Month: October 2022

Moggia, Giulia; Schalck, Jonathan; Daems, Nick; Breugelmans, Tom published the artcile< Two-steps synthesis of D-glucaric acid via D-gluconic acid by electrocatalytic oxidation of D-glucose on gold electrode: Influence of operational parameters>, Electric Literature of 87-73-0, the main research area is synthesis glucaric gluconic acid electrocatalysis oxidation glucose gold electrode.

Glucose electrooxidation to glucaric acid, a highly valuable platform chem., was conducted, for the 1st time, in two consecutive steps employing a bare Au electrode in a batch reactor. The 1st step, at low potential, enabled the effective formation of the intermediate, gluconic acid, promoted by the oxidation of the aldehyde group on C1. For this reaction step, except for the reaction time, all the operational parameters had a strong impact on the selectivity. At the optimal conditions of pH 11.3, 5° and 0.04M initial glucose, a maximum selectivity of 97.6% was obtained, the highest reported to date for the electrochem. process, with a conversion of 25%. At higher potential, gluconic acid was further converted to glucaric acid by the oxidation of the hydroxymethyl group on C6. For this oxidation step, the variation of the operational parameters (pH, gluconic acid initial concentration, reaction temperature and time) had no conspicuous effect on the selectivity, while the applied potential had a major role: at 1.1 VRHE, a maximum selectivity of 89.5% to glucaric acid was obtained, which is one of the highest values reported in literature so far. In all experiments, irresp. of conditions and reaction time, a maximum concentration of ∼1.2 mM of glucaric acid was achieved, and a drastic decrease of the c.d. was observed in the 1st hours of electrolysis. Addnl. control experiments revealed a poisoning process caused by glucaric acid that, once formed, remains strongly bonded to the catalyst’s active sites, thus deactivating it.

Electrochimica Acta published new progress about Cyclic voltammetry. 87-73-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C6H10O8, Electric Literature of 87-73-0.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Lu, Jianwu; Shi, Yinfei; Li, Xiao; Liang, Xiaomin; Wang, Yinquan; Yuan, Shun; Wu, Taizhi published the artcile< Understanding and Controlling the Formation of an N-Alkyl Impurity in Olmesartan Medoxomil: A Derivative via Michael-Type Addition between Tetrazole and Mesityl Oxide In Situ Generated from Acetone>, COA of Formula: C19H16O, the main research area is olmesartan medoxomil API impurity quality by design definitive screening.

An unknown impurity was detected in olmesartan medoxomil active pharmaceutical ingredient (API), which was determined as 2-methyl-4-oxopentan-2-yl-protected olmesartan medoxomil by NMR and mass spectrometry (MS). The formation mechanism of this impurity was investigated. In summary, the tetrazole of the final product was condensed with the potential genotoxic compound mesityl oxide generated from acetone self-condensation in acidic conditions to form the N-Alkyl impurity. Further quality control of the reaction was investigated using statistical methods (design of experiment, DoE) via a definitive screening design. The key factors of the reaction were determined to control the process parameters. Three batches of validation experiments showed that the generation of the N-Alkyl impurity was suppressed (<0.1%) and the residual mesityl oxide was not detected (<2.5 ppm). Organic Process Research & Development published new progress about Antihypertensives. 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, COA of Formula: C19H16O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Cui, Jianchao; Ke, Sen; Zhao, Jia; Wu, Shufeng; Luo, Wencheng; Xu, Shinuo; Su, Xiaolong; Li, Yi published the artcile< Photocatalytic access to aromatic keto sulfonyl fluorides from vinyl fluorosulfates>, Reference of 627-27-0, the main research area is aromatic keto sulfonyl fluoride preparation; vinyl fluorosulfate preparation rearrangement iridium photocatalyst.

An efficient photocatalytic transformation of vinyl fluorosulfates I [R = H, 5-Br, 6-Me, 7-(phenanthren-1-yl), etc.; X = -CH2-, -O-, -CH(CH3)-], and 1H-inden-3-yl sulfofluoridate, 6-bromo-1H-inden-3-yl sulfofluoridate to aromatic β-keto sulfonyl fluorides II, III (R = H, Br) with 1 mol% of iridium catalyst under the irradiation of 3 W blue LEDs was presented. Preliminary mechanistic studies proposed a direct radical fragmentation and recombination of vinyl fluorosulfates through a free fluorosulfonyl radical (FSO2). This methodol. provides a facile approach to aromatic β-keto sulfonyl fluorides, featuring sustainable conditions and a broad substrate scope (32 examples) with 33%-90% isolated yields.

Organic Chemistry Frontiers published new progress about Cyclic voltammetry. 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Reference of 627-27-0.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Comotti, A.; Castiglioni, F.; Bracco, S.; Perego, J.; Pedrini, A.; Negroni, M.; Sozzani, P. published the artcile< Fluorinated porous organic frameworks for improved CO2 and CH4 capture>, SDS of cas: 76-84-6, the main research area is fluoropolymer polyacetylene synthesis adsorbent carbon dioxide methane adsorption.

A porous 3D selectively fluorinated framework (F-PAF1), robust yet flexible and with a surface area of 2050 M2 g-1, was synthesized by condensation of an ad hoc prepared fluorinated tetraphenylmethane (TPM) monomer to ensure homogeneously distributed C-F dipoles in the swellable architecture. Tetradentate TPM was also the comonomer for the reaction with fluorinated difunctional monomers to obtain frameworks (FMFs) with a controlled amount of regularly spaced reorientable C-F dipoles. The isosteric heat of adsorption of CO2 was increased by 53% by even moderate C-F dipole insertion, with respect to the non-fluorinated frameworks. CO2/N2 selectivity was also increased up to a value of 50 for the difluoro-containing comonomer. Moreover, methane shows optimal interaction energies of 24 kJ mol-1.

Chemical Communications (Cambridge, United Kingdom) published new progress about Adsorbents. 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, SDS of cas: 76-84-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Pandey, Bedraj; Xu, Shi; Ding, Keying published the artcile< Switchable β-alkylation of Secondary Alcohols with Primary Alcohols by a Well-Defined Cobalt Catalyst>, Electric Literature of 403-41-8, the main research area is alkylation primary secondary alc preparation cobalt triphosphine pyridine catalyst; switchable ketone secondary alc preparation alkylation benzenemethanol cobalt catalyst.

β-Alkylation of secondary alcs. R1CH(OH)Me with primary alcs. R2CH2OH catalyzed by cobalt(I) triphosphine-pyridine complex in the presence of KOtBu selectively generate either alcs. R1CH(OH)CH2CH2R2 or ketones R1COCH2CH2R2 in dependence of catalyst and base loadings and hydrogen presence or removal. Remarkably, a low catalyst loading of 0.7 mol% can be employed for the reaction. More significantly, this study represents the first Co-catalyzed switchable alc./ketone synthesis by simply manipulating the reaction parameters. In addition, the transformation is environmentally friendly, with water as the only byproduct.

Organometallics published new progress about Alkylation. 403-41-8 belongs to class alcohols-buliding-blocks, and the molecular formula is C8H9FO, Electric Literature of 403-41-8.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Baars, Julian; Grimm, Isabelle; Blunk, Dirk; Neudorfl, Jorg-Martin; Schmalz, Hans-Guenther published the artcile< Enantioselective Total Synthesis and Structural Revision of Dysiherbol A>, Recommanded Product: But-3-en-1-ol, the main research area is dysiherbol A enantiomer enantioselective synthesis addition cyclization cyclopropane opening; cyclization; enantioselectivity; gold catalysis; natural products; rearrangement.

A 12-step total synthesis of the natural product dysiherbol A, a strongly anti-inflammatory and anti-tumor avarane meroterpene isolated from the marine sponge Dysidea sp., was elaborated. As key steps, the synthesis features an enantioselective Cu-catalyzed 1,4-addition/enolate-trapping opening move, an Au-catalyzed double cyclization to build up the tetracyclic core-carbon skeleton, and a late installation of the C5-bridgehead Me group via proton-induced cyclopropane opening associated with spontaneous cyclic ether formation. The obtained pentacyclic compound I (corresponding to an anhydride of the originally suggested structure for dysiherbol A) showed identical spectroscopic data as the natural product, but an opposite mol. rotation. CD-spectroscopic measurements finally confirmed that both the constitution and the absolute configuration of the originally proposed structure of (+)-dysiherbol A need to be revised.

Angewandte Chemie, International Edition published new progress about 1,4-Addition reaction catalysts (stereoselective). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Recommanded Product: But-3-en-1-ol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Sun, Peng-Wei; Zhang, Ze; Wang, Xinyao; Li, Linshan; Li, Yuxin; Li, Zhengming published the artcile< Cobalt-Catalyzed Intermolecular Hydroamination of Unactivated Alkenes Using NFSI as Nitrogen Source>, Application of C4H8O, the main research area is diphenylsulfonimide preparation chemoselective regioselective; alkene fluorobenzenesulfonimide cobalt hydroamination.

Comprehensive Summary : Cheap metal (Fe, Mn, and Co)-catalyzed hydroamination of alkenes has been an attractive method for synthesis of amines because of biocompatibility of metal, excellent Markovnikov selectivity and chemoselectivity. However, most reports are limited to unsaturated nitrogen sources (nitric oxide, azos, azides, cyano, etc.), for which aminated products are very limited. Notably, while used widely for fluorinating reaction, N-fluorobenzenesulfonimide (NFSI) as amine source for hydroamination has seldom been reported. Here authors developed a cobalt-catalyzed intermol. hydroamination of unactivated alkenes using NFSI as nitrogen source under mild conditions. The reaction exhibits excellent chemo- and regio-selectivity with no hydrofluorination or linear-selectivity products. Notably, the reaction proceeded with excellent yield even though the amount of Co(salen) catalyst was reduced to 0.2 mol%. Recently, a similar work was also reported by Zhang and coworkers (reference 19).

Chinese Journal of Chemistry published new progress about Aryl alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Application of C4H8O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Rodriguez Tzompantzi, Tomasa; Amaro Hernandez, Aldo Guillermo; Meza-Leon, Rosa Luisa; Bernes, Sylvain published the artcile< Deciphering the hydrogen-bonding scheme in the crystal structure of triphenylmethanol: a tribute to George Ferguson and co-workers>, Quality Control of 76-84-6, the main research area is triphenylmethanol crystal structure hydrogen bond; alcohol; crystal structure; disorder; hydrogen bond; topological chirality; triphenylmethanol.

The crystal structure of triphenylmethanol, C19H16O, has been redetermined using data collected at 295 and 153 K, and is compared to the model published by Ferguson et al. over 25 years ago [Ferguson et al. (1992). Acta Crystalline C48, 1272-1275] and that published by Serrano-Gonzalez et al., using neutron and X-ray diffraction data [Serrano-Gonzalez et al. (1999). J. Phys. Chem. B, 103, 6215-6223]. As predicted by these authors, the hydroxy groups are involved in weak intermol. hydrogen bonds in the crystal, forming tetrahedral tetramers based on the two independent mols. in the asym. unit, one of which is placed on the threefold symmetry axis of the R [inline formula omitted] space group. However, the reliable determination of the hydroxy H-atom positions is difficult to achieve, for two reasons. Firstly, a positional disorder affects the full asym. unit, which is split over two sets of positions, with occupancy factors of ca 0.74 and 0.26. Secondly, all hydroxy H atoms are further disordered, either by symmetry, or through a positional disorder in the case of parts placed in general positions. We show that the correct description of the hydrogen-bonding scheme is possible only if diffraction data are collected at low temperature The prochiral character of the hydrogen-bonded tetrameric supramol. clusters leads to enantiomorphic three-dimensional graphs in each tetramer. The crystal is thus a racemic mixture of supS and supR motifs, consistent with the centrosym. nature of the R [inline formula omitted] space group.

Acta Crystallographica, Section C: Structural Chemistry published new progress about Crystal structure. 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Quality Control of 76-84-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ghosh, Enakshi; Venkatesan, Radhika published the artcile< Plant Volatiles Modulate Immune Responses of Spodoptera litura>, Recommanded Product: 3,7-Dimethylocta-1,6-dien-3-ol, the main research area is Herbivory; Insect immunity; Linalool; Ocimene; Plant volatiles; Tritrophic interaction.

Plants emit a specific blend of volatiles in response to herbivory and these volatiles, which often attract predators and parasitoids function as an indirect plant defense. The impact of plant volatiles in shaping herbivore defenses is unclear. Here, we report that specific plant volatiles induce immune responses in the polyphagous herbivore, Spodoptera litura. We characterized the hemocyte profile and established their functional significance with respect to ontogeny and exposure to specific plant volatiles. Fifth instar larvae showed the highest number and hemocytes diversity. We characterized seven different types of hemocytes, of which granulocytes performed phagocytosis, oenocytoids showed melanization activity, and plasmatocytes along with granulocytes and oenocytoids were found to be involved in encapsulation. Among the six volatiles tested, exposure to (E)-β-ocimene caused the highest increase in total hemocytes number (THC) followed by linalool and (Z)-3-hexenyl acetate exposure. Although THC did not differ between these three volatile treatments, circulating hemocytes diversity varied significantly. (E)-β-ocimene exposure showed higher number of plasmatocytes and phenol oxidase activity. The interaction of the parasitic wasp Bracon brevicornis with (E)-β-ocimene exposed larvae was poor in terms of delayed paralysis and lower egg deposition. In choice assays, the wasp showed clear preference towards control larvae indicating (E)-β-ocimene treatment renders the host unattractive. Hemocyte profiles post-parasitoid exposure and (E)-β-ocimene treatment were similar indicating cue-based priming. When challenged with Bacillus thuringiensis, linalool exposure resulted in the highest survival as compared to other volatiles. Our results show that specific HIPVs can modulate cellular immunity of S. litura, revealing a new role for HIPVs in tri-trophic interactions.

Journal of Chemical Ecology published new progress about 78-70-6. 78-70-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C10H18O, Recommanded Product: 3,7-Dimethylocta-1,6-dien-3-ol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Markov, Andrey V.; Sen’kova, Aleksandra V.; Popadyuk, Irina I.; Salomatina, Oksana V.; Logashenko, Evgeniya B.; Komarova, Nina I.; Ilyina, Anna A.; Salakhutdinov, Nariman F.; Zenkova, Marina A. published the artcile< Novel 3'-substituted-1',2',4'-oxadiazole derivatives of 18βH-glycyrrhetinic acid and their O-acylated amidoximes: synthesis and evaluation of antitumor and anti-inflammatory potential in vitro and in vivo>, Recommanded Product: N-Hydroxypropionimidamide, the main research area is oxadiazolyl oleanen preparation antitumor anti inflammatory agent SAR; acetoxy oxooleanen amidoxime preparation antitumor anti inflammatory agent SAR; 18βH-glycyrrhetinic acid; anti-inflammatory activity; antitumor activity; apoptosis; derivatives; heterocyclic moiety; metastasis; molecular docking; oxadiazole; target prediction.

A series of novel 18βH-glycyrrhetinic acid (GA) derivatives containing 3′-(alkyl/phenyl/pyridin(-2”, -3”, and -4”)-yl)-1′,2′,4′-oxadiazole moieties at the C-30 position were synthesized by condensation of triterpenoid’s carboxyl group with corresponding amidoximes and further cyclization. Screening of the cytotoxicity of novel GA derivatives on a panel of tumor cell lines showed that the 3-acetoxy triterpenoid intermediates-O-acylated amidoxime I [R = Me, Et, i-Pr, t-Bu, etc]display better solubility under bioassay conditions and more pronounced cytotoxicity compared to their 1′,2′,4′-oxadiazole analogs II [R = 2-pyridine, 3-pyridine, 4-pyridine] (median IC50 = 7.0 and 49.7μM, resp.). Subsequent replacement of the 3-acetoxy group by the hydroxyl group of pyridin(-2”, 3”, and -4”)-yl-1′,2′,4′-oxadiazole-bearing GA derivatives produced compounds III [R = 2-pyridine, 3-pyridine, 4-pyridine], showing the most pronounced selective toxicity toward tumor cells (median selectivity index (SI) > 12.1). Further detailed anal. of the antitumor activity of hit derivative III [R = 2-pyridine] revealed its marked proapoptotic activity and inhibitory effects on clonogenicity and motility of HeLa cervical carcinoma cells in vitro, and the metastatic growth of B16 melanoma in vivo. Addnl., the comprehensive in silico study revealed intermediate I [R = t-Bu], bearing the tert-Bu moiety in O-acylated amidoxime, as a potent anti-inflammatory candidate, which was able to effectively inhibit inflammatory response induced by IFNγ in macrophages in vitro and carrageenan in murine models in vivo, probably by primary interactions with active sites of MMP9, neutrophil elastase, and thrombin. Taken together, our findings provide a basis for a better understanding of the structure-activity relationship of 1′,2′,4′-oxadiazole-containing triterpenoids and reveal two hit mols. with pronounced antitumor III [R = 2-pyridine] and anti-inflammatory I [R = t-Bu] activities.

International Journal of Molecular Sciences published new progress about Amidoximes Role: PAC (Pharmacological Activity), RCT (Reactant), SPN (Synthetic Preparation), THU (Therapeutic Use), BIOL (Biological Study), RACT (Reactant or Reagent), PREP (Preparation), USES (Uses). 29335-36-2 belongs to class alcohols-buliding-blocks, and the molecular formula is C3H8N2O, Recommanded Product: N-Hydroxypropionimidamide.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts