Month: October 2022

Application of 301673-14-3In 2022 ,《Enantioselective Reductive N-Cyclization-Alkylation Reaction of Alkene-Tethered Oxime Esters and Alkyl Iodides by Nickel Catalysis》 appeared in Journal of the American Chemical Society. The author of the article were Jia, Xue-Gong; Yao, Qi-Wei; Shu, Xing-Zhong. The article conveys some information:

Asym. cross-electrophile difunctionalization of tethered alkenes has become a powerful tool for the production of chiral cyclic scaffolds; however, the current studies all focus on carbocyclization reactions. Herein, an N-cyclization-alkylation reaction and showcase on the potential of heterocyclization for accessing new enantioenriched cyclic architectures is reported. This work establishes a new approach for enantioselective aza-Heck cyclization/cross-coupling sequence, which remains a long-standing unsolved challenge for the synthetic community. The reaction proceeds with primary, secondary, and a few tertiary alkyl iodides, and the use of newly defined ligands gave highly enantioenriched pyrrolines with improved mol. diversity under mild conditions. The presence of imine functionality allows for further structural variations. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Application of 301673-14-3)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Application of 301673-14-3

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Category: iodides-buliding-blocksIn 2019 ,《Synthesis and exploration of in-silico and in-vitro α-glucosidase and α-amylase inhibitory activities of N-(3-acetyl-2-methyl-4-phenylquinolin-6-yl)arylamides》 appeared in Journal of the Iranian Chemical Society. The author of the article were Kumar, L. Jyothish; Suresh, Y.; Rajasekaran, R.; Reddy, S. Rajeswara; Vijayakumar, V.. The article conveys some information:

Nitro function of 1-(2-methyl-6-nitro-4-phenylquinolin-3-yl)ethanone was converted into amine by grinding it with zinc dust and ammonium chloride which in turn successfully converted into the N-(3-acetyl-2-methyl-4-phenylquinolin-6-yl)arylamides I [R = H, 3-F, 2-O2N, etc.] by treating it with benzoic acids using coupling reagents such as EDC, HATU and DCC. The compounds I were found to afford excellent yields with HATU, moderate in EDC and very less in DCC and hence HATU was considered as a suitable coupling reagent. All the synthesized compounds I were evaluated for their in-silico and in-vitro α-glucosidase and α-amylase inhibitory activity using acarbose as standard to treat type II diabetes and all compounds showed pos. results by in-silico and in-vitro α-amylase inhibition assay. Among the tested compounds, compounds I [R = 2-I, 2-O2N] in α-glucosidase as well as in α-amylase were found to have least binding energy value and form more stable ligand-receptor complex. In addition, the compounds I [R = 2-I, 2-O2N] exhibited 56.90 ± 0.77% and 59.46 ± 0.61% of the higher potent α-glucosidase inhibitory activity with IC50 values 171.75 ± 3.95 μmol/mL and 171.67 ± 1.57 μmol/mL significantly (p < 0.05) compared to remaining seven test samples. And similarly, the compound I [R = 2-I, 2-O2N] possessed α-amylase inhibitory activity at a concentration of 100 μg/mL (55.42 ± 0.42% and 55.42 ± 1.14%) with IC50 values 138.92 ± 4.44 μmol/mL and 158.78 ± 2.34 μmol/mL. In the experiment, the researchers used 2-Iodobenzoic acid(cas: 88-67-5Category: iodides-buliding-blocks)

2-Iodobenzoic acid(cas: 88-67-5) belongs to organic iodides. Generally organic iodides can be divided into two classes of alkyl iodides and aryl iodides. Category: iodides-buliding-blocks Typical reactions of alkyl iodides include nucleophilic substitution, elimination, reduction, and the formation of organometallics.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 1,2-DiiodoethaneIn 2018 ,《Radical Anions from Urea-type Carbonyls: Radical Cyclizations and Cyclization Cascades》 appeared in Angewandte Chemie, International Edition. The author of the article were Huang, Huan-Ming; McDouall, Joseph J. W.; Procter, David J.. The article conveys some information:

Radical anions generated from urea carbonyls by reductive electron transfer are exploited in carbon-carbon bond formation. New radical cyclizations of urea radical anions deliver complex nitrogen heterocycles and, depending upon the proton source used in the reactions, a chemoselective switch between reaction pathways can deliver two heterobicyclic scaffolds. A computational study has been used to investigate the selectivity of the urea radical processes. Furthermore, radical cyclization cascades involving urea radical anions deliver unusual spirocyclic aminal architectures. After reading the article, we found that the author used 1,2-Diiodoethane(cas: 624-73-7Reference of 1,2-Diiodoethane)

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Reference of 1,2-Diiodoethane

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Quality Control of 1-Bromo-3-iodobenzeneIn 2021 ,《Hypsochromic Shift of Multiple-Resonance-Induced Thermally Activated Delayed Fluorescence by Oxygen Atom Incorporation》 was published in Angewandte Chemie, International Edition. The article was written by Tanaka, Hiroyuki; Oda, Susumu; Ricci, Gaetano; Gotoh, Hajime; Tabata, Keita; Kawasumi, Ryosuke; Beljonne, David; Olivier, Yoann; Hatakeyama, Takuji. The article contains the following contents:

Herein, we reported an ultrapure blue multiple-resonance-induced thermally activated delayed fluorescence (MR-TADF) material (ν-DABNA-O-Me) with a high photoluminescence quantum yield and a large rate constant for reverse intersystem crossing. Because of restricted π-conjugation of the HOMO rather than the LUMO induced by oxygen atom incorporation, ν-DABNA-O-Me shows a hypsochromic shift compared to the parent MR-TADF material (ν-DABNA). An organic light-emitting diode based on this material exhibits an emission at 465 nm, with a small full-width at half-maximum of 23 nm and Commission Internationale de l’Eclairage coordinates of (0.13, 0.10), and a high maximum external quantum efficiency of 29.5%. Moreover, ν-DABNA-O-Me facilitates a drastically improved efficiency roll-off and a device lifetime compared to ν-DABNA, which demonstrates significant potential of the oxygen atom incorporation strategy. In the experiment, the researchers used many compounds, for example, 1-Bromo-3-iodobenzene(cas: 591-18-4Quality Control of 1-Bromo-3-iodobenzene)

1-Bromo-3-iodobenzene(cas: 591-18-4) has been used in the preparation of 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene.Quality Control of 1-Bromo-3-iodobenzene

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

《Cu-Catalyzed Hydrocarbonylative C-C Coupling of Terminal Alkynes with Alkyl Iodides》 was written by Cheng, Li-Jie; Mankad, Neal P.. Recommanded Product: 301673-14-3This research focused onunsym dialkyl ketone regioselective synthesis; copper catalyzed hydrocarbonylative coupling terminal alkyne unactivated alkyl iodide. The article conveys some information:

A Cu-catalyzed hydrocarbonylative C-C coupling of terminal alkynes with unactivated alkyl iodides has been developed, enabling highly chemo- and regioselective synthesis of unsym. dialkyl ketones. A variety of functional groups are tolerated, and both primary and secondary alkyl iodides react well. An autotandem sequence of two Cu-catalyzed processes is proposed: first hydrocarbonylative coupling of the alkyne and the alkyl iodide, followed by reduction of the intermediate unsaturated ketone to the saturated product. Mechanistic experiments indicate that an alkenylcopper intermediate activates the alkyl iodide by single electron transfer to enable a radical carbonylation pathway. In the experiment, the researchers used many compounds, for example, tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Recommanded Product: 301673-14-3)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. The carbon-iodine bond is weaker than other carbon-halogen bonds due to the poor electronegative nature of the iodine atom. In general, organic iodides are light-sensitive and turn yellow during storage, owing to the formation of iodine. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles.Recommanded Product: 301673-14-3

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2015,Zhang, Wei; Dourado, Daniel F. A. R.; Mannervik, Bengt published 《Evolution of the active site of human glutathione transferase A2-2 for enhanced activity with dietary isothiocyanates》.Biochimica et Biophysica Acta, General Subjects published the findings.Quality Control of 1,2-Diiodoethane The information in the text is summarized as follows:

Organic isothiocyanates (ITCs) are produced by plants, in which they are released from glucosinolates by myrosinase. ITCs are generally toxic and serve as a chem. defense against herbivorous insects and against infections by microorganisms. In mammalian tissues subtoxic concentrations of ITCs can provide protective effects against cancer and other diseases partially by induction of glutathione transferases (GSTs) and other detoxication enzymes. Thus, human consumption of edible plants rich in ITCs is presumed to provide health benefits. ITCs react with intracellular glutathione to form dithiocarbamates, catalyzed by GSTs. Formation of glutathione conjugates is central to the biotransformation of ITCs and leads to a route for their excretion. Clearly, the emergence of ITC conjugating activity in GSTs is essential from the biol. and evolutionary perspective. In the present investigation an active-site-focused mutant library of GST A2-2 has been screened for enzyme variants with enhanced ITC activity. Significantly superior activities were found in 34 of the approx. 2000 mutants analyzed, and the majority of the superior GSTs featured His and Gly residues in one of the three active-site positions subjected to mutagenesis. We explored the propensity of GSTs to obtain altered substrate selectivity and moreover, identified a specific pattern of mutagenesis in GST for enhanced PEITC detoxification, which may play an important role in the evolution of adaptive responses in organisms subjected to ITCs. The facile acquisition of enhanced ITC activity demonstrates that this important detoxication function can be promoted by numerous evolutionary trajectories in sequence space. The results came from multiple reactions, including the reaction of 1,2-Diiodoethane(cas: 624-73-7Quality Control of 1,2-Diiodoethane)

1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Quality Control of 1,2-Diiodoethane

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2016,Anka-Lufford, Lukiana L.; Huihui, Kierra M. M.; Gower, Nicholas J.; Ackerman, Laura K. G.; Weix, Daniel J. published 《Nickel-Catalyzed Cross-Electrophile Coupling with Organic Reductants in Non-Amide Solvents》.Chemistry – A European Journal published the findings.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate The information in the text is summarized as follows:

Cross-electrophile coupling of aryl halides with alkyl halides has thus far been primarily conducted with stoichiometric metallic reductants in amide solvents. This report demonstrates that the use of tetrakis(dimethylamino)ethylene (TDAE) as an organic reductant enables the use of non-amide solvents, such as acetonitrile or propylene oxide, for the coupling of benzyl chlorides and alkyl iodides with aryl halides. Furthermore, these conditions work for several electron-poor heterocycles that are easily reduced by manganese. Finally, the authors demonstrate that TDAE addition can be used as a control element to ‘hold’ a reaction without diminishing yield or catalyst activity. The experimental part of the paper was very detailed, including the reaction process of tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate)

tert-Butyl 4-iodopiperidine-1-carboxylate(cas: 301673-14-3) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the Simmons–Smith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.Recommanded Product: tert-Butyl 4-iodopiperidine-1-carboxylate

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

In 2019,Angewandte Chemie, International Edition included an article by Diehl, Claudia J.; Scattolin, Thomas; Englert, Ulli; Schoenebeck, Franziska. Synthetic Route of C6H4BrI. The article was titled 《C-I-Selective Cross-Coupling Enabled by a Cationic Palladium Trimer》. The information in the text is summarized as follows:

While there is a growing interest in harnessing synergistic effects of more than one metal in catalysis, relatively little is known beyond bimetallic systems. This report describes the straightforward access to an air-stable Pd trimer and presents unambiguous reactivity data of its privileged capability to differentiate C-I over C-Br bonds in C-C bond formations (arylation and alkylation) of polyhalogenated arenes, which typical Pd0 and PdI-PdI catalysts fail to deliver. Exptl. and computational reactivity data, including the first location of a transition state for bond activation by the trimer, are presented, supporting direct trimer reactivity to be feasible. In addition to this study using 1-Bromo-3-iodobenzene, there are many other studies that have used 1-Bromo-3-iodobenzene(cas: 591-18-4Synthetic Route of C6H4BrI) was used in this study.

1-Bromo-3-iodobenzene(cas: 591-18-4) has been used in the preparation of 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodec-1-ene and 1-(3′-bromophenyl)-3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooct-1-ene.Synthetic Route of C6H4BrI Further, it is involved in the preparation of oxygen-tethered 1,6-enynes.

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The author of 《Biosynthesis of Pd/MnO2 nanocomposite using Solanum melongena plant extract and its application for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides》 were Nasrollahzadeh, Mahmoud; Ghorbannezhad, Fatemeh; Sajadi, S. Mohammad. And the article was published in Applied Organometallic Chemistry in 2019. Electric Literature of C5H4IN The author mentioned the following in the article:

In this work, for the first time, Solanum melongena plant extract was used for the green synthesis of Pd/MnO2 nanocomposite via reduction of Pd(II) ions to Pd(0) and their immobilization on the surface of manganese dioxide (MnO2) nanoparticles (NPs) as an effective support. The synthesized nanocomposite was characterized by various anal. techniques such as Fourier transform IR (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), field emission SEM (FESEM), energy dispersive X-ray spectroscopy (EDS), and UV-Vis spectroscopy. Pd/MnO2 nanocomposite was used as a heterogeneous catalyst for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides containing various electron-donating or electron-withdrawing groups in the presence of K4[Fe(CN)6] as non-toxic cyanide source and sodium azide. The products were obtained in good yields via a simple methodol. and easy work-up. The nanocatalyst can be recycled and reused several times with no remarkable loss of activity. The results came from multiple reactions, including the reaction of 4-Iodopyridine(cas: 15854-87-2Electric Literature of C5H4IN)

4-Iodopyridine(cas: 15854-87-2) is used as a reagent in the synthesis of indazolylamides as glucocorticoid receptor agonists. 4-Iodopyridine is a halogenated heterocycle that is a building block for proteomics research.Electric Literature of C5H4IN

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

The author of 《Orthogonal Nanoparticle Catalysis with Organogermanes》 were Fricke, Christoph; Sherborne, Grant J.; Funes-Ardoiz, Ignacio; Senol, Erdem; Guven, Sinem; Schoenebeck, Franziska. And the article was published in Angewandte Chemie, International Edition in 2019. Computed Properties of C7H7I The author mentioned the following in the article:

Although nanoparticles are widely used as catalysts, little is known about their potential ability to trigger privileged transformations as compared to homogeneous mol. or bulk heterogeneous catalysts. The authors herein demonstrate (and rationalize) that nanoparticles display orthogonal reactivity to mol. catalysts in the cross-coupling of aryl halides with aryl germanes. While the aryl germanes are unreactive in LnPd0/LnPdII catalysis and allow selective functionalization of established coupling partners in their presence, they display superior reactivity under Pd nanoparticle conditions, outcompeting established coupling partners (such as ArBPin and ArBMIDA) and allowing air-tolerant, base-free, and orthogonal access to valuable and challenging biaryl motifs. As opposed to the notoriously unstable polyfluoroaryl- and 2-pyridylboronic acids, the corresponding germanes are highly stable and readily coupled. The authors’ mechanistic and computational studies provide unambiguous support of nanoparticle catalysis and suggest that owing to the electron richness of aryl germanes, they preferentially react by electrophilic aromatic substitution, and in turn are preferentially activated by the more electrophilic nanoparticles. After reading the article, we found that the author used 1-Iodo-4-methylbenzene(cas: 624-31-7Computed Properties of C7H7I)

1-Iodo-4-methylbenzene(cas: 624-31-7) is used in wide range of medicals industrial applications as well as in pharmaceutical intermediates, polarizing films for Liquid Crystal Display (LCD) chemicals.Computed Properties of C7H7I

Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com