327972
Aceanthrenequinone
96%
Synonym(s):
1,2-Aceanthrylenedione
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All Photos(2)
About This Item
Empirical Formula (Hill Notation):
C16H8O2
CAS Number:
Molecular Weight:
232.23
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
96%
form
solid
mp
270-273 °C (lit.)
SMILES string
O=C1C(=O)c2c3ccccc3cc4cccc1c24
InChI
1S/C16H8O2/c17-15-12-7-3-5-10-8-9-4-1-2-6-11(9)14(13(10)12)16(15)18/h1-8H
InChI key
YAIBDWAANBTYIA-UHFFFAOYSA-N
General description
Aceanthrenequinone is a cyclic α-diketone. It reacts with hexaethyltriaminophosphine in the presence of fullerene C(60), to yield methanofullerene derivatives. Hydroxyalkylation reactions of aceanthrenequinone with a series of arenes was reported.
Application
Aceanthrenequinone was used in synthesis of spiro-tricyclic porphodimethenes.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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M Harmjanz et al.
Organic letters, 3(15), 2281-2284 (2001-07-21)
[structure: see text] Acid-catalyzed [2 + 2] condensation reactions of polycyclic aromatic vicinal diketones including aceanthrenequinone, phenathrenequinone, and pyrene-4,5-dione with 5-mesityldipyrromethanes are outlined, and this methodology provides a flexible entry to spiro-tricyclic porphodimethenes. The porphodimethene products have been fully characterized
Irina P Romanova et al.
The Journal of organic chemistry, 76(8), 2548-2557 (2011-03-12)
The reactions of such cyclic α-diketones as acenaphthenequinone, aceanthrenequinone, and N-alkylisatins, with hexaethyltriaminophosphine in the presence of the fullerene C(60), lead to the formation of methanofullerene derivatives under mild conditions. This process proceeds via deoxygenation of the dicarbonyl compound by
Douglas A Klumpp et al.
Applied catalysis. A, General, 336(1-2), 128-132 (2008-03-01)
The hydroxyalkylation reactions of aceanthrenequinone (6) and acenapthenequinone (7) with a series of arenes have been studied. In reactions with the Brønsted superacid CF(3)SO(3)H (triflic acid), the condensation products are formed in good yields (58-99%, 10 examples) with high regioselectivity.
Janice L Hyatt et al.
Journal of medicinal chemistry, 50(23), 5727-5734 (2007-10-19)
Carboxylesterases (CE) are ubiquitous enzymes responsible for the detoxification of xenobiotics, including numerous clinically used drugs. Therefore, the selective inhibition of these proteins may prove useful in modulating drug half-life and bioavailability. Recently, we identified 1,2-diones as potent inhibitors of
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