Tag: 100-200

Wang, Dongjie; Xu, Xu; Zhang, Jingyu; Zhao, Yingsheng published their research in Journal of Organic Chemistry in 2021. The article was titled 《Ligand Promoted Olefination of Anilides for Indirectly Introducing Fluorinated Functional Groups via Palladium Catalyst》.Reference of Ethyl oxalyl monochloride The article contains the following contents:

A palladium-catalyzed, ligand promoted, C-H fluorine-containing olefination of anilides with 4-bromo-3,3,4,4-tetrafluorobutene as the fluorinated reagent, which was a potential transformation into other compounds due to its -CF2CF2Br functional group. -CF2CF2H was obtained by using the mild reducing agent sodium borohydride. Bioactive compounds such as aminoglutethimide derivative and propham were well-tolerated in this reaction, both of which highlighted the synthetic importance of this method. In addition to this study using Ethyl oxalyl monochloride, there are many other studies that have used Ethyl oxalyl monochloride(cas: 4755-77-5Reference of Ethyl oxalyl monochloride) was used in this study.

Ethyl oxalyl monochloride(cas: 4755-77-5) belongs to acyl chlorides. In the laboratory, acyl chlorides are generally prepared by treating carboxylic acids with thionyl chloride (SOCl2). The reaction is catalyzed by dimethylformamide and other additives.Reference of Ethyl oxalyl monochloride

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

Huang, Ya-Qing; Huang, Xiong-Zhi; Huang, Pei-Qiang published their research in Journal of Organic Chemistry in 2021. The article was titled 《Synthesis of 5-(1-Alkoxyalkylidene)tetronates by Direct Condensation Reactions of Tetronates with Thionolactones and Thionoesters》.Category: esters-buliding-blocks The article contains the following contents:

We report a two-step approach to bicyclic and monocyclic 5-(1-alkoxyalkylidene)tetronates starting from lactones/esters. The method features the use of thionolactones and thionoesters as activated forms of lactones/esters that allows the direct condensation with tetronates via one-pot enolate formation, nucleophilic addition, S-methylation, and DBU-promoted elimination. The value of the method was demonstrated by the stereoselective syntheses of two natural products: 5,6-Z-fadyenolide (Z/E ratio = 6:1) and 9,10-methylenedioxy-5,6-Z-fadyenolide (Z/E ratio = 9:1). The results came from multiple reactions, including the reaction of Methyl 4-fluorobenzoate(cas: 403-33-8Category: esters-buliding-blocks)

Methyl 4-fluorobenzoate(cas: 403-33-8) is an organic fluorinated building block used for the synthesis of various pharmaceutical compounds. It can be used for the preparation of Blonanserin.Category: esters-buliding-blocks

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

《Structure-Based Design, Synthesis, and Biological Evaluation of New Triazolo[1,5-a]Pyrimidine Derivatives as Highly Potent and Orally Active ABCB1 Modulators》 was written by Wang, Shuai; Wang, Sai-Qi; Teng, Qiu-Xu; Yang, Linlin; Lei, Zi-Ning; Yuan, Xiao-Han; Huo, Jun-Feng; Chen, Xiao-Bing; Wang, Mengru; Yu, Bin; Chen, Zhe-Sheng; Liu, Hong-Min. Computed Properties of C7H12O3 And the article was included in Journal of Medicinal Chemistry in 2020. The article conveys some information:

ABCB1 is a promising therapeutic target for overcoming multidrug resistance (MDR). In this work, we reported the structure-based design of triazolo[1,5-a]pyrimidines as new ABCB1 modulators, of which WS-691 significantly increased sensitization of ABCB1-overexpressed SW620/Ad300 cells to paclitaxel (PTX) (IC50 = 22.02 nM). Mechanistic studies indicated that WS-691 significantly increased the intracellular concentration of PTX and [3H]-PTX while decreasing the efflux of [3H]-PTX in SW620/Ad300 cells by inhibiting the efflux function of ABCB1. The cellular thermal shift assay suggested that WS-691 could stabilize ABCB1 by directly binding to ABCB1. WS-691 could stimulate the activity of ABCB1 ATPase but had almost no inhibitory activity against CYP3A4. Importantly, WS-691 increased the sensitivity of SW620/Ad300 cells to PTX in vivo without observed toxicity. Collectively, WS-691(I) is a highly potent and orally active ABCB1 modulator capable of overcoming MDR. The triazolo[1,5-a]pyrimidine may be a promising scaffold for developing more potent ABCB1 modulators.Ethyl 3-oxopentanoate(cas: 4949-44-4Computed Properties of C7H12O3) was used in this study.

Ethyl 3-oxopentanoate(cas: 4949-44-4) belongs to ketone compounds. They are most widely used as solvents, especially in industries manufacturing explosives, lacquers, paints, and textiles. Ketones are also used in tanning, as preservatives, and in hydraulic fluids.Computed Properties of C7H12O3

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

《Complexation of methyl salicylate with β-cyclodextrin and its release characteristics for active food packaging》 was written by Lee, Myungho; Dey, Kartick Prasad; Lee, Youn Suk. Name: Methyl Salicylate And the article was included in Food Science and Biotechnology in 2020. The article conveys some information:

A series of Me salicylate (MeSA)/β-cyclodextrin (β-CD) inclusion complexes (ICs) were prepared at different MeSA concentrations by the co-precipitation method using Me salicylate for maintaining the quality of fresh produce. The formation of IC was confirmed through FTIR, 1H NMR, TGA, and SEM measurements. Among the grades applied, IC with 1:1 grade showed the highest MeSA entrapment efficiency (59%). The release rate of MeSA from an IC was greater at higher temperature and higher relative humidity. In addition, the MeSA release from ICs of all grades followed a diffusive nature and first-order kinetics at 25°C under all RH conditions, except at 7°C. These results indicate that the use of a MeSA/β-CD IC in active packaging applications can effective maintain the quality of fresh produce. In the experiment, the researchers used Methyl Salicylate(cas: 119-36-8Name: Methyl Salicylate)

Methyl Salicylate(cas: 119-36-8) is a natural herbivore-induced plant volatile. It is a naturally occurring product in trees, legumes, exotic plants, vegetables, berries, and the primary constituent of the oil of wintergreen.Methyl Salicylate is produced from salicylic acid.Name: Methyl Salicylate

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

《C-F bond arylation of fluoroarenes catalyzed by Pd0 phosphine complexes: theoretical insight into regioselectivity, reactivity, and prediction of ligands》 was written by Zhong, Rong-Lin. Recommanded Product: Methyl 4-fluorobenzoate And the article was included in Organic Chemistry Frontiers in 2020. The article conveys some information:

Palladium-catalyzed C-F bond arylation of pentafluorobenzene was theor. investigated as an example of aryl-F bond functionalization. DFT computations show that C3-regioselective arylation of pentafluorobenzene occurs more favorably than C1 and C2-ones as reported exptl., through oxidative addition of the C-F bond to Pd0 species, transmetalation and reductive elimination of the C-C bond. Oxidative addition of the C-F bond is the rate-determining and regioselectivity-determining step. The lower energy transition state of the oxidative addition of the C3-F bond (TS-C3) arises from a larger stabilization energy between Pd0(BrettPhos) and distorted pentafluorobenzene moieties in TS-C3 than those in TS-C1 and TS-C2. The larger stabilization energy is a result of a lower σ* orbital energy of the distorted C3-F bond than those of C1-F and C2-F bonds, which leads to a larger charge transfer from the Pd dπ orbital to the σ* orbital of the C3-F bond. The results suggest that both σ* orbital energy and bond dissociation energy are important factors for determining the reactivity of the C-F bond. Also, the activation barriers of the C-F bond with different substitution groups follow the order: NO2 < COOMe < CN ~CF3 < F, which is approx. consistent with the order of electron-withdrawing ability of these groups. It is theor. predicted here that NMe2-substituted BrettPhos is better for C-F bond cleavage than BrettPhos, where three NMe2 groups are introduced to BrettPhos instead of the iso-Pr groups. The experimental part of the paper was very detailed, including the reaction process of Methyl 4-fluorobenzoate(cas: 403-33-8Recommanded Product: Methyl 4-fluorobenzoate)

Methyl 4-fluorobenzoate(cas: 403-33-8) can be used in the synthesis of trisubstituted imidazole derivatives containing a 4-fluorophenyl group, a pyrimidine ring, and a CN- or CONH2-substituted benzyl moiety.Recommanded Product: Methyl 4-fluorobenzoate

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

The author of 《Late-stage peptide C-H alkylation for bioorthogonal C-H activation featuring solid phase peptide synthesis》 were Schischko, Alexandra; Kaplaneris, Nikolaos; Rogge, Torben; Sirvinskaite, Giedre; Son, Jongwoo; Ackermann, Lutz. And the article was published in Nature Communications in 2019. Computed Properties of C10H10O2 The author mentioned the following in the article:

Methods for the late-stage diversification of structurally complex peptides hold enormous potential for advances in drug discovery, agrochem. and pharmaceutical industries. While C-H arylations emerged for peptide modifications, they are largely limited to highly reactive, expensive and/or toxic reagents, such as silver(I) salts, in superstoichiometric quantities. In sharp contrast, we herein establish the ruthenium(II)-catalyzed C-H alkylation on structurally complex peptides. The additive-free ruthenium(II)carboxylate C-H activation manifold is characterized by ample substrate scope, racemization-free conditions and the chemo-selective tolerance of otherwise reactive functional groups, such as electrophilic ketone, bromo, ester, amide and nitro substituents. Mechanistic studies by experiment and computation feature an acid-enabled C-H ruthenation, along with a notable protodemetalation step. The transformative peptide C-H activation regime sets the stage for peptide ligation in solution and proves viable in a bioorthogonal fashion for C-H alkylations on user-friendly supports by means of solid phase peptide syntheses. In addition to this study using Benzyl acrylate, there are many other studies that have used Benzyl acrylate(cas: 2495-35-4Computed Properties of C10H10O2) was used in this study.

Benzyl acrylate(cas: 2495-35-4) is a reagent that can be used in the preparation of 2-(Phosphonomethyl)pentanedioic Acid, a selective glutamate carboxypeptidase 2 (GCP-II) inhibitor. It can also be used in the preparation of high refractive index polyacrylates.Computed Properties of C10H10O2

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

In 2019,Organic Chemistry Frontiers included an article by Jiao, Meng-Jie; Liu, Dan; Hu, Xiu-Qin; Xu, Peng-Fei. Category: esters-buliding-blocks. The article was titled 《Photocatalytic decarboxylative [2+2+1] annulation of 1,6-enynes with N-hydroxyphthalimide esters for the synthesis of indene-containing polycyclic compounds》. The information in the text is summarized as follows:

An efficient photoredox-mediated [2+ 2+1] cascade annulation of 1,6-enynes with N-hydroxyphthalimide esters was reported for the synthesis of a series of indene-containing polycyclic frameworks such as I [R1 = t-Bu, Ph, 2-thienyl, etc.; R2 = H, 5-Me, 5-Cl, 5-F, 6-Cl; R3 = CN, CO2Me, CO2Bn; R4 = R5 = Me; R4R5 = (CH2)4, (CH2)2O(CH2)2, (CH2)2C(O)(CH2)2, etc.] through a sequence of radical addition, 5-exo-dig cyclization, 1,n-H shift and 5-endo-trig cyclization. This protocol exhibited excellent functional group tolerance for establishing spiro and non-spiro polycyclic architectures under mild conditions. Moreover, this transformation could also be achieved smoothly via a simple phosphine/iodide-based photoredox system.Benzyl acrylate(cas: 2495-35-4Category: esters-buliding-blocks) was used in this study.

Benzyl acrylate(cas: 2495-35-4) has been used in preparation of high refractive index polyacrylates. Benzyl acrylate is used in the preparation of heptanoic acid benzyl ester. It is used to prepare polybenzylacrylate using azobisisobutyronitrile as initiator.Category: esters-buliding-blocks

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

In 2019,Journal of Organic Chemistry included an article by Wang, Xue-Mei; Liu, Yi-Wen; Ma, Rui-Jun; Si, Chang-Mei; Wei, Bang-Guo. HPLC of Formula: 4248-19-5. The article was titled 《Synthesis of 1,4- and 1,5-Amino Alcohols via Nucleophilic Addition of Semicyclic N,O-Acetal with Organozinc Reagents》. The information in the text is summarized as follows:

An efficient approach to access functionalized 1,4- and 1,5-amino alcs. was developed through the nucleophilic addition of semicyclic N,O-acetal with organozinc reagents. A number of substituted benzyl zinc reagents (including nitrile and ester substituted) could react with semicyclic N,O-acetals 1 and 2, affording the desired products in good to excellent yields. In the experiment, the researchers used many compounds, for example, tert-Butyl carbamate(cas: 4248-19-5HPLC of Formula: 4248-19-5)

tert-Butyl carbamate(cas: 4248-19-5) belongs to anime.Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one.HPLC of Formula: 4248-19-5

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

In 2019,Advanced Synthesis & Catalysis included an article by Zheng, Chao; Wang, Guang-Zu; Shang, Rui. Formula: C10H10O2. The article was titled 《Catalyst-free decarboxylation and decarboxylative Giese additions of alkyl carboxylates through photoactivation of electron donor-acceptor complex》. The information in the text is summarized as follows:

A catalyst-free method to perform decarboxylative conjugated addition and hydrodecarboxylation of aliphatic N-(acyloxy) phthalimides e.g., I (redox active esters, RAEs) through photoactivation of electron-donor-acceptor (EDA) complex with Hantzsch ester (HE) in N,N-dimethylacetamide (DMA) solution was reported. The reactions present a green method to decarboxylatively construct carbon-carbon bond and to perform hydrodecarboxylation with broad substrate scope and functional group tolerance under mild blue light irradiation condition without recourse of popularly used photo-redox catalysts. The experimental part of the paper was very detailed, including the reaction process of Benzyl acrylate(cas: 2495-35-4Formula: C10H10O2)

Benzyl acrylate(cas: 2495-35-4) has been used in preparation of high refractive index polyacrylates. Benzyl acrylate is used in the preparation of heptanoic acid benzyl ester. It is used to prepare polybenzylacrylate using azobisisobutyronitrile as initiator.Formula: C10H10O2

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

In 2017,Yao, Po-Hsin Eric; Kumar, Sunil; Liu, Yu-Li; Fang, Chiu-Ping; Liu, Chia-Chen; Sun, Chung-Ming published 《Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization》.ACS Combinatorial Science published the findings.Related Products of 329-59-9 The information in the text is summarized as follows:

Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramol. cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray anal. and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney D-amino acid oxidase (pkDAO). In the part of experimental materials, we found many familiar compounds, such as Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9Related Products of 329-59-9)

Methyl 4-fluoro-3-nitrobenzoate(cas: 329-59-9) belongs to methyl benzoate. Methyl benzoate reacts at both the ring and the ester, depending on the substrate. Electrophiles attack the ring, illustrated by acid-catalysed nitration with nitric acid to give methyl 3-nitrobenzoate.Related Products of 329-59-9Methyl 4-fluoro-3-nitrobenzoate is used to prepare dimethyl 3-nitro-3′,4-oxydibenzoate by reacting with 3-hydroxy-benzoic acid methyl ester.

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