Tag: 200-300

Synthesis, Spectroscopy and Crystal Structure Analysis of N¹,N³-dicyclohexyl-N¹-(all-trans-retinoyl)urea was written by Vachlioti, Eleanna;Kalantzi, Stefania;Papaioannou, Dionissios;Nastopoulos, Vassilios. And the article was included in Journal of Chemical Crystallography in 2022.Application of 2387-23-7 This article mentions the following:

The title compound, C₃₃H₅₀N₂O₂, was a side product in the reaction of all-trans-retinoic acid (atRA) with N-hydroxysuccinimide, in the presence of the coupling agent N,N’-dicyclohexylcarbodiimide, which produced the ‘active’ ester succinimidyl all-trans-retinoate as the product. It crystallized in the orthorhombic Pbca space group. The compound was characterized by ¹H-NMR, ¹³C-NMR, ESI-MS and IR spectroscopy and its structure was determined by single-crystal X-ray diffraction. For example in the ¹³C-NMR spectrum, diagnostic peaks are those of the two amide carbonyl C atoms at δ 169.5 and 154.2 ppm, the ten olefinic C atoms of the unsaturated chain of atRA moiety at δ 149.0, 139.3, 137.7, 137.3, 134.9, 130.2, 130.0, 129.4, 128.5 and 121.5 ppm and the two methine C atoms of the N,N’-dicyclohexylurea moiety at δ 57.9 and 49.5 ppm. Detailed anal. of its mol. and supramol. structure showed that close-packing principles (elongated shape/large hydrophobic region of the mol.) together with chem. factors (N-H···O and C-H···O intermol. interactions) direct the 3D self-assembly process in the crystalline state. Hirshfeld surface anal. was employed, a powerful approach to quickly and easily gain insight into mol. environments in the crystalline state. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Application of 2387-23-7

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

Evidence and isolation of tetrahedral intermediates formed upon the addition of lithium carbenoids to Weinreb amides and N-acylpyrroles was written by Castoldi, Laura;Holzer, Wolfgang;Langer, Thierry;Pace, Vittorio. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Reference of 116332-61-7 This article mentions the following:

The tetrahedral intermediates generated upon the addition of halolithium carbenoids (LiCH₂X and LiCHXY) to Weinreb amides have been intercepted and fully characterized as O-TMS heminals. The com. available N-trimethylsilyl imidazole is the ideal trapping agent whose employment, combined with a straightforward neutral Alox chromatog. purification, enables the isolation of such labile species. The procedure could be advantageously extended also for obtaining O-TMS heminals from N-acylpyrroles. These intermediates manifest interesting reactivity including as precursors of more complex carbenoids. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Reference of 116332-61-7).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Reference of 116332-61-7

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

An assessment of chemical and biological product use in aquaculture in Bangladesh was written by Ali, Hazrat;Rico, Andreu;Murshed-e-Jahan, Khondker;Belton, Ben. And the article was included in Aquaculture in 2016.Related Products of 10543-57-4 This article mentions the following:

The aim of this study is to describe current chem. use practices in the aquaculture sector of Bangladesh and to identify the factors that influence them. A survey on the use of chem. and biol. products was conducted between Nov. 2011 and June 2012 using structured questionnaires administered to operators of nine farm groups, including homestead ponds, carps, tilapias, koi fish, shrimps, shrimps and prawns, prawns, rice and fish, and pangas. Farm type and farm owner characteristics were used as independent variables to explain observed chem. use. Forty-six chem. and biol. products (7 water and sediment treatment compounds, 13 disinfectants, 7 antibiotics, 7 pesticides, 8 fertilizers and 4 feed additives and probiotics) were reported to be applied in aquaculture. The use of disinfectants and antibiotics was found to be highest in intensive koi and pangas farms as compared to other farm groups, whereas the use of fertilizers was lowest in these farm groups. A higher percentage of prawn and shrimp/prawn farmers applied pesticides than other farm groups. A multivariate anal. showed that patterns of use of chem. and biol. products were significantly different across aquaculture farm groups, with the largest number of chem. compounds used by the intensive koi farm group. The study shows that, despite rapid expansion of com. aquaculture in Bangladesh, use of chem. and biol. products is still relatively low compared to other aquaculture producing countries in Asia. However, despite this finding, the study identified a large number of compounds that are currently in use, and that require further regulation and evaluation regarding their potential environmental and human health impacts, as already done in most developed countries. Chem. use practices in Bangladesh. In the experiment, the researchers used many compounds, for example, N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4Related Products of 10543-57-4).

N,N-(Ethane-1,2-diyl)bis(N-acetylacetamide) (cas: 10543-57-4) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Related Products of 10543-57-4

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

Deacylation-aided C-H alkylative annulation through C-C cleavage of unstrained ketones was written by Zhou, Xukai;Xu, Yan;Dong, Guangbin. And the article was included in Nature Catalysis in 2021.Synthetic Route of C9H10BrNO2 This article mentions the following:

Arene- and heteroarene-fused rings are pervasive in biol. active mols. Direct annulation between a C-H bond on the aromatic core and a tethered alkyl moiety provides a straightforward approach to access these scaffolds; however, such a strategy is often hampered by the need of special reactive groups and/or less compatible cyclization conditions. It would be synthetically appealing if a common native functional group can be used as a handle to enable a general C-H annulation with diverse aromatic rings. A deacylative annulation strategy for preparing a large variety of aromatic-fused rings from linear simple ketone precursors was demonstrated. The reaction starts with homolytic cleavage of the ketone α C-C bond via a pre-aromatic intermediate, followed by a radical-mediated dehydrogenative cyclization. Using widely available ketones as the robust radical precursors, this deconstructive approach allows streamlined assembly of complex polycyclic structures with broad functional group tolerance. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Synthetic Route of C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Synthetic Route of C9H10BrNO2

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

Formamides as Isocyanate Surrogates: A Mechanistically Driven Approach to the Development of Atom-Efficient, Selective Catalytic Syntheses of Ureas, Carbamates, and Heterocycles was written by Bruffaerts, Jeffrey;von Wolff, Niklas;Diskin-Posner, Yael;Ben-David, Yehoshoa;Milstein, David. And the article was included in Journal of the American Chemical Society in 2019.Reference of 2387-23-7 This article mentions the following:

Despite the hazardous nature of isocyanates, they remain key building blocks in bulk and fine chem. synthesis. By surrogating them with less potent and readily available formamide precursors, we herein demonstrate an alternative, mechanistic approach to selectively access a broad range of ureas, carbamates, and heterocycles via ruthenium-based pincer complex catalyzed acceptorless dehydrogenative coupling reactions. The design of these highly atom-efficient procedures was driven by the identification and characterization of the relevant organometallic complexes, uniquely exhibiting the trapping of an isocyanate intermediate. D. functional theory (DFT) calculations further contributed to shed light on the remarkably orchestrated chain of catalytic events, involving metal-ligand cooperation. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Reference of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Reference of 2387-23-7

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

A Mild Heteroatom (O-, N-, and S-) Methylation Protocol Using Trimethyl Phosphate (TMP)-Ca(OH)₂ Combination was written by Tang, Yu;Yu, Biao. And the article was included in Synthesis in 2022.Application In Synthesis of N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide This article mentions the following:

A mild heteroatom methylation protocol using tri-Me phosphate (TMP)-Ca(OH)₂ combination was developed, which proceeded in DMF, or water, or under neat conditions, at 80°C or at room temperature A series of O-, N-, and S-nucleophiles, including phenols, sulfonamides, N-heterocycles, such as 9H-carbazole, indole derivatives, and 1,8-naphthalimide, and aryl/alkyl thiols, were suitable substrates for this protocol. The high efficiency, operational simplicity, scalability, cost-efficiency, and environmentally friendly nature of this protocol made it an attractive alternative to the conventional base-promoted heteroatom methylation procedures. In the experiment, the researchers used many compounds, for example, N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6Application In Synthesis of N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide).

N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide (cas: 1146-43-6) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Application In Synthesis of N-(4-Hydroxyphenyl)-4-methylbenzenesulfonamide

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

A CO₂-Catalyzed Transamidation Reaction was written by Yang, Yang;Liu, Jian;Kamounah, Fadhil S.;Ciancaleoni, Gianluca;Lee, Ji-Woong. And the article was included in Journal of Organic Chemistry in 2021.Safety of 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Herein, a report on the use of CO₂ as a traceless catalyst: in the presence of catalytic amounts of CO₂, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular, N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO₂-catalyzed transamidation vs. a N₂ atmosphere. Comparative Hammett studies and kinetic anal. were conducted to elucidate the catalytic activation mechanism of mol. CO₂, which was supported by DFT calculations The pos. effect of CO₂ in the transamidation reaction was attributed to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO₂. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Safety of 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Safety of 4-Bromo-N-methoxy-N-methylbenzamide

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

Synthesis and structure-activity relationships of benzophenone-bearing diketopiperazine-type anti-microtubule agents was written by Yamazaki, Yuri;Sumikura, Makiko;Masuda, Yurika;Hayashi, Yoshiki;Yasui, Hiroyuki;Kiso, Yoshiaki;Chinen, Takumi;Usui, Takeo;Yakushiji, Fumika;Potts, Barbara;Neuteboom, Saskia;Palladino, Michael;Lloyd, George Kenneth;Hayashi, Yoshio. And the article was included in Bioorganic & Medicinal Chemistry in 2012.Product Details of 116332-61-7 This article mentions the following:

KPU-105 (4), a potent anti-microtubule agent that contains a benzophenone was derived from the diketopiperazine-type vascular disrupting agent (VDA) plinabulin 3, which displays colchicine-like tubulin depolymerization activity. To develop derivatives with more potent anti-microtubule and cytotoxic activities, we further modified the benzophenone moiety of 4. Accordingly, we obtained a 4-fluorobenzophenone derivative 16j that inhibited tumor cell growth in vitro with a subnanomolar IC₅₀ value against HT-29 cells (IC₅₀ = 0.5 nM). Next, the effect of 16j on mitotic spindles was evaluated in HeLa cells. Treatment with 3 nM of 16j partially disrupted the interphase microtubule network. By contrast, treatment with the same concentration of CA-4 barely affected the microtubule network, indicating that 16j exhibited more potent anti-mitotic effects than did CA-4. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Product Details of 116332-61-7).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. The amide group is called a peptide bond when it is part of the main chain of a protein, and an isopeptide bond when it occurs in a side chain, such as in the amino acids asparagine and glutamine. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Product Details of 116332-61-7

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

Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes was written by Dale, Harvey J. A.;Nottingham, Chris;Poree, Carl;Lloyd-Jones, Guy C.. And the article was included in Journal of the American Chemical Society in 2021.Electric Literature of C10H10F3NO2 This article mentions the following:

Alkylidene carbenes undergo rapid inter- and intramol. reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of ¹³C-labeled precursors. Herein we report on the rearrangement of ¹³C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [¹³C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (¹³C{¹H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally. In the experiment, the researchers used many compounds, for example, N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7Electric Literature of C10H10F3NO2).

N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide (cas: 116332-61-7) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Electric Literature of C10H10F3NO2

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

Palladium-Catalyzed meta-Selective C-H Functionalization by Noncovalent H-Bonding Interaction was written by Li, Guoshuai;Yan, Yifei;Zhang, Pengfei;Xu, Xiaohua;Jin, Zhong. And the article was included in ACS Catalysis in 2021.Application of 2387-23-7 This article mentions the following:

Herein, a palladium-catalyzed meta-selective C-H olefination of aromatic carbonyl compounds such as acetophenone, benzaldehyde, Me benzoate, N,N-diisopropylbenzamide, etc. by noncovalent hydrogen-bonding interaction was reported. N,N’-Substituted ureas RNHC(O)NHR¹ [R = cyclohexyl, 3,5-bis(trifluoromethyl)phenyl; R¹ = cyclohexyl, 2-(2-cyanophenoxy)ethyl, 2-phenoxyethyl, etc.] were engineered to serve as a H-bonding donor for binding to the substrates and, meanwhile, achieve site-selective control by the integrated directing group. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Application of 2387-23-7).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Application of 2387-23-7

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