Dienestrol: Difference between revisions
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==Synthesis== |
==Synthesis== |
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[[File:Dienestrol.png|center|thumb|700px|Dienestrol synthesis:<ref>{{Cite doi|10.1098/rspb.1939.0015}}</ref>]] |
[[File:Dienestrol.png|center|thumb|700px|Dienestrol synthesis:<ref>{{Cite doi|10.1098/rspb.1939.0015}}</ref>]] |
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#[[Pinacol coupling]] of |
#[[Pinacol coupling]] of ''[[para isomer|p]]''-[[acetoxy]]-[[propiophenone]]. |
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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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Revision as of 17:59, 26 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.
Hexestrol
The addition reaction of HBr to anethole yields 1-bromo-1-(p-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.
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. - ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1098/rspb.1940.0009, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1098/rspb.1940.0009instead. - ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/ja01867a067, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1021/ja01867a067instead. - ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jo01158a010, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1021/jo01158a010instead.
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