-17-methylandrost-4-en-3-one (I) with thiophenol (A) and formaldehyde by means of triethylamine in refluxing ethanol gives 17beta-hydroxy-17-methy-4-(phenylthiomethyl)androst-4-en-3-one (II), which is desulfurized by treatment with Raney-Ni in water yielding 17beta-hydroxy-4,17-dimethylandrost-4-en-3-one (III). The reaction of (III) with methyl formate by means of sodium methoxide in methanol affords 17beta-hydroxy-4,17-dimethyl-2-hydroxymethyleneandrost-4-en-3-one (IV), which by cyclization with hydroxylamine in acetic acid-sodium acetate is converted into 4,17-dimethylandrosta-2,4-dieno[2,3-d]isoxazol-17beta-ol (V). The epoxidation of (V) with m-chloroperbenzoic acid in methylene chloride gives 4alpha,5alpha-epoxy-4,17-dimethylandrost-2-eno [2,3-d]isoxazol-17beta-ol (VI), which is finally isomerized by treatment with sodium methoxide in THF.

Cyanide and its compounds are on the Community Right-To-Know List.

Experimental reproductive effects. A steroid. When 4,17-Dimethyltrilostane (CAS NO.71507-79-4) is heated to decomposition, it emits toxic fumes of NO_x and CN⁻. See also NITRILES.