6768-21-4

Usage

Uses

Used in Organic Synthesis:
(m-Chlorobenzylidene)malonic acid diethyl ester is used as a reagent for the formation of various organic compounds, including dyes, pharmaceuticals, and agrochemicals. Its synthetic versatility and ability to participate in condensation reactions make it a valuable component in the development of these products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (m-Chlorobenzylidene)malonic acid diethyl ester is used as a key intermediate in the synthesis of certain drugs. Its reactivity and structural properties allow for the creation of novel pharmaceutical compounds with potential therapeutic applications.
Used in Agrochemical Industry:
(m-Chlorobenzylidene)malonic acid diethyl ester is also utilized in the agrochemical industry for the synthesis of various agrochemical products, such as pesticides and herbicides. Its role in these applications is to provide a stable and reactive starting material for the development of effective and targeted agrochemicals.
Safety Precautions:
It is crucial to handle and use (m-Chlorobenzylidene)malonic acid diethyl ester with caution, as it may pose health and environmental risks if not managed properly. Proper safety measures, including the use of personal protective equipment and adherence to safety protocols, should be taken to minimize potential hazards.

Upstream product

• 587-04-2 m-Chlorobenzaldehyde 
• 105-53-3 diethyl malonate 

Downstream Products

• 19051-28-6 4-(2-(3-chloro-phenyl)-1-cyanovinyl)benzonitrile 
• 1374878-07-5 tert-butyl 2-(1-(3-chlorophenyl)-3-ethoxy-2-(ethoxycarbonyl)-3-oxopropyl)-5-oxo-2H-pyrrole-1(5H)-carboxylate 
• 1309167-01-8 diethyl 2,3-diphenyl-5-(m-chloro-phenyl)-4,4-isoxazolidine-dicarboxylate 
• 1309359-52-1 2-(3-chlorophenyl)-4-vinyl-2,5-dihydrofuran-3-carboxylic acid 
• 1309359-65-6 2-(3-chlorophenyl)-4-ethylfuran-3-carboxylic acid 
• 1146217-37-9 ethyl 2-ethoxycarbonyl-3-(3-indolyl)-3-(m-chlorophenyl)propanoate 

Relevant academic research and scientific papers

Unnatural α-amino ethyl esters from diethyl malonate or ethyl β-bromo-α-hydroxyiminocarboxylate

We have explored here the scope of the age-old diethyl malonate-based accesses to α-amino esters involving Knoevenagel condensations of diethyl malonate on aldehydes, reductions of the resulting alkylidenemalonates, the preparation of the corresponding α-hydroxyimino esters and their final reduction. This synthetic pathway turned out to be general although some unexpected limitations were encountered. The synthetic modifications of some of the intermediates - using Suzuki-Miyaura coupling or cycloadditions - before undertaking the oximation step - provided accesses to further α-amino esters. Moreover, other pathways to α-hydroxyimino esters were explored including an attempt to improve the cycloadditions between ethyl β-bromo-α-hydroxyiminocarboxylate and various alkylfuranes.

Lipase-Catalysed Addition of Pyrrolidine to Chalcone and Benzylidene Malonate Derivatives

The porcine pancreas lipase (PPL) type II catalyzes the aminolysis of benzylidene malonates by regiospecific amidation of substrates and afforded the Z-isomer; no E-isomer or diamide byproducts were observed. PPL also catalyzes Michael addition of acetophenone to various derivatives of chalcones.

Synthesis of 3-(3-aryl-pyrrolidin-1-yl)-5-aryl-1,2,4-triazines that have antibacterial activity and also inhibit inorganic pyrophosphatase

Inorganic pyrophosphatases are potential targets for the development of novel antibacterial agents. A pyrophosphatase-coupled high-throughput screening assay intended to detect o-succinyl benzoic acid coenzyme A (OSB CoA) synthetase inhibitors led to the unexpected discovery of a new series of novel inorganic pyrophosphatase inhibitors. Lead optimization studies resulted in a series of 3-(3-aryl-pyrrolidin-1-yl)-5-aryl-1,2,4-triazine derivatives that were prepared by an efficient synthetic pathway. One of the tetracyclic triazine analogues 22h displayed promising antibiotic activity against a wide variety of drug-resistant Staphylococcus aureus strains, as well as activity versus Mycobacterium tuberculosis and Bacillus anthracis, at a concentration that was not cytotoxic to mammalian cells.

Chiral-Zn(NTf2)2-complex-catalyzed diastereo- and enantioselective direct conjugate addition of arylacetonitriles to alkylidene malonates

Chiral N,N′-dioxide/Zn(NTf2)2 complexes were demonstrated to be highly effective in the direct asymmetric conjugate addition of arylacetonitriles to alkylidene malonates under mild conditions. A wide range of substrates were tolerated to afford their corresponding products in moderate-to-good yields with high diastereoselectivities (82:18->99:1 d.r.) and enantioselectivities (81-99 % ee). The reactions performed well, owing to the high Lewis acidity of the metal triflimidate and a ligand-acceleration effect. The N,N′-dioxide also benefited the deprotonation process as a Bronsted base. The catalytic reaction could be performed on the gram-scale with retention of yield, diastereoselectivity, and enantioselectivity. The products that contained functional groups were ready for further manipulation. In addition, a possible catalytic model was proposed to explain the origin of the asymmetric induction. Copyright

Synthesis and anti-tumor activity of novel ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates

A series of ethyl 3-aryl-4-oxo-3,3a,4,6-tetrahydro-1H-furo[3,4-c]pyran-3a- carboxylates were prepared through the metal-catalyzed domino reaction of alkylidene malonates and 1,4-butynediol under a one-pot reaction condition at room temperature. Their in vitro anti-proliferative activities were subsequently evaluated in A549, QGY and HeLa cells. The majority of the compounds showed potent anti-tumor activity against HeLa cells. In particular, compound 3l was the most potent compound with IC50 value of 5.4 μM. For the first time, the X-ray structure of the anti-tumor ethyl 3-aryl-4-oxo-3,3a,4,6- tetrahydro-1H-furo[3,4-c]pyran-3a-carboxylates is determined.

Determination of the electrophilicity parameters of diethyl benzylidenemalonates in dimethyl sulfoxide: Reference electrophiles for characterizing strong nucleophiles

The second-order rate constants of the reactions of nine substituted diethyl benzylidenemalonates 1a-i with the carbanions 2a-e have been determined spectrophotometrically in dimethyl sulfoxide (DMSO). Product studies show that the nucleophiles attack regioselectively at the electrophilic C=C double bond of the Michael acceptors to form the carbanionic adducts 4. The correlation log k(20°C) = s(N+E) allows the determination of the electrophilicity parameters E for the electrophiles 1a-i from the rate constants determined in this work and the previously published N and s parameters for the nucleophiles 2a-e. The electrophilicities E for compounds 1a-i cover a range of six units (-17.7> E >-23.8) and correlate excellently with Hammett's substituent constants σp. The title compounds are roughly ten orders of magnitude less reactive than analogously substituted benzylidene Meldrum's acids, their cyclic analogues. Due to their low reactivities, compounds 1a-i are suitable reference electrophiles for determining the reactivities of highly reactive nucleophiles, such as carbanions with 16N30.