64-82-4

Basic information

• Product Name: 17-beta-hydroxy-5alpha-androst-1-en-3-one acetate
• Synonyms: 17-beta-hydroxy-5alpha-androst-1-en-3-one acetate;17β-(Acetyloxy)-5α-androst-1-en-3-one;Einecs 200-595-9;17β-Acetyloxy-5α-androstenone;(5α,17β)-17-(Acetyloxy)-androst-1-en-3-one;17β-Acetoxy-5α-androst-1-en-3-one;17β-Hydroxy-5α-androst-1-en-3-one acetate;ZK 5777
• CAS NO: 64-82-4
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.4611
• EINECS: 200-595-9
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 64-82-4.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 17-beta-hydroxy-5alpha-androst-1-en-3-one acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 17-beta-hydroxy-5alpha-androst-1-en-3-one acetate(64-82-4)
• EPA Substance Registry System: 17-beta-hydroxy-5alpha-androst-1-en-3-one acetate(64-82-4)

Safety Data

• Hazardous Substances Data: 64-82-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 68522-43-0 3-Trimethylsiloxy-5α-androst-2-en-17β-ylacetat 
• 73033-72-4 1α-phenylthio-17β-acetoxy-5α-androstan-3-one 
• 1350714-40-7 17β-acetoxy-1α-[4'-cyclohexyl-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 1350714-39-4 17β-acetoxy-1α-[4'-cyclopentyl-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 1350714-38-3 17β-acetoxy-1α-[4'-cyclopropyl-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 1350714-36-1 17β-acetoxy-1α-[4'-(4''-tert-butylphenyl)-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 1350714-35-0 17β-acetoxy-1α-[4'-(4''-ethylphenyl)-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 1350714-23-6 17β-acetoxy-1α-[4'-phenyl-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 1350714-34-9 17β-acetoxy-1α-[4'-(4''-tolyl)-1'H-1',2',3'-triazol-1'-yl]-5α-androstan-3β-ol 
• 5846-70-8 17β-acetoxy-1α-hydroxy-5α-androst-2-ene 
• 1164-91-6 stanolone acetate 
• 952222-37-6 (5S,8R,9S,10S,13S,14S,17S)-2-bromo-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate 
• 14291-94-2 17α-Acetoxy-5α-androst-1-en-3α-ol 
• 73033-74-6 1α-(2-iodophenylthio)-17β-acetoxy-5α-androstan-3-one 

Downstream Products

• 4062-46-8 17β-acetyloxy-1α-methyl-5α-androstan-3-one 
• 1164-91-6 stanolone acetate 
• 73033-74-6 1α-(2-iodophenylthio)-17β-acetoxy-5α-androstan-3-one 
• 73033-72-4 1α-phenylthio-17β-acetoxy-5α-androstan-3-one 
• 1229-06-7 5α-Androst-2-ene-1α,17α-diol 
• 5846-70-8 17β-acetoxy-1α-hydroxy-5α-androst-2-ene 
• 51505-46-5 (3β,5α,17β)-3-hydroxyandrost-1-en-17-yl acetate 
• 65-06-5 1-testosterone 
• 571-40-4 5α-androst-1-ene-3,17-dione 
• 14291-95-3 1ξ-Fluor-17β-acetoxy-5α-androst-2-en 
• 23633-63-8 5α-androst-1-en-3β-ol-17-one 
• 1350714-44-1 1α-[4'-(4''-tolyl)-1'H-1',2',3'-triazol-1'-yl]-5α-androstane-3β,17β-diol 
• 1350714-46-3 1α-[4'-(4''-ethylphenyl)-1'H-1',2',3'-triazol-1'-yl]-5α-androstane-3β,17β-diol 
• 1350714-47-4 1α-[4'-(4''-tert-butylphenyl)-1'H-1',2',3'-triazol-1'-yl]-5α-androstane-3β,17β-diol 

Relevant articles and documents

ANTI-CANCER NUCLEAR HORMONE RECEPTOR-TARGETING COMPOUNDS

The disclosure relates to anti-cancer compounds which are anti-cancer PARP inhibitors of formula Al, A2, A3 or A4 conjugated by a linker to a steroid, whereby the steroid targets the conjugate to the nucleus, as well as to methods for their preparation and use. (I)

An efficient synthesis of 5α-androst-1-ene-3,17-dione

5α-Androst-1-ene-3,17-dione (5) as a prodrug of 1-testosterone (4) was prepared in four steps from 17β-Acetoxy-5α-androstan-3-one (stanolone acetate) (1) in high yield. Thus, stanolone acetate (1) was brominated in the presence of hydrogen chloride in acetic acid to give 17β-acetoxy-2-bromo-5α-androstan-3-one (2), which underwent dehydrobromination using lithium carbonate as base with lithium bromide as an additive to give 17β-acetoxy-5α-androst-1-en-3-one (3) in almost quantitative yield with 97% of purity. Compound (3) was hydrolyzed with sodium hydroxide to give 17β-hydroxy-5α-androst-1-en-3-one (4,1-testosterone), which was oxidized with chromium trioxide to afford 5α-androst-1-ene-3,17-dione (5). The overall yield of 5 was 78.2% with purity of 99%. In this method, the formation of 4-ene was diminished when 1-ene was introduced, and its mechanism was also discussed.

α-FLUORINATION OF KETONES BY XENON AND IODOBENZENE DIFLUORIDES: A STEREOCHEMICAL EVIDENCE DEMONSTRATING THEIR MECHANISTIC DIFFERENCES

Xenon difluoride reacts smoothly with various steroid silyl enol ethers in the absence of any acid catalyst to afford stereoselectively α-oriented α-fluoroketones in good yields while iodotoluene difluoride reacts rather sluggishly with these silyl enol ethers to competitively produce β-oriented α-fluoro ketones, elimination and other nucleophilic substitution products.The observed stereochemical contrast clearly suggest an electrophilic and nucleophilic mechanism for these reactions, respectively.