13934-61-7

Basic information

• Product Name: Andrenolactone
• CAS NO: 13934-61-7
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• EINECS: 237-709-1
• Mol File: 13934-61-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Andrenolactone(CAS DataBase Reference)
• NIST Chemistry Reference: Andrenolactone(13934-61-7)
• EPA Substance Registry System: Andrenolactone(13934-61-7)

Safety Data

• Hazardous Substances Data: 13934-61-7(Hazardous Substances Data)

Upstream product

• 156894-83-6 21,24-dinor-3β,17β-dihydroxy-chol-5-en-22-yne 
• 169306-26-7 3β-<(tert-butyldimethylsilyl)oxy>-17β-hydroxy-17α-allyl-5-androstene 
• 42151-23-5 (3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one 
• 53-43-0 dehydroepiandrosterone 
• 50775-60-5 Allyl Tetramethylphosphorodiamidate 
• 19637-35-5 3-tetrahydropyran-2-yloxy-androst-5-en-17-one 

Downstream Products

• 103208-71-5 3β-tosyloxy-17α-pregn-5-ene-21,17-carbolactone 
• 976-71-6 canrenone 
• 52-01-7 SPIRONOLACTONE 
• 34681-78-2 C₂₂H₃₂BrClO₃ 
• 34681-77-1 5α-bromo-6β-chloro-3β,17α-dihydroxypregnane-21-carboxylic acid χ-lactone 

Relevant articles and documents

Lactonization at the 17β-position of steroids

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One-Pot γ-Lactonization of Homopropargyl Alcohols via Intramolecular Ketene Trapping

A one-pot γ-lactonization of homopropargyl alcohols via an alkyne deprotonation/boronation/oxidation sequence has been developed. Oxidation of the generated alkynyl boronate affords the corresponding ketene intermediate, which is trapped by the adjacent hydroxy group to furnish the γ-lactone. We have optimized the conditions as well as examined the substrate scope and synthetic applications of this efficient one-pot lactonization.

Ruthenium-catalyzed cycloisomerization - Oxidation of homopropargyl alcohols. A new access to γ-butyrolactones

Vinylidenemetal species, which readily form from terminal alkynes under mild conditions, have rarely been utilized as reactive intermediates in a catalytic cycle. The conversion of homopropargyl alcohols via such intermediates to metal-complexed oxacarbenes led to the development of an oxidant compatible with a ruthenium complex capable of performing the cycloisomerization, that would convert them to lactones. None of the oxidants known to stoichiometrically convert isolated metallooxacarbenes to esters are effective. The unconventional oxidants , N-hydroxyimides, proved to be capable of effecting the desired transformation, with N-hydroxysuccinimide being the oxidant of choice. The procedure of choice employs cyclopentadienyl (1,4-cyclooctadiene) ruthenium chloride and trifuryl phosphine as the precatalyst in the presence of tetra-n-butylammonium bromide or hexafluorophosphate with N-hydroxysuccinimide as the oxidant in DMF-water at 95°. In this way, a wide diversity of homopropargyl alcohols were converted to γ-butyrolactones with excellent chemoselectivity. Lactones synthesized include an intermediate toward a platelet aggregation inhibitor, a fruit flavor principle, an inhibitor of binding of phorbol esters to PKC-α, a tobacco constituent, a wood constituent (quercus lactone), an aldosterone antagonist (spironolactone) precursor, and an acetogenin known for pesticidal and antitumor activities (muricatacin).