63104-44-9

Usage

General Description

2,2-di-(prop-2-ynyl)-malonic acid dimethyl ester is a chemical compound with the molecular formula C10H12O4. It is a ester derivative of malonic acid, containing two propynyl groups and two methyl groups. 2,2-di-(prop-2-ynyl)-malonic acid dimethyl ester is used in organic synthesis as a reagent for the preparation of various organic compounds. It is also used in pharmaceutical and agrochemical industries for the synthesis of active pharmaceutical ingredients and crop protection chemicals. Additionally, it has potential applications in the production of polymers and materials with specific properties. However, it is important to handle this chemical with care, as it may pose health and environmental risks.

Upstream product

• 95124-07-5 dimethyl (prop-2-yn-1-yl)malonate 
• 106-96-7 propargyl bromide 
• 96740-23-7 1,5-dimethoxypentane-2,4-dione 
• 108-59-8 malonic acid dimethyl ester 
• 18424-76-5 dimethyl malonate sodium salt 

Downstream Products

• 253784-01-9 5-{[(2-iodo-phenyl)-(2-methyl-acryloyl)-amino]-methyl}-indan-2,2-dicarboxylic acid dimethyl ester 
• 253784-03-1 5-{[(2-iodo-benzoyl)-(2-methyl-allyl)-amino]-methyl}-indan-2,2-dicarboxylic acid dimethyl ester 
• 276888-00-7 indan-2,2-dicarboxylic acid, dimethyl ester 
• 206008-32-4 dimethyl 5-(2,2-bis(methoxycarbonyl)pent-4-yn-1-yl)-1,3-dihydro-2H-indene-2,2-dicarboxylate 

Relevant academic research and scientific papers

Acid promoted metal free synthesis of triazole-fused heterocycles via intramolecular [3+2] cycloaddition

A practical and efficient protocol for the synthesis of triazole-fused heterocycles through intramolecular metal free [3+2] azide-alkyne cycloaddition reaction is described. Range of acids was selected to demonstrate the reaction conditions. Organic azides and propargyl cations generated by acids gave fused triazoles including multivariate rings and heterocycles. Various fused triazoles and bistriazoles were obtained in good yields under mild reaction conditions.

Iridium complex-catalyzed [2+2+2] cycloaddition of α,ω-diynes with monoynes and monoenes

[Ir(cod)Cl]2/DPPE was found to be a new catalyst for the cycloaddition of α,ω-diynes with monoynes to give polysubstituted benzene derivatives in high yields. Internal monoynes as well as terminal monoynes could be used. The reaction tolerates a broad range of functional groups such as alcohol, amine, alkene, ether, halogen, and nitrile. The reaction of 1,6-octadiyne derivatives with 1-alkynes gives ortho products and meta products. The regioselectivity could be controlled by the choice of ligand. The reaction with DPPE was meta selective, with meta selectivity of up to 82%. The reaction with DPPF was ortho selective, with ortho selectivity of up to 88%. We propose a mechanism to account for this regioseleetive cycloaddition. [Ir(cod)Cl]2/DPPE also catalyzed the cycloaddition of α,ω-diynes with 2,5-dihydrofuran to give bicyclic cyclohexadiene derivatives. The reaction with 2,3-dihydrofuran and n-butyl vinyl ether gave benzene derivatives instead of cyclohexadiene derivatives. We also propose a mechanism to account for this novel aromatization that includes cleavage of the C-O bond.

Energetic interpenetrating polymer network based on orthogonal azido-alkyne click and polyurethane for potential solid propellant

High energetic propellants with synergistic mechanical strength are the prerequisites for aerospace industry and missile technology; though glycidyl azide polymer (GAP) is a renowned and a promising energetic polymer which shows poor mechanical and low-temperature properties. In order to overcome these problems, a novel energetic interpenetrating polymer network (IPN) of acyl-terminated glycidyl azide polymer (Acyl-GAP) and hydroxyl terminated polybutadiene (HTPB) is effectively synthesized and characterized via an "in situ" polymerization by triazole and urethane curing system respectively. Acyl-GAP and dimethyl 2,2-di(prop-2-ynyl)malonate (DDPM) have been synthesized and well characterized by using FT-IR, 1H NMR, 13C NMR and GPC. The maximum tensile strength ～5.26 MPa and elongation 318% are achieved with HTPB-PU/Acyl-GAP triazole in 50 : 50 weight ratios. The solvent resistance properties have been investigated by the equilibrium swelling method and the glass transition temperature (Tg), morphology and thermal stability are evaluated by DSC, SEM and TGA-DTG respectively. Thus, HTPB-PU/Acyl-GAP triazole is a futuristic binder for the composite solid propellant.

Nbcl5/zN/PCy3-system-catalyzed intramolecular [2 + 2 + 2] cycloadditions of diynes and alkenes to form bicyclic cyclohexadienes

A NbCl5, Zn, and PCy3 catalytic system that generated low-valent Nb species is used for the synthesis of bicyclic cyclohexadienes from diynes and simple alkenes. A phosphine ligand is important for stabilizing low-valent Nb in the cycloaddition. The bicyclic cyclohexadiene skeleton is important in transition-metal-catalyzed intramolecular cycloadditions.

Synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids

Unique chiral spiro ionic liquids based on 1,2,3-triazolium salts were synthesized via an intramolecular double Huisgen reaction. The optical resolution of the liquid precursors and subsequent dialkylations leads to chiral spiro triazolium salts on a gram

Cyclopolymerization of dimethyl dipropargylmalonate in supercritical carbon dioxide to give a highly regular polyene containing predominantly five-membered rings

Poly(dimethyl dipropargylmalonate) synthesized in scCO2 contained more than 95% five-membered rings, i.e., highly regular polyene was produced, which shows carbon dioxide as a reaction medium plays a significant role in determining a highly selective polymer structure. The Royal Society of Chemistry 2005.

First examples of cobalt-mediated formal Alder ene reaction of allenynes

CpCo(CO)2 catalyzes the Alder ene reaction of allenynes 1 to afford six-membered carbocycles in a totally regioselective manner through, presumably, η3-allyl hydride complexes mechanism.

Epoxyanthracene Derivatives and Dicarbonylation on Benzene Ring via Hexadehydro-Diels-Alder (HDDA) Derived Benzynes with Oxazoles

A capture reaction of hexadehydro-Diels-Alder (HDDA) derived benzyne with various substituted oxazoles is reported. With methyl, hydrogen, or phenyl as the substituent at 2-position of oxazole, tetraynes afforded epoxyanthracene derivatives or underwent dicarbonylation on benzene ring. The reaction does not require any catalyst or additive. The mechanism behind the reaction was investigated. The obtained polycyclic product structure has potential application value in optoelectronic materials. The availability of dicarbonylated arene implies the uniqueness of HDDA benzyne reaction compared with traditional benzyne.

SPIROCYCLIC ANDROGEN RECEPTOR PROTEIN DEGRADERS

The present disclosure provides compounds represented by Formula( I ) and the salts or solvates thereof, wherein R3a, E, L, A1, B1, X1, X2, Z1, and Z2 are as defined in the specification. Compounds having Formula (I) are androgen receptor degraders useful for the treatment of cancer and other diseases.

Synthesis of [6,6,m]-Tricyclic Compounds via [4+2] Cycloaddition with Au or Cu Catalyst

We synthesized [6,6,6]- and [6,6,7]-tricyclic compounds via intramolecular [4+2] cycloaddition by gold or copper catalysts. Substrates for cyclization were prepared by coupling reactions between eight types of diyne and four types of aromatic moieties. We have successfully synthesized eleven tricyclic compounds.