5-chloro-5 beta-cholestane, the first simple 5 beta-chlorosteroid.
The life, times, and the main achievements in the steroid field of Julius Mauthner are briefly described. Three attempts by the author to isolate and to characterise 5-chloro-5 beta-cholestane are enumerated; the last attempt was successful, and furnished 5-chloro-5 beta-cholestane in two polymorphic forms: m.p. 72-75 degrees C, [alpha]20D + 37 degrees (labile above 0 degrees C) and m.p. 94-95 degrees C, [alpha]20D + 34 degrees (stable up to 75 degrees C). Possible mechanisms of the spontaneous, solid-state dehydrochlorination above 0 degrees C of the polymorph, m.p. 72-75 degrees C, are discussed.
D002776:Cholestanes / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009904:Optical Rotation; D013329:Structure-Activity Relationship
D002776:Cholestanes; D007202:Indicators and Reagents; C039007:5-chlorocholestane