19317-98-7Relevant articles and documents
7-METHANESULFONYLOXY-3α,5-CYCLO-5α-CHOLESTANES
Kohout, Ladislav
, p. 1028 - 1035 (2007/10/02)
Acetolysis and hydrogenolysis of 7-methanesulfonyloxy-3α,5-cyclo-5α-cholestanes was studied.The 7β-methanesulfonyloxy derivative VI is hydrogenolysed more readily than its 7α-isomer III.The acetolysis gives products of elimination, substitution and rearrangement with participation of the cyclopropane ring.Whereas the 7α-derivative III predominantly reacts with elimination, the 7β-derivative VI is more susceptible to the participation reaction.
SYNTHESIS OF 5,6-CYCLOPROPANOCHOLESTANE DERIVATIVES WITH AN OXYGEN FUNCTION IN POSITION 7
Kohout, Ladislav
, p. 1828 - 1838 (2007/10/02)
Synthesis of all four possible isomeric 7-hydroxy-5,6-cyclopropanocholestane derivatives is described starting from 5-cholesten-7-one and using Simmons-Smith methylenation.
Photo-induced Transformations. Part 50. The Photo-Beckmann Rearrangement of 3α,5-Cyclo-5α-cholestan-7-one Oxime, a βγ-Cyclopropyl Ketone Oxime
Suginome, Hiroshi,Shea, Chi-Ming
, p. 2268 - 2271 (2007/10/02)
Photolysis of the title βγ-cyclopropyl ketone oxime in methanol gave 7-aza-3α,5-cyclo-B-homo-5α-cholestan-7a-one (3), 7a-aza-3α,5-cyclo-B-homo-5α-cholestan-7-one (4), and 3α,5-cyclo-7,8-seco-5α-cholestan-7-amide (5), together with the parent ketone (2), with no olefinic products resulting from cleavage of the cyclopropane ring.The results entirely parallel those obtained in the photolysis of cyclic ketone oximes and are compatible with the suggested mechanism that the normal photo-Beckmann rearrangement of cyclic ketone oximes does not involve any intimate radical pair or diradical species resulting from α-fission.The seco-amide (5) was identified by its synthesis from methyl 3α,5-cyclo-7,8-seco-5α-cholestan-7-oate (7) prepared by the photolysis of 3α,5-cyclo-5α-cholestan-7-one in methanol.