718-08-1 Usage
Description
3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER, also known as Ethyl 3-oxo-4-phenylbutanoate, is a synthetic intermediate with a wide range of applications in various industries. It is an organic compound characterized by its ester functional group and a phenyl ring attached to a butyric acid chain. Its unique structure and properties make it a valuable component in the synthesis of various pharmaceutical and chemical compounds.
Uses
Used in Pharmaceutical Industry:
3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER is used as a synthetic intermediate for the preparation of pyrazolone derivatives, which are known for their antiprion properties. These compounds have the potential to inhibit the formation of prion proteins, which are associated with neurodegenerative diseases such as Creutzfeldt-Jakob disease and bovine spongiform encephalopathy (BSE), commonly known as mad cow disease.
Used in Biochemical Research:
In the field of biochemical research, 3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER is used as a precursor for the synthesis of pyrrolinylaminopyrimidine analogs. These analogs act as inhibitors of AP-1 and NF-κB mediated gene expression, which are crucial for regulating various cellular processes, including inflammation, immune response, and cell proliferation. By inhibiting these pathways, pyrrolinylaminopyrimidine analogs can potentially be used to develop treatments for various diseases and conditions, such as cancer and inflammatory disorders.
Used in Chemical Synthesis:
3-OXO-4-PHENYL-BUTYRIC ACID ETHYL ESTER is also utilized in the chemical synthesis industry as a versatile building block for the creation of various organic compounds. Its reactivity and functional groups make it suitable for use in a wide range of chemical reactions, allowing for the development of new and innovative products.
Synthesis Reference(s)
Journal of Medicinal Chemistry, 44, p. 78, 2001 DOI: 10.1021/jm001034kChemical and Pharmaceutical Bulletin, 30, p. 2440, 1982 DOI: 10.1248/cpb.30.2440
Synthesis
The synthesis of Ethyl 3-oxo-4-phenylbutanoate is as follows:Monoethyl monopotassium malonate (12.9 g, 2.3 equivalents) was mixed with tetrahydrofuran (200 ml), and the mixture was cooled to 5°C. Triethylamine (8.2 g, 2.5 equivalents) and magnesium chloride (8.62 g, 2.8 equivalents) were added, and the mixture was stirred at 5 to 20°C for 3 hours. The reaction mixture was cooled to 5°C. Phenacyl chloride (5 g, 32 mmol, 1 equivalent) was gradually added, and the mixture was stirred at 5 to 20°C for 63 hours. The mixture was cooled to 5°C, and 1 N hydrochloric acid (30 ml) was added. Tetrahydrofuran was evaporated away under reduced pressure, and extraction was carried out with ethyl acetate (50 ml). The organic layer was washed with 1 N hydrochloric acid (30 ml), water (10 ml), saturated aqueous solution of sodium hydrogencarbonate (30 ml) and water (10 ml) in order. The solvent was evaporated away under reduced pressure to obtain the Ethyl 3-oxo-4-phenylbutanoate as a pale yellow oil (5.82 g, yield: 86 %).
Check Digit Verification of cas no
The CAS Registry Mumber 718-08-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 7,1 and 8 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 718-08:
(5*7)+(4*1)+(3*8)+(2*0)+(1*8)=71
71 % 10 = 1
So 718-08-1 is a valid CAS Registry Number.
InChI:InChI=1/C12H14O3/c1-2-15-12(14)9-11(13)8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3
718-08-1Relevant articles and documents
Non-metal Lewis acid-catalyzed cross-Claisen condensation for β-keto esters
Han, Zhengyu,Huang, Hai,Meng, Fuliang,Yang, Zhenkun,Zhang, Tianyu,Zhou, Dapeng
supporting information, p. 9163 - 9166 (2021/11/16)
In this work, we disclose a new catalytic and highly chemoselective cross-Claisen condensation of esters. In the presence of TBSNTf2 as a non-metal Lewis acid, various esters can undergo cross-Claisen condensation to form β-keto esters which are important building blocks. Compared with the traditional Claisen condensation, this process, employing silyl ketene acetals (SKAs) as carbonic nucleophiles to achieve cross-Claisen condensation, requires mild conditions and has good tolerance of functional groups. This journal is
Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds
Pallesen, Jakob S.,Narayanan, Dilip,Tran, Kim T.,Solbak, Sara M. ?.,Marseglia, Giuseppe,S?rensen, Louis M. E.,H?j, Lars J.,Munafò, Federico,Carmona, Rosa M. C.,Garcia, Anthony D.,Desu, Haritha L.,Brambilla, Roberta,Johansen, Tommy N.,Popowicz, Grzegorz M.,Sattler, Michael,Gajhede, Michael,Bach, Anders
supporting information, p. 4623 - 4661 (2021/05/07)
Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.
General [4 + 1] Cyclization Approach to Access 2,2-Disubstituted Tetrahydrofurans Enabled by Electrophilic Bifunctional Peroxides
Gao, Min,Zhao, Yukun,Zhong, Chen,Liu, Shengshu,Liu, Pengkang,Yin, Qi,Hu, Lin
supporting information, p. 5679 - 5684 (2019/08/01)
A general [4 + 1] cyclization reaction of carbonyl nucleophiles with 2-iodomethylallyl peroxides, which function as unique electrophilic oxygen synthons, for the synthesis of a broad range of 2,2-disubstituted tetrahydrofurans is achieved under operationally simple conditions. The unprecedented asymmetric version of such reaction is also realized via chiral auxiliary-assisted cyclization, thus providing a distinct approach to access chiral tetrahydrofurans with high diastereoselectivities. The new method can be applied to the synthesis of core structure of posaconazole drug.
