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327972

Sigma-Aldrich

Aceanthrenequinone

96%

Sinónimos:

1,2-Aceanthrylenedione

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About This Item

Fórmula empírica (notación de Hill):
C16H8O2
Número de CAS:
6373-11-1
Peso molecular:
232.23
MDL number:
MFCD00013265
UNSPSC Code:
12352100
PubChem Substance ID:
24859705
NACRES:
NA.22

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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
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.
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
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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