(+)-Wieland-Miescher ketone
Basic information
- CAS
33878-99-8- Standard SMILES
C[C@]12CCC(=O)C=C1CCCC2=O- InChIKey
DNHDRUMZDHWHKG-NSHDSACASA-N- Molecular formula
- C11H14O2
- Average molar mass
- 178.23 g/mol
- Monoisotopic mass
- 178.09937969
Names & identifiers
- Preferred name
- (+)-Wieland-Miescher ketone
- IUPAC
- (8aS)-8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione
- English name
- (S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione
- Molecular formula
- C11H14O2
- Molecular weight
- 178.23
Names & synonyms
33878-99-8(+)-Wieland-Miescher ketoneRefChem:203662(S)-8A-methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione(S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione(8as)-8a-methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2h,7h)-dioneMFCD00213797(8aS)-8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione(8aS)-(+)-8a-Methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione(8aS)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione9-(S)-Methyl-.delta.-5(10)-octalin-1,6-dione(8aS)-8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione
Show more names
(s)-(+)-9-methyl-e(WIELAND-MIESCHER KETONE(S)-Wieland-MiescherketoneWIELAND-MIESCHER KETONE, S-(+)-ISOMERS(+)-9-methyl-5(10)-octaline-1,6-dione9(S)-Methyl-delta-5(10)-octalin-1,6-dione(S)-(+)-9-Methyl-delta-(5,10)-octalin-1,6-dioneS(+)-8A-methyl-3,4,8,8A-tetrahydro-1,6-naphthalenedione8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione
1,6(2H,7H)-Naphthalenedione, 3,4,8,8a-tetrahydro-8a-methyl-, (8aS)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione #CHEMBL344139SCHEMBL4232967DNHDRUMZDHWHKG-NSHDSACASA-NDTXSID001310367AKOS015916397PS-4916
Database identifiers
- CAS
33878-99-8- PubChem CID
- 736069
- DTXSID
DTXSID001310367- ChEMBL
CHEMBL344139- Nikkaji
- J352.498A
Properties
Computed structural properties
- XLogP
- 0.6
- Topological polar surface area
- 34.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 301
Physicochemical properties
- Melting point
- 50 · 50-52 °C(lit.)
- storage temp.
- 2 · 2-8°C
- form
- crystalline powder
- color
- Cream
- BRN
- 1569979 · 1569979
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 280 · P280-P261-P271
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- F
- 10 · 10
- HS Code
- 2914290090 · 2914290090
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10
- wgk
- 3
- hs_code
- 2914290090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P280-P261-P271
Chemistry & industry
Applications
Uses(S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE is a key intermediate in the total synthesis of macrocyclic diterpene lactones (+)-cleomeolides. A chiral structural unit used for the enantioselective synthesis of the A and C rings of paclitaxel. 3,4,5 A novel class of palladium complexes was used as catalysts to study the selective hydrogenation of carbon-carbon double bonds in α,β-unsaturated ketones.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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