(±)-Wieland-Miescher ketone
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(±)-Wieland-Miescher ketone
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CAS No:
20007-72-1
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Formula:
C11H14O2
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Chemical Name:
(±)-Wieland-Miescher ketone
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Synonyms:
1,6(2H,7H)-Naphthalenedione,3,4,8,8a-tetrahydro-8a-methyl-;3,4,8,8a-Tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione;9-Methyl-Δ5,10-octalin-1,6-dione;9-Methyl-1,6-dioxo-1,2,3,4,6,7,8,9-octahydronaphthalene;9-Methyl-5(10)-octalin-1,6-dione;Wieland-Miescher ketone;MODX;(±)-8a-Methyl-1,2,3,4,6,7,8,8a-octahydro-1,6-naphthalenedione;(R/S)-Wieland-Miescher ketone;NSC 87581;(±)-Wieland-Miescher ketone;8a-Methyl-3,4,8,8a-tetrahydronaphthalene-1,6(2H,7H)-dione;20007-99-2
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CAS No:
Description
BEIGE TO BROWN ADHERING CRYSTALLINE POWDER
The Wieland–Miescher ketone is a racemic bicyclic diketone (enedione) and is a versatile synthon which has so far been employed in the total synthesis of more than 50 natural products, predominantly sesquiterpenoids, diterpenes and steroids possessing possible biological properties including anticancer, antimicrobial, antiviral, antineurodegenerative and immunomodulatory activities. The reagent is named after two chemists from Ciba Geigy, Karl Miescher and Peter Wieland (not to be confused with Heinrich Otto Wieland). Examples of syntheses performed using the optically active enantiomer of this diketone as a starting material are that of ancistrofuran and the Danishefsky total synthesis of Taxol.
Characteristics
34.14000
2.03500
BEIGE TO BROWN ADHERING CRYSTALLINE POWDER
1.1 g/cm3
41.5-42.5 °C @ Solvent: Diisopropyl ether
106-108 °C @ Press: 1 x 10-3 Torr
122ºC
1.519
0-6ºC
0.000229mmHg at 25°C
Computed Properties
Molecular Weight:178.23
XLogP3:0.6
Hydrogen Bond Acceptor Count:2
Exact Mass:178.099379685
Monoisotopic Mass:178.099379685
Topological Polar Surface Area:34.1
Heavy Atom Count:13
Complexity:301
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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