95124-07-5

Usage

Uses

Used in Pharmaceutical Industry:
DIMETHYL PROPARGYLMALONATE is used as a reactant for the synthesis of Nitro methylenecyclopentanes through a [3+2] annulation reaction with various nitroalkenes in the presence of Triton B. These synthesized compounds have potential applications in the development of pharmaceuticals and other bioactive molecules.
Used in Chemical Synthesis:
DIMETHYL PROPARGYLMALONATE is used as a precursor for the preparation of Propargylmalonamides intermediates, which are applicable in the synthesis of "click BOX" ligands. This is achieved through a copper-catalyzed cycloaddition and oxazoline ring formation reaction, allowing for the creation of diverse and complex organic structures.
Used in Organic Chemistry Research:
DIMETHYL PROPARGYLMALONATE is used in the synthesis of Cyclopentene derivatives by reacting with various α, β-unsaturated ketones. This reaction employs a combination of organocatalysts and transition metal catalysts, enabling the formation of valuable intermediates and final products in organic chemistry research and development.

InChI:InChI=1/C8H10O4/c1-4-5-6(7(9)11-2)8(10)12-3/h1,6H,5H2,2-3H3

Upstream product

• 108-59-8 malonic acid dimethyl ester 
• 659-86-9 propargyl iodide 
• 1180611-55-5 dimethyl 2-(phenyl(tosylamino)methyl)-2-(prop-2-ynyl)malonate 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 624-65-7 2-propynyl chloride 
• 106-96-7 propargyl bromide 
• 18424-76-5 dimethyl malonate sodium salt 

Downstream Products

• 130860-69-4 dimethyl 2-[(E)-cinnamyl]-2-propargylmalonate 
• 153933-65-4 dimethyl 2-[2-(phenylsulfonyl)buta-2,3-dienyl]-2-(prop-2-ynyl)malonate 
• 160977-65-1 propanedioic acid, <2-(benzyloxy)-2,3-dihydro-6H-pyran-3-yl>-2-propynyl-dimethyl ester 
• 176589-99-4 2-((3R,6R)-6-Benzyloxy-3,6-dihydro-2H-pyran-3-yl)-2-prop-2-ynyl-malonic acid dimethyl ester 
• 697288-08-7 dimethyl 2-(4-phenyl-3-butenyl)-2-(2-propynyl)malonate 
• 697288-02-1 dimethyl 2-(3-phenyl-3-butenyl)-2-(2-propynyl)malonate 
• 745071-83-4 2-phenethyl-2-prop-2-ynylmalonic acid dimethyl ester 
• 909797-76-8 1,3-dimethyl 2-benzyl-2-(prop-2-yn-1-yl)propanedioate 
• 884492-09-5 (E)-dimethyl 2-(3-(4-methoxyphenyl)allyl)-2-(prop-2-ynyl)malonate 

Relevant academic research and scientific papers

CARBENE LIGANDS AS ANTHRACYCLINONESYNTHONS-II CHROMIUM MEDIATED CYCLOADDITION OF ALKYNES, CARBENES AND CARBON MONOXIDE: APPLICATION TO RING B SYNTHESIS IN ANTHRACYCLINONES

The cycloaddition of Cr-co-ordinated alkyne, carbene and carbonyl ligands provides a variable route to the anthracyclinone skeleton.The key step of a formal total synthesis of 4-demethoxydaunomycinone (1) is based on the reaction of carbonyl-carbene complex 15 -used as a CD ring synthon- and alkyne 9 leading to the formation of ring B.

A chemical probe for lysine malonylation

Tag! You′re it! MalAM-yne is a chemical reporter for malonylation of lysines within proteins (see scheme), a newly identified posttranslational modification. MalAM-yne is cell-permeable and metabolically incorporated into proteins in living cells. Subsequent bioorthogonal tag conjugation allows the fluorescent visualization of cellular malonylation and profiling of malonylated proteins. Copyright

Silver oxide(I) promoted Conia-ene/radical cyclization for a straightforward access to furan derivatives

A novel access to fused furan cores using silver oxide(I) has been developed. Mechanistic investigations indicate the involvement of a Conia-ene reaction/radical cyclization for an expedient path to complex furan derivatives. The reaction is broad in scop

Iron-Catalyzed [2+2+2] Annulation of Aliphatic Bridged 1,n-Enynes with Aldehydes for the Synthesis of Fused Pyrans

An iron-catalyzed [2+2+2] annulation of aliphatic bridged 1,n-enynes with aldehydes was developed. Aldehydes play a dual role as the precursors of acyl radicals to trigger the cascade cyclization but also as the radical acceptors to terminate the annulation. This two-in-one strategy overcomes the limitation in [2+2+m] cyclization that requires a rigid benzene skeleton as the essential linker, thus enabling the efficient synthesis of functionalized fused [5.6] and [6.6] pyran skeletons.

Visible-Light Mediated Hydrosilylative and Hydrophosphorylative Cyclizations of Enynes and Dienes

Described herein is a visible-light mediated intermolecular radical cyclization approach to access heterocycles. Heteroatom radicals, such as silicon and phosphorus atom radicals, were generated via direct hydrogen atom abstraction by the photoexcited catalyst species with hydro-silanes and phosphine oxides. The radical addition/cyclization/HAT (hydrogen atom transfer) reaction sequences of 1,6-enynes and 1,6-dienes were highly efficient delivering the desired heterocycles in good yields.

SUBSTITUTED HETEROCYCLES AS c-MYC TARGETING AGENTS

Disclosed are substituted heterocycle compounds including substituted pyrazoles, substituted pyrimidines, and substitute triazoles. The substituted heterocycles disclosed herein are shown to be useful in inhibiting c-MYC and may be utilized as therapeutics for treating cancer and cell proliferative disorders.

Enantioselective α-Amination of Acyclic 1,3-Dicarbonyls Catalyzed by N-Heterocyclic Carbene

Herein, we describe a method for the catalytic enantioselective α-amination of α-substituted acyclic 1,3-ketoamides and 1,3-amidoesters that affords the products possessing N-substituted quaternary stereocenters with a chiral N-heterocyclic carbene (NHC). The reaction is based on the utilization of an intrinsic Br?nsted base characteristic of NHC that enables the catalytic formation of a chiral ion pair comprising the enolate and the azolium ion. A series of challenging open-chain α-substituted 1,3-dicarbonyls are aminated via this method with ee's of ≤99%.

Complementary Reactivity of 1,6-Enynes with All-Metal Aromatic Trinuclear Complexes and Carboxylic Acids

The distinct reactivity of 1,6-enynes in the presence of a trinuclear metal complex activated by a carboxylic acid is presented. The triplatinum catalyst enables the cyclization of the substrate and subsequent incorporation of a nucleophile in the final product. In contrast, sequential cyclization/double bond shift occurs under analogous conditions in the presence of the corresponding tripalladium complex.

Au-Cavitand Catalyzed Alkyne-Acid Cyclizations

Supramolecular cavitands that contain inwardly directed functional groups have yielded specialized transformations and trapping of reactive intermediates. A recently reported 3-wall Au cavitand provides exciting opportunities for supramolecular catalysis. In this study, a variety of substituted γ-alkynoic acids were reacted to give lactones. The interaction of peripheral “R” groups revealed differential catalyst behavior. Extremely large and small groups reacted with appreciable rate. Intermediate sized groups however, slowed significantly: giving support that size-specific binding is at play when using cavitands as a scaffold for gold catalysis. These results serve as some of the first evidence of the interplay between substrate and cavitand interior in the catalytic sphere.

Cobalt-catalyzed versus uncatalyzed intramolecular Diels-Alder cycloadditions

The intramolecular [4+2] cycloadditions of dienynes was investigated using cobalt-based catalysts. Substrates without substitution on alkyne moiety were found to react under thermal activation. The use of a cobalt salt as catalyst made reactions cleaner by limiting the formation of byproducts. Cycloadditions with dienynes possessing a substituent on the alkyne pattern occurred only in presence of a cobalt catalyst which displayed a moderate to good activity depending on the substrate patterns.