20007-99-2

Basic information

• Product Name: Wieland-Miescher ketone
• CAS NO: 20007-99-2
• Molecular Weight: 178.231
• Mol File: 20007-99-2.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: Wieland-Miescher ketone(CAS DataBase Reference)
• NIST Chemistry Reference: Wieland-Miescher ketone(20007-99-2)
• EPA Substance Registry System: Wieland-Miescher ketone(20007-99-2)

Safety Data

• Hazardous Substances Data: 20007-99-2(Hazardous Substances Data)

Upstream product

• 1193-55-1 2-methylcyclohexane-1,3-dione 
• 78-94-4 methyl vinyl ketone 
• 504-02-9 1,3-cylohexanedione 
• 2550-28-9 5-hexyn-2-one 
• 109-87-5 Dimethoxymethane 
• 4242-00-6 (±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one) 
• 112251-15-7 8a-methyl-6-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-3,7,8,8a-tetrahydronaphthalen-1(2H)-one 
• 112251-14-6 4a-methyl-5-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-4,4a,7,8-tetrahydronaphthalen-2(3H)-one 
• 102547-88-6 3-hydroxy-2-methyl-1-cyclohexanone 
• 5073-65-4 2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione 
• 42541-87-7 2-(but-3'-ynyl)-2-methyl-1,3-dioxolane 
• 6838-66-0 1,2-bis((trimethylsilyl)oxy)cyclopent-1-ene 
• 67257-30-1 diethyl 2-oxo-3-butenylphosphonate 
• 3299-38-5 4-(diethylamino)butan-2-one 

Downstream Products

• 112251-14-6 4a-methyl-5-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-4,4a,7,8-tetrahydronaphthalen-2(3H)-one 
• 112251-15-7 8a-methyl-6-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-3,7,8,8a-tetrahydronaphthalen-1(2H)-one 
• 112251-16-8 8a-methyl-3,8-bis-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-1,2,6,8a-tetrahydronaphthalen 
• 57234-61-4 γ-<3-Keto-6-methylcyclohexen-(1)-yl-(1)>-buttersaeuremethylester 
• 101328-30-7 methyl 4-(2,6-dimethyl-3-oxocyclohex-1-enyl)butyrate 
• 19133-70-1 8-hydroxy-5-methyl-1,2,3,4-tetrahydronaphtalene-1-one 
• 117803-32-4 [(4S,5S)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 33878-99-8 (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione 
• 100348-93-4 (R)-Wieland-Miescher ketone 
• 137744-76-4 methyl 4-(5-methoxy-2-methylphenyl)butanoate 
• 6694-96-8 (1α,8aα)-(8a-Methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-1-naphthyl)-p-toluolsulfonat 
• 70499-17-1 9-Methyl-Δ⁵⁽¹⁰⁾-octalin-1,6-dione 1,6-bis(ethylene-dithioacetal) 
• 70499-16-0 4a′-methyl-4′,4a′,7′,8′-tetrahydro-3′H-spiro[[1,3]dithiolane-2,2′-naphthalen]-5′(6′H)-one 
• 128242-25-1 4a-<6-(tert-butyldiphenylsiloxy)-1-hexen-1-yl>-8a-methyldecahydronaphthalene-1,6-dione 

Relevant articles and documents

Annulative Ring Expansions. Direct Conversion of ω-Alkynyl Acetals to Polycyclic Unsaturated Ketones

Geminal acylation of ω-acetylenic acetals and bis(silyloxy)cycloalkenes under Lewis acid conditions preceded cationic cyclization of the alkyne onto the ketone to produce polycyclic unsaturated ketones.

A synthetic approach to (±)-aristomakine

We describe the synthesis of trans-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol (2) in five steps from the Wieland-Miescher ketone 3 in 17% overall yield. The N-benzyl analogue (trans-11-Benzyl-11b-methyl-2,3,4,6,11,11b-hexahydro-1H-benzo[a]carbazol-3-ol) 15 was likewise prepared. Attempts thus far to fashion (±)-aristomakine (1) from 2, 15, or derivatives have not been successful.

Prolinamide/PPTS-catalyzed Hajos-Parrish annulation: Efficient approach to the tricyclic core of cylindricine-type alkaloids

A series of Wieland-Miescher ketone analogues bearing highly functionalized substituents are efficiently constructed in high enantioselectivities and good yields using catalytic amounts of prolinamide and PPTS. We have successfully utilized this reaction as a key step to synthesize the tricyclic core of cylindricine type alkaloids. Georg Thieme Verlag Stuttgart.