4660-80-4

Usage

Uses

Used in Organic Synthesis:
ETHYL 2,3-EPOXYPROPANOATE is used as a key intermediate in the synthesis of various organic compounds, contributing to the development of pharmaceuticals, agrochemicals, and other specialty chemicals. Its reactivity with different chemical agents makes it a valuable building block in the creation of complex molecules.
Used in Food Production:
ETHYL 2,3-EPOXYPROPANOATE is used as a flavoring agent in the food industry, providing a fruity aroma to various food products. Its ability to enhance the taste and smell of food items makes it a popular choice among food manufacturers, despite the need for careful handling due to its potential health risks.
Used in Pharmaceutical Industry:
ETHYL 2,3-EPOXYPROPANOATE is used as a starting material in the synthesis of certain pharmaceutical compounds, playing a crucial role in the development of new drugs. Its versatility in reacting with various chemical groups allows for the creation of a wide range of therapeutic agents.
Used in Agrochemical Industry:
ETHYL 2,3-EPOXYPROPANOATE is used as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its ability to form stable compounds with other chemical entities makes it an essential component in the development of effective crop protection products.

InChI:InChI=1/C5H8O3/c1-2-5(3-8-5)4(6)7/h2-3H2,1H3,(H,6,7)/p-1

Upstream product

• 140-88-5 ethyl acrylate 
• 74-96-4 ethyl bromide 
• 82044-23-3 R-oxiranecarboxylic acid potassium salt 
• 56-45-1 L-serin 
• 75-03-6 ethyl iodide 
• 64-67-5 diethyl sulfate 
• 82079-45-6 potassium de l'acide (S)-(-)-epoxy-2,3 propionique 
• 312-84-5 D-Serine 
• 73245-23-5 dimethyl 1'-methyl-8'-tert-butyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate 
• 73245-21-3 dimethyl 1',8'-dimethyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate 
• 73245-18-8 dimethyl 8'-7',8'-dimethyl-2'-oxospiro(oxirane-2,3'-bicyclo<2,2,2>octa<5,7>diene)-5',6'-dicarboxylate 

Downstream Products

• 111289-58-8 3-(2-Amino-phenylamino)-2-hydroxy-propionic acid ethyl ester 
• 623-72-3 ethyl 3-hydroxypropanoate 
• 145487-86-1 ethyl (2RS)-2-hydroxy-3-N-(R-tetrahydropapaverinyl)propionate 
• 108-95-2 phenol 
• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 
• 1448674-10-9 3-(4-cyanophenoxy)-2-hydroxypropionic acid ethyl ester 
• 1448674-69-8 (R)-3-(4-cyanophenoxy)-2-hydroxypropionic acid ethyl ester 
• 1383618-17-4 C₃₇H₄₄O₁₀P₂ 
• 1010398-42-1 ethyl 3-[6-{[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridin-3-yl}amino]-2-hydroxypropanoate 
• 110994-96-2 (R)-(-)-(Z)-(t-butyldiphenylsiloxy)-2 decene-4 oate d'ethyle 
• 1310717-17-9 C₁₆H₂₄O₄ 
• 1310717-21-5 C₃₇H₄₄O₁₀P₂ 
• 1006376-61-9 (1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester 

Relevant academic research and scientific papers

RUTHENIUM COMPLEX AND PRODUCTION METHOD THEREOF, CATALYST, AND PRODUCTION METHOD OF OXYGEN-CONTAINING COMPOUND

PROBLEM TO BE SOLVED: To provide a ruthenium complex that is particularly useful as a catalyst for oxidizing a substrate having a carbon-hydrogen bond. SOLUTION: The ruthenium complex represented by the general formula (i) or a cis conformer thereof is provided. In the general formula (i), R1 represents H, a phenyl group or a substituted phenyl group; R2 represents H, a phenyl group or an alkyl group; L1 represents halogen or water molecule; L2 represents triphenylphosphine, pyridine, imidazole or dimethylsulfoxide; X represents halogen; and n represents 1 or 2. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT

Poly(Alkyl Glycidate Carbonate)s as Degradable Pressure-Sensitive Adhesives

Insertion of CO2 into the polyacrylate backbone, forming poly(carbonate) analogues, provides an environmentally friendly and biocompatible alternative. The synthesis of five poly(carbonate) analogues of poly(methyl acrylate), poly(ethyl acrylate), and poly(butyl acrylate) is described. The polymers are prepared using the salen cobalt(III) complex catalyzed copolymerization of CO2 and a derivatized oxirane. All the carbonate analogues possess higher glass-transition temperatures (Tg=32 to ?5 °C) than alkyl acrylates (Tg=10 to ?50 °C), however, the carbonate analogues (Td≈230 °C) undergo thermal decomposition at lower temperatures than their acrylate counterparts (Td≈380 °C). The poly(alkyl carbonates) exhibit compositional-dependent adhesivity. The poly(carbonate) analogues degrade into glycerol, alcohol, and CO2 in a time- and pH-dependent manner with the rate of degradation accelerated at higher pH conditions, in contrast to poly(acrylate)s.

SELECTIVE INHIBITORS OF NLRP3 INFLAMMASOME

The present disclosure relates to compounds of Formula (I): (I); and to their pharmaceutically acceptable salts, pharmaceutical compositions, methods of use, and methods for their preparation. The compounds disclosed herein are useful for inhibiting the maturation of cytokines of the IL-1 family by inhibiting inflammasomes and may be used in the treatment of disorders in which inflammasome activity is implicated, such as autoinflammatory and autoimmune diseases and cancers.

Α coccidiosis production of acrylic acid ester

PROBLEM TO BE SOLVED: To provide a production method with which α-acyloxy acrylate can be obtained at high yield using commodity chemicals as raw materials and which is thereby suitable to be used industrially as a method for producing the α-acyloxy acrylate. SOLUTION: The method for producing the α-acyloxy acrylate includes a process for obtaining the α-acyloxy acrylate, which has a specific structure, using glycidic esters that have a specific structure. COPYRIGHT: (C)2012,JPOandINPIT

Total Synthesis of Solandelactone i

Since the marine natural products solandelactones A-I were isolated from the hydroid Solanderia secunda and investigated by Seo et al. in 1996, considerable synthetic efforts toward these marine oxylipins followed. However, the structure elucidation of solandelactone I remained incomplete, and no synthesis has been reported. On the basis of our retrosynthetic analysis, the key building blocks were combined in a Horner-Wadsworth-Emmons reaction to create two common intermediates for the stereodivergent synthesis of all four diastereomers 1-4 matching the proposed structure of solandelactone I. Comparison of the published analytical data of natural product solandelactone I and data obtained from the synthetic endeavor toward diastereomers 1-4 enabled the structure assignment of isomer 3; the proposed biosynthetic pathway for marine oxylipins also supports the result.

Facile synthesis of glycidates via oxidation of acrylates with aqueous solution of naocl in the presence of ammonium salts

Various glycidates were obtained in high yields via green oxidation of acrylates with aqueous solution of NaOCl in the presence of ammonium salts. The appropriate choice of ammonium salts fitting to the polarity of the substrates and the reaction under slightly basic conditions were essential for efficient reactions.

Efficient epoxidation of electron-deficient alkenes with hydrogen peroxide catalyzed by [γ-PW10O38V2(μ-OH) 2]3-

A divanadium-substituted phosphotungstate, [γ-PW10O 38V2(μ-OH)2]3- (I), showed the highest catalytic activity for the H2O2-based epoxidation of allyl acetate among vanadium and tungsten complexes with a turnover number of 210. In the presence of I, various kinds of electron-deficient alkenes with acetate, ether, carbonyl, and chloro groups at the allylic positions could chemoselectively be oxidized to the corresponding epoxides in high yields with only an equimolar amount of H2O2 with respect to the substrates. Even acrylonitrile and methacrylonitrile could be epoxidized without formation of the corresponding amides. In addition, I could rapidly (min) catalyze epoxidation of various kinds of terminal, internal, and cyclic alkenes with H;bsubesubbsubesub& under the stoichiometric conditions. The mechanistic, spectroscopic, and kinetic studies showed that the I-catalyzed epoxidation consists of the following three steps: 1) The reaction of I with H;bsubesubbsubesub& leads to reversible formation of a hydroperoxo species [I;circbsubesubbsubesubbsubesubcirccircbsupesup& (II), 2) the successive dehydration of II forms an active oxygen species with a peroxo group [ 2:2-O2)]3- (III), and 3) III reacts with alkene to form the corresponding epoxide. The kinetic studies showed that the present epoxidation proceeds via III. Catalytic activities of divanadium-substituted polyoxotungstates for epoxidation with H 2O2 were dependent on the different kinds of the heteroatoms (i.e., Si or P) in the catalyst and I was more active than [γ-SiW10O38V2(μ-OH)2] 4-. On the basis of the kinetic, spectroscopic, and computational results, including those of [γ-SiW10O38V 2(μ-OH)2]4-, the acidity of the hydroperoxo species in II would play an important role in the dehydration reactivity (i.e., k3). The largest k3 value of I leads to a significant increase in the catalytic activity of I under the more concentrated conditions. Copyright

Potent inhibitors of a shikimate pathway enzyme from Mycobacterium tuberculosis: Combining mechanism- and modeling-based design

Tuberculosis remains a serious global health threat, with the emergence of multidrug-resistant strains highlighting the urgent need for novel antituberculosis drugs. The enzyme 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase (DAH7PS) catalyzes the first step of the shikimate pathway for the biosynthesis of aromatic compounds. This pathway has been shown to be essential in Mycobacterium tuberculosis, the pathogen responsible for tuberculosis. DAH7PS catalyzes a condensation reaction between P-enolpyruvate and erythrose 4-phosphate to give 3-deoxy-D-arabino-heptulosonate 7-phosphate. The enzyme reaction mechanism is proposed to include a tetrahedral intermediate, which is formed by attack of an active site water on the central carbon of P-enolpyruvate during the course of the reaction. Molecular modeling of this intermediate into the active site reported in this study shows a configurational preference consistent with water attack from the re face of P-enolpyruvate. Based on this model, we designed and synthesized an inhibitor of DAH7PS that mimics this reaction intermediate. Both enantiomers of this intermediate mimic were potent inhibitors of M. tuberculosis DAH7PS, with inhibitory constants in the nanomolar range. The crystal structure of the DAH7PS-inhibitor complex was solved to 2.35 A. Both the position of the inhibitor and the conformational changes of active site residues observed in this structure correspond closely to the predictions from the intermediate modeling. This structure also identifies a water molecule that is located in the appropriate position to attack the re face of P-enolpyruvate during the course of the reaction, allowing the catalytic mechanism for this enzyme to be clearly defined.

Epoxidation of α,β-unsaturated esters by dimejhyldioxirane

Kinetic data for the epoxidation of a series of α,β-unsaturated esters, 2-10, by dimethyldioxirane in dried acetone are reported. These epoxidations are less sensitive to steric effects and occur with lower k 2 values than those for simple alkenes. Relative reactivity could be modeled based on a spiro transition state mechanism. The density function calculations were in good agreement with the krel values except for those compounds with cis-β-substituents.

A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1- tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2- fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, starting from ethyl acrylate. The successful radiosynthesis of [18F]-1 and [18F]-ent-1 is also reported.