Esters-buliding-blocks

Barbituric acids. I. Synthesis of methylenebis(5-alkyl-barbituric acids) was written by Levina, R. Ya.;Godovikov, N. N.. And the article was included in Zhurnal Obshchei Khimii in 1954.Product Details of 10203-58-4 This article mentions the following:

CH₂(CO₂Et)₂ with paraform and 10% alc. KOH gave 60-70% CH₂[CH(CO₂Et)₂]₂ (I), b₅ 174-5°, n²⁰_D 1.4425, d₂₀ 1.119; mercuration with Hg(OAc)₂ gave the di-HgCl derivative, decompose 165-7° (from EtOH-Me₂CO). I (34 g.) added to 4.6 g. Na in 150 ml. dry EtOH, then RX added dropwise (the heating being interrupted for the addition), and the mixture heated until the basic reaction had nearly disappeared gave by the usual treatment the following (EtO₂C)₂CRCH₂CR'(CO₂Et)₂, (R, R’, % yield, b.p./mm., and n²⁰_D shown): Me, Me, 30.8, 190-1°/10, 1.4470; H, Me, 11.5, 78-9°/10, 1.4132; H, Et, 30.5, 74-5°/3, 1.4152; Et, Et, -, – (m. 62-3°), -; H, Pr, 32.3, 114-16°/3, 1.4198; Pr, Pr, 40, 206-8°/11 (m. 41-2°), -; Bu, Bu, 37.4, 198-9°/5, 1.4522; H, Bu, 30, 124-8°/18, 1.4226; H, PhCH₂, not isolated; PhCH₂,PhCH₂, 17, 240-5°/4 (m. 44°), -. The reactions yielded minor amounts of the polymers of I, m. 156° [cf. Bottomley and Perkin, J. Chem. Soc. 77, 306(1900)]. Alkylation attempts with iso-PrX, iso-BuX, iso-AmX (where X is halide), and cyclohexyl chloride, failed; only the corresponding RCH(CO₂Et)₂, polymer of I, and unreacted starting material were isolated. The reaction of the dialkylated esters with urea in the presence of EtONa yielded the following, 5,5′-methylenebis(5,1-alkylbarbituric acids) (alkyl group shown): H, 45%, decompose 300°; Me, 44.8%, m. 252-3°; Et, 61.7%, decompose 364-5°; Pr, 56.2%, decompose 358-9°; Bu, 25.4%, m. 235-8°; PhCH₂, 15.3%, m. 210-11°. The ring closures were run 18 hrs. at 120°. In the experiment, the researchers used many compounds, for example, Diethyl isobutylmalonate (cas: 10203-58-4Product Details of 10203-58-4).

Diethyl isobutylmalonate (cas: 10203-58-4) 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.Product Details of 10203-58-4

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

Combined bioderivatization and engineering approach to improve the efficiency of geraniol production was written by Wang, Xun;Xiao, Longjie;Zhang, Xinyi;Zhang, Jia;Zhang, Yu;Wang, Fei;Li, Xun. And the article was included in Green Chemistry in 2022.Recommanded Product: (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate This article mentions the following:

Constructing microbial factories offers a sustainable strategy for terpenoid synthesis; however, the accumulation of terpenoid products is often toxic to cells and hampers production yields. Here, we developed a bioderivatization strategy that successfully alleviates the toxicity of the end-product and maximizes the biochem. production of geraniol in Escherichia coli. We observed that the conversion of geraniol to less toxic geranyl acetate, which is an esterified derivative of geraniol, had a significant pos. effect on productivity. Subsequently, the high concentration and purity of geraniol was recovered by the combined hydrolysis of geranyl acetate and solid phase adsorption. These findings demonstrate that a combination of bioderivatization and engineering approaches for the biosynthesis of a relatively toxic chem. (geraniol) can mitigate cytotoxicity while further promoting production efficiency. Finally, the maximal titer of these engineering strategies accumulated 13.19 g L^-1 of geraniol by fed-batch fermentation in a 10-L fermentor. This study highlights the ability of this system to address the challenges associated with toxic geraniol accumulation. More broadly, the developed approach could also be considered for metabolic engineering of other similar chems. In the experiment, the researchers used many compounds, for example, (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3Recommanded Product: (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate).

(E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3) 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.Recommanded Product: (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate

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

[Bis(2-methoxyethyl)amino]sulfur trifluoride, the Deoxo-Fluor reagent: application toward one-flask transformations of carboxylic acids to amides was written by White, Jonathan M.;Tunoori, Ashok Rao;Turunen, Brandon J.;Georg, Gunda I.. And the article was included in Journal of Organic Chemistry in 2004.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate This article mentions the following:

The use of the Deoxo-Fluor reagent is a versatile method for acyl fluoride generation and subsequent one-flask amide coupling. It provides mild conditions and facile purification of the desired products in good to excellent yields. The utility of this reagent was explored for the one-flask conversion of acids to amides and Weinreb amides and as a peptide-coupling reagent. 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 In Synthesis 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 typically have a pleasant smell; those of low molecular weight are commonly used as fragrances and are found in essential oils and pheromones. 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.Application In Synthesis of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

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

Evaluation of stereochemically dense morpholine-based scaffolds as proline surrogates in β-turn peptides was written by Sladojevich, Filippo;Guarna, Antonio;Trabocchi, Andrea. And the article was included in Organic & Biomolecular Chemistry in 2010.Product Details of 133467-01-3 This article mentions the following:

Four peptides differing for the structure of the new morpholine-based heterocyclic compound acting as a turn inducer were synthesized in solution phase, and the conformational preferences were assessed by means of NMR anal. All spectroscopic data revealed an adaptive behavior of the turn peptides in generating turn conformations stabilized by intramol. hydrogen-bonds, despite the conformational changes of the turn inducer. Thus, this study suggests the possibility of functionalizing morpholine-containing β-turn peptides with no significant loss of the secondary framework. The 3,4-dihydro-2H-[1,4]oxazine-containing peptide showed a more compact structure stabilized by an addnl. γ-turn-forming hydrogen-bond experienced by the Gly amide proton. In the experiment, the researchers used many compounds, for example, Boc-D-Leu-OMe (cas: 133467-01-3Product Details of 133467-01-3).

Boc-D-Leu-OMe (cas: 133467-01-3) belongs to esters. Carboxylic acid esters of low molecular weight are colourless, volatile liquids with pleasant odours, slightly soluble in water. 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.Product Details of 133467-01-3

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

Synthesis of Glycosylated 1-Deoxynojirimycins Starting from Natural and Synthetic Disaccharides was written by Liu, Bing;van Mechelen, Jeanine;van den Berg, Richard J. B. H. N.;van den Nieuwendijk, Adrianus M. C. H.;Aerts, Johannes M. F. G.;van der Marel, Gijsbert A.;Codee, Jeroen D. C.;Overkleeft, Herman S.. And the article was included in European Journal of Organic Chemistry in 2019.Synthetic Route of C16H22O11 This article mentions the following:

Iminosugars are an important class of natural products and have been subject to extensive studies in organic synthesis, bio-organic chem. and medicinal chem., yet only a limited number of these studies are on glycosylated iminosugars. Here, a general route of synthesis is presented towards glycosylated 1-deoxynojirimycin derivatives based on the oxidation-reductive amination protocol that in the past has also been shown to be a versatile route towards 1-deoxynojirimycin. The strategy can be applied on com. disaccharides, as shown in four examples, as well as on disaccharides that are not com. available and are synthesized for this purpose, as shown by a fifth example. 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: 4163-60-4Synthetic Route of C16H22O11).

(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. 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.Synthetic Route of C16H22O11

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

Tipranavir analogous 3-sulfonylanilidotetronic acids: new synthesis and structure-dependent anti-HIV activity was written by Schobert, Rainer;Stehle, Ralf;Walter, Hauke. And the article was included in Tetrahedron in 2008.Computed Properties of C11H14O3 This article mentions the following:

Sulfonamide-containing tetronic acids I [R¹ = Me, Ph, R² = Me, H, R¹R² = (CH₂)₅, R³ = H, F, Cl, Me], structural analogs of the HIV-1 protease inhibitor tipranavir, were synthesized in five steps including a microwave-assisted Claisen rearrangement of cinnamyl tetronates and a modified Charette cyclopropanation of the so-formed 3-allyltetronic acids. Compounds I with two non-H residues (R¹, R²) at C-5 of the tetronate core exhibited structure-dependent antiviral activity in two HIV strains. Derivatives I (R¹ = R² = Me, R³ = Cl) and I [R¹R² = (CH₂)₅, R³ = Me] were most active (IC₅₀<10 μM) in the sensitive strain HIV_NL4-3. In the experiment, the researchers used many compounds, for example, Benzyl 2-hydroxy-2-methylpropanoate (cas: 19444-23-6Computed Properties of C11H14O3).

Benzyl 2-hydroxy-2-methylpropanoate (cas: 19444-23-6) 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. Computed Properties of C11H14O3

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

Metal- and Additive-Free Intermolecular Aziridination of Olefins Using N-Boc-O-tosylhydroxylamine was written by Jat, Jawahar L.;Chandra, Dinesh;Kumar, Puneet;Singh, Vikram;Tiwari, Bhoopendra. And the article was included in Synthesis in 2022.Synthetic Route of C12H20O2 This article mentions the following:

A metal and additive-free stereospecific direct N-H and N-Me aziridination of inactivated olefins was disclosed using N-Boc- O-tosylhydroxylamine (TsONHBoc) as an aminating agent in hexafluoroisopropanol (HFIP) to gave aziridine derivatives such as I [R¹ = H, Me; R² = Et, Bz, octyl, etc.; R³ = H, Me; R⁴ = H, Me, Ph, etc.; R²R⁴ = (CH₂)₄, (CH₂)₆]. The use of TsONHBoc, which generates the free aminating agent in situ under the reaction conditions, had several inherent advantages over other similar agents, such as low cost, easy access, and stability (non-explosiveness) during storage over a longer time. In the experiment, the researchers used many compounds, for example, (E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3Synthetic Route of C12H20O2).

(E)-3,7-Dimethylocta-2,6-dien-1-yl acetate (cas: 105-87-3) 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. 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.Synthetic Route of C12H20O2

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

Signaling in the tomato immunity against Fusarium oxysporum was written by Hernandez-Aparicio, Francisco;Lison, Purificacion;Rodrigo, Ismael;Belles, Jose Maria;Lopez-Gresa, M. Pilar. And the article was included in Molecules in 2021.Name: Ethyl 2-hydroxybenzoate This article mentions the following:

New strategies of control need to be developed with the aim of economic and environmental sustainability in plant and crop protection. Metabolomics is an excellent platform for both understanding the complex plant-pathogen interactions and unraveling new chem. control strategies. GC-MS-based metabolomics, along with a phytohormone anal. of a compatible and incompatible interaction between tomato plants and Fusarium oxysporum f. sp. lycopersici, revealed the specific volatile chem. composition and the plant signals associated with them. The susceptible tomato plants were characterized by the over-emission of methyl- and ethyl-salicylate as well as some fatty acid derivatives, along with an activation of salicylic acid and abscisic acid signaling. In contrast, terpenoids, benzenoids, and 2-ethylhexanoic acid were differentially emitted by plants undergoing an incompatible interaction, together with the activation of the jasmonic acid (JA) pathway. In accordance with this response, a higher expression of several genes participating in the biosynthesis of these volatiles, such as MTS1, TomloxC, TomloxD, and AOS, as well as JAZ7, a JA marker gene, was found to be induced by the fungus in these resistant plants. The characterized metabolome of the immune tomato plants could lead to the development of new resistance inducers against Fusarium wilt treatment. In the experiment, the researchers used many compounds, for example, Ethyl 2-hydroxybenzoate (cas: 118-61-6Name: Ethyl 2-hydroxybenzoate).

Ethyl 2-hydroxybenzoate (cas: 118-61-6) 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 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.Name: Ethyl 2-hydroxybenzoate

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

Palladium-Catalyzed Decarboxylative γ-Arylation for the Synthesis of Tetrasubstituted Chiral Allenes was written by Scheipers, Ina;Mueck-Lichtenfeld, Christian;Studer, Armido. And the article was included in Angewandte Chemie, International Edition in 2019.Name: Methyl2-methylbutyrate This article mentions the following:

An enantiospecific palladium-catalyzed decarboxylative coupling of acyclic β,γ-alkynoic acids with various aryl iodides to chiral tetrasubstituted allenes is described. The coupling reaction comprises a decarboxylative γ-palladation of α,α-disubstituted carboxylic acids to provide the tetrasubstituted allenes with complete point-to-axial chirality transfer in excellent yields. In the experiment, the researchers used many compounds, for example, Methyl2-methylbutyrate (cas: 868-57-5Name: Methyl2-methylbutyrate).

Methyl2-methylbutyrate (cas: 868-57-5) 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. Name: Methyl2-methylbutyrate

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

Carbon suboxide and some of its reactions. XX. Reaction of carbon suboxide with sodium alcoholates was written by Dashkevich, L. B.;Pechenyuk, V. A.. And the article was included in Zhurnal Obshchei Khimii in 1965.Recommanded Product: malonic acid dibutyl ester This article mentions the following:

Passage of C₃O₂ into RONa in ROH gave colorless precipitates, which heated with EtI 4-6 hrs. gave CH₂(CO₂R)₂ and EtCH(CO₂R)₂, resp. (R shown): Me, 91%, b₇₆₂ 179-81°, and 0%; Et, 95%, b₇₅₂ 197-8°, and 0%; Pr, 80%, b₇₆₂ 229-30°, d²⁰₂₀ 0.9798, n²⁰_D 1.4204, and 13.9%, b₇₆₂ 240-1°, 0.9863, 1.4219; Bu, 56%, b₅ 118-20°, 0.9650, 1.4265, and 37.3%, b₅ 130-2°, 0.9531, 1.4281; n-C₆H₁₃, 41.6%, b₆ 143-5°, 0.9211, 1.4370, and 53%, b₆ 168-70°, 0.9053, 1.4310; n-C₇H₁₅, 38.8%, b₇ 173-5°, 0.9228, 1.4365, and 61%, b₇ 190-2°, 0.9159, 1.4388; cyclohexyl, 38.2%, b₁₀ 168-70°, 1.0154, 1.4725, and 46%, b₁₀ 190-1°, 1.0289, 1.4742; n-C₈H₁₇, 0%, and 84.5%, b₇ 209-11°, –, 1.4430. In the experiment, the researchers used many compounds, for example, malonic acid dibutyl ester (cas: 1190-39-2Recommanded Product: malonic acid dibutyl ester).

malonic acid dibutyl ester (cas: 1190-39-2) 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. 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.Recommanded Product: malonic acid dibutyl ester

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