6827-40-3

Usage

Uses

Used in Organic Synthesis:
[(4-Chlorophenyl)methylene]malonic acid diethyl ester serves as a reagent in organic synthesis, facilitating the preparation of a variety of organic compounds. Its unique structure allows for versatile reactions and the formation of diverse chemical products.
Used in Pharmaceutical Drug Synthesis:
In the pharmaceutical industry, [(4-Chlorophenyl)methylene]malonic acid diethyl ester is utilized as a key building block for the synthesis of drugs. Its incorporation into drug molecules can contribute to the development of new therapeutic agents with specific pharmacological properties.
Used in Agrochemical Synthesis:
Similarly, in agrochemical applications, [(4-Chlorophenyl)methylene]malonic acid diethyl ester is employed in the synthesis of various agrochemicals. Its structural features can be leveraged to create compounds with pesticidal or herbicidal activity, contributing to agricultural productivity and crop protection.

InChI:InChI=1/C14H15ClO4/c1-3-18-13(16)12(14(17)19-4-2)9-10-5-7-11(15)8-6-10/h5-9H,3-4H2,1-2H3

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 105-53-3 diethyl malonate 
• 110-89-4 piperidine 
• 95-76-1 m,p-dichloroaniline 
• 104-86-9 4-chlorobenzylamine 
• 37556-13-1 diethyl (4-chlorobenzyl)malonate 
• 685-87-0 Diethyl 2-bromomalonate 
• 631-22-1 diethyl dibromomalonate 

Downstream Products

• 40877-57-4 ethyl 3-(4-chlorophenyl)-3-cyanopropanoate 
• 22730-52-5 <α-(O,O-Diethyl-phosphono)-4-chlor-benzyl>-malonsaeure-diethylester 
• 22399-10-6 2-[(4-Chloro-phenyl)-(diethoxy-thiophosphorylsulfanyl)-methyl]-malonic acid diethyl ester 
• 74444-83-0 2-(4-chlorophenyl)cyclopropane-1,1-dicarboxylic acid diethyl ester 
• 37556-13-1 diethyl (4-chlorobenzyl)malonate 
• 130944-14-8 ethyl 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carboxylate 
• 130944-06-8 ethyl 2-amino-4-(4-chlorophenyl)-7-hydroxy-4H-chromene-3-carboxylate 
• 63140-98-7 acide amino-1 parachlorophenyl-2 cyclopropanecarboxylique cis 
• 63141-02-6 acide amino-1 parachlorophenyl-2 cyclopropanecarboxylique trans chlorhydrate 
• 74444-87-4 acide parachlorophenyl-2 ethoxycarbonyl-1 cyclopropane carboxylique 
• 74444-88-5 2-(4-Chloro-phenyl)-1-isocyanato-cyclopropanecarboxylic acid ethyl ester 
• 74444-85-2 1-Azidocarbonyl-2-(4-chloro-phenyl)-cyclopropanecarboxylic acid 
• 74444-84-1 Potassium; 2-(4-chloro-phenyl)-1-ethoxycarbonyl-cyclopropanecarboxylate 

Relevant academic research and scientific papers

Ball-Milling-Enabled Reactivity of Manganese Metal**

Efforts to generate organomanganese reagents under ball-milling conditions have led to the serendipitous discovery that manganese metal can mediate the reductive dimerization of arylidene malonates. The newly uncovered process has been optimized and its mechanism explored using CV measurements, radical trapping experiments, EPR spectroscopy, and solution control reactions. This unique reactivity can also be translated to solution whereupon pre-milling of the manganese is required.

Metal free biomimetic deaminative direct C-C coupling of unprotected primary amines with active methylene compounds

An unprecedented direct C-C coupling reaction of unprotected primary amines with active methylene compounds is reported. The reaction involves a biomimetic deamination of amines which was achieved under conditions free of metallic reagents and strong oxidizing agents. A wide range of primary amines was reacted with different active methylene compounds to provide structurally diverse trisubstituted alkenes and dihydropyridines. A kinetic study revealed an activation barrier of 10.1 kcal mol-1 for the conversion of a key intermediate of the reaction.

Solvent-Free FeCl3-Assisted Electrophilic Fluorine-Catalyzed Knoevenagel Condensation to Yield α,β-Unsaturated Dicarbonyl Compounds and Coumarins

A highly environmentally friendly procedure was developed for the Knoevenagel condensation of aromatic aldehydes with diethyl malonate in the presence of FeCl3 and N-fluorobenzenesulfonimide as a source of electrophilic fluorine under solvent-free conditions. The scope of the reaction was explored using commercially available substrates. The reaction with substituted salicylaldehydes afforded the corresponding coumarin derivatives which attract interest due to their potential medicinal importance.

Organic photocatalysis for the radical couplings of boronic acid derivatives in batch and flow

We report an acridium-based organic photocatalyst as an efficient replacement for iridium-based photocatalysts to oxidise boronic acid derivatives by a single electron process. Furthermore, we applied the developed catalytic system to the synthesis of four active pharmaceutical ingredients (APIs). A straightforward scale up approach using continuous flow photoreactors is also reported affording gram an hour throughput.

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.

Diastereoselective construction of spirocyclic pyrrolidines bearing two quaternary centers via CuII-P, N-Ligand catalyzed 1,3-dipolar cycloaddition

Here, we report a convenient access to diastereoselective synthesis of polysubstituted pyrrolidines bearing a unique spiro quaternary center at the C-2 position and another quaternary center at C-4. The synthesis system, CuII/P, N-Ligand-cataly

Synthesis of monosubstituted 1,1-dicarbonyl ester 1,3-dienes

The synthesis of various electron-deficient 1,1-dicarbonyl ester 1,3-dienes substituted in position 2 or 3 of the diene moiety has been developed. Georg Thieme Verlag Stuttgart. New York.

Design and synthesis of 6-oxo-1,4,5,6-tetrahydropyrimidine-5-carboxylate derivatives as neuraminidase inhibitors

A series of 6-oxo-1,4,5,6-tetrahydropyrimidine-5-carboxylate derivatives were prepared to evaluate their ability of inhibiting neuraminidase (NA) of influenza A virus. All the compounds were synthesized in good yields starting from aldehyde by using a suitable synthetic strategy, which showed moderate inhibitory activity against influenza A NA. Compound 6g exhibited the strongest inhibitory activity against influenza virus A NA (IC50 = 17.64 μM), which indicated pyrimidine ring could be used as a core structure to design novel influenza NA inhibitors.

Synthesis of nitrogen heterocycles via α-aminoalkyl radicals generated from α-silyl secondary amines under visible light irradiation

We have succeeded in the visible light-mediated synthetic use of α-aminoalkyl radicals derived from α-silyl secondary amines toward addition to α,β-unsaturated carbonyl compounds. The resulting γ-aminocarbonyl compounds are converted into γ-lactams and pyrroles in a one-pot process. This journal is the Partner Organisations 2014.

Integration of heterogeneous catalysts into complex synthetic routes: Sequential vs. one-pot reactions in a (Knoevenagel + Mukaiyama-Michael + hydrogenation + transesterification) sequence

Heterogeneous catalysts of different nature can be combined in one-pot tandem reactions, but the compatibility issues of catalysts with reagents, products, and by-products make more convenient the application of a sequential procedure, in which the catalyst is filtered after each reaction and the crude is used in the following reaction without purification. In this way the recovery and reuse of each catalyst can be optimized to obtain the maximum productivity. The nature of the reactions, and the catalysts involved in them, conditions the maximum number of successive steps in the sequence. In the case of the (Knoevenagel + Mukaiyama-Michael + hydrogenation + transesterification) process tested in this work, the optimal results are obtained when the sequential method is applied to only three reactions, whereas the four reactions sequence shows limitations in the yield of the last transesterification step. The Royal Society of Chemistry 2013.