30122-70-4

Basic information

• Product Name: androst-4-ene-6,17-dione
• Synonyms: androst-4-ene-6,17-dione
• CAS NO: 30122-70-4
• Molecular Formula: C19H26O2
• Molecular Weight: 286.41
• Mol File: 30122-70-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: androst-4-ene-6,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: androst-4-ene-6,17-dione(30122-70-4)
• EPA Substance Registry System: androst-4-ene-6,17-dione(30122-70-4)

Safety Data

• Hazardous Substances Data: 30122-70-4(Hazardous Substances Data)

Upstream product

• 103232-88-8 3-ethylthio-2,4-androstadiene-6,17-dione 
• 103232-83-3 3,3-ethylenedithio-4-androstene-6,17-dione 
• 169560-43-4 4β-hydroxyandrost-5-en-17-one 
• 169560-45-6 6β-hydroxyandrost-4-en-17-one 
• 169560-44-5 6α-hydroxyandrost-4-en-17-one 
• 30122-67-9 3β-hydroxy-5α,6α-androstan-17-one methanesulfonate 
• 25824-80-0 5-androsten-17-one 
• 23640-45-1 5α-bromo-6β-hydroxyandrost-17-one 
• 131768-90-6 6β-acetoxyandrost-4-en-17-one 
• 95331-36-5 4β-Acetoxyandrost-5-en-17-one 
• 166116-86-5 6α-acetoxyandrost-4-en-17-one 
• 169560-48-9 5α,6β-dibromoandrost-17-one 
• 204330-77-8 5β,6α-dibromoandrostan-17-one 
• 2243-06-3 androst-4-ene-3,6,17-trione 

Relevant articles and documents

Reaction of androst-5-en-17-one with hypobromous acid and its use for synthesis of 19-oxygenated 5-ene and 4-en-6-one steroids

Reaction of androst-5-en-17-one (1) with hypobromous acid using a short reaction time (30 min) along with a careful isolation procedure gave, for the first time, the addition product, 5α-bromo-6β-hydroxyandrostan-17-one (3), in 43% yield. This bromohydrin was much more reactive than 5α-bromo-3β- acetoxy-6β-hydroxyandrostan-17-one (4) towards KHCO3 and HClO4. The high reactivity of compound 3 was found to be a principal reason for the difficulty in isolating this compound by the addition reaction so far. 19- Hydroxyandrost-5-en-17-one (16) and androst-5-ene-17,19-dione (18), as well as 19-hydroxyandrost-4-ene-6,17-dione (28) and androst-4-ene-6,17,19-trione (29), were synthesized through hypoiodite reaction of the bromohydrin 3 as a key reaction.

Competing pathway involved in allylic acetoxylation of androst-5-en-17-one, and oxidation of allylic alcohols with chromium oxides

Allylic acetoxylation of androst-5-en-17-one (1) with bromine and silver acetate gave 6α- and 6β-acetoxyandrost-4-en-17-ones and 5α-bromo-6β-acetoxy steroid 8 (4percent) along with the expected product 4β-acetoxy derivative 2 (45percent).Treatment of 5α,6β-bromide 12, an intermediate of the acetoxylation reaction, with silver acetate also produced the acetates 2,4,5,and 8 in relative yields similar to those above.These results indicate that the 6=acetates 4 and 5 are produced through a competing pathway involving formation of a bridged carbonium ion 13 followed by attack of an acetate anion.Oxidation of the axial allylic alcohol, 5-en-4β-ol 3, with Jones reagent yielded no trace of the previously reported androst-5-ene-4,17-dione (18) but instead gave a 1:4 mixture of 5β,6β-epoxy-4-one 16 and 4β,5β-epoxy-6-one 17 in high yield.In contrast, a 1:4 mixture of androst-4-ene-6,17-dione (10) and compound 18 was obtained upon treatment with chromium trioxide in pyridine.Similar results were also found with the oxidation of another axial allylic alcohol, 4-en-6β-ol 7. (Steroid 60:499-505, 1995)

Androsta-2,4-diene-6,17-dione.

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