Category: esters-buliding-blocks

Zinc-Catalyzed Synthesis of Acylsilanes Using Carboxylic Acids and a Silylborane in the Presence of Pivalic Anhydride was written by Tatsumi, Kenta;Tanabe, Sae;Tsuji, Yasushi;Fujihara, Tetsuaki. And the article was included in Organic Letters in 2019.Computed Properties of C12H22O4 This article mentions the following:

Zn-catalyzed synthesis of acylsilanes using carboxylic acids and a silylborane was achieved in the presence of pivalic anhydride. Various carboxylic acids were converted to the corresponding acylsilanes. The in situ formation of mixed anhydrides was essential in the present reaction. In the experiment, the researchers used many compounds, for example, Dimethyl decanedioate (cas: 106-79-6Computed Properties of C12H22O4).

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. Computed Properties of C12H22O4

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

Synthesis of new “benzyl”-thiourea derivatives and their cyclic analogs with diuretic and saluretic activity was written by Reiter, J.;Toldy, L.;Schaefer, I.;Szondy, E.;Borsy, J.;Lukovits, I.. And the article was included in European Journal of Medicinal Chemistry in 1980.Name: 4-Fluorobenzylisothiocyanate This article mentions the following:

RR¹CHNHCSNR²R³ [I; R = optionally substituted Ph; R¹ = H, Me, Et, Pr, CHMe₂, (CH₂)₆Me, cyclopropyl; R² = H, Me, Et, Bu, cyclohexyl, CH₂CH₂OH; R³ = (CH₂)₃OH, CH₂CHMeOH, CH₂CMe₂OH, CHEtCH₂OH, allyl, CH₂CMe:CH₂, CH₂CH₂OH] and their cyclic derivatives II (X = CH₂, CH₂CH₂, CH₂CHMe, CH₂CMe₂, CHEtCH₂, CH₂CH:CH) with diuretic and saluretic activity were prepared Thus, RR¹CHNH₂ were converted to RR¹CHNCS or RR¹CHNHCS₂Me, which were treated with R²R³NH to give I. Acidic cyclizaton of I using HCl gave II. The quant. structure activity relationships for I and II were determined using the Free-Wilson approach. In the experiment, the researchers used many compounds, for example, 4-Fluorobenzylisothiocyanate (cas: 2740-88-7Name: 4-Fluorobenzylisothiocyanate).

4-Fluorobenzylisothiocyanate (cas: 2740-88-7) 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. 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.Name: 4-Fluorobenzylisothiocyanate

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

Lewis Acid Regulated Divergent Catalytic Reaction between Quinone Imine Ketals (QIKs) and 1,3-Dicarbonyl Compounds: Switchable Access to Multiple Products Including 2-Aryl-1,3-Dicarbonyl Compounds, Indoles, and Benzofurans was written by Chen, Xingyu;Lu, Sixian;Deng, Ping;Chang, Xiaoqiang;Zhao, Yifan;Ma, Yue;Zhang, Dong;Xia, Fei;Yang, Lan;Wang, Jigang;Sun, Peng. And the article was included in Advanced Synthesis & Catalysis in 2022.HPLC of Formula: 13669-10-8 This article mentions the following:

A catalytic Lewis acid regulated reaction between quinone imine ketals (QIKs) and 1,3-dicarbonyl compounds provided a divergent and tunable approach to a variety of skeletons, including a series of 2-aryl-1,3-dicarbonyl compounds, indoles and benzofurans. The use of lithium chloride and ferrous bromide gave C3- or C2-alkylation products of the QIKs. The combination of ferrous bromide and trifluoromethanesulfonic acid delivered indole derivatives Sequential hydrolysis and C3-alkylation occurred in the presence of ytterbium(III) trifluoromethanesulfonate and stoichiometric amounts of water. When the reaction was performed with trifluoromethanesulfonic acid and stoichiometric amounts of water, benzofurans are obtained. This protocol utilizes mild conditions, exhibits regio- and chemoselectivity and has broad functional group tolerance. In the experiment, the researchers used many compounds, for example, Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8HPLC of Formula: 13669-10-8).

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (cas: 13669-10-8) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. 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.HPLC of Formula: 13669-10-8

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

Enantioselective Type II Cycloaddition of Alkynes via C-C Activation of Cyclobutanones: Rapid and Asymmetric Construction of [3.3.1] Bridged Bicycles was written by Hou, Si-Hua;Yu, Xuan;Zhang, Rui;Deng, Lin;Zhang, Mengxi;Prichina, Adriana Y.;Dong, Guangbin. And the article was included in Journal of the American Chemical Society in 2020.Product Details of 98231-07-3 This article mentions the following:

Synthesis of bridged scaffolds via Type II cyclization constitutes substantial challenges due to the intrinsic ring strain accumulated in reaction transition states. Catalytic enantioselective Type II-cyclization methods are even rarer. Here, a detailed study of developing a Rh(I)-catalyzed enantioselective intramol. Type II cyclization of alkynes via C-C activation of cyclobutanones is described. This method offers a rapid approach to access a wide range of functionalized [3.3.1]-bridged bicycles along with an exocyclic olefin and an all-carbon quaternary stereocenter. Excellent enantioselectivity has been achieved using a combination of cationic rhodium(I) and DTBM-segphos. Attributed to the redox neutral and strong acid/base-free reaction conditions, high chemoselectivity has also been observed For the oxygen-tethered substrates, the reaction can proceed at room temperature In addition, partial kinetic resolution has been achieved for substrates with existing stereocenters, forging interesting chiral tricyclic scaffolds. The methylalkyne-derived substrates gave unexpected dimeric structures in good yield with excellent enantioselectivity and complete diastereoselectivity. Furthermore, the bridged bicyclic products can be diversely functionalized through simple transformations. Finally, mechanistic studies reveal a surprising reaction pathway that involves forming a metal-stabilized anti-Bredt olefin intermediate. In the experiment, the researchers used many compounds, for example, Methyl 3,3-dimethoxycyclobutanecarboxylate (cas: 98231-07-3Product Details of 98231-07-3).

Methyl 3,3-dimethoxycyclobutanecarboxylate (cas: 98231-07-3) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. 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.Product Details of 98231-07-3

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

Synthesis of tetrasubstituted symmetrical pyrazines from β-keto γ-amino esters: A mild strategy for self-dimerization of peptides was written by Ganesh Kumar, Mothukuri;Thombare, Varsha J.;Bhaisare, Rupal D.;Adak, Anindita;Gopi, Hosahudya N.. And the article was included in European Journal of Organic Chemistry in 2015.Safety of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate This article mentions the following:

A facile synthesis of highly sym. tetrasubstituted pyrazines through simple aerial oxidation of β-keto γ-amino esters is reported. The scope of the reaction was examined by use of various amino acid side-chain functional groups and peptides. The mild and efficient transformation of β-keto γ-amino esters into pyrazines may serve as an attractive strategy for self-dimerization of peptides. 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: 87694-53-9Safety 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 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. 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. Safety of (S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate

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

Probing α-Amino Aldehydes as Weakly Acidic Pronucleophiles: Direct Access to Quaternary α-Amino Aldehydes by an Enantioselective Michael Addition Catalyzed by Bronsted Bases was written by Garcia-Urricelqui, Ane;de Cozar, Abel;Mielgo, Antonia;Palomo, Claudio. And the article was included in Chemistry – A European Journal in 2021.COA of Formula: C16H24N2O4 This article mentions the following:

The chem. of α-amino aldehydes was expanded beyond their limits by documenting the first direct α-alkylation of α-branched α-amino aldehydes with nitroolefins. The reaction produced densely functionalized products bearing up to two, quaternary and tertiary, vicinal stereocenters with high diastereo- and enantioselectivity. DFT modeling lead to the proposal that intramol. hydrogen bonding between the NH group and the carbonyl oxygen atom in the starting α-amino aldehyde was key for reaction stereocontrol. 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: 87694-53-9COA of Formula: C16H24N2O4).

(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate (cas: 87694-53-9) belongs to esters. Volatile esters with characteristic odours are used in synthetic flavours, perfumes, and cosmetics. Certain volatile esters are used as solvents for lacquers, paints, and varnishes. 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.COA of Formula: C16H24N2O4

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

Concise Stereoselective Synthesis of β-Hydroxy-γ-lactones: (4R,5R)-4-Hydroxy-γ-decalactone from the Japanese Orange Fly and Enantiomers of Arachnid Harvestmen Isolates was written by Gangani, Ashvin J.;Kumar, Praveen;Fernandes, Rodney A.. And the article was included in Journal of Natural Products in 2021.Quality Control of 5-Hexyldihydrofuran-2(3H)-one This article mentions the following:

The naturally occurring (4R,5R)-4-hydroxy-γ-decalactone from the Japanese orange fly and the antipode of (4S,5R)-4-hydroxy-γ-dodecalactone from the harvestmen arachnid and their stereoisomers are synthesized from the chiral pool material D-glucono-δ-lactone in a few steps. The one-pot conversion of the latter to γ-vinyl-β-hydroxy-γ-lactone, cross-metathesis with requisite olefin, and hydrogenation enabled the synthesis of syn-lactones in just a two-pot operation. An addnl. efficient Pd-catalyzed allylic isomerization of γ-vinyl-β-hydroxy-γ-lactone led to the anti-lactones in high yields. In the experiment, the researchers used many compounds, for example, 5-Hexyldihydrofuran-2(3H)-one (cas: 706-14-9Quality Control of 5-Hexyldihydrofuran-2(3H)-one).

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. 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.Quality Control of 5-Hexyldihydrofuran-2(3H)-one

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

S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides was written by Blaszczyk, Stephanie A.;Xiao, Guozhi;Wen, Peng;Hao, Hua;Wu, Jessica;Wang, Bo;Carattino, Francisco;Li, Ziyuan;Glazier, Daniel A.;McCarty, Bethany J.;Liu, Peng;Tang, Weiping. And the article was included in Angewandte Chemie, International Edition in 2019.Product Details of 4163-60-4 This article mentions the following:

The site-selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site-selective acylation at the C2 position of S-glycosides through dispersion interactions between the adamantyl C-H bonds and the π system of the cationic acylated catalyst, which may have broad implications in many other chem. reactions. Because of their stability, chem. orthogonality, and ease of activation for glycosylation, the site-selective acylation of S-glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis. 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: 4163-60-4Product Details of 4163-60-4).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) 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, including apples, durians, pears, bananas, pineapples, and strawberries. 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. Product Details of 4163-60-4

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

An Efficient One-Pot Protocol for Direct Access to Diarylmethyl Thioglycosides with para-Quinone Methides via S -Glycosyl Isothiouronium Salts was written by Dubey, Atul;Mandal, Pintu Kumar. And the article was included in Synlett in 2020.Application of 4163-60-4 This article mentions the following:

An efficient one-pot protocol has been developed for the direct preparation of diarylmethyl thioglycosides starting from per-O-acetylated sugars via glycosyl isothiouronium salts. The one-pot reaction conditions involve rapid conversion of the per-O-acetylated sugar with thiourea in the presence of boron trifluoride etherate as catalyst to give the corresponding glycosyl isothiouronium salt, which is subsequently treated with a para-quinone methide in the presence of a base to give the a diarylmethyl thioglycoside in excellent yield. 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 of 4163-60-4).

(2S,3R,4S,5S,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (cas: 4163-60-4) 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. 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. Application of 4163-60-4

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

Design and synthesis of a peptide that binds specific DNA sequences through simultaneous interaction in the major and minor groove was written by Vazquez, M. Eugenio;Caamano, Ana M.;Martinez-Costas, Jose;Castedo, Luis;Mascarenas, Jose L.. And the article was included in Angewandte Chemie, International Edition in 2001.Formula: C7H8N2O4 This article mentions the following:

A peptide derivative capable of binding to DNA with nanomolar affinity through a bivalent, major-minor groove recognition motif, was synthesized. Distamycin A, a well known tripyrrole antibiotic that binds DNA preferentially at A-T rich sites, was used for the minor groove and the basic region of GCN4, a bZIP protein which binds specifically to the cAMP response element site, for the major groove. A suitable linking of a b-ZIP basic region to a minor groove binding tripyrrole enabled for specific binding to its cognate DNA site. The hybrid compound revealed significantly higher affinity for its designated target DNA sequence than that of its isolated components for their resp. cognate subsites. In the experiment, the researchers used many compounds, for example, Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7Formula: C7H8N2O4).

Ethyl 4-nitro-1H-pyrrole-2-carboxylate (cas: 5930-92-7) 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, 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.Formula: C7H8N2O4

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