Tag: 100-200

In 2019,Journal of Materials Chemistry C: Materials for Optical and Electronic Devices included an article by Szukalski, Adam; Moffa, Maria; Camposeo, Andrea; Pisignano, Dario; Mysliwiec, Jaroslaw. Product Details of 17201-43-3. The article was titled 《All-optical switching in dye-doped DNA nanofibers》. The information in the text is summarized as follows:

All-optical switches are introduced which are based on DNA (DNA) in the form of electrospun fibers, where DNA is semi-intercalated with a push-pull, luminescent nonlinear pyrazoline derivative Optical birefringence is found in the organic nanofibers, with fully reversible switching controlled through continuous-wave laser irradiation The photoinduced signal is remarkably large, with birefringence highlighted by optically-driven refractive index anisotropy approaching 0.001. Sub-millisecond characteristic switching times are found. Integrating dye-intercalated DNA complex systems in organic nanofibers, as a convenient and efficient approach to template mol. organization and control it by external stimuli, might open new routes for realizing optical logic gates, reconfigurable photonic networks and sensors through phys.-transient biopolymer components.4-Cyanobenzyl bromide(cas: 17201-43-3Product Details of 17201-43-3) was used in this study.

4-Cyanobenzyl bromide(cas: 17201-43-3) is a white solid. Its melting point is 113-117°C, and flash point is 125.1°C. It is insoluble in water at 20°C. It is stable under normal temperatures and pressures. It should be stored at 0-5°C.Product Details of 17201-43-3

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《Organocatalytic Enantioselective Aminoalkylation of 5-Aminopyrazole Derivatives with Cyclic Imines》 was written by Carceller-Ferrer, Laura; Gonzalez del Campo, Aleix; Vila, Carlos; Blay, Gonzalo; Munoz, M. Carmen; Pedro, Jose R.. Product Details of 614-16-4 And the article was included in European Journal of Organic Chemistry in 2020. The article conveys some information:

In this communication, an efficient asym. aminoalkylation of 5-aminopyrazole derivatives with cyclic benzoxathiazine 2,2-dioxides catalyzed by a quinine-derived squaramide in dichloromethane has been established. This is the first example of 5-aminopyrazole derivatives in asym. catalysis. A variety of chiral sulfamidates bearing an aminopyrazole moiety were obtained in good yields (up to 98%) and moderate to excellent enantioselectivities (up to 99%ee).3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Product Details of 614-16-4) was used in this study.

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Product Details of 614-16-4

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In 2011,de Koning, Pieter D.; Murtagh, Lorraine; Lawson, Jon P.; Vonder Embse, Richard A.; Kunda, Sastry A.; Kong, Wei published 《Development an efficient route to the 5-lipoxygenase inhibitor PF-04191834》.Organic Process Research & Development published the findings.Application In Synthesis of 2-(3-Bromophenyl)acetonitrile The information in the text is summarized as follows:

A convergent six-step process for the synthesis of PF-04191834 (I), a potent and selective 5-lipoxygenase inhibitor, has been developed and used to deliver over 20 kg of API. The process uses the same bond-forming steps as the initial medicinal chem. route, including the use of two consecutive Pd-catalyzed Ar-S couplings to form the key diaryl thioether linkage. The reaction conditions and downstream processing have been optimized to eliminate column chromatog. and aqueous work-ups and to minimize disproportionation of I, to ensure successful scale-up. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Application In Synthesis of 2-(3-Bromophenyl)acetonitrile)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands or 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione.Application In Synthesis of 2-(3-Bromophenyl)acetonitrile

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Formula: C8H6BrNIn 2021 ,《Synthesis and pharmacological evaluation of novel resorcinol biphenyl ether analogs as small molecule inhibitors of PD-1/PD-L1 with benign toxicity profiles for cancer treatment》 appeared in Biochemical Pharmacology (Amsterdam, Netherlands). The author of the article were Cao, Hao; Cheng, Binbin; Liu, Ting; Chen, Jianjun. The article conveys some information:

Programmed death protein 1 (PD-1)/programmed death protein ligand 1 (PD-L1) pathway is one of the most actively pursued targets in cancer immunotherapy. In a continuation of authors research interest in this pathway, synthesized and evaluated the pharmacol. activities of a series of resorcinol biphenyl ether analogs as small mol. PD-1/PD-L1 inhibitors for cancer treatment. Among the 27 newly synthesized compounds, I was found to have the highest inhibitory effect against PD-1/PDL-1 with an IC50 value of 56.58 nM in the HTRF (homogeneous time-resolved fluorescence) assay. In addition, I dose-dependently promoted HepG2 cell death in a co-culture model of HepG2/hPD-L1 and Jurkat T cells. Furthermore, mol. modeling study indicated that I binds with high affinity to the binding interface of PD-L1. Moreover, I effectively inhibited tumor growth (TGI of 76.4% at 90 mg/kg) in an immune checkpoint humanized mouse model with no obvious toxicity. Finally, I did not cause in vivo cardiotoxicity and bone marrow suppression (myelosuppression) to BALB/c mice. Taken together, these results suggest that I deserves further investigation as a potent and safe PD-1/PDL-1 inhibitor for cancer treatment. In the part of experimental materials, we found many familiar compounds, such as 4-Cyanobenzyl bromide(cas: 17201-43-3Formula: C8H6BrN)

4-Cyanobenzyl bromide(cas: 17201-43-3) can reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)methyl]benzonitrile. And it may be used in the synthesis of ligands containing a chelating pyrazolyl-pyridine group with a pendant aromatic nitrile.Formula: C8H6BrN

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Electric Literature of C7H4BrNIn 2021 ,《Design of an Electron-Withdrawing Benzonitrile Ligand for Ni-Catalyzed Cross-Coupling Involving Tertiary Nucleophiles》 appeared in Journal of the American Chemical Society. The author of the article were Mills, L. Reginald; Edjoc, Racquel K.; Rousseaux, Sophie A. L.. The article conveys some information:

The design of new ligands for cross-coupling is essential for developing new catalytic reactions that access valuable products such as pharmaceuticals. In this report, we exploit the reactivity of nitrile-containing additives in Ni catalysis to design a benzonitrile-containing ligand for cross-coupling involving tertiary nucleophiles. Kinetic and Hammett studies are used to elucidate the role of the optimized ligand, which demonstrate that the benzonitrile moiety acts as an electron-acceptor to promote reductive elimination over β-hydride elimination and stabilize low-valent Ni. With these conditions, a protocol for decyanation-metalation and Ni-catalyzed arylation is conducted, enabling access to quaternary α-arylnitriles from disubstituted malononitriles. Safety: cyanide handling. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Electric Literature of C7H4BrN)

2-Bromobenzonitrile(cas: 2042-37-7) belongs to a group of ortho-substituted bromobenzenes that have varying hepatotoxicity effects in the presence of rat liver microsomes in vitro. 2-Bromobenzonitrile is also used as a starting material to synthesize novel benzothiophene derivatives that were found to exhibit antibacterial and antifungal activity.Electric Literature of C7H4BrN

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In 2022,Liu, Wei; Zhang, Le; Liu, Ye; Fan, Shi-Lu; Dai, Jian-Jun; Tao, Wei; Zhu, Hui-Xia; Xiao, Hua published an article in Chemical Communications (Cambridge, United Kingdom). The title of the article was 《Chemoselective tandem SN2’/SN2”/inter- or intramolecular Diels-Alder reaction of γ-vinyl MBH carbonates with phenols and o-hydroxychalcones》.Recommanded Product: 3-Oxo-3-phenylpropanenitrile The author mentioned the following in the article:

An unprecedented consecutive SN2’/SN2” addition of phenol to γ-vinyl MBH carbonate formed a reactive diene intermediate, followed by a dimerization/elimination process to give functionalized exocyclohexenes I [R = (CF3)2CH, Ph, 2-MeC6H4, etc.] with excellent chemoselectivity. When using o-hydroxychalcones as pronucleophiles, an SN2’/SN2”/intramol. Diels-Alder reaction sequence occurred, selectively producing a series of pharmaceutically intriguing tricyclic chromane derivatives II [R1 = H, 4-Me, 2-Cl, etc.; R2 = OEt, Ph, 1-naphthyl, etc.] with good diastereoselectivity. The good nucleophilicity and fair nucleofugicity exhibited by phenoxy anion played a pivotal role in the SN2” addition step. In the experiment, the researchers used 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Recommanded Product: 3-Oxo-3-phenylpropanenitrile)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Recommanded Product: 3-Oxo-3-phenylpropanenitrile

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Trowse, Benjamin R.; Byrne, Fergal P.; Sherwood, James; O’Brien, Peter; Murray, Jane; Farmer, Thomas J. published their research in ACS Sustainable Chemistry & Engineering in 2021. The article was titled 《Study on 2,2,5,5-Tetramethyloxolane (TMO) as a Solvent for Buchwald-Hartwig Aminations》.Product Details of 2042-37-7 The article contains the following contents:

Herein, the successful application of 2,2,5,5-tetramethyloxolane (TMO), a solvent with a similar property profile to toluene, for Buchwald-Hartwig amination reactions for coupling a wide range of primary and secondary amines with aryl bromides was demonstrated. When NaOt-Bu was used as the base, similar yields were obtained in toluene and TMO. In contrast, using Cs2CO3, TMO outperformed toluene significantly for electron-deficient aryl bromides that could be susceptible to nucleophilic attack. To showcase the use of TMO as a solvent for Buchwald-Hartwig aminations, the synthesis of a key intermediate in the route to smoothened (SMO) receptor antagonist drug candidate SEN826 was successfully accomplished in TMO. Improved metrics and reduction in residual palladium in the isolated amines demonstrate further benefits in the substitution of toluene with TMO in Buchwald-Hartwig aminations. In the part of experimental materials, we found many familiar compounds, such as 2-Bromobenzonitrile(cas: 2042-37-7Product Details of 2042-37-7)

2-Bromobenzonitrile(cas: 2042-37-7) is a precursor to the quinazolinones, a class of drugs used to treat autoimmune diseases and coronary heart disease. In addition, 2-bromobenzonitrile can be used for the Suzuki coupling reaction.Product Details of 2042-37-7

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《Enantioselective Aryl-Iodide-Catalyzed Wagner-Meerwein Rearrangements》 was written by Sharma, Hayden A.; Mennie, Katrina M.; Kwan, Eugene E.; Jacobsen, Eric N.. Product Details of 31938-07-5 And the article was included in Journal of the American Chemical Society in 2020. The article conveys some information:

We report a strategy for effecting catalytic, enantioselective carbocationic rearrangements through the intermediacy of alkyl iodanes as stereodefined carbocation equivalent Asym. Wagner-Meerwein rearrangements of β-substituted styrenes are catalyzed by the C2-sym. aryl iodide 1 to provide access to enantioenriched 1,3-difluorinated mols. possessing interesting and well-defined conformational properties. Hammett and kinetic isotope effect studies, in combination with computational investigations, reveal that two different mechanisms are operative in these rearrangement reactions, with the pathway depending on the identity of the migrating group. In reactions involving alkyl-group migration, intermol. fluoride attack is product- and enantio-determining In contrast, reactions in which aryl rearrangement occurs proceed through an enantiodetermining intramol. 1,2-migration prior to fluorination. The fact that both pathways are promoted by the same chiral aryl iodide catalyst with high enantioselectivity provides a compelling illustration of generality across reaction mechanisms in asym. catalysis. In the experiment, the researchers used many compounds, for example, 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Product Details of 31938-07-5)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Product Details of 31938-07-5

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《Enantioselective dearomative [3+2] annulation of 5-amino-isoxazoles with quinone monoimines》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Liu, Hui; Yan, Yingkun; Zhang, Jiayan; Liu, Min; Cheng, Shaobing; Wang, Zhouyu; Zhang, Xiaomei. Computed Properties of C9H7NO The article mentions the following:

The first enantioselective dearomative [3+2] annulation of 5-aminoisoxazoles with quinone monoimines was realized using a chiral phosphoric acid as catalyst. Various novel (bridged) isoxazoline fused dihydrobenzofurans bearing two continuous quaternary stereocenters were achieved in moderate to good yields (up to 94%) with moderate to good enantioselectivities (up to 98% ee). The absolute configurations of two products were assigned by X-ray crystal structural analyses and a plausible reaction mechanism was proposed. In the part of experimental materials, we found many familiar compounds, such as 3-Oxo-3-phenylpropanenitrile(cas: 614-16-4Computed Properties of C9H7NO)

3-Oxo-3-phenylpropanenitrile(cas: 614-16-4) has been used to produce 2-benzoyl-3-furan-2-yl-acrylonitrile. It is an active methylene compound, useful in heterocyclic synthesis, e.g. polyfunctional pyridines and pyrimidines.Computed Properties of C9H7NO

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In 2018,Kavala, Veerababurao; Yang, Zonghan; Konala, Ashok; Yang, Tang-Hao; Kuo, Chun-Wei; Ruan, Jian-Yao; Yao, Ching-Fa published 《Synthesis of 1,2,3-Fused Indole Polyheterocycles by Copper-Catalyzed Cascade Reaction》.European Journal of Organic Chemistry published the findings.Related Products of 31938-07-5 The information in the text is summarized as follows:

A one-pot reaction has been developed for the preparation of 1,2,3-fused indole polyheterocycles, e.g., I, by starting from 2-iodobenzamide and 2-iodobenzyl cyanide in the presence of a copper catalyst. The cascade process involves the efficient formation of one C-C and three C-N bonds. A broad substrate scope, good yields, and short reactions times are key features of this strategy. The experimental process involved the reaction of 2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5Related Products of 31938-07-5)

2-(3-Bromophenyl)acetonitrile(cas: 31938-07-5) has been used in the synthesis of 2-(1-cyano-1-(3-bromophenyl))methylidene-3-phenylthiazolidine-4,5-dione or a series of aminoethylbiphenyls, novel 5-HT7 receptor ligands.Related Products of 31938-07-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts