36600-72-3

Basic information

• Product Name: 2-(4-CHLOROBENZYL)ACETOACETIC ACID ETHYL ESTER
• Synonyms: 2-(4-CHLOROBENZYL)ACETOACETIC ACID ETHYL ESTER;2-(4-Chlorobenzyl)-acetic acid ethyl ester;Ethyl 2-(4-chlorobenzyl)-3-oxobutanoate;2-(4-chlorobenzyl)-3-keto-butyric acid ethyl ester;2-[(4-chlorophenyl)methyl]-3-oxobutanoic acid ethyl ester;ethyl 2-[(4-chlorophenyl)methyl]-3-oxobutanoate;ethyl 2-[(4-chlorophenyl)methyl]-3-oxo-butanoate
• CAS NO: 36600-72-3
• Molecular Formula: C₁₃H₁₅ClO₃
• Molecular Weight: 254.71
• Mol File: 36600-72-3.mol

Chemical Properties

• Boiling Point: 180 °C
• Flash Point: 129.5°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 0.000105mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: 2-(4-CHLOROBENZYL)ACETOACETIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-CHLOROBENZYL)ACETOACETIC ACID ETHYL ESTER(36600-72-3)
• EPA Substance Registry System: 2-(4-CHLOROBENZYL)ACETOACETIC ACID ETHYL ESTER(36600-72-3)

Safety Data

• Hazardous Substances Data: 36600-72-3(Hazardous Substances Data)

Usage

Uses

Given the lack of specific applications provided in the materials, the following uses are speculative and would require validation through research and practical application:
Used in Pharmaceutical Industry:
2-(4-Chlorobenzyl)acetoacetic acid ethyl ester could be used as an intermediate in the synthesis of pharmaceutical compounds for [specific medical condition or treatment] due to its unique molecular structure that may allow for specific binding or reactivity with biological targets.
Used in Chemical Research:
In the field of chemical research, 2-(4-Chlorobenzyl)acetoacetic acid ethyl ester might serve as a subject for studying the effects of chlorine substitution on aromatic rings and ester functionalities, potentially leading to new insights into chemical reactivity and compound design.
Used in Material Science:
2-(4-CHLOROBENZYL)ACETOACETIC ACID ETHYL ESTER could be explored in material science applications, such as in the development of new polymers or coatings, where its aromatic and ester groups might contribute to desired material properties like stability, solubility, or adhesion.

InChI:InChI=1/C13H15ClO3/c1-3-17-13(16)12(9(2)15)8-10-4-6-11(14)7-5-10/h4-7,12H,3,8H2,1-2H3

Upstream product

• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 141-97-9 ethyl acetoacetate 
• 622-95-7 4-chlorobenzyl bromide 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 95314-46-8 C₁₉H₁₇ClN₃O₉^(1-)*C₆H₁₅N*H⁽¹⁺⁾ 
• 960312-14-5 3-(4-chlorobenzyl)-5-hydroxy-4,7-dimethylchromen-2-one 
• 219552-28-0 3-(4-Chlorobenzyl)-5,7-dihydroxy-4-methyl-2H-1-benzopyran-2-one 
• 932706-95-1 8-chloro-3-(4-chlorobenzyl)-5-hydroxy-2-methyl-1H-quinolin-4-one 
• 932707-02-3 3-(4-chlorobenzyl)-5-hydroxy-4,7-dimethyl-1H-quinolin-2-one 
• 1034982-05-2 methyl 2-(4-(4-chlorobenzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylate 
• 1091602-31-1 C₁₇H₁₈ClN₃O₄S 
• 95314-45-7 C₁₉H₁₈ClN₃O₉ 
• 611196-98-6 2-(4-chlorobenzyl)-3-methyl-1-oxo-1H,5H-pyrido[1,2-a]benzimidazole-4-carbonitrile 
• 1310264-37-9 6-[(4-chlorophenyl)methyl]-5-methylpyrazolo[1,5-a]pyrimidin-7-ol 
• 702670-02-8 6-[(4-chlorophenyl)methyl]-7-hydroxy-5-methylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid 
• 1370227-02-3 6-[(4-chlorophenyl)methyl]-7-hydroxy-N,5-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1370227-04-5 6-[(4-chlorophenyl)methyl]-7-hydroxy-N,N,5-trimethylpyrazolo[1,5-a]pyrimidine-3-carboxamide 
• 1370227-06-7 6-[(4-chlorophenyl)methyl]-7-hydroxy-5-methyl-N-[(2R)-oxolan-2-ylmethyl]pyrazolo-[1,5-a]pyrimidine-3-carboxamide 

Relevant articles and documents

Development of coumarine derivatives as potent anti-filovirus entry inhibitors targeting viral glycoprotein

Filoviruses, including Ebolavirus (EBOV), Marburgvirus (MARV) and Cuevavirus, cause hemorrhagic fevers in humans with up to 90% mortality rates. In the 2014–2016 West Africa Ebola epidemic, there are 15,261 laboratory confirmed cases and 11,325 total deaths. The lack of effective vaccines and medicines for the prevention and treatment of filovirus infection in humans stresses the urgency to develop antiviral therapeutics against filovirus-associated diseases. Our previous study identified a histamine receptor antagonist compound CP19 as an entry inhibitor against both EBOV and MARV. The preliminary structure-activity relationship (SAR) studies of CP19 showed that its piperidine, coumarin and linker were related with its antiviral activities. In this study, we performed detailed SAR studies on these groups with synthesized CP19 derivatives. We discovered that 1) the piperidine group could be optimized with heterocycles, 2) the substitution groups of C3 and C4 of coumarin should be relatively large hydrophobic groups and 3) the linker part should be least substituted. Based on the SAR analysis, we synthesized compound 32 as a potent entry inhibitor of EBOV and MARV (IC50 = 0.5 μM for EBOV and 1.5 μM for MARV). The mutation studies of Ebola glycoprotein and molecular docking studies showed that the coumarin and its substituted groups of compound 32 bind to the pocket of Ebola glycoprotein in a similar way to the published entry inhibitor compound 118a. However, the carboxamide group of compound 32 does not have strong interaction with N61 as compound 118a does. The coumarin skeleton structure and the binding model of compound 32 elucidated by this study could be utilized to guide further design and optimization of entry inhibitors targeting the filovirus glycoproteins.

TELOMERASE REVERSE TRANSCRIPTASE DEGRADERS AND METHODS OF USE THEREOF

The present disclosure provides TERT inhibitor compounds, a TERT inhibitor linked to a ubiquitin ligase ligand, as well as pharmaceutical compositions thereof. The present disclosure also provides methods of inhibiting telomerase reverse transcriptase (TERT) and methods of treating or preventing a disease or disorder using said compounds and/or compositions.

α-Arylation of Carbonyl Compounds through Oxidative C?C Bond Activation

A synthetically useful approach for the direct α-arylation of carbonyl compounds through a novel oxidative C?C bond activation is reported. This mechanistically unusual process relies on a 1,2-aryl shift and results in all-carbon quaternary centers. The transformation displays broad functional-group tolerance and can in principle also be applied as an asymmetric variant.

Biocatalytic dynamic kinetic reductive resolution with ketoreductase from: Klebsiella pneumoniae: The asymmetric synthesis of functionalized tetrahydropyrans

Ketoreductase from growing cells of Klebsiella pneumoniae (NBRC 3319) acts as an efficient reagent for converting racemic α-benzyl/cinnamyl substituted-β-ketoesters to the corresponding β-hydroxy esters with excellent yields and stereoselectivities (ee and de >99 %). The reactions described herein followed a biocatalytic dynamic kinetic reductive resolution (DKRR) pathway, which is reported for the first time with such substrates. It was found that the enzyme system can accept substituted mono-aryl rings with different electronic natures. In addition, it also accepts a substituted naphthyl ring and heteroaryl ring in the α-position of the parent β-ketoester. The synthesized enantiopure β-hydroxy esters were then synthetically manipulated to valuable tetrahydropyran building blocks.

Five Roads That Converge at the Cyclic Peroxy-Criegee Intermediates: BF3-Catalyzed Synthesis of β-Hydroperoxy-β-peroxylactones

We have discovered synthetic access to β-hydroperoxy-β-peroxylactones via BF3-catalyzed cyclizations of a variety of acyclic precursors, β-ketoesters and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals, with H2O2. Strikingly, independent of the choice of starting material, these reactions converge at the same β-hydroperoxy-β-peroxylactone products, i.e., the peroxy analogues of the previously elusive cyclic Criegee intermediate of the Baeyer-Villiger reaction. Computed thermodynamic parameters for the formation of the β-hydroperoxy-β-peroxylactones from silyl enol ethers, enol acetates, and cyclic acetals confirm that the β-peroxylactones indeed correspond to a deep energy minimum that connects a variety of the interconverting oxygen-rich species at this combined potential energy surface. The target β-hydroperoxy-β-peroxylactones were synthesized from β-ketoesters, and their silyl enol ethers, alkyl enol ethers, enol acetates, and cyclic acetals were obtained in 30-96% yields. These reactions proceed under mild conditions and open synthetic access to a broad selection of β-hydroperoxy-β-peroxylactones that are formed selectively even in those cases when alternative oxidation pathways can be expected. These β-peroxylactones are stable and can be useful for further synthetic transformations.

Antischistosomal Activity of Pyrido[1,2-a]benzimidazole Derivatives and Correlation with Inhibition of β-Hematin Formation

The extensive use of praziquantel against schistosomiasis raises concerns about drug resistance. New therapeutic alternatives targeting critical pathways within the parasite are therefore urgently needed. Hemozoin formation in Schistosoma presents one such target. We assessed the in vitro antischistosomal activity of pyrido[1,2-a]benzimidazoles (PBIs) and investigated correlations with their ability to inhibit β-hematin formation. We further evaluated the in vivo efficacy of representative compounds in experimental mice and conducted pharmacokinetic analysis on the most potent. At 10 μM, 48/57 compounds resulted in >70% mortality of newly transformed schistosomula, whereas 37 of these maintained >60% mortality of adult S. mansoni. No correlations were observed between β-hematin inhibitory and antischistosomal activities against both larval and adult parasites, suggesting possible presence of other target(s) or a mode of inhibition of crystal formation that is not adequately modeled by the assay. The most active compound in vivo showed 58.7 and 61.3% total and female worm burden reduction, respectively. Pharmacokinetic analysis suggested solubility-limited absorption and high hepatic clearance as possible contributors to the modest efficacy despite good in vitro activity. The PBIs evaluated in this report thus merit further optimization to improve their efficacy and to elucidate their possible mode of action.

PYRAZOLOPYRIMIDINE DERIVATIVES AND THE COMPOSITIONS AND METHODS OF TREATMENT REGARDING THE SAME

The present disclosure is directed to pyrazolo[1,5-a]pyrimidine compounds of formula (I), pharmaceutical compositions thereof and methods for modulating or activating a Parkin ligase The present disclosure is also directed to methods of treating and/or reducing the incidence of diseases or conditions related to the activation of Parkin ligase. R21, R22, R23, R24 and R25 are as defined herein.

Alkynylation of heterocyclic compounds using hypervalent iodine reagent

The alkynylation of various nitrogen- and/or sulphur-containing heterocyclic compounds using hypervalent iodine TMS-EBX by utilization of tertiary amines under mild conditions is described. The developed metal-free methodology furnishes the corresponding alkynylated heterocycles bearing quaternary carbon in high yields.

NOVEL BENZIMIDAZOLE DERIVATIVE AND USE THEREOF

The present invention aims to provide a compound capable of inhibiting PCA-1 that can be a target for a novel treatment method of various diseases, and pharmaceutical use of the compound. A compound represented by the formula (I): wherein each symbol is a

Fe(HSO4)3 : An efficient, heterogeneous and reusable catalyst for C-alkylation of β-dicarbonyl compounds

Fe(HSO4)3(FHS) was used as an efficient catalyst for the heterogeneous addition of a series of benzylic and allylic alcohols to various β-dicarbonyl compounds, which afforded moderate to excellent yields of C-alkylated products in 1,2-dichloroethane. In comparison with the previous methods, the present research surprisingly exhibited higher reaction yields without formation of any by-products which could be formed by self-condensation of alcohols. Moreover, the catalyst can be readily recovered and reused up to five times with almost maintained reactivity and yields.