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Merck

210145

Sigma-Aldrich

2,2-Dimethyl-1,3-dioxan-4,6-dion

98%

Synonym(e):

Malonsäure-cycl.-isopropylidenester, cycl.-Isopropyliden-malonat, ‘Meldrum’s Säure’

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About This Item

Empirische Formel (Hill-System):
C6H8O4
CAS-Nummer:
Molekulargewicht:
144.13
Beilstein:
117310
EG-Nummer:
MDL-Nummer:
UNSPSC-Code:
12352100
PubChem Substanz-ID:
NACRES:
NA.22

Assay

98%

Form

solid

mp (Schmelzpunkt)

92-96 °C (lit.)

Löslichkeit

dioxane: soluble 5%, clear to very slightly hazy, colorless to faintly yellow

Funktionelle Gruppe

ester

Lagertemp.

2-8°C

SMILES String

CC1(C)OC(=O)CC(=O)O1

InChI

1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3

InChIKey

GXHFUVWIGNLZSC-UHFFFAOYSA-N

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Allgemeine Beschreibung

Benzyl substituted Meldrum′s acids, available via aldol condensation and reduction with triethylammonium formate, were used to form indanones upon hydrolysis, loss of CO2, and Friedel-Crafts cyclization with chlorosulfonic acid. Knoevenagel condensations between aldehydes and Meldrum′s acid are accelerated in ionic liquids.

Anwendung

Used in an efficient synthesis of isofraxidin.

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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Aaron M Dumas et al.
Accounts of chemical research, 43(3), 440-454 (2009-12-17)
Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) is a molecule with a unique history, owing to its originally misassigned structure, as well as a unique place among acylating agents, owing to its high acidity and remarkable electrophilicity. In this Account, we outline the work
Songlei Zhu et al.
Molecules (Basel, Switzerland), 17(12), 13856-13863 (2012-11-24)
A series of 4-aryl-6-methyl-3,4-dihydro-2H-pyrano[3,2-c]quinolin-2,5(6H)-diones were synthesized via the three-component reactions of aromatic aldehydes, 4-hydroxy-1-methylquinolin-2(1H)-one, and Meldrum's acid catalyzed by L-proline. The structures of the products were identified by spectroscopic analysis. A mechanism for this three-component reaction catalyzed by L-proline was
Davood Nematollahi et al.
Chemical & pharmaceutical bulletin, 58(1), 23-26 (2010-01-05)
Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates
The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives.
Lermer L, et al.
Canadian Journal of Chemistry, 70(5), 1427-1445 (1992)
New multicomponent domino reactions (MDRs) in water: highly chemo-, regio-and stereoselective synthesis of spiro {[1, 3] dioxanopyridine}-4, 6-diones and pyrazolo [3, 4-b] pyridines.
Ma N, et al.
Green Chemistry, 12?(8), 1357-1361 (2010)

Artikel

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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