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Merck
모든 사진(1)

주요 문서

210145

Sigma-Aldrich

2,2-Dimethyl-1,3-dioxane-4,6-dione

98%

동의어(들):

Malonic acid cyclic isopropylidene ester, Meldrum’s acid, cycl-Isopropylidene malonate

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About This Item

실험식(Hill 표기법):
C6H8O4
CAS Number:
Molecular Weight:
144.13
Beilstein:
117310
EC Number:
MDL number:
UNSPSC 코드:
12352100
PubChem Substance ID:
NACRES:
NA.22

Quality Level

분석

98%

형태

solid

mp

92-96 °C (lit.)

solubility

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

작용기

ester
ketal

저장 온도

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

InChI key

GXHFUVWIGNLZSC-UHFFFAOYSA-N

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일반 설명

2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pKa 4.83) and steric rigidity. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.

Meldrum′s acid is used as a valuable starting material to synthesize heterocycles and as intermediates in organic synthesis reactions.

애플리케이션

2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:
  • macrocyclic β-keto lactone
  • 4-pyridyl-substituted heterocycles
  • 2-substituted indoles
  • isofraxidin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


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이미 열람한 고객

Slide 1 of 1

1 of 1

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
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)
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)
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
C, O-Dialkylation of Meldrum's Acid: Synthesis and Reactivity of 1, 3, 7, 7-Tetramethyl-4 H, 10 H-6, 8, 9-trioxa-2-thiabenz [f] azulen-5-one
Snyder CA, et al.
The Journal of Organic Chemistry, 68(19), 7455-7459 (2013)

문서

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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