Category: 2557-13-3

Schierle, Simone; Chaikuad, Apirat; Lillich, Felix F.; Ni, Xiaomin; Woltersdorf, Stefano; Schallmayer, Espen; Renelt, Beatrice; Ronchetti, Riccardo; Knapp, Stefan; Proschak, Ewgenij; Merk, Daniel published the artcile< Oxaprozin Analogues as Selective RXR Agonists with Superior Properties and Pharmacokinetics>, Formula: C9H7F3O2, the main research area is oxaprozin analog RXR agonist pharmacokinetic SAR.

The retinoid X receptors (RXR) are ligand-activated transcription factors involved in multiple regulatory networks as universal heterodimer partners for nuclear receptors. Despite their high therapeutic potential in many pathologies, targeting of RXR has only been exploited in cancer treatment as the currently available RXR agonists suffer from exceptional lipophilicity, poor pharmacokinetics (PK), and adverse effects. Aiming to overcome the limitations and to provide improved RXR ligands, we developed a new potent RXR ligand chemotype based on the nonsteroidal anti-inflammatory drug oxaprozin. Systematic structure-activity relationship anal. enabled structural optimization toward low nanomolar potency similar to the well-established rexinoids. Cocrystal structures of the most active derivatives demonstrated orthosteric binding, and in vivo profiling revealed superior PK properties compared to current RXR agonists. The optimized compounds were highly selective for RXR activation and induced RXR-regulated gene expression in native cellular and in vivo settings suggesting them as excellent chem. tools to further explore the therapeutic potential of RXR.

Journal of Medicinal Chemistry published new progress about Crystal structure. 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Formula: C9H7F3O2.

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

Qiao, Zhi; Fu, Wen; Zhang, Yongchao; Chen, Ruijia; Xu, Zhiping; Li, Zhong; Shao, Xusheng published the artcile< Azobenzene-Semicarbazone Enables Optical Control of Insect Sodium Channels and Behavior>, HPLC of Formula: 2557-13-3, the main research area is azobenzene semicarbazone optical photoswitching sodium channel insect behavior; invertebrates; metaflumizone; photopharmacology; photoswitches; sodium channels.

Photopharmacol. uses mol. photoswitches to establish control over the action of bioactive mols. The application of photopharmacol. in the research of invertebrate sodium channels has not been investigated. Here we report several photochromic ligands of metaflumizone. One ligand, termed ABM04 (I), underwent reversible trans-cis isomerization under UV or blue light irradiation cis-ABM04 had excellent larvicidal activity against mosquito larvae with an LC50 value of 4.39 μM and showed insecticidal activity against Mythimna separata with an LC50 value of 7.19 μM. However, trans-ABM04 was not found to have biol. activity. ABM04 (10 μM) can induce depolarization of dorsal unpaired median neurons and enable the real-time photoregulation of mosquito larval behavior. The precise regulation of invertebrate sodium channels is realized for the first time, which provides a new strategy for the basic and accurate research of invertebrate sodium channels.

Journal of Agricultural and Food Chemistry published new progress about Aedes albopictus. 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, HPLC of Formula: 2557-13-3.

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

Liu, Jing; Wan, Cong; Zheng, Aili; Wang, Lianyue; Yin, Kaiyue; Liu, Dandan; Wang, Shengde; Ren, Lanhui; Gao, Shuang published the artcile< α-Oxygenation of Benzylic Ethers to Esters Using MnOx-N@C Catalyst>, Category: esters-buliding-blocks, the main research area is benzoic ester preparation chemoselective green chem; benzylic ether oxidation manganese catalyst.

A catalytic system for the oxidation of benzylic ethers 2-R-3-R1-4-R2-5-R3-6-R4C6CH2OR5 (R = H, OH, Cl, OMe, etc.; R1 = H, Me, OMe, CF3; RR1 = -CH=CH-CH=CH-; R2 = H, i-Pr, Cl, Ph, etc.; R1R2 = -OCH2O-; R3 = H; R4 = H, Cl; R3R4 = -CH=CH-CH=CH-; R5 = Me, Et, Bn; R4R5 = -(CH2)2-, -CH2-) to esters 2-R-3-R1-4-R2-5-R3-6-R4C6C(O)OR5 has been developed utilizing reusable MnOx-N@C as catalyst and tert-Bu hydroperoxide (TBHP) as benign oxidant under neat condition. The catalytic oxidation system has good functional groups tolerance and excellent chemoselectivity, and this catalytic procedure can also be scaled up.

Youji Huaxue published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Category: esters-buliding-blocks.

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

Zhao, Haiwei; Herbert, Simon; Kinzel, Tom; Zhang, Wei; Shen, Qilong published the artcile< Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation>, Application of C9H7F3O2, the main research area is fluoromethyl palladium imidazolinylidene complex preparation crystal structure fluoromethylation catalyst; crystal structure fluoromethyl palladium arylimidazolinylidene complex; mol structure fluoromethyl palladium arylimidazolinylidene complex; hetero arene borylation difluoromethylation palladium catalyst; fluoromethylated heteroarene preparation.

A process for the concurrent transfer of both the NHC ligand and difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc and OPiv) for the preparation [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the 1st 1-pot C-H borylation and difluoromethylation for the preparation of difluoromethylated (hetero)arenes was developed.

Journal of Organic Chemistry published new progress about Aromatic hydrocarbons Role: RCT (Reactant), RACT (Reactant or Reagent). 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Application of C9H7F3O2.

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

Demonti, Luca; Saffon-Merceron, Nathalie; Mezailles, Nicolas; Nebra, Noel published the artcile< Cross-Coupling through Ag(I)/Ag(III) Redox Manifold>, Application In Synthesis of 2557-13-3, the main research area is silver trifluoromethyl tervalent argentate preparation reductive elimination arylboronate; trifluoromethyl arene preparation coupling arylboronate trifluoromethylargentate reductive elimination; crystal mol optimized electronic structure tervalent trifluoromethyl argentate complex; AgIII chemistry; cross-coupling; fluorine; high-valent species; trifluoromethylation.

Trifluoromethyl argentates(III) undergo reductive elimination with arylboronic acids, yielding trifluoromethylarenes. In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e- redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: (i) easy AgI/AgIII 2e- oxidation mediated by air; (ii) bpy/phen ligation to AgIII; (iii) boron-to-AgIII aryl transfer; and (iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]- (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]- intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.

Chemistry – A European Journal published new progress about Boronic acids, esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (arylboronates). 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Application In Synthesis of 2557-13-3.

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

Gu, Yuanyun; Zhang, Zhen; Wang, Yan-En; Dai, Ziteng; Yuan, Yaqi; Xiong, Dan; Li, Jie; Walsh, Patrick J.; Mao, Jianyou published the artcile< Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe3)2/Cs+ System>, Related Products of 2557-13-3, the main research area is aryl acetophenone preparation; methyl benzoate Weinreb amide toluene benzylic aroylation.

Chemoselective deprotonative functionalization of benzylic C-H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)-H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes to Weinreb amides mediated by LiN(SiMe3)2/CsF for the synthesis of a diverse array of 2-arylacetophenones. Surprisingly, simple Me benzoates also react with toluenes under similar conditions to form 2-arylacetophenones without double addition to give tertiary alc. products. This finding greatly increases the practicality and impact of this chem. Some challenging substrates with respect to benzylic deprotonations, such as fluoro and methoxy substituted toluenes, are selectively transformed to 2-aryl acetophenones. The value of benzylic deprotonation of 3-fluorotoluene is demonstrated by the synthesis of a key intermediate in the preparation of Polmacoxib.

Journal of Organic Chemistry published new progress about Acetophenones Role: SPN (Synthetic Preparation), PREP (Preparation) (2-aryl). 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Related Products of 2557-13-3.

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

Nishiyama, Yoshitake; Misawa, Yoshihiro; Hazama, Yuki; Oya, Kazuhiro; Yoshida, Suguru; Hosoya, Takamitsu published the artcile< Synthesis of diverse 3-Azido-5-(azidomethyl)benzene derivatives via formal C-H azidation and functional group-selective transformations>, Reference of 2557-13-3, the main research area is aliphatic aromatic diazido building block preparation; disubstituted benzene regioselective borylation deborylative azidation key step.

3-Azido-5-(azidomethyl)benzene derivatives are useful compounds for preparing diverse bistriazole compounds and photoaffinity probes for target identification of bioactive compounds To more easily synthesize a diverse range of diazido compounds, a facile method for synthesizing diazido compounds bearing a transformable functional group, such as iodo, bromo, methoxycarbonyl, or cyano group, was developed. This method is based on formal C-H azidation of 1,3-disubstituted benzenes via regioselective borylation followed by deborylative azidation with subsequent transformations, such as that of a one-carbon unit on the benzene ring to an azidomethyl group. The functional groups of the diazido compounds were efficiently transformed to various connecting groups, including carboxy, (succinimidyloxy)carbonyl, hydroxymethyl, formyl, bromomethyl, tosylthiomethyl, ethynyl, diazoacetyl, bromoacetyl, boryl, hydroxy, aminocarbonyl, amino, and isothiocyanato groups, leaving the azido groups untouched. Several diazido building blocks were used to prepare diazido compounds by forming amide, thiourea, and sulfide bonds via conjugation at the connecting groups. These results show that the method described here would facilitate diazido probe syntheses and bistriazole library construction.

Heterocycles published new progress about Azidation. 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Reference of 2557-13-3.

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

Wang, Zheng; Zhao, Ziwei; Li, Yong; Zhong, Yanxia; Zhang, Qiuyue; Liu, Qingbin; Solan, Gregory A.; Ma, Yanping; Sun, Wen-Hua published the artcile< Ruthenium-catalyzed hydrogenation of CO2 as a route to methyl esters for use as biofuels or fine chemicals>, Name: Methyl 3-(trifluoromethyl)benzoate, the main research area is carbon dioxide hydrogenation methyl ester ruthenium catalyst.

A novel robust diphosphine-ruthenium(II) complex has been developed that can efficiently catalyze both the hydrogenation of CO2 to methanol and its in situ condensation with carboxylic acids to form Me esters; a TON of up to 3260 is achievable for the CO2 to methanol step. Both aromatic and aliphatic carboxylic acids can be transformed to their corresponding Me esters with high conversion and selectivity (17 aliphatic and 18 aromatic examples). On the basis of a series of experiments, a mechanism has been proposed to account for the various steps involved in the catalytic pathway. More importantly, this approach provides a promising route for using CO2 as a C1 source for the production of biofuels, fine chems. and methanol.

Chemical Science published new progress about Biofuels. 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Name: Methyl 3-(trifluoromethyl)benzoate.

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

Manfrin, Alessandro; Hanggli, Aline; van den Wildenberg, Jeroen; McNeill, Kristopher published the artcile< Substituent Effects on the Direct Photolysis of Benzotrifluoride Derivatives>, Name: Methyl 3-(trifluoromethyl)benzoate, the main research area is benzotrifluoride derivative direct photolysis substituent effect.

The chem. class of benzotrifluoride derivatives is widely used in active ingredients of various com. products, such as pharmaceuticals, pesticides, herbicides, and crop protection agents. Past studies have shown that some benzotrifluorides are not stable under UV irradiation in water and convert into benzoic acids due to C-F bond hydrolysis. It was also observed, but never systematically studied, that the ring substituents play an important role on the direct photochem. reactivity of the CF3 moiety. In the present work, we explore the structure-reactivity relationship between ring substituent and direct photodefluorination for 16 different substituents, by determining fluoride production rates, quantum yields, and half-lives, and found that strong electron-donating groups enhance the reactivity toward hydrolysis. In addition, flufenamic acid, travoprost, dutasteride, cyflumetofen, flutoanil, and teriflunomide were also examined, finding that their direct photochem. reactivity could be qual. predicted based on their ring substituents. We provide here a tool to evaluate the environmental persistence of benzotrifluoride contaminants, as well as to design more photodegradable new active ingredients.

Environmental Science & Technology published new progress about Defluorination. 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Name: Methyl 3-(trifluoromethyl)benzoate.

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

Karmel, Caleb; Hartwig, John F. published the artcile< Mechanism of the Iridium-Catalyzed Silylation of Aromatic C-H Bonds>, Electric Literature of 2557-13-3, the main research area is arene silylation mechanism iridium catalysis.

Phenanthroline ligands and [Ir(cod)(OMe)]2 form complexes that catalyze the silylation of aromatic and aliphatic C-H bonds. However, no exptl. data on the identity of complexes related to the mechanism of this process or the mechanisms by which they react to functionalize C-H bonds have been reported. Herein, we describe our studies on the mechanism of the iridium-catalyzed silylation of aryl C-H bonds. The resting state of the catalyst is an iridium disilyl hydride complex (phenanthroline)Ir(SiMe(OTMS)2)2(H)(L), in which L varies with the arene and additives. An iridium disilyl hydride complex was isolated, characterized, and allowed to react with arenes to form aryl silanes. The kinetics of the reactions of electron-rich and electron-poor arenes showed that the rate-limiting step varies with the electronic properties of the arene. Computational studies on related iridium silyl complexes revealed that the high activity of iridium complexes with sterically encumbered phenanthroline ligands is due to a change in the number of silyl groups bound to iridium between the resting state of the catalyst containing the hindered phenanthroline and that containing less hindered phenanthroline.

Journal of the American Chemical Society published new progress about Aromatic hydrocarbons Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), PROC (Process), RACT (Reactant or Reagent), PREP (Preparation). 2557-13-3 belongs to class esters-buliding-blocks, and the molecular formula is C9H7F3O2, Electric Literature of 2557-13-3.

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