Stenbolone
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| Stenbolone | ||
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| IUPAC name (5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-2,10,13-trimethyl-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one | ||
| Other names Deacetylanatrofin; 17β-Hydroxy-2-methyl-5α-androst-1-en-3-one | ||
| Identifiers | ||
| CAS number | 5197-58-0  | |
| PubChem | 234454 | |
| Jmol-3D images | {{#if:CC1=C[C@]2([C@@H](CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C)CC1=O)C|Image 1 | |
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| Properties | ||
| Molecular formula | C20H30O2 | |
| Molar mass | 302.45 g/mol | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Stenbolone is an anabolic steroid. It is structurally similar to 1-Testosterone.
Synthesis
DHT () with one equivalent of bromine under carefully controlled conditions afford 2a bromide (). The bromoketone is then dehydrobrominated by means of lithium carbonate in dimethyl formamide to give the unusual enone (). The conjugate addition of methyl Grignard reagent in the presence of cuprous iodide goes directly to the 1b methyl derivative mesterolone ();[1] the reaction in this case goes directly to the energetically favored equatorial isomer.
References
- ↑ Wiechert, R.; 1968, U.S. Patent 3,361,773.
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