Category: esters-buliding-blocks

Identification, optimisation and in vivo evaluation of oxadiazole DGAT-1 inhibitors for the treatment of obesity and diabetes was written by McCoull, William;Addie, Matthew S.;Birch, Alan M.;Birtles, Susan;Buckett, Linda K.;Butlin, Roger J.;Bowker, Suzanne S.;Boyd, Scott;Chapman, Stephen;Davies, Robert D. M.;Donald, Craig S.;Green, Clive P.;Jenner, Chloe;Kemmitt, Paul D.;Leach, Andrew G.;Moody, Graeme C.;Morentin Gutierrez, Pablo;Newcombe, Nicholas J.;Nowak, Thorsten;Packer, Martin J.;Plowright, Alleyn T.;Revill, John;Schofield, Paul;Sheldon, Chris;Stokes, Steve;Turnbull, Andrew V.;Wang, Steven J. Y.;Whalley, David P.;Matthew Wood, J.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.Synthetic Route of C14H11NOS This article mentions the following:

A novel series of DGAT-1 inhibitors was discovered from an oxadiazole amide high throughput screening (HTS) hit. Optimization of potency and ligand lipophilicity efficiency (LLE) resulted in a carboxylic acid containing clin. candidate 53 (AZD3988, I), which demonstrated excellent DGAT-1 potency (0.6 nM), good pharmacokinetics and pre-clin. in vivo efficacy that could be rationalised through a PK/PD relationship. In the experiment, the researchers used many compounds, for example, 3-Benzyloxyphenylisothiocyanate (cas: 206559-36-6Synthetic Route of C14H11NOS).

3-Benzyloxyphenylisothiocyanate (cas: 206559-36-6) 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. 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.Synthetic Route of C14H11NOS

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

Nickel-catalyzed hydroalkylation of 1,3-dienes with malonates using a homoallyl carbonate as the 1,3-diene and hydride source was written by Tsuji, Hiroaki;Takahashi, Yoshiyuki;Kawatsura, Motoi. And the article was included in Tetrahedron Letters in 2021.Electric Literature of C11H20O4 This article mentions the following:

The nickel-catalyzed hydroalkylation of 1,3-dienes with malonates using homoallyl carbonates RCH(OCOOCH₃)CH₂CH=CH₂ (R = 4-chlorophenyl, piperonyl, cyclohexyl, etc.) as the 1,3-diene and hydride source was reported. A broad range of homoally carbonates and malonate derivatives R¹CH(COOR²)₂ (R¹ = H, Ph, Me, i-Bu, etc.; R² = Et, i-Pr, Me, Bn, t-Bu) was well tolerated under a Ni/DPEphos catalyst system, providing the corresponding 1,2-hydroalkylation products RCH=CH₂CH(CH₃)CH((COOCH₃)₂)CH₃ in 40-94% yields with excellent regioselectivity. Also, suggested the possible reaction mechanism for the nickel-catalyzed hydroalkylation of in situ generated 1,3-dienes with malonates is suggested. In the experiment, the researchers used many compounds, for example, Diethyl isobutylmalonate (cas: 10203-58-4Electric Literature of C11H20O4).

Diethyl isobutylmalonate (cas: 10203-58-4) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. 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. Electric Literature of C11H20O4

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

Intravenous anesthetics of thiobarbital series. VI. Synthesis of sodium 5-allyl-5-isobutyl-2-thiobarbiturate was written by Abe, Kyuji;Matsui, Kazuo. And the article was included in Tanabe Seiyaku Kenkyu Nenpo in 1957.Related Products of 10203-58-4 This article mentions the following:

Na (11.5 g.) in 200 cc. EtOH is warmed with 80 g. CH₂(CO₂Et)₂ at 40-50°, and the mixture treated with 102 g. iso-BuI over 4 hrs. to afford 74.5 g. di-Et isobutylmalonate (I), b₇ 95-8°. I (45 g.), 4.8 g. Na, and 150 cc. EtOH is warmed to 40-50°, 24.8 g. allyl bromide added over 1 hr., and the mixture boiled 3 hrs. to afford 45.6 g. di-Et isobutylallylmalonate (II), b₇ 114-16°. Isobutylation of di-Et allylmalonate also affords II in 81.9% yield. NCCH₂CO₂Et (57 g.) in a mixture of 11.5 g. Na and 300 cc. alc. treated with 102 g. iso-BuI affords 46.7 g. Et isobutylcyanoacetate (III), b₉ 93-7°. α-Chloroisocaproic acid (15 g.) in 50 cc. H₂O is neutralized by NaHCO₃, heated with 13 g. KCN, evaporated to dryness, a mixture of 26 cc. alc. and 20 cc. concentrated H₂SO₄ added, and the solution boiled 4 hrs. and distilled in vacuo to afford 7.5 g. III. III (42 g.), 5.7 g. Na, and 200 cc. EtOH is treated with 31 g. allyl bromide to afford 41.6 g. Et isobutylallylcyanoacetate (IV), b₁₀ 114-16°. IV (41.6 g.) and 30 g. thiourea in a mixture of 9.2 g. Na and 150 cc. EtOH boiled 6 hrs. and worked up gave 5-isobutyl-5-allyl-4-imino-2-thiobarbiturate (V), yellow, m. 276-8° (dioxane). V is boiled with 150 g. 30% H₂SO₄ to yield 24 g. 5-isobutyl-5-allyl-2-thiobarbiturate (VI), leaves, m. 145-7° (benzene). II (185 g.) and 110 g. thiourea boiled 7 hrs. with a mixture of 33.2 g. Na and 700 cc. MeOH yield VI. VI Na salt, a light yellow powder, is very hygroscopic and soluble in H₂O, and useful as an ultra-short-acting intravenous anesthetic. In the experiment, the researchers used many compounds, for example, Diethyl isobutylmalonate (cas: 10203-58-4Related Products of 10203-58-4).

Diethyl isobutylmalonate (cas: 10203-58-4) 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. 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.Related Products of 10203-58-4

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

Convenient synthesis of 5-arylidene-2-imino-4-thiazolidinone derivatives using microwave irradiation was written by Sarkis, Manal;Tran, Diem-Ngan;Dasso Lang, Maria Chiara;Garbay, Christiane;Braud, Emmanuelle. And the article was included in Synlett in 2014.Quality Control of 4-Fluorobenzylisothiocyanate This article mentions the following:

A concise approach for the preparation of 5-arylidene-2-imino-4-thiazolidinone derivatives, e.g., I, is described. Structurally diverse amines, isothiocyanates, aldehydes, and chloroacetyl chloride were combined under microwave irradiation to afford new 5-arylidene-2-imino-4-thiazolidinone derivatives The one-pot synthesis involves the in situ formation of a thiourea followed by reaction with chloroacetyl chloride and an aldehyde to generate the target compounds In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Quality Control of 4-Fluorobenzylisothiocyanate).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) 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. 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.Quality Control of 4-Fluorobenzylisothiocyanate

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

Machine learning-based prediction of toxicity of organic compounds towards fathead minnow was written by Chen, Xingmei;Dang, Limin;Yang, Hai;Huang, Xianwei;Yu, Xinliang. And the article was included in RSC Advances in 2020.Application In Synthesis of Ethyl 2-hydroxybenzoate This article mentions the following:

Predicting the acute toxicity of a large dataset of diverse chems. against fathead minnows (Pimephales promelas) is challenging. In this paper, 963 organic compounds with acute toxicity towards fathead minnows were split into a training set (482 compounds) and a test set (481 compounds) with an approx. ratio of 1 : 1. Only six mol. descriptors were used to establish the quant. structure-activity/toxicity relationship (QSAR/QSTR) model for 96 h pLC₅₀ through a support vector machine (SVM) along with genetic algorithm. The optimal SVM model (R² = 0.756) was verified using both internal (leave-one-out cross-validation) and external validations. The validation results (q_int² = 0.699 and q_ext² = 0.744) were satisfactory in predicting acute toxicity in fathead minnows compared with other models reported in the literature, although our SVM model has only six mol. descriptors and a large data set for the test set consisting of 481 compounds In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxybenzoate (cas: 118-61-6Application In Synthesis of Ethyl 2-hydroxybenzoate).

Ethyl 2-hydroxybenzoate (cas: 118-61-6) 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. 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.Application In Synthesis of Ethyl 2-hydroxybenzoate

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

Synthesis of 2-arylimidazo[4,5-d][1,2,3]triazoles from a 4-nitroimidazol-5-yl phosphoramidate and aryl isocyanates was written by Taher, A.;Eichenseher, S.;Weaver, G. W.. And the article was included in Tetrahedron Letters in 2000.Quality Control of 3-Cyanophenylisocyanate This article mentions the following:

The synthesis of a series of 2-aryl-2H,4H-imidazo[4,5-d][1,2,3]triazoles is reported. These compounds are obtained in moderate to good yield by reaction of tri-Et N-1-ethyl-2-methyl-4-nitro-1H-imidazol-5-yl phosphoramidate with aryl isocyanates. In the experiment, the researchers used many compounds, for example, 3-Cyanophenylisocyanate (cas: 16413-26-6Quality Control of 3-Cyanophenylisocyanate).

3-Cyanophenylisocyanate (cas: 16413-26-6) 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. 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.Quality Control of 3-Cyanophenylisocyanate

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

Palladium catalyzed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives was written by Krishna Reddy, Singarajanahalli Mundarinti;Prasanna Kumari, Subramaniyan;Selva Ganesan, Subramaniapillai. And the article was included in Tetrahedron Letters in 2021.Reference of 33166-79-9 This article mentions the following:

Palladium catalyzed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biol. significant 4-arylquinolin-2-one or pyrazolone derivatives The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety in the acetonitrile also converted to the corresponding acetophenone derivative In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(m-tolyl)propanoate (cas: 33166-79-9Reference of 33166-79-9).

Ethyl 3-oxo-3-(m-tolyl)propanoate (cas: 33166-79-9) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. 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. Reference of 33166-79-9

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

Effects of highland barley powders with different peeling rates on the rheological properties of dough and sensory, volatile flavor evaluation of bread was written by Zong, Yao;Tian, Shuangqi;Zhang, Yan;Liu, Zixuan;Chen, Zhicheng. And the article was included in Journal of Food Processing and Preservation.HPLC of Formula: 706-14-9 This article mentions the following:

Highland barley has the nutritional characteristics of high protein, high fiber, high vitamin, low fat, and low sugar and is a high-quality cereal crop. In this study, the effect of highland barley powders with different peeling rates on the rheol. properties of dough and bread quality was studied. The ash content in QK0 was as high as 2.19%. After peeling, the ash content decreased significantly. The oil holding capacity of QK4-35% and QK5-35% was lower than that of the control group. From the perspective of health, it was beneficial to the production and promotion of food. The G′ and G” of samples QK4-35% and QK5-35% were relatively close to the control group. The creep and recovery abilities of samples QK4-35% and QK5-35% were better than other highland barley compound doughs. With the increase of the peeling rate of highland barley powder, the overall acceptability of highland barley bread samples increased from 34.9 to 60.1. Highland barley is rich in dietary fiber and β-glucan. To study the influences of highland barley with different peeling rates on the rheol. properties of dough and bread quality, highland barley powder was added with different peeling rates to bread flour. In general, it can be concluded that the addition of highland barley powder endows the bread with more unique flavor substances, thus making the bread more popular among consumers. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9HPLC of Formula: 706-14-9).

5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9) 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. Esterification is the general name for a chemical reaction in which two reactants (typically an alcohol and an acid) form an ester as the reaction product. Esters are common in organic chemistry and biological materials.HPLC of Formula: 706-14-9

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

Towards a better understanding of the evolution of odour-active compounds and the aroma perception of sparkling wines during ageing was written by Martinez-Garcia, Rafael;Mauricio, Juan Carlos;Garcia-Martinez, Teresa;Peinado, Rafael A.;Moreno, Juan. And the article was included in Food Chemistry in 2021.Related Products of 706-14-9 This article mentions the following:

A native veil-forming yeast and a com. yeast strain were used to elaborate sparkling wines by the Champenoise method with a grape variety traditionally used for the production of still wines. Wines aged on lees for fifteen months were sampled at five points and their physicochem. and sensory indexes were analyzed. Unsupervised and supervised statistical techniques were used to establish a comparison between 81 volatile compounds and eight odor descriptors (chem., fruity, floral, fatty, balsamic, vegetal, empyreumatic and spicy). Principal component anal. of both datasets showed good separation among the samples in relation to ageing time and yeast strain. By using a partial least squares regression-based criterion, 38 odor active compounds were selected as the most influential for the ageing factor and out of them, only 27 were unique to certain aroma descriptors. These results contribute to a better understanding of the aroma perception of sparkling wines. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9Related Products of 706-14-9).

5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9) 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.Related Products of 706-14-9

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

Synthesis of sp³-Enriched β-Fluoro Sulfonyl Chlorides was written by Gurbanov, Rustam;Sokolov, Andriy;Golovach, Sergey;Melnykov, Kostiantyn;Dobrydnev, Alexey V.;Grygorenko, Oleksandr O.. And the article was included in Synthesis in 2021.Application of 145576-28-9 This article mentions the following:

A three-step approach to the synthesis of sp³-enriched β-fluoro sulfonyl chlorides starting from alkenes is reported. The method was successfully applied to a wide range of acyclic and cyclic substrates, bearing either an exocyclic or an endocyclic double bond. The procedure worked with a wide range of substrates and tolerated a number of functional and protecting groups. Moreover, the target cyclic compounds were obtained as single cis diastereomers on a multigram scale. The title compounds are promising building blocks for drug discovery that can be used to obtain sp ³-enriched β-fluoro and α,β-unsaturated sulfonamides. In the experiment, the researchers used many compounds, for example, Ethyl 4-methylenecyclohexanecarboxylate (cas: 145576-28-9Application of 145576-28-9).

Ethyl 4-methylenecyclohexanecarboxylate (cas: 145576-28-9) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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 of 145576-28-9

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