6155-08-4

Basic information

• Product Name: (+)-Lupa-1-ene-3-one
• Synonyms: (+)-Lupa-1-ene-3-one
• CAS NO: 6155-08-4
• Molecular Formula: C30H48O
• Molecular Weight: 424.70152
• Mol File: 6155-08-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-Lupa-1-ene-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Lupa-1-ene-3-one(6155-08-4)
• EPA Substance Registry System: (+)-Lupa-1-ene-3-one(6155-08-4)

Safety Data

• Hazardous Substances Data: 6155-08-4(Hazardous Substances Data)

Upstream product

• 3186-72-9 lupanone 
• 3186-72-9 lupan-3-one 
• 3186-86-5 lupanol 
• 545-47-1 lupenol 
• 6610-70-4 Dihydroglochidiol-diacetat 
• 151593-07-6 lup-1(2)-en-3α-ol 
• 20097-24-9 2α-bromolupanone 

Relevant articles and documents

Studies on reaction of 2-bromo-3-ketotriterpenoids: Part IV - Debromination and dehydrobromination of 2α-bromo and 2,2-dibromo derivatives of lupanone and methyl dihydrobetulonate

2α-bromolupanone/methyl 2α-dibromodihydrobetulonate (1/1') and 2,2-dibromolupanone/methyl 2,2-dibromodihydrobetulonate (2/2') on refluxing with dimethylaniline (DMA) for 6 hr afford lupanone/methyl dihydrobetulonate (3/3') whereas 6 hr reflux of 1/1' and 2/2' with LiBr in dimethylformamide (DMF) furnish lup-1(2)-en-3-one/28-carbomethoxylup-1(2)-en-3-one (4/4') and 2-bromolup-1(2)-en-3-one/2-bromo-28-carbomethoxylup-1(2)-en-3-one (5/5'), respectively.On the other hand Wolff-Kishner reduction of 1/2 results in the formation of lupane (6).

Oxidation of triterpenoids: Part XV - Action of hydrogen peroxide on lup-1(2)-en-3α-ol in the presence of p-toluenesulfonic acid

Treatment of lup-1(2)-en-3α-ol (1a) in CH2Cl2 with hydrogen peroxide and p-toluenesulfonic acid in t-BuOH furnishes lup-1(2)-en-3-one (1), 3α-chloro-1α,2α-epoxylupane (2), 3α-t-butoxy-1α,2α-epoxylupane (2a), 1α,2α-epoxylupan-3-one (2b) and 1α,2α-epoxy-3α-hydroxylupane (2c).

Oxidation of triterpenoids: Part IX - Oxidation of lupanone with selenium dioxide in t-butanol

Lupanone (1) on prolonged heating with selenium dioxide in t-butanol furnishes six products, lup-1-en-3-one (2), lup-1(2)-en-3-one-2-selenide (3), lup-1(2)-en-3-one-2-bis-selenide (4), 3-carboxy-1β,3α-dihydroxy-A-norlupane (5), A-norlupan anhydride (6), 1-hydroxylupan anhydride (7) and 1-hydroxy-A-norlup-2-carb-4-olide (8).Oxidation of 3/4 with alkaline H2O2 affords 1α,2α-epoxy-lup-3-one (9).The structures of the compounds have been established on the basis of analytical and spectral data.

Hydrogen Peroxide Oxidation of Lupanone in Presence of Selenium Dioxide

The oxidation of lupanone (Ia) with molar proportion of hydrogen peroxide and catalytic amount of selenium dioxide in t-butanol affords lup-1-ene-3-one (Ib), lupane dicarboxylic acid (Ic) and 2α-carboxyl-A-nor-lupane (Id); with excess of hydrogen peroxide, Ia furnishes 4,23,24-tri-nor-lupane-3->5-olide, a δ-lactone (Ie) together with lupane dicarboxylic acid (Ic).