151424-85-0

Basic information

• Product Name: 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene-17-one
• Synonyms: 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene-17-one
• CAS NO: 151424-85-0
• Molecular Weight: 494.628
• Mol File: 151424-85-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene-17-one(151424-85-0)
• EPA Substance Registry System: 3,3-ethylenedioxy-5α-hydroxy-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene-17-one(151424-85-0)

Safety Data

• Hazardous Substances Data: 151424-85-0(Hazardous Substances Data)

Upstream product

• 5571-36-8 ethylene deltenone 
• 4360-68-3 2-(4-bromophenyl)-2-methyl-1,3-dioxolane 
• 39931-88-9 (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one 
• 39575-67-2 (4-(2-methyl-1,3-dioxolan-2-yl)phenyl)magnesium bromide 

Downstream Products

• 1421037-50-4 11β-(4'-acetylphenyl)-17β-hydroxy-17-(1,1-difluoroprop-2-enyl)-estra-4,9-diene-3-one 
• 1421037-46-8 11β-(4'-acetylphenyl)-17β-hydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-estra-4,9-diene-3-one 
• 1421037-52-6 11β-(4'-acetyl-phenyl)-17β-hydroxy-17-(1,1-difluoropropyl)-estra-4,9-diene-3-one 
• 1421036-64-7 3,3-ethylenedioxy-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estra-4,9-diene-17-one 
• 1421036-60-3 3,3-ethylenedioxy-5a,17β-dihydroxy-17-(3,3,3-trifluoroprop-1(E)-enyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene 
• 1421036-55-6 11β-(4'-acetylphenyl)-17β-hydroxy-17-(3,3,3-trifluoro-1-propynyl)-estra-4,9-diene-3-one 
• 1421036-59-0 3,3-ethylenedioxy-5α,17β-dihydroxy-17-(3,3,3-trifluoro-1-propynyl)-11β-{4'-[1',1'-(ethylenedioxy)-ethyl]phenyl}-estr-9-ene 
• 646037-63-0 3-ethylenedioxy-5α-hydroxy-11β-(4'-acetyl-phenyl)-estr-9-ene-17-one 
• 216372-21-3 3,3-ethylenedioxy-11β-[4-(2-methyl-1,3-dioxolan-2-yl)phenyl]spiro[estr-9-en-17β,2'-oxirane] 

Relevant articles and documents

Hydrolytic behavior of 5α-hydroxy-11β- and 5β-hydroxy- 11α-substituted 19-norsteroids

Teutsch G. and Bélanger A. treated 5α,10α epoxides with Grignard-reagents catalyzed by copper(I) ions. The reaction with steroidal epoxides proceeded with complete regio- and stereospecificity, leading exclusively to the 11β-substituted compounds. According to our synthetic strategy, the 5,10 epoxide isomers were not separated; instead, the pure 11β, and in some cases, 11α-substituted molecules were isolated after the conjugate addition of the Grignard-reagents, followed by deketalization and dehydration. Surprisingly, appearance of a third compound was generally observed beside the expected deprotected products, and this compound turned out to have a 3-keto-5(10),9(11) structural unit. Starting from pure 3-ethylenedioxy-5α,10α-epoxy-estr-9(11)-ene-17-one and 3-ethylenedioxy-5β,10β-epoxy-estr-9(11)-ene-17-one, four model compounds were synthesized (11α- and 11β-{4-[1,1-(ethylenedioxy)- ethyl]phenyl}-estra-, as well as 11α- and 11β-cyclohexyl-estra- derivatives) to study the process of deprotection and dehydration. 3-keto-5(10),9(11)-derivatives were found to form after deketalization and dehydration only from 11α-substituted derivatives, while 11β-derivatives resulted in only the expected 3-keto-5,9-diene structure. After observing this remarkable difference between the behavior of 11α-, 11β-substituted isomers we decided to take a closer look at the processes of deketalization and dehydration. In order to carry out the hydrolysis under mild conditions, pyridinium paratoluenesulfonate, a weakly acidic salt, was applied. All the intermediate products observed by TLC were isolated. The outcome of the deprotection and elimination reactions can be rationalized by two factors: conjugation of olefins (with the 3-oxo-group or the 11-phenyl group) and orientation of groups to be eliminated.