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437026

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

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

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

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₄O₂

CAS Number:

33878-99-8

Molecular Weight:

178.23

PubChem Substance ID:

24867341

UNSPSC Code:

12352115

Beilstein/REAXYS Number:

1569979

MDL number:

MFCD00213797

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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

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

07621JD

17528BN

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Sommovigo, M. Alper, H.

Tetrahedron Letters, 34, 59-59 (1993)

Arseniyadis, S. et al.

Tetrahedron Letters, 35, 99-99 (1994)

Paquette, L.A. et al.

Journal of the American Chemical Society, 116, 3367-3367 (1994)

L.A. Paquette et al.

Tetrahedron Letters, 34, 3523-3523 (1993)

M. Golinski et al.

Tetrahedron Letters, 34, 55-55 (1993)

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