Back to Search
Start Over
Steroids. V. Conjugated steroid nitriles via phosphonates (1,2)
- Source :
- Steroids. 11:27-35
- Publication Year :
- 1968
- Publisher :
- Elsevier BV, 1968.
-
Abstract
- Steroid ketones were found to react with diethyl cyanomethylphosphonate in the presence of dimsyl anion and dimethyl sulfoxide at room temperature forming conjugated nitriles. Ketones at positions 2,4,6,7,12, and 15 readily afforded unsaturated nitriles. The yield of Δ 4 -3-cyano-methylene steroids from Δ 4 -3-ketosteroids was high under these conditions. The sterically hindered ketone from lanosterol also could be converted to an unsaturated nitrile. Ketones at positions 1 and 11 were found to be unreactive even when dimsyl anion and dimethyl sulfoxide were used. 16-Ketoprogesterone did not react, probably because it is a β -diketone.
- Subjects :
- Steric effects
Ketone
Chemical Phenomena
Nitrile
medicine.medical_treatment
Clinical Biochemistry
Organophosphonates
Conjugated system
Biochemistry
Steroid
chemistry.chemical_compound
Endocrinology
Nitriles
medicine
Organic chemistry
Molecular Biology
Pharmacology
chemistry.chemical_classification
Dimethyl sulfoxide
Lanosterol
Organic Chemistry
Ketones
Chemistry
Sterols
chemistry
Yield (chemistry)
Steroids
Subjects
Details
- ISSN :
- 0039128X
- Volume :
- 11
- Database :
- OpenAIRE
- Journal :
- Steroids
- Accession number :
- edsair.doi.dedup.....e039170b6ffbfbf8aa4fb6c79dd26922
- Full Text :
- https://doi.org/10.1016/s0039-128x(68)80049-2