17947-03-4

Basic information

• Product Name: 3-hydroxy-D:A-friedoolean-3-en-2-one
• CAS NO: 17947-03-4
• Molecular Weight: 440.71
• Mol File: 17947-03-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-D:A-friedoolean-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-D:A-friedoolean-3-en-2-one(17947-03-4)
• EPA Substance Registry System: 3-hydroxy-D:A-friedoolean-3-en-2-one(17947-03-4)

Safety Data

• Hazardous Substances Data: 17947-03-4(Hazardous Substances Data)

Upstream product

• 559-74-0 3-oxofriedelane 
• 75-65-0 tert-butyl alcohol 
• 67895-85-6 cerin 

Downstream Products

• 113376-09-3 A⁽¹⁾-norfriedelan-3-en-3-yl benzoate 

Relevant articles and documents

Studies on oxidation of triterpenoids: Part XI - Oxygenation of friedelin in presence of potassium t-butoxide in t-butanol

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Terpenoids and Related Compounds: Part XXIII - Mechanism of Some Transformation Reactions of Friedelin and Its Derivatives

DDQ dehydrogenation of friedelin (I) affords friedel-1-ene-3-one (III) in a very low yield (9percent).Treatment of 2α-bromofriedel-3-one (IV) with LiBr and Li2CO3 furnishes (III) (20percent) along with I (15percent).Reaction of IV with AgOAc and glacial HOAc leads to the formation of 3-hydroxyfriedel-3-ene-2-one (V) (66percent).Baeyer-Villiger oxidation of I with p-nitroperbenzoic acid produces the ε-lactone (IX) (41percent) while NiO2 oxidation of cerin (II) affords (V) (20percent) and 3α-hydroxyfriedel-2-one (VI) (15percent).The mechanism of these reactions are discussed.