Meldrum's acid

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H8O4
Molecular Weight	144.1253
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=GXHFUVWIGNLZSC-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H8O4
Molecular Weight	144.1253
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Synthesis of functionalized chromenes from Meldrum's acid, 4-hydroxycoumarin, and ketones or aldehydes.	2010-11	20615198
Ketene functionalized polyethylene: control of cross-link density and material properties.	2010-10-27	20923158
(E)-2,2-Dimethyl-5-(3-phenyl-allyl-idene)-1,3-dioxane-4,6-dione.	2010-10-23	21589113
5-(4-Fluoro-benzyl-idene)-2,2-dimethyl-1,3-dioxane-4,6-dione.	2010-08-21	21588707
5-(4-Hy-droxy-benzyl-idene)-2,2-dimethyl-1,3-dioxane-4,6-dione.	2010-08-18	21588666
Synthesis and biological evaluation of arylidene analogues of Meldrum's acid as a new class of antimalarial and antioxidant agents.	2010-08-01	20621497
Short malonyl dehydro peptides as potential scaffolds for peptidomimetics by an efficient Knoevenagel reaction.	2010-07	20094741
4-[2-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-yl-idene)hydrazin-1-yl]benzo-nitrile.	2010-06-26	21587996
rac-2-Methyl-3,4,5,6-tetra-hydro-2H-2,6-methano-1,3-benzoxazocin-4-one.	2010-05-22	21579481
Meldrum's acids and 5-alkylidene Meldrum's acids in catalytic carbon-carbon bond-forming processes.	2010-03-16	20000793
Synthesis of zwitterionic salts of pyridinium-Meldrum acid and barbiturate through unique four-component reactions.	2010-03-08	20092329
A facile route to ketene-functionalized polymers for general materials applications.	2010-03	21124478
Polymer synthesis: facilitating functionality.	2010-03	21124472
Practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors: access to chiral beta-alkynyl acids.	2010-01-20	20020682
Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid. Synthesis and kinetic evaluation.	2010-01	20045960
Microwave-assisted solid phase conversion study of Meldrum's acid to ethylenetetracarboxylic dianhydride (C6O6).	2010-01	19945911
Synthetic routes to pyrrolizine-1,5-dione derivatives by flash vacuum pyrolysis of amidomethylene derivatives of Meldrum's acid.	2009-12-07	19907784
4-(4-Chloro-phen-yl)-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-2,5(3H,6H)-dione.	2009-12-04	21580158
4-(4-Methoxy-phen-yl)-7,7-dimethyl-5-oxo-5,6,7,8-tetra-hydrochromene-2,5-dione.	2009-11-25	21578924
Asymmetric synthesis of all-carbon benzylic quaternary stereocenters via conjugate addition to alkylidene and indenylidene Meldrum's acids.	2009-11-20	19824691
Hydrogenolysis of unstrained carbon-carbon sigma bonds: stereoselective entry into benzylic tertiary centers.	2009-11-04	19810747
One hundred years of Meldrum's acid: advances in the synthesis of pyridine and pyrimidine derivatives.	2009-11	19381852
5-(2-Fluoro-benzyl-idene)-2,2-dimethyl-1,3-dioxane-4,6-dione.	2009-09-30	21578023
2,2-Dimethyl-5-(2-naphthyl-amino-methyl-ene)-1,3-dioxane-4,6-dione.	2009-09-30	21578013
6-Methyl-sulfanyl-4H-pyrimido[1,6-a]pyrimidin-4-one.	2009-09-30	21578009
2,2-Dimethyl-5-[(3-nitro-anilino)methyl-ene]-1,3-dioxane-4,6-dione.	2009-08-15	21577577
A novel one-pot three-(in situ five-)component condensation reaction: an unexpected approach for the synthesis of tetrahydro-2,4-dioxo-1H-benzo[b][1,5]diazepine-3-yl-2-methylpropanamide derivatives.	2009-08-06	19719182
A new domino autocatalytic reaction leading to polyfunctionalized spiro[5.5]undecanes and dispiro[4.2.5.2]pentadecanes.	2009-05-21	19421460
Multi-catalysis cascade reactions based on the methoxycarbonylketene platform: diversity-oriented synthesis of functionalized non-symmetrical malonates for agrochemicals and pharmaceuticals.	2009-05-21	19421442
5-[(3,4-Dimethoxy-benzyl)-aminomethyl-ene]-2,2-dimethyl-1,3-dioxane-4,6-dione.	2009-05-14	21583157
5-[(4-Acetyl-phenyl)-aminomethyl-ene]-2,2-dimethyl-1,3-dioxane-4,6-dione.	2009-05-14	21583156
7,14-Bis(4-bromo-phen-yl)-2,11,11-trimethyl-1,4,10,12-tetra-oxa-dispiro-[4.2.5.2]penta-decane-9,13-dione.	2009-04-30	21583954
7,14-Bis(4-methoxy-phen-yl)-11,11-dimethyl-1,4,10,12-tetra-oxa-dispiro-[4.2.5.2]penta-decane-9,13-dione.	2009-04-18	21583891
Chemical bonding and structure-reactivity correlation in Meldrum's acid: a combined experimental and theoretical electron density study.	2009-03-20	19231871
Probing persistent intramolecular C-H...X (X = O, S, Br, Cl, and F) bonding in solution using benzyl Meldrum's acid derivatives.	2009-02-06	19113820
New potential inhibitors of DNA topoisomerase. Part II: Design and synthesis of alpha-lapachone derivatives under microwave irradiation.	2009-02-01	19112020
LAS0811: from combinatorial chemistry to activation of antioxidant response element.	2009	19794825
4-Phenyl-1,2,3,4-tetra-hydro-pyrimido[1,2-a]benzimidazol-2-one.	2008-10-18	21581003
Mechanism and regioselectivity of the cycloaddition of thiones derived from Meldrum's acid, malonates, or other dicarbonyls.	2008-10-03	18771325
Meldrum's acid catalyzed reaction of tetracyanoethylene and aldehydes in water: a novel approach to arylidenemalononitrile.	2008-10	18827396
A novel method for the synthesis of substituted 3,4-dihydrocoumarin derivatives via isocyanide-based three-component reaction.	2008-08-10	18830678
Asymmetric synthesis of carboxylic acid derivatives having an all-carbon alpha-quaternary center through Cu-catalyzed 1,4-addition of dialkylzinc reagents to 2-aryl acetate derivatives.	2008-07-03	18510334
Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives.	2008-06-19	18503292
Kinetic study of electrochemically induced michael reactions of o-quinones with Meldrum's acid derivatives. Synthesis of highly oxygenated catechols.	2008-05-02	18396907
Meldrum's acid and related compounds in the synthesis of natural products and analogs.	2008-04	18362984
7-Chloro-4-(2,5-dichloro-phen-yl)-1-phenyl-1H-thio-chromeno[2,3-b]pyridine-2,5(3H,4H)-dione.	2008-03-05	21202064
Ab initio structure determination of 5-anilinomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione from laboratory powder data--a combined use of X-ray, molecular and solid-state DFT study.	2007-06	17507761
Carboxyketenes, methyleneketenes, vinylketenes, oxetanediones, ynols, and ylidic ketenes from Meldrum's acid derivatives.	2007-05-07	17464413
Studies on the synthesis of (-)-gymnodimine. Subunit synthesis and coupling.	2007-03-02	17263581
Reactions of 3-formylchromone with active methylene and methyl compounds and some subsequent reactions of the resulting condensation products.	2005-08-31	18007363

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:20:44 GMT 2025` Edited by `admin` on `Mon Mar 31 21:20:44 GMT 2025`
Record UNII	DD139RP1SC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Meldrum's acid

Common Name

English

NSC-688343

Preferred Name

English

N,N-Dimethyl-1-4-aminobilidine

Systematic Name

English

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

Systematic Name

English

MELDRUMIC ACID

Common Name

English

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

Systematic Name

English

Isopropylidene malonate

Systematic Name

English

NSC-71902

Code

English

2,2-Propanediol cyclic malonate

Common Name

English

MELDRUM'S ACID [MI]

Common Name

English

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

Systematic Name

English

Malonic acid, cyclic isopropylidene ester

Common Name

English

2,2-Dimethyl-m-dioxane-4,6-dione

Systematic Name

English

Cyclic isopropylidene malonate

Common Name

English

Code System Code Type Description

NSC

71902