437026

(S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione

98%

• Synonym(s): (S)-(+)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione, (S)-(+)-9-Methyl-5(10)-octaline-1,6-dione, (S)-Miescher-Wieland ketone, Wieland-Miescher ketone
• Empirical Formula (Hill Notation): C₁₁H₁₄O₂
• CAS Number: 33878-99-8
• Molecular Weight: 178.23
• Beilstein/REAXYS Number: 1569979
• MDL number: MFCD00213797
• UNSPSC Code: 12352115
• PubChem Substance ID: 24867341

Properties

• assay: 98%
• optical activity: [α]20/D +98°, c = 1.1 in benzene
• mp: 50-52 °C (lit.)
• SMILES string: C[C@]12CCC(=O)C=C1CCCC2=O
• 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
• InChI key: DNHDRUMZDHWHKG-NSHDSACASA-N

Description

Application

Key intermediate in the total synthesis of the macrocyclic diterpene lactone, (+)-cleomeolide. Chiral building block for enantioselective approaches to the A and C rings of taxol. 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.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)