Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C6H6O4 |
| Molecular Weight | 142.1094 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC(=O)C#CC(=O)OC
InChI
InChIKey=VHILMKFSCRWWIJ-UHFFFAOYSA-N
InChI=1S/C6H6O4/c1-9-5(7)3-4-6(8)10-2/h1-2H3
| Molecular Formula | C6H6O4 |
| Molecular Weight | 142.1094 |
| 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 |
|---|---|---|
| An efficient synthesis of substituted 2-iminothiazolidin-4-one and thiadiazoloquinazolinone derivatives. | 2009-08 |
|
| Generation and trapping of a terminal chlorophosphinidene complex. | 2009-06-10 |
|
| Synthesis and chemistry of 4,5-dihydrothieno[3,2-b]pyrrol-6-one--a heteroindoxyl. | 2009-06-05 |
|
| Reaction of an oxaruthenacycle with DMAD. Stoichiometric transformations of 2,6-xylenol to allylic phenols and benzopyrans via sp(3) C-H bond cleavage reaction. | 2009-05-07 |
|
| Oxidative reactions of tetrametal Pd(0)...Mo(II)-Mo(II)...Pd(0) clusters: electrochemical communication of two Pd(0) centers through the Mo(2) moiety and oxidative formation of a Pd(I)-Mo(II)-Mo(II)-Pd(I) array. | 2009-03-02 |
|
| Tandem electrophilic cyclization-[3+2] cycloaddition-rearrangement reactions of 2-alkynylbenzaldoxime, DMAD, and Br2. | 2009-01-16 |
|
| Reactions of ruthenium vinylidene and acetylide complexes containing trichloromethyl groups: preparation of a cyclobutenonyl complex by solid-state photolysis. | 2009 |
|
| A new class of sulfido/oxo(dithiolene)-molybdenum(IV) complexes derived from sulfido/oxo-bis(tetrasulfido)molybdenum(IV) anions. | 2008-11-03 |
|
| Intermolecular sequential [4 + 2]-cycloaddition-aromatization reaction of aryl-substituted allenes with DMAD affording phenanthrene and naphthalene derivatives. | 2008-10-07 |
|
| An efficient low-temperature route to polycyclic isoquinoline salt synthesis via C-H activation with [Cp*MCl2]2 (M = Rh, Ir). | 2008-09-17 |
|
| Photooxygenation of 5-dialkylamino-4-pyrrolin-3-ones. Synthesis of highly functionalized ureas, 2-oxazolidinones, and 2-oxazolinones. | 2008-09-05 |
|
| Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds. | 2008-05 |
|
| Regioselectivity and tautomerism of novel five-membered ring nitrogen heterocycles formed via cyclocondensation of acylthiosemicarbazides. | 2008-03-01 |
|
| Rh-catalyzed intermolecular and enantioselective [4 + 2] cycloaddition of 1,3-dienes with dimethyl acetylenedicarboxylate. | 2008-02-07 |
|
| Cycloaddition/Ring opening reaction sequences of N-alkenyl aziridines: influence of the aziridine nitrogen on stereoselectivity. | 2008-01-03 |
|
| Reactions of 16e CpCo half-sandwich complexes containing a chelating 1,2-dicarba-closo-dodecaborane-1,2-dichalcogenolate ligand with ethynylferrocene and dimethyl acetylenedicarboxylate. | 2008 |
|
| The unprecedented ring transformation from thiazoline-spiro-thiophene to thieno[2,3-b]pyrazine involved in the reaction of 2-thiocarbamoyl thiazolium salts with dimethyl acetylenedicarboxylate. | 2007-12-21 |
|
| Remote monitoring of a multi-component liquid-phase organic synthesis by infrared emission spectroscopy: the recovery of pure component emissivities by band-target entropy minimization. | 2007-10 |
|
| Mechanistic twist of the [8+2] cycloadditions of dienylisobenzofurans and dimethyl acetylenedicarboxylate: stepwise [8+2] versus [4+2]/[1,5]-vinyl shift mechanisms revealed through a theoretical and experimental study. | 2007-09-05 |
|
| Microwave assisted condensation reactions of 2-aryl hydrazonopropanals with nucleophilic reagents and dimethyl acetylenedicarboxylate. | 2007-08-24 |
|
| Preparation and Diels-Alder chemistry of 4-vinylimidazoles. | 2007-05-11 |
|
| An unprecedented tandem 1,3-dipolar cycloaddition-cheletropic elimination: a facial approach to novel push-pull olefins. | 2007-04-21 |
|
| Synthesis, structure, and reactivity of mononuclear RE(I) oximato complexes. | 2007-04-02 |
|
| A versatile strategy for divergent and diastereoselective synthesis of natural product-like polyhydroxylated indolizidines. | 2007-03-16 |
|
| Reaction of the Mo3S4 cluster with dimethylacetylenedicarboxylate: an ESR-active cluster and an organometallic cluster formed by alpha,beta-conjugate addition. | 2007-01-22 |
|
| Imaging GABAc receptors with ligand-conjugated quantum dots. | 2007 |
|
| Investigations on the coupling of ethylene and alkynes in [IrTp Me2] compounds: water as an effective trapping agent. | 2007 |
|
| Substrate-controlled and site-selective [3+2] cycloadditions of N-heterocyclic carbene derived ambident dipoles. | 2007 |
|
| Novel multicomponent reaction of [60]fullerene: the first example of 1,4-dipolar cycloaddition reaction in fullerene chemistry. | 2006-11-21 |
|
| Synthesis and reaction of alpha-dithiolactone. | 2006-10-10 |
|
| Synthesis of new 2-vinylation products of indole via a Michael-type addition reaction with dimethyl acetylenedicarboxylate and their Diels-Alder reactivity as precursors of new carbazoles. | 2006-09-29 |
|
| On the [2+2] cycloaddition of 2-aminothiazoles and dimethyl acetylenedicarboxylate. Experimental and computational evidence of a thermal disrotatory ring opening of fused cyclobutenes. | 2006-07-07 |
|
| Novel annulation reactions of aryl methyl ketenes with zwitterions derived from dimethyl acetylenedicarboxylate and N-alkylimidazoles. | 2006-07-06 |
|
| 1-Borabarrelene derivatives via Diels-Alder additions to borabenzenes. | 2006-06-22 |
|
| 1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products. | 2006-06-21 |
|
| A one-pot entry to a novel 3-H-benzo[d]pyrazolo[1,5-b]isothiazole ring system. | 2006-05 |
|
| A N-heterocyclic carbene derived highly regioselective ambident C-C-S and C-C-N 1,3-dipolar system. | 2006-03-21 |
|
| Reaction of dimethoxycarbene-DMAD zwitterion with 1,2-diones and anhydrides: a novel synthesis of highly substituted dihydrofurans and spirodihydrofurans. | 2006-03-17 |
|
| Three-component reaction between triphenylphosphine, dialkyl acetylenedicarboxylates and urea or N-methylurea. | 2006-02 |
|
| Bridgehead nitrogen heterocycles which contain the quinazoline moiety -- synthesis and cycloaddition of 1,2-dihydroquinazoline 3-oxides. | 2005-12-21 |
|
| Trapping evidence for the thermal cyclization of di-(o-acetylphenyl)acetylene to 3,3'-dimethyl-1,1'-biisobenzofuran. | 2005-12-09 |
|
| Synthesis and characterisation of second-generation metallodithiolene complexes of the type [Tp*ME(dithiolene)](M=Mo, W; E=O, S) and a novel 'organoscorpionate' complex of tungsten. | 2005-11-07 |
|
| Domino 6pi-electrocyclization/Diels-Alder reactions on 1,6-disubstituted (E,Z,E)-1,3,5-hexatrienes: versatile access to highly substituted tri- and tetracyclic systems. | 2005-11-04 |
|
| Facile synthesis of highly substituted 3-aminofurans from thiazolium salts, aldehydes, and dimethyl acetylenedicarboxylate. | 2005-10-28 |
|
| Unprecedented coordination modes and demetalation pathways for unbridged polyenyl ligands. Ruthenium eta1,eta4-cycloheptadienyl complexes from allyl/alkyne cycloaddition. | 2005-10-19 |
|
| Engaging the pyridine-DMAD zwitterion in a novel strategy for the selective synthesis of highly substituted benzene and cyclopentenedione derivatives. | 2005-10-13 |
|
| DABCO-catalyzed reaction of alpha-halo carbonyl compounds with dimethyl acetylenedicarboxylate: a novel method for the preparation of polysubstituted furans and highly functionalized 2H-pyrans. | 2005-09-30 |
|
| Synthesis and structure of cyclopropano-annelated homosesquinorbornene derivatives containing pyramidalized double bonds: evidence for the sterical effect of a cyclopropyl group on the degree of C=C double-bond pyramidalization. | 2005-07-08 |
|
| Unexpected reaction of dimethyl acetylenedicarboxylate with in situ generated arylketenes catalyzed by 1-methylimidazole. | 2005-05-26 |
|
| Synthesis, molecular structure and reactivity of 5-methylidene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolines. | 2004-02-28 |
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:43:06 GMT 2025
by
admin
on
Mon Mar 31 21:43:06 GMT 2025
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| Record UNII |
7HZA2PL15F
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| Record Status |
Validated (UNII)
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| Record Version |
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101119
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7HZA2PL15F
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762-42-5
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C022918
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14912
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Acetylenedicarboxylic acid dimethyl ester
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DTXSID0061088
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212-098-4
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12980
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