181770-90-1

Basic information

• Product Name: (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(E)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one
• CAS NO: 181770-90-1
• Molecular Weight: 450.737
• Mol File: 181770-90-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(E)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(E)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one(181770-90-1)
• EPA Substance Registry System: (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(E)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one(181770-90-1)

Safety Data

• Hazardous Substances Data: 181770-90-1(Hazardous Substances Data)

Upstream product

• 51467-38-0 6β-hydroxy-5β-androstane-3,17-dione 
• 4966-70-5 3,3,17,17-diethylenedioxyandrost-5-ene 
• 571-36-8 5-androstenedione 
• 53-43-0 dehydroepiandrosterone 
• 181770-92-3 (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(Z)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one 
• 768-33-2 phenyldimethylsilyl chloride 

Downstream Products

• 181770-92-3 (5R,6R,8R,9S,10R,13S,14S)-6-(Dimethyl-phenyl-silanyloxy)-3-eth-(Z)-ylidene-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-one 

Relevant articles and documents

Antenna-initiated photochemistry in polyfunctional steroids. Intramolecular singlet and triplet energy transfer between aryl, ketone, and alkene groups in 6β-(Dimethylphenylsiloxy)-5β-androstanes 1

Steroids have been prepared that bear a dimethylphenylsiloxy (DPSO) group and additional C3 and/or C17 ketone functionalities. The DPSO group has been used to harvest 266 nm photons and then activate the ketone functionalities through intramolecular singlet-singlet energy transfer (intra-SSET). Thus, the monoketones 3,3-(ethylenedioxy)-6β-(DPSO)-5β-androstan-17-one (6) and 6β-(DPSO)-5β-androstan-3-one (8) both exhibit DPSO-initiated photochemistry at the carbonyl groups. Irradiation of the diketone, 6β-(DPSO)-5β-androstane-3,17-dione (5), gives two ring D-derived photoproducta, an epimer (19) and an enal (18), both coming from the C17 ketone excited singlet state. Here Φintra-SSET from the aryl antenna to the carbonyl groups is ca. 88% efficients and occurs with a rate of ca. 6.5 × 109 s-1, with the chemistry indicative of facile intra-SSET between the C3 and C17 ketones. The alkylidene group at C3 (i.e., as in 6β-(DPSO)-3(E)-ethylidene-5β-androstan-17-one (33) and its Z isomer (34)) has no effect on the rate or efficiency of aryl activation of the C17 ketone.