Month: February 2023

A Novel Base-Solvent Controlled Chemoselective Azide Attack on an Ester Group versus Keto in Alkyl 3-Substituted 3-Oxopropanoates: Mechanistic Insights was written by Pokhodylo, Nazariy T.;Shyyka, Olga Ya.;Matiychuk, Vasyl S.;Obushak, Mykola D.;Pavlyuk, Volodymyr V.. And the article was included in ChemistrySelect in 2017.Recommanded Product: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate This article mentions the following:

During the exploration of arylazides reactions with alkyl 3-substituted-3-oxopropanoates under the Dimroth reaction conditions (MeONa-MeOH) azide attack on ester group vs. keto was found out in few examples yielding stable 3-alkyl-2-diazo-3-oxo-N-(aryl)propanamides instead of obvious target 1-aryl-5-alkyl-1H-1,2,3-triazole-4-carboxylic acids. The formation of diazo compounds was observed in case of 3-(4,4-diethoxymethyl)-, isopropyl-, cyclopropyl-3-oxopropanoate in the reaction with arylazides, especially, those containing electron-withdrawing substituents. Influence of the base-solvent system on yields of diazo products was investigated and mechanistic insights of Dimroth reaction were discussed. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8Recommanded Product: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate).

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Liquid esters of low volatility serve as softening agents for resins and plastics. Esters also include many industrially important polymers. Polymethyl methacrylate is a glass substitute sold under the names Lucite and Plexiglas; polyethylene terephthalate is used as a film (Mylar) and as textile fibres sold as Terylene, Fortrel, and Dacron.Recommanded Product: Ethyl 3-oxo-3-(thiophen-2-yl)propanoate

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

Three-component coupling using arynes and DMF: straightforward access to coumarins via ortho-quinone methides was written by Yoshida, Hiroto;Ito, Yu;Ohshita, Joji. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2011.SDS of cas: 1190-39-2 This article mentions the following:

ortho-Quinone methides, arising from a formal [2+2] cycloaddition between arynes and DMF, were found to facilely undergo a [4+2] cycloaddition with ester enolates or ketenimine anions to produce diverse coumarins in a straightforward manner. E.g., coumarin derivative I was prepared with 79% yield by reacting CH₂(CO₂Et)₂ and F₃CSO₂O-2-C₆H₄SiMe₃ with Me₂NCHO using KF at 80°. In the experiment, the researchers used many compounds, for example, malonic acid dibutyl ester (cas: 1190-39-2SDS of cas: 1190-39-2).

malonic acid dibutyl ester (cas: 1190-39-2) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.SDS of cas: 1190-39-2

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

Aglycone Ebselen and β-D-Xyloside Primed Glycosaminoglycans Co-contribute to Ebselen β-D-Xyloside-Induced Cytotoxicity was written by Tang, Yang;Zhang, Siqi;Chang, Yajing;Fan, Dacheng;De Agostini, Ariane;Zhang, Lijuan;Jiang, Tao. And the article was included in Journal of Medicinal Chemistry in 2018.Application In Synthesis of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate This article mentions the following:

Most β-D-xylosides with hydrophobic aglycons are nontoxic primers for glycosaminoglycan assembly in animal cells. However, when Ebselen was conjugated to D-xylose, D-glucose, D-galactose, and D-lactose (8A-D), only Ebselen β-D-xyloside (8A) showed significant cytotoxicity in human cancer cells. The following facts indicated that the aglycon Ebselen and β-D-xyloside primed glycosaminoglycans co-contributed to the observed cytotoxicity: 1. Ebselen induced S phase cell cycle arrest, whereas 8A induced G2/M cell cycle arrest; 2. 8A augmented early and late phase cancer cell apoptosis significantly compared to that of Ebselen and 8B-D; 3. Both 8A and phenyl-β-D-xyloside primed glycosaminoglycans with similar disaccharide compositions in CHO-pgsA745 cells; 4. Glycosaminoglycans could be detected inside of cells only when treated with 8A, indicating Ebselen contributed to the unique property of intracellular localization of the primed glycosaminoglycans. Thus, 8A represents a lead compound for the development of novel antitumor strategy by targeting glycosaminoglycans. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4Application In Synthesis of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Polyesters are important plastics, with monomers linked by ester moieties. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Application In Synthesis of (2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

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

Aggregation behavior of polystyrene-b-poly(acrylic acid) at the air-water interface was written by Wang, Xiaolu;Ma, Xiaoyan;Zang, Duyang. And the article was included in Soft Matter in 2013.Recommanded Product: Benzyl benzodithioate This article mentions the following:

The aggregation behavior of amphiphilic block copolymer polystyrene-b-poly(acrylic acid) (PS-b-PAA) at the air-water interface was investigated through surface pressure measurements (isotherms, compression-expansion hysteresis and compression relaxation experiments), Brewster Angle Microscopy (BAM) imaging and Atomic Force Microscopy (AFM) imaging. It is found that PS-b-PAA (M_n = 11 490 g mol^-1, PAA wt%∼62%) forms a stable Langmuir monolayer on the water surface (pH = 7) by using N,N-dimethylformamide (DMF) as the spreading solvent. The aggregation of block copolymer is induced by an initial diffusion of DMF into water from the interface. Upon compression of the film, the pseudoplateau observed in the Langmuir isotherm corresponds to a “pancake-to-brush” transition with the PAA chains gradually dissolving in the water subphase and stretching underneath the PS cores. Based on the isotherms and the BAM images, it is suggested that the polymer chain dynamics in spreading solutions with different concentrations at the time of solvent diffusion influence the interfacial behavior of block copolymers significantly. The Langmuir-Blodgett (LB) films prepared at different surface pressures from different spreading solution concentrations were scanned by AFM. A variety of morphologies such as wormlike, porous and reticulate structures, and dots were observed The isotherms and AFM images show the spreading solution concentration and surface pressure dependence of the aggregation behavior of PS-b-PAA copolymer at the air-water interface. In the experiment, the researchers used many compounds, for example, Benzyl benzodithioate (cas: 27249-90-7Recommanded Product: Benzyl benzodithioate).

Benzyl benzodithioate (cas: 27249-90-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Recommanded Product: Benzyl benzodithioate

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

One-pot ozonolytic synthesis of acyclic α,ω-bifunctional compounds from methyl 10-undecenoate and 10-undecen-1-ol was written by Legostaeva, Yu. V.;Botsman, L. P.;Nazarov, I. S.;Yakovleva, M. P.;Garifullina, L. R.;Khalikov, R. M.;Ishmuratov, G. Yu.. And the article was included in Russian Journal of Applied Chemistry in 2015.Category: esters-buliding-blocks This article mentions the following:

Transformations of peroxy products formed by ozonolysis of undecylenic acid derivatives (Me ester and hydride reduction product, 10-undecen-1-ol) in various protic and aprotic solvents (MeOH, PrⁱOH, THF, 1: 5 AcOH-CH₂Cl₂ mixture), occurring under the action of such reductants as hydroxylamine and semicarbazide hydrochlorides, were studied. These reductants exhibit high performance and in some cases high chemoselectivity, which allowed the development of a number of one-pot procedures for the synthesis of acyclic α,ω-bifunctional compounds, the majority of which are widely used in medicine, perfumery, cosmetics, engineering, and chem. industry, e.g., as block synthons in targeted organic synthesis. In the experiment, the researchers used many compounds, for example, Dimethyl decanedioate (cas: 106-79-6Category: esters-buliding-blocks).

Dimethyl decanedioate (cas: 106-79-6) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Category: esters-buliding-blocks

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

LMP2 Inhibitors as a Potential Treatment for Alzheimer’s Disease was written by Bhattarai, Deepak;Lee, Min Jae;Baek, Ahruem;Yeo, In Jun;Miller, Zachary;Baek, Yu Mi;Lee, Sukyeong;Kim, Dong-Eun;Hong, Jin Tae;Kim, Kyung Bo. And the article was included in Journal of Medicinal Chemistry in 2020.Application of 87694-53-9 This article mentions the following:

The immunoproteasome (iP), an inducible proteasome variant harboring three immunosubunits, low mol. mass polypeptide-2 (LMP2), multicatalytic endopeptidase complex subunit-1, and low mol. mass polypeptide-7 (LMP7), is involved in multiple facets of inflammatory responses. We recently reported that YU102, a dual inhibitor of the iP subunit LMP2 and the constitutive proteasome catalytic subunit β1, ameliorates cognitive impairments in mouse models of Alzheimer’s disease (AD) independently of amyloid deposits. To investigate whether inhibition of LMP2 is sufficient to improve the cognitive functions of AD mice, here we prepared 37 YU102 analogs and identified a potent LMP2 inhibitor DB-310 (28) (IC₅₀: 80.6 nM) with improved selectivity and permeability in cells overexpressing ABCB1 transporters. We show that DB-310 induces suppression of IL-1α production in microglia cells and improves cognitive functions in the Tg2576 transgenic mouse model of AD. This study supports that inhibition of LMP2 is a promising therapeutic strategy for treatment of AD. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Application of 87694-53-9).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Application of 87694-53-9

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

Monomer release from surgical guide resins manufactured with different 3D printing devices was written by Kessler, Andreas;Reichl, Franz-Xaver;Folwaczny, Matthias;Hoegg, Christof. And the article was included in Dental Materials in 2020.Application In Synthesis of Dicyclohexyl phthalate This article mentions the following:

The aim of this study was to assess the post curing monomer release of resins applicable for 3D printing of surgical implant guides in dependency of printing technique and storing media using high performance liquidchromatog.Specimens of Nextdent SG, Freeprint Splint. The highest eluted concentration for MMA in methanol was 20.27 ± 8.60μg/mL followed by 12.66 ± 3.38μg/mL of HPMA. HEMA was found at concentration of 11.17 ± 2.43μg/mL in methanol and 1.15 ± 0.11μg/mL in water. TPGDA and TEGDMA reached maximum concentration in methanol of 4.29 ± 0.54μg/mL and 5.07 ± 0.93μg/mL and in water of 0.79 ± 0.19μg/mL and 0.36 ± 0.14μg/mL, resp. Significant difference was found for the material Nextdent SG manufactured on SLA and DLP printing device for THFMA (p = 0.041), TEGDMA (p = 0.026), TPGDA (p = 0.05) and EGDMA (p = 0.06). The amount of monomers released into water did not reach the detection threshold for V-print SG.The study revealed significant influence of the printing technique and resin material on the elution of monomers. The elution in methanol and water was significantly different. While the relative amount of eluted monomers from 3D printed guides is comparable to conventional direct composites and below toxic relevant concentrations, the absolute amount of monomer can rise in a clinic situation due to the size of the guides. In the experiment, the researchers used many compounds, for example, Dicyclohexyl phthalate (cas: 84-61-7Application In Synthesis of Dicyclohexyl phthalate).

Dicyclohexyl phthalate (cas: 84-61-7) belongs to esters. Esters typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. Because of their lack of hydrogen-bond-donating ability, esters do not self-associate. Consequently, esters are more volatile than carboxylic acids of similar molecular weight.Application In Synthesis of Dicyclohexyl phthalate

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

Lipase-catalyzed synthesis of polymeric prodrugs of nonsteroidal anti-inflammatory drugs was written by Qian, Xueqi;Wu, Qi;Xu, Fangli;Lin, Xianfu. And the article was included in Journal of Applied Polymer Science in 2013.Formula: C12H22O4 This article mentions the following:

Because of the potential application of prodrugs of nonsteroidal anti-inflammatory drugs (NSAIDs), Candida antarctica lipase B (CAL-B) catalyzed polycondensation of profen-containing diol monomers and diesters were designed to prepare a series of biodegradable polymeric prodrugs composed of NSAID branches and poly(amide-co-ester) backbone. The structure of the products was confirmed by Fourier transform IR spectroscopy, NMR, and gel permeation chromatog. (GPC). The reaction conditions of polymerization, such as the enzyme source, amount of catalyst, and temperature, were optimized. The mol. weights of resultant copolymers were 2170-13,270 g/mol, with corresponding polydispersities from 1.17 to 2.4. The copolymers had relatively high drug loadings of 44.7-59.7 wt % because every repeat unit contained one drug mol. The strategy of enzymic polymerization appeared to be quite general and accommodated a large number of comonomer substrates with various chain lengths and substituents. The optically pure (R)-naproxen monomer was demonstratively incorporated into the corresponding copolymers with the developed synthesis strategy. The in vitro study showed that the polyester could release the drug effectively under physiol. conditions with enzyme, which indicated that the obtained product could be a promising prodrug for extending pharmacol. effects by delayed drug release. With GPC anal., we confirmed that the prodrug was completely degradable in aqueous solution The attractive features of the copolymer were its high drug loading, biodegradability, and biocompatibility. The high tolerance of the CAL-B toward drug groups, as described in this article, provides a new route for synthesizing polymeric drugs with potential biomedical applications in mild conditions and for reducing environmental impact. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2012. In the experiment, the researchers used many compounds, for example, Dimethyl decanedioate (cas: 106-79-6Formula: C12H22O4).

Dimethyl decanedioate (cas: 106-79-6) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. Esters are more polar than ethers but less polar than alcohols. They participate in hydrogen bonds as hydrogen-bond acceptors, but cannot act as hydrogen-bond donors, unlike their parent alcohols. This ability to participate in hydrogen bonding confers some water-solubility.Formula: C12H22O4

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

Two Functional Porous Metal-Organic Frameworks Constructed from Expanded Tetracarboxylates for Gas Adsorption and Organosulfurs Removal was written by Luo, Xiaolong;Kan, Liang;Li, Xiang;Sun, Libo;Li, Guanghua;Zhao, Jun;Li, Dong-Sheng;Huo, Qisheng;Liu, Yunling. And the article was included in Crystal Growth & Design in 2016.Recommanded Product: Dimethyl 5-ethynylisophthalate This article mentions the following:

Two fof-type porous metal-organic frameworks (MOFs), [Cu₂(bdfdpa)(H₂O)₂]·8DMF·2H₂O (JLU-Liu29) and [Cu₂(btadpa)(H₂O)₂]·7DMF·8H₂O (JLU-Liu30) (H₄bdfdpa = 5,5′-(benzo[1,2-b:4,5-b’]difuran-2,6-diyl)diisophthalic acid and H₄btadpa = 5,5′-(benzo[c][1,2,5]thiadiazole-4,7-diylbis(ethyne-2,1-diyl))diisophthalic acid), have been successfully synthesized by using different expanded tetracarboxylate ligands. Both of them exhibit good permanent porosity and high surface areas of 2205 and 1791 m²g^-1, resp. Due to open metal sites, different functional groups, and suitable pore spaces, the two porous MOFs exhibit high adsorption performance for small mol. gases (CO₂, CH₄, C₂H₆, and C₃H₈) and removal of refractory organosulfur compounds In the experiment, the researchers used many compounds, for example, Dimethyl 5-ethynylisophthalate (cas: 313648-56-5Recommanded Product: Dimethyl 5-ethynylisophthalate).

Dimethyl 5-ethynylisophthalate (cas: 313648-56-5) belongs to esters. Esters perform as high-grade solvents for a broad array of plastics, plasticizers, resins, and lacquers, and are one of the largest classes of synthetic lubricants on the commercial market. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.Recommanded Product: Dimethyl 5-ethynylisophthalate

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

Metathesis cascade strategies (ROM-RCM-CM): a DOS approach to skeletally diverse sultams was written by Jeon, Kyu Ok;Rayabarapu, Dinesh;Rolfe, Alan;Volp, Kelly;Omar, Iman;Hanson, Paul R.. And the article was included in Tetrahedron in 2009.Quality Control of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate This article mentions the following:

The development of a ring-opening metathesis/ring-closing metathesis/cross-metathesis (ROM-RCM-CM) cascade strategy to the synthesis of a diverse collection of bi- and tricyclic sultams is reported. In this study, functionalized sultam scaffolds derived from intramol. Diels-Alder (IMDA) reactions undergo metathesis cascades to yield a collection of tricyclic sultams, e.g. I. Addnl. appendage-based diversity was achieved by utilizing a variety of CM partners. In the experiment, the researchers used many compounds, for example, (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9Quality Control of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Acyl chlorides and acid anhydrides alcoholysis is another way to produce esters. Acyl chlorides and acid anhydrides react with alcohols to produce esters. Anydrous conditions are recommended since both acyl chlorides and acid anhydrides react with water.Quality Control of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

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