Dienestrol: Difference between revisions
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#[[Dehydration]] of the thus-obtained [[glycol]] with a mixture of [[acetyl chloride]] and [[acetic anhydride]] leads to the [[wikt:transoid|transoid]] [[diene]] system ([[bis]]-''β''-Methyl[[styrene]]-type). |
#[[Dehydration]] of the thus-obtained [[glycol]] with a mixture of [[acetyl chloride]] and [[acetic anhydride]] leads to the [[wikt:transoid|transoid]] [[diene]] system ([[bis]]-''β''-Methyl[[styrene]]-type). |
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#[[Saponification]] removes the acetate groups and thus affords dienestrol. |
#[[Saponification]] removes the acetate groups and thus affords dienestrol. |
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==[[Hexestrol]]== |
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[[File:Hexestrol synthesis.svg|thumb|center|700px|[[Hexestrol]] synthesis:<ref>{{Cite doi|10.1098/rspb.1940.0009}}</ref><ref>{{Cite doi|10.1021/ja01867a067}}</ref><ref>{{Cite doi|10.1021/jo01158a010}}</ref> {{US patent|2357985}} {{Cite patent|GB|523320}}]] |
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The [[addition reaction]] of [[hydrogen bromide|HBr]] to [[anethole]] yields 1-bromo-1-(''p''-[[wikt:anisyl|anisyl]])propane. This is the subject of a [[Wurtz coupling]] reaction in the presence of sodium, magnesium, aluminium, or iron. Subsequent removal of the methoxy groups in the resulting dimerization product using [[hydroiodic acid]] gives hexestrol. |
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==See also== |
==See also== |
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Revision as of 12:26, 27 December 2014
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| Clinical data | |
|---|---|
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| ATC code | |
| Pharmacokinetic data | |
| Protein binding | 50 to 80% |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.001.381 |
| Chemical and physical data | |
| Formula | C18H18O2 |
| Molar mass | 266.334 g/mol g·mol−1 |
| 3D model (JSmol) | |
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  (what is this?) (verify) | |
Dienestrol is a synthetic estrogen.
Synthesis
- Pinacol coupling of p-acetoxy-propiophenone.
- Dehydration of the thus-obtained glycol with a mixture of acetyl chloride and acetic anhydride leads to the transoid diene system (bis-β-Methylstyrene-type).
- Saponification removes the acetate groups and thus affords dienestrol.
See also
References
- ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1098/rspb.1939.0015, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1098/rspb.1939.0015instead.
 | This drug article relating to the genito-urinary system is a stub. You can help Wikipedia by expanding it. |