(8aS)-8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione

• ChemBase ID: 87851
• Molecular Formular: C11H14O2
• Molecular Mass: 178.22766
• Monoisotopic Mass: 178.09937969
• SMILES: O=C1C=C2CCCC(=O)[C@]2(CC1)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CCCC2=O)C
• InChI: InChI=1S/C11H14O2/c1-11-6-5-9(12)7-8(11)3-2-4-10(11)13/h7H,2-6H2,1H3/t11-/m0/s1
• InChIKey: DNHDRUMZDHWHKG-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8aS)-8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene-1,6-dione
• IUPAC Traditional name: (8aS)-8a-methyl-3,4,7,8-tetrahydro-2H-naphthalene-1,6-dione
• Synonyms: (S)-(+)-9-Methyl-5(10)-octaline-1,6-dione; (S)-Miescher-Wieland ketone; (S)-(+)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione; Wieland-Miescher ketone; (S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione; (S)-(+)-9-Methyl-Δ(5,10)-octalin-1,6-dione; (S)-Wieland-Miescher ketone; (8aS)-(+)-8a-Methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione; (S)-Miescher-Wieland 酮; (S)-(+)-8a-甲基-3,4,8,8a-四氢-1,6(2H,7H)-萘二酮; Wieland-Miescher 酮; (S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6(2H,7H)-萘二酮; (S)-(+)-3,4,8,8a-四氢-8a-甲基-1,6-(2H,7H)-萘二酮

Database IDs

• CAS Number: 33878-99-8
• MDL Number: MFCD00213797
• Beilstein Number: 1569979
• PubChem SID: 24867341; 162074891
• PubChem CID: 736069

CALCULATED PROPERTIES

• Acid pKa: 17.79769
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0745733
• LogD (pH = 7.4): 2.0745733
• Log P: 2.0745733
• Molar Refractivity: 50.7394 cm^3
• Polarizability: 19.4364 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 48-52°C; 50-51°C; 50-52 °C(lit.)
• Optical Rotation: [α]20/D +98°, c = 1.1 in benzene; +100 (c=1 in benzene)

Safety Information

• Storage Warning: Irritant
• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%; 99%
• Empirical Formula (Hill Notation): C11H14O2
• Classification: Derivatives & analogs of Natural Compounds

DETAILS

Sigma Aldrich - 437026

Application
Key intermediate in the total synthesis of the macrocyclic diterpene lactone, (+)-cleomeolide.1,2 Chiral building block for enantioselective approaches to the A and C rings of taxol.3,4,5 Used to study selective hydrogenations of the carbon-carbon double bonds in α,β-unsaturated ketones with a new class of palladium complexes as catalysts.6

REFERENCES

• Key intermediate in enantioselective steroid syntheses; see, e.g.: Angew. Chem. Int. Ed., 10, 496 (1971); Chem. Ber., 106, 3636 (1973); J. Org. Chem., 45, 2204 (1980).
• For an example of use in synthesis of a diterpene, see: J. Chem. Soc., Perkin 1, 2151 (1986), and of taxane intermediates: J. Org. Chem., 57, 3274 (1992).