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  • 437026 - (S)-(+)-3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione

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437026 Sigma-Aldrich

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

98%

Synonym: (S)-Miescher-Wieland ketone, (S)-(+)-8a-Methyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione, (S)-(+)-9-Methyl-5(10)-octaline-1,6-dione, Wieland-Miescher ketone

  • CAS Number 33878-99-8

  • Empirical Formula (Hill Notation) C11H14O2

  • Molecular Weight 178.23

  •  Beilstein/REAXYS Number 1569979

  •  MDL number MFCD00213797

  •  PubChem Substance ID 24867341

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks, Ketones, Organic Building Blocks More...
InChI Key   DNHDRUMZDHWHKG-NSHDSACASA-N
assay   98%
optical activity   [α]20/D +98°, c = 1.1 in benzene
mp   50-52 °C (lit.)

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 & Documentation

Safety Information

WGK Germany 
3

Documents

Certificate of Analysis

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Protocols & Articles
Peer-Reviewed Papers
15

References

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