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

• 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 
• 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 
• 67340-74-3 7α-(phenylthio)androst-4-ene-3,17-dione 
• 67340-75-4 (7R,8R,9S,10R,13S,14S)-7-Benzylsulfanyl-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 95589-91-6 (7R,8R,9S,10R,13S,14S)-10,13-Dimethyl-7-p-tolylsulfanyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 95589-96-1 (7R,8R,9S,10R,13S,14S)-7-(4-Bromo-phenylsulfanyl)-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-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

Methoxylation of Enolizable Steroidal 4-Ene-3-ones using Hypervalent Iodine

Reaction of androst-4-ene-3,17-dione (1) with o-iodosylbenzoic acid in methanolic potassium hydroxide gave the methoxylated products, the 4- and 6β-methoxides (2) and (3), along with the dehydrogenated compound, the 4,6-dienone (4).