609-08-5 Archives - Page 2 of 9 - Esters-buliding-blocks

Bagum, Halima’s team published research in Tetrahedron in 2019 | CAS: 609-08-5

Diethyl 2-methylmalonate(cas: 609-08-5) belongs to aliphatic hydrocarbons. Aliphatic hydrocarbons belong to the most abundant fraction in crude oil. Aliphatics molecules are linear or branched open-chain structures such as n-alkanes, isoalkanes, cycloalkanes (naphthenes), terpenes and steranes.Reference of Diethyl 2-methylmalonate

Reference of Diethyl 2-methylmalonateIn 2019 ,《Synthetic access to 3,4-disubstituted pyroglutamates from tetramate derivatives from serine, allo-threonine and cysteine》 appeared in Tetrahedron. The author of the article were Bagum, Halima; Christensen, Kirsten E.; Genov, Miroslav; Pretsch, Alexander; Pretsch, Dagmar; Moloney, Mark G.. The article conveys some information:

A route allowing the conversion of substituted tetramates to 3,4-disubstituted pyroglutamates, making use of Suzuki coupling on an enol mesylate, followed by reduction, is both general and fully stereoselective. In the experiment, the researchers used many compounds, for example, Diethyl 2-methylmalonate(cas: 609-08-5Reference of Diethyl 2-methylmalonate)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Zhang, Jiaxing’s team published research in Tetrahedron in 2019 | CAS: 609-08-5

In 2019,Tetrahedron included an article by Zhang, Jiaxing; Zhao, Gang. Computed Properties of C8H14O4. The article was titled 《Enantioselective Mannich reaction of γ-malonate-substituted α,β-unsaturated esters with N-Boc imines catalyzed by chiral bifunctional thiourea-phosphonium salts》. The information in the text is summarized as follows:

A novel enantioselective Mannich reaction of γ-malonate-substituted α,β-unsaturated esters with N-protected aryl aldimines was realized by using asym. phase-transfer catalysis (APTC). With amino acid-derived bifunctional thiourea-phosphonium salts as a catalyst, a series of enantio-enriched Mannich products were synthesized under very mild and simple reaction conditions with high yields and enantioselectivities. In addition to this study using Diethyl 2-methylmalonate, there are many other studies that have used Diethyl 2-methylmalonate(cas: 609-08-5Computed Properties of C8H14O4) was used in this study.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Faundez, Rodrigo’s team published research in Synthesis in 2019 | CAS: 609-08-5

In 2019,Synthesis included an article by Faundez, Rodrigo; Castillo, Francisco; Preite, Marcelo; Schott, Eduardo; Zarate, Ximena; Manriquez, Juan Manuel; Molins, Elies; Morales-Verdejo, Cesar; Chavez, Ivonne. Name: Diethyl 2-methylmalonate. The article was titled 《Novel and Convenient Synthesis of 2,7-Dialkyl-1,8-dihydro-as-indacenes》. The information in the text is summarized as follows:

A novel and convenient synthetic route towards dialkyl as-indacenes was achieved by alkylation of malonic esters with o-xylylene dibromide, to give the corresponding tetraester, and related diacid. The alkyl groups on the central benzene ring induce intramol., regiospecific cycloeliminations leading selectively to the diketones, the precursors of the corresponding 1,8-dihydro-as-indacenes. The structure of the 2,7-dimethyl-1,8-dihydro-as-indacene was determined by x-ray diffraction. The compound 2,7-diethyl-1,8-dihydro-as-indacene was characterized by 1H NMR, 13C NMR, FT-IR, UV/Vis measurements, electrochem., and elemental anal. On the other hand, quantum chem. computations based on DFT methods were carried out to get insight into the mol. and electronic structures of the studied ligands. TDDFT approach was employed to calculate the vertical excitations and characterize the nature the UV/Vis absorption bands present in the experiments showing a very good agreement between exptl. and calculated values. Finally, the reactivity of the compounds was assessed using the chem. potential (μ), chem. hardness (η), and electrophilicity (ω). Also, the electron-donating (ω -), electron-accepting (ω +), and the net electrophilicity powers (ω ±) indexes were studied. The experimental part of the paper was very detailed, including the reaction process of Diethyl 2-methylmalonate(cas: 609-08-5Name: Diethyl 2-methylmalonate)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Roy, Ashis’s team published research in ChemistrySelect in 2020 | CAS: 609-08-5

Application of 609-08-5In 2020 ,《Novel Pyrimidinone Derivatives Show Anticancer Activity and Induce Apoptosis: Synthesis, SAR and Putative Binding Mode》 appeared in ChemistrySelect. The author of the article were Roy, Ashis; Kundu, Mrinalkanti; Dhar, Pranab; Chakraborty, Arnish; Mukherjee, Soumen; Naskar, Jayatri; Rarhi, Chhanda; Barik, Rajib; Mondal, Susanta Kumar; Wani, Mushtaq Ahmad; Gajbhiye, Rahul; Roy, Kuldeep K.; Maiti, Arup; Manna, Priyadarshi; Adhikari, Susanta. The article conveys some information:

A series of novel bicyclic, substituted pyrimidinone compounds I (R1 = Br, Me, cyclopropyl, etc.; R2 = 4-ClC6H4, cyclohexyl, 1,3-benzothiazol-2-yl, etc.) were designed, synthesized and characterized. In vitro anti-proliferative activity of the synthesized compounds was evaluated against six different human cancer cell lines using MTT assay. Among all twenty four compounds tested, compound II (R3 = Me; R4 = 4-phenylphenyl) exhibited significant cell growth inhibition of human liver cancer cells HepG2 with GIC50 (50% growth inhibitory concentration) value of 120+10 nM and was found to be selective over healthy human embryonic kidney (HEK) cell line (33.1% inhibition at 20μM). Further studies demonstrated that compound II (R3 = Me; R4 = 4-phenylphenyl) induced cell apoptosis in HepG2 cells and resulted in similar effect to Staurosporine, a well known proapoptopic compound widely used to induce apoptosis in various cancer cell lines. Compound II (R3 = Me; R4 = 4-phenylphenyl) also rendered acceptable aqueous solubility (3.5+0.37μM, at pH 7.4) and attractive metabolic stability against human liver microsomes with a half-life of 34.63+0.33 min. Based on the similarity observed between the known tankyrase-1 inhibitors available in literature and compound II (R3 = Me; R4 = 4-phenylphenyl), in silico docking study was performed and the results suggested that the compound interacted with the key amino acid residues present in the tankyrase-1 enzyme active site. After reading the article, we found that the author used Diethyl 2-methylmalonate(cas: 609-08-5Application of 609-08-5)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Morita, Shunya’s team published research in Tetrahedron in 2021 | CAS: 609-08-5

Recommanded Product: 609-08-5In 2021 ,《Intermolecular domino Michael/aldol reactions of α,β-unsaturated esters, aromatic aldehydes, and various nucleophiles promoted with a catalytic amount of a guanidine base in DMSO》 was published in Tetrahedron. The article was written by Morita, Shunya; Yoshimura, Tomoyuki; Matsuo, Jun-ichi. The article contains the following contents:

In DMSO, a catalytic amount of Barton’s base (2-t-butyl-1,1,3,3-tetramethylguanidine, BTMG) effectively catalyzed intermol. three-component reactions of α-unsaturated esters, aldehydes, and carbon-, sulfur-, or nitrogen-pronucleophiles to give three-component addition products with the formation of two new σ-bonds: pronucleophiles and aldehydes reacted with α,β-unsaturated esters at their β-positions and α-positions, resp. Mechanism studies suggested that these reactions proceeded by the first intermol. Michael addition of anionic nucleophiles that were formed from pronucleophiles with a catalytic amount of BTMG, followed by intermol. aldol reactions of transient ester enolates even in the presence of more than stoichiometric amounts of acidic pronucleophiles. High nucleophilicity over Bronsted basicity of transient enolates in polar solvents was observed for transient ester enolates rather than ketone enolates. In the part of experimental materials, we found many familiar compounds, such as Diethyl 2-methylmalonate(cas: 609-08-5Recommanded Product: 609-08-5)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Sarkar, Ramkrishna’s team published research in Langmuir in 2021 | CAS: 609-08-5

SDS of cas: 609-08-5In 2021 ,《Probing Polymer Chain Folding in Solution Using Second Harmonic Light Scattering》 appeared in Langmuir. The author of the article were Sarkar, Ramkrishna; Mishra, Kamini; Harshita; Das, Puspendu Kumar; Ramakrishnan, S.. The article conveys some information:

Periodically grafted amphiphilic copolymers (PGACs) were earlier shown by us to adopt a zigzag folded conformation in the solid state, which enabled the backbone and pendant segments to segregate and occupy alternate layers in a lamellar structure. The conformational transition from a random coil to a zigzag folded chain in solution is an interesting problem, which is largely unexplored. To examine this, an orthogonally clickable parent polyester was sequentially clicked with two types of poly(ethylene glycol) (PEG) segments: one is a simple PEG and the other is a PEG that carries a dipolar chromophore. These two hydrophilic PEG segments, installed in a periodic and alternating fashion along the hydrocarbon-rich (HC) polyester backbone, ensure that the Janus folded chains are formed upon folding and carry chromophoric dipoles oriented along the same direction, thereby generating a large net dipole. The folding-induced alignment of chromophores in solution was followed using second harmonic light scattering (SHLS), wherein the intensity of the frequency-doubled scattered light (I2ω) is measured. Folding was induced by adding a polar solvent, like methanol, to a chloroform solution of the polymer; methanol desolvates the HC backbone but solubilizes the pendant PEG segments, thus inducing folding. The second harmonic intensity (I2ω) increased initially with methanol concentration and then saturated; in contrast, I2ω remained invariant with the solvent composition in the case of an analogous model chromophore. Furthermore, in a model PGAC carrying chromophore-bearing PEG segments on every repeat unit, I2ω decreased with increasing methanol composition, revealing the formation of a centrosym. folded chain, wherein the chromophoric dipoles on either side cancel each other. Thus, this study clearly reveals that the zigzag chain folding of PGACs can be induced by a segment-selective solvent, resulting in the rather elusive directional ordering of chromophoric dipoles in solution The experimental part of the paper was very detailed, including the reaction process of Diethyl 2-methylmalonate(cas: 609-08-5SDS of cas: 609-08-5)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Ma, Jiajia’s team published research in Nature Catalysis in 2022 | CAS: 609-08-5

Application In Synthesis of Diethyl 2-methylmalonateIn 2022 ,《Facile access to fused 2D/3D rings via intermolecular cascade dearomative [2+2] cycloaddition/rearrangement reactions of quinolines with alkenes》 appeared in Nature Catalysis. The author of the article were Ma, Jiajia; Chen, Shuming; Bellotti, Peter; Wagener, Tobias; Daniliuc, Constantin; Houk, Kendall N.; Glorius, Frank. The article conveys some information:

Two types of energy-transfer-mediated cascade dearomative [2+2] cycloaddition/rearrangement reactions of quinoline derivatives with alkenes, which provide a straightforward avenue to 2D/3D pyridine-fused 6-5-4-3- and 6-4-6-membered ring systems are reported. Notably, this energy-transfer-mediated strategy features excellent diastereoselectivity that bypasses the general reactivity and selectivity issues of photochem. [2+2] cycloaddition of various other aromatics Tuning the aza-arene substitutions enabled selective diversion of the iridium photocatalyzed energy transfer manifold towards either cyclopropanation or cyclobutane-rearrangement products. D. functional theory calculations revealed a cascade energy transfer scenario to be operative. In addition to this study using Diethyl 2-methylmalonate, there are many other studies that have used Diethyl 2-methylmalonate(cas: 609-08-5Application In Synthesis of Diethyl 2-methylmalonate) was used in this study.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Lim, Jieyan’s team published research in Organic Letters in 2021 | CAS: 609-08-5

Category: esters-buliding-blocksIn 2021 ,《Synthesis of the C1-C27 Fragment of Stambomycin D Validates Modular Polyketide Synthase-Based Stereochemical Assignments》 was published in Organic Letters. The article was written by Lim, Jieyan; Chintalapudi, Venkaiah; Gudmundsson, Haraldur G.; Tran, Minh; Bernasconi, Alice; Blanco, Araceli; Song, Lijiang; Challis, Gregory L.; Anderson, Edward A.. The article contains the following contents:

The stambomycins are a family of bioactive macrolides isolated from Streptomyces ambofaciens. Aside from two stereocenters installed through cytochrome P 450 oxidations, their stereochem. has been predicted by sequence anal. of the polyketide synthase. We report a synthesis of the C1-C27 fragment (I) of stambomycin D, the spectroscopic data of which correlates well with that of the natural product, further validating predictive sequence anal. as a powerful tool for stereochem. assignment of complex polyketide natural products.Diethyl 2-methylmalonate(cas: 609-08-5Category: esters-buliding-blocks) was used in this study.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Pickl, Mathias’s team published research in ACS Catalysis in 2019 | CAS: 609-08-5

The author of 《Mechanistic Studies of Fatty Acid Activation by CYP152 Peroxygenases Reveal Unexpected Desaturase Activity》 were Pickl, Mathias; Kurakin, Sara; Cantu Reinhard, Fabian G.; Schmid, Philipp; Poecheim, Alexander; Winkler, Christoph K.; Kroutil, Wolfgang; de Visser, Sam P.; Faber, Kurt. And the article was published in ACS Catalysis in 2019. Reference of Diethyl 2-methylmalonate The author mentioned the following in the article:

The majority of cytochrome P 450 enzymes (CYPs) predominantly operate as monooxygenases, but recently a class of P 450 enzymes was discovered, that can act as peroxygenases (CYP152). These enzymes convert fatty acids through oxidative decarboxylation, yielding terminal alkenes, and through α- and β-hydroxylation to yield hydroxy-fatty acids. Bioderived olefins may serve as biofuels, and hence understanding the mechanism and substrate scope of this class of enzymes is important. In this work, we report on the substrate scope and catalytic promiscuity of CYP OleTJE (CYP152L1) and two of its orthologues from the CYP152 family, utilizing α-monosubstituted branched carboxylic acids. We identify α,β-desaturation as an unexpected dominant pathway for CYP OleTJE with 2-methylbutyric acid. To rationalize product distributions arising from α/β-hydroxylation, oxidative decarboxylation, and desaturation depending on the substrate’s structure and binding pattern, a computational study was performed based on an active site complex of CYP OleTJE containing the heme cofactor in the substrate binding pocket and 2-methylbutyric acid as substrate. It is shown that substrate positioning determines the accessibility of the oxidizing species (Compound I) to the substrate and hence the regio- and chemoselectivity of the reaction. Furthermore, the results show that, for 2-methylbutyric acid, α,β-desaturation is favorable because of a rate-determining α-hydrogen atom abstraction, which cannot proceed to decarboxylation. Moreover, substrate hydroxylation is energetically impeded due to the tight shape and size of the substrate binding pocket. The results came from multiple reactions, including the reaction of Diethyl 2-methylmalonate(cas: 609-08-5Reference of Diethyl 2-methylmalonate)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Xu, Pengwei’s team published research in Nature Chemistry in 2021 | CAS: 609-08-5

Reference of Diethyl 2-methylmalonateIn 2021 ,《Catalytic reductive desymmetrization of malonic esters》 appeared in Nature Chemistry. The author of the article were Xu, Pengwei; Huang, Zhongxing. The article conveys some information:

Here, a dinuclear zinc complex with a tetradentate ligand could selectively hydrosilylate one of the carbonyls of malonic esters to give α-quaternary β-hydroxyesters I [R1 = Me, CH2F, allyl, etc.; R2 = Ph, 3-thienyl, 1-naphthyl, etc.] was reported, providing a promising alternative to the desym. hydrolysis using carboxylesterases. The asym. reduction features excellent enantiocontrol that could differentiate sterically similar substituents and high chemoselectivity toward the diester motif of substrates. Together with the versatile preparation of malonic ester substrates and post-reduction derivatization, the desym. reduction had enabled the synthesis of a diverse array of quaternary stereocenters with distinct structural features. After reading the article, we found that the author used Diethyl 2-methylmalonate(cas: 609-08-5Reference of Diethyl 2-methylmalonate)

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics