633-34-1

Basic information

• Product Name: 4,6-ANDROSTADIEN-3,17-DIONE
• Synonyms: 6-DEHYDROANDROSTENEDIONE;4,6-ANDROSTADIEN-3,17-DIONE;4,6-androstadiene-3,17-dione;Androsta-4,6-diene-3,17-dione;Δ4,6-Androgen;(8R,9S,10R,13S,14S)-10,13-dimethyl-9,10,11,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,8H)-dione(WX116144)
• CAS NO: 633-34-1
• Molecular Formula: C₁₉H₂₄O₂
• Molecular Weight: 284.39
• Mol File: 633-34-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 449.3 °C at 760 mmHg
• Flash Point: 167.5 °C
• Appearance: /
• Density: 1.14 g/cm³
• Vapor Pressure: 2.88E-08mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: 4,6-ANDROSTADIEN-3,17-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-ANDROSTADIEN-3,17-DIONE(633-34-1)
• EPA Substance Registry System: 4,6-ANDROSTADIEN-3,17-DIONE(633-34-1)

Safety Data

• Hazardous Substances Data: 633-34-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H24O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h3-4,11,14-16H,5-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

Upstream product

• 67-56-1 methanol 
• 63-05-8 Androstenedione 
• 38632-00-7 6β-bromoandrost-4-ene-3,17-dione 
• 53-43-0 dehydroepiandrosterone 

Downstream Products

• 1229-12-5 androstane-3,17-dione 
• 633-35-2 1,4,6-androstatriene-3,17-dione 
• 95589-98-3 (7R,8R,9S,10R,13S,14S)-7-Cyclohexylsulfanyl-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 95589-93-8 (7R,8R,9S,10R,13S,14S)-7-(4-Fluoro-phenylsulfanyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 67340-80-1 (7R,8R,9S,10R,13S,14S)-7-(4-Methoxy-phenylsulfanyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 95589-97-2 (7R,8R,9S,10R,13S,14S)-7-(4-Acetyl-phenylsulfanyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 95589-95-0 (7R,8R,9S,10R,13S,14S)-7-(4-Chloro-phenylsulfanyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 67340-72-1 7α-<(4-aminophenyl)thio>androst-4-ene-3,17-dione 
• 140421-65-4 3β-hydroxy-16E-oximinoandrost-5-en-17-one 
• 81-25-4 cholic acid 
• 81-23-2 dehydrocholic acid 
• 2243-06-3 androst-4-ene-3,6,17-trione 
• 95589-99-4 7α-<<4-(3,3-dimethylazido)phenyl>thio>androst-4-ene-3,17-dione 
• 95589-94-9 7α-<(4-iodophenyl)thio>androst-4-ene-3,17-dione 

Relevant articles and documents

Platinum-Catalyzed α,β-Desaturation of Cyclic Ketones through Direct Metal–Enolate Formation

The development of a platinum-catalyzed desaturation of cyclic ketones to their conjugated α,β-unsaturated counterparts is reported in this full article. A unique diene-platinum complex was identified to be an efficient catalyst, which enables direct metal-enolate formation. The reaction operates under mild conditions without using strong bases or acids. Good to excellent yields can be achieved for diverse and complex scaffolds. A wide range of functional groups, including those sensitive to acids, bases/nucleophiles, or palladium species, are tolerated, which represents a distinct feature from other known desaturation methods. Mechanistically, this platinum catalysis exhibits a fast and reversible α-deprotonation followed by a rate-determining β-hydrogen elimination process, which is different from the prior Pd-catalyzed desaturation method. Promising preliminary enantioselective desaturation using a chiral-diene-platinum complex has also been obtained.

Reactions of Enolizable Steroidal 4-En-3-ones and 17-Ones with Hypervalent Iodine

Reaction of the 3-oxo-4-androsten-derivative 1 or 4 with 1.2 eq. of o-iodosylbenzoic acid in methanolic KOH gave the methoxy products, the 4-methoxide 2 or 5 and the 6β-methoxide 3 or 6, along with dehydrated compound, the 4,6-dienone 7 or 8, respectively.Treatment of the 6-methoxide 3 or 6 with trimethylsilyl iodide yielded the 5α-androstane-3,6-dioxo derivative 11 or 12 in high yield.The same hypervalent oxidation of the 17-oxo steroid 15, 18, 21 or 24 using excess iodine and a longer reaction time produced the corresponding 16α-hydroxy-17,17-dimethylacetal 16, 19,22 or 25, which was converted into the 16α-hydroxy-17-one 17, 20, 23 or 26 by treatment with diluted HCl in every case.Keywords - hypervalent iodine oxidation; o-iodosylbenzoic acid; 4-en-3-oxo steroid; 17-oxo steroid; methoxylation; dehydration; 16α-hydroxy-17,17-dimethoxy steroid; 16α-hydroxy-17-oxo steroid; 5α-saturated 3,6-dioxo steroid

CHROMIUM(VI) BASED OXIDANTS-1. CHROMIUM PEROXIDE COMPLEXES AS VERSATILE, MILD, AND EFFICIENT OXIDANTS IN ORGANIC SYNTHESIS.

The preparation of 2,2'-bipyridylchromium peroxide, pyridinechromium peroxide, and chromium peroxide etherate is described. 2,2'-Bipyridylchromium peroxide converts different classes of alcohols to the carbonyl compounds.In 1,2-diols C-C bond cleavage occurs extensively. α-Hydroxy acids are decarboxylated quantitatively.Oximes are converted to their carbonyl compounds and thiols to their disulfides, dihydroxy phenolic compounds to quinones, benzyl amine to benzaldehyde, aromatic amines to their azo compounds, anthracene and phenanthrene to their quinones.Pyridinechromium peroxide converts different classes of alcohols efficiently to the carbonyl compounds, thiols to their disulfides, anthracene to anthraquinone.Mandelic and benzilic acids are decarboxylated very efficiently.Chromium peroxide etherate is an efficient reagent for the oxidation of different classes of alcohols to their carbonyl compounds.