64244-87-7

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLOROCARBONYL-2-METHYL-PROPIONIC ACID ETHYL ESTER is used as a chemical intermediate for the synthesis of various pharmaceuticals, leveraging its reactivity to facilitate the production of different medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 2-CHLOROCARBONYL-2-METHYL-PROPIONIC ACID ETHYL ESTER is utilized as a precursor in the manufacturing of insecticides, herbicides, and fungicides, capitalizing on its ability to undergo chemical reactions to yield other compounds essential for crop protection.
Given the compound's hazardous nature and flammability, it is imperative that 2-CHLOROCARBONYL-2-METHYL-PROPIONIC ACID ETHYL ESTER is handled with caution to ensure safety in both industrial and laboratory settings.

InChI:InChI=1/C7H11ClO3/c1-4-11-6(10)7(2,3)5(8)9/h4H2,1-3H3

Upstream product

• 75-44-5 phosgene 
• 600-00-0 ethyl 2-bromoisobutyrate 
• 1619-62-1 2,2-dimethylmalonic acid diethyl ester 
• 5471-77-2 3-ethoxy-2,2-dimethyl-3-oxopropanoic acid 
• 105-53-3 diethyl malonate 
• 74-88-4 methyl iodide 

Downstream Products

• 7507-43-9 ethyl 2,2-dimethyl-3-oxo-3-(phenylamino)propanoate 
• 24161-58-8 ethyl 2-nitrophenyl dimethylmalonate 
• 135473-84-6 N-(4-N',N'-dimethylaminophenyl)-2-carboethoxy-2-methylpropionamide 
• 135473-85-7 N-(4-fluorophenyl)-2-carboethoxy-2-methylpropionamide 
• 138683-46-2 N-(2,6-Diisopropyl-phenyl)-2,2-dimethyl-malonamic acid ethyl ester 
• 229636-60-6 3-[6-(3-benzylureido)indolin-1-yl]-2,2-dimethyl-3-oxopropanoic acid 
• 403599-98-4 ethyl 3-[6-(3-benzylureido)indolin-1-yl]-2,2-dimethyl-3-oxopropanoate 
• 1026913-43-8 (R,S)-ethyl 3-{3-[6-(3-benzylureido)indolin-1-yl]-2,2-dimethyl-3-oxopropanoylamino}-3-(pyridin-3-yl)propanoate 
• 511-68-2 2,2-dimethyl-cyclohexane-1,3,5-trione 
• 135473-83-5 2-(dimethylamino)-2-oxo-3-(4-dimethylaminophenyl)-5,5-dimethyl-1,3,2-oxazaphosphorinane 
• 135473-82-4 2-(dimethylamino)-2-oxo-3-(4-fluorophenyl)-5,5-dimethyl-1,3,2-oxazaphosphorinane 
• 151451-95-5 2-(Dimethylamino)-3-(p-N,N-dimethylanilino)-5,5-dimethyl-1,3,2-oxazaphosphorinane 
• 135473-86-8 N-(4-N',N'-dimethylaminophenyl)-2-(hydroxymethyl)-2-methylpropylamine 
• 135473-87-9 N-(4-fluorophenyl)-2-(hydroxymethyl)-2-methylpropylamine 

Relevant academic research and scientific papers

Structure-Activity Relationship of Phenylpyrazolones against Trypanosoma cruzi

Chagas disease is a neglected parasitic disease caused by the parasitic protozoan Trypanosoma cruzi and currently affects around 8 million people. Previously, 2-isopropyl-5-(4-methoxy-3-(pyridin-3-yl)phenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (NPD-0227) was discovered to be a sub-micromolar inhibitor (pIC50=6.4) of T. cruzi. So far, SAR investigations of this scaffold have focused on the alkoxy substituent, the pyrazolone nitrogen substituent and the aromatic substituent of the core phenylpyrazolone. In this study, modifications of the phenyldihydropyrazolone scaffold are described. Variations were introduced by installing different substituents on the phenyl core, modifying the geminal dimethyl and installing various bio-isosteres of the dihydropyrazolone group. The anti T. cruzi activity of NPD-0227 could not be surpassed as the most potent compounds show pIC50 values of around 6.3. However, valuable additional SAR data for this interesting scaffold was obtained, and the data suggest that a scaffold hop is feasible as the pyrazolone moiety can be replaced by a oxazole or oxadiazole with minimal loss of activity.

L-alanine derivatives as a5beta1 antagonists

The present invention relates to compounds that inhibit of a5b1 function, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments

Novel malonamide derivatives as αvβ3 antagonists. Syntheses and evaluation of 3-(3-indolin-1-yl-3-oxopropanoyl)aminopropanoic acids on vitronectin interaction with αvβ3

In attempt to find novel integrin of αvβ3 antagonists, we selected SC65811 and its guanidine analogue (1) as lead compounds. Modification of the glycine part of SC65811 led to a new series of malonamide derivatives that exhibited αvβ3 inhibitory activity. Among them, (R,S)-3-{3-[6-(3-benzylureido)indolin-1-yl]-3-oxopropanoylamino}-3- (pyridin-3-yl)propanoic acid (43a) showed not only potent activity with an IC50 value of 3.0 nM but also good selectivity for αvβ3 relative to αIIbβ3, α5β1, and αvβ5 with IC50 values of 19000, 11000, and 14 nM, respectively. Furthermore, optimization of 43a led to the most potent αvβ3 antagonist, (R,S)-3-(3-{6-[(4,5-dihydro-1H-imidazol-2-yl)aminoindolin-1-yl}- 3-oxopropanoylamino)-3-(quinolin-3-yl)propanoic acid (431) with an IC50 value of 0.42 nM. The synthesis and the structure-activity relationships of these malonamide derivatives are presented.

A novel enantioselective synthetic route to omuralide analogues with the potential for species selectivity in proteasome inhibition.

[reaction in text] The building blocks shown can be combined for an enantioselective construction of the simplified omuralide analogue 4 in nine steps, with the use of (R)-atrolactic acid as a recoverable chiral controller.

α-substituted malonester amides: Tools to define the relationship between ACAT inhibition and adrenal toxicity

We prepared a series of α-substituted malonester amides that were evaluated for their ability to inhibit acyl-CoA:cholesterol O-acyl transferase activity in vitro and to lower plasma total cholesterol levels in a variety of cholesterol-fed animal models.

Behaviour of ot-carbethoxy radical generated from the ester of N-hydroxy-2-thiopyridone

Studies on the behaviour of α-carbethoxy radical generated from the ester of N-hydroxy-2-thiopyridone is described.

Study of the Conformational Equilibria of 2-Z-3-Methyl-1,3,2-oxazaphosphorinanes. Steric and Stereoelectronic Influences on the Orientation of the Me2N Substituent on Three-Coordinate Phosphorus

The conformations of a series of 1,3,2-oxazaphosphorinanes containing tree-coordinate phosphorus, 1-9, have been determined by the use of 1H, 31P, and 13C NMR spectroscopy.The rings were substituted at ring nitrogen, N(3), with a methyl group to compare its effect on conformational energies with those of 1,3,2-oxazaphosphorinanes reported earlier that featured a larger substituent at N(3), Ph or i-Pr.Quite expectedly, like those rings previously studied with Ph or i-Pr at N(3), a MeO or (CF3)2CHO substituent at phosphorus has a strong preference to be axial on a chair-form ring, 1-4, cis-7, and cis-8, or pseudoaxial on a ring in a twist/boat conformation, trans-7.However, when Me2N is attached to phosphorus, the newly studied N(3)Me rings display a chair-chair conformational equilibrium, 10 ->///- 11 is opposite to that found for four-coordinate phosphorus containing 1,3,2-oxazaphosphorinanes in which Me2NP(ax)/N(3)Ph repulsions that destabilize 10 appear to be dominant.

CONFORMATIONS OF SATURATED SIX-MEMBERED-RING PHOSPHORUS HETEROCYCLES. SYNTHESES AND X-RAY CRYSTAL STRUCTURES OF TWO 2-(DIMETHYLAMINO)-2-OXO-3-ARYL-5,5-DIMETHYL-1,3,2-OXAZAPHOSPHORINANES

The crystal and molecular structures have been determined for 2-(dimethylamino)-2-oxo-3-(4-fluorophenyl)-5,5-dimethyl-1,3,2-oxazaphosphorinane, 1, and 2-(dimethylamino)-2-oxo-3-(4-dimethylaminophenyl)-5,5-dimethyl-1,3,2-oxazaphosphorinane, 2.Compound 1 cr

An Efficient Synthesis of Some Substituted Vinylic Chloroformates: Reaction Scope and Limitations

2,2-Dichlorovinyl chloroformate is isolated in 50percent distilled yield when chloral is treated with phosgene and zinc dust in 2:1 methyl acetate/ether.The reaction has been extended to other α-chloro and α-bromo aldehydes and ketones in which both other α-positions are occupied by either halo and/or alkyl groups.The reaction fails with hydrogen in an α-position.Examples include the synthesis of Cl2C=C(Me)OC(=O)Cl in 23percent yield, MeC(Cl)=CHOC(=O)Cl (56percent, E:Z=1:1.1), Cl2C=C(C6H5)OC(=O)Cl (66percent), and 2-methyl-1-cyclohexenyl chloroformate (68percent).Similar treatment of α-halo esters gives only the C-acylated products expected from a Reformatsky type reaction, while ketenes are the well known products from α-halo acid chlorides.However, acyl cyanides and acyl phosphonates, with leaving groups intermediate between fluoride and alkoxide, are converted to chloroformates; e.g., Me2C=C(CN)OC(=O)Cl in 67percent yield and Me2C=COC(=O)Cl in 83percent yield.Carbonates and urethans from these chloroformates are of interest as monomers, pesticides, and chemical intermediates.

NITRIC ACID OXIDATION OF 3-PHOSPHONO-3,5,5-TRIMETHYLCYCLOHEXANONE

Ammonium metavanadate catalysed nitric acid oxidation of 3-phosphono-3,5,5-trimethylcyclohexanone 1 gave a mixture of the three dicarboxylic acids 2, 3 and 4 which were characterised by isolation (2) or synthesis (3,4).