Category: 627-27-0

Li, Sifan; Wang, Yu; Wu, Zibo; Shi, Weiliang; Lei, Yibo; Davies, Paul W.; Shu, Wei published the artcile< A Radical-Initiated Fragmentary Rearrangement Cascade of Ene-Ynamides to [1,2]-Annulated Indoles via Site-Selective Cyclization>, Name: But-3-en-1-ol, the main research area is annulated indole regioselective preparation; ene ynamide fragmentary rearrangement cascade radical initiated.

Herein, a radical triggered fragmentary cyclization cascade reaction of ene-ynamides was presented, providing a rapid access into [1,2]-annulated indoles I [R = H, Me, SMe, etc.; R1 = Ph, 4-MeC6H4, 3-pyridyl, etc.; R2 = H, Me, n-Bu; n = 1,2,3] by an intermol. radical addition, intramol. cyclization, desulfonylative aryl migration, and site-selective C(sp2)-N cyclization sequence. DFT calculations support oxidation of N-centered radical species to cations prior to the C-N bond formation, followed by an unusual aza-Nazarov cyclization.

Organic Letters published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Name: But-3-en-1-ol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Michalak, Michal; Bisek, Bartosz; Nowacki, Michal; Gorecki, Marcin published the artcile< Base-Catalyzed, Solvent-Free Synthesis of Rigid V-Shaped Epoxydibenzo[b,f][1,5]diazocines>, Product Details of C4H8O, the main research area is fluorinated aminophenone tetramethylguanidine catalyst autocondensation cross condensation; epoxydibenzo diazocine preparation.

A novel method for the synthesis of epoxydibenzo[b,f][1,5]diazocines exhibiting a V-shaped mol. architecture is reported. The unique approach is based on unprecedented base-catalyzed, solvent-free autocondensation and cross-condensation of fluorinated o-aminophenones. The structure of the newly synthesized diazocines was confirmed independently by X-ray anal. and chiroptical methods. The rigidity of the diazocine scaffold allowed for the separation of the racemate into single enantiomers that proved to be thermally stable up to 140°C. Furthermore, the inertness of the diazocine scaffold was demonstrated by performing a series of typical transformations, including transition metal-catalyzed reactions, proceeding without affecting the bis-hemiaminal subunit.

Journal of Organic Chemistry published new progress about Condensation reaction. 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Product Details of C4H8O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Quach, Linda; Dutta, Subhabrata; Pflueger, Philipp M.; Sandfort, Frederik; Bellotti, Peter; Glorius, Frank published the artcile< Visible-Light-Initiated Hydrooxygenation of Unactivated Alkenes-A Strategy for Anti-Markovnikov Hydrofunctionalization>, Name: But-3-en-1-ol, the main research area is unactivated alkene hydrooxygenation visible light anti Markovnikov hydrofunctionalization.

Hydrofunctionalization of unactivated alkenes is an indispensable mean in synthetic chem. Given that addition of electrophilic species into alkenes intrinsically follows the Markovnikov rule, a regioselectivity switch presents a major challenge. Herein, authors present a visible-light-promoted strategy for the selective anti-Markovnikov hydrooxygenation of unactivated alkenes. Therefore, an innovative reagent was carefully designed to release a highly reactive and strongly underdeveloped alkoxycarbonyloxyl radical upon reduction, which selectively adds into alkenes. Hydrogen atom abstraction from 2-phenylmalononitrile is the key to form the product. Authors believe that this methodol. enlarges the toolbox for regioselective hydrofunctionalization and could serve as a complementary strategy to the established hydroboration/oxidation protocol.

ACS Catalysis published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Name: But-3-en-1-ol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Nishimura, Taiki; Katsuhara, Satoshi; Lee, Chaehun; Ree, Brian J.; Borsali, Redouane; Yamamoto, Takuya; Tajima, Kenji; Satoh, Toshifumi; Isono, Takuya published the artcile< Fabrication of Ultrafine, Highly Ordered Nanostructures Using Carbohydrate-Inorganic Hybrid Block Copolymers>, Application of C4H8O, the main research area is carbohydrate inorganic hybrid block copolymer ultrafine fabrication; block copolymer; gyroid structure; microphase-separated structure; organic–inorganic hybrid; self-assembly.

Block copolymers (BCPs) have garnered considerable interest due to their ability to form microphase-separated structures suitable for nanofabrication. For these applications, it is critical to achieve both sufficient etch selectivity and a small domain size. To meet both requirements concurrently, we propose the use of oligosaccharide and oligodimethylsiloxane as hydrophilic and etch-resistant hydrophobic inorganic blocks, resp., to build up a novel BCP system, i.e., carbohydrate-inorganic hybrid BCP. The carbohydrate-inorganic hybrid BCPs were synthesized via a click reaction between oligodimethylsiloxane with an azido group at each chain end and propargyl-functionalized maltooligosaccharide (consisting of one, two, and three glucose units). In the bulk state, small-angle X-ray scattering revealed that these BCPs microphase separated into gyroid, asym. lamellar, and sym. lamellar structures with domain-spacing ranging from 5.0 to 5.9 nm depending on the volume fraction. Addnl., we investigated microphase-separated structures in the thin film state and discovered that the BCP with the most asym. composition formed an ultrafine and highly oriented gyroid structure as well as in the bulk state. After reactive ion etching, the gyroid thin film was transformed into a nanoporous-structured gyroid SiO2 material, demonstrating the material’s promising potential as nanotemplates.

Nanomaterials published new progress about Annealing. 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Application of C4H8O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chen, Xueyuan; Zhong, Junyang; Jiang, Xinlin; He, Ziqing; Quan, Yusi; Zhong, Songjing; Li, Guangji; Huang, Yugang published the artcile< Structure and Oxidation Effects on Conformation and Thermoresponsiveness of the OEGylated Poly(glutamic acid)-Bearing Side-Chain Thioether Linkers>, Application of C4H8O, the main research area is structure conformation thermoresponsiveness polyglutamic acid side chain thioether linker.

A series of side-chain thioether-linked OEGylated poly(glutamic acid) (PGAs) have been synthesized by “”thiol-ene”” synthetic methodol., where both the oligo-ethylene glycol (OEG) length and the hydrophobic linkers at the side chains are varied to learn how these structural features affect the secondary structure and thermoresponsive behaviors in water. Before side-chain oxidation, the structural factors affecting the α-helicity include the backbone length, the OEG length, and the hydrophobic linkers’ length at the side chains; however, the OEG length plays the most crucial role among these factors because longer OEG around the peripheral side chains can stop water penetration into the backbone to disturb the intramol. H bonds, which finally allows stabilizing the α-helix; after the oxidation, the polypeptides show increased α-helicity because of the enhanced hydrophilicity. More interestingly, a rare oxidation-induced conformation transition from the ordered β-sheet to the ordered α-helix can be achieved. In addition, only the OEGylated poly(glutamic acids) (PGAs) with shorter hydrophobic linkers and longer OEG can display the thermoresponsive properties before the oxidation but the subsequent oxidation can cause the polypeptides bearing longer hydrophobic linkers to exhibit the thermosensitivity since sulfone formation at the side chain can lead to final hydrophilicity-hydrophobicity balance. This work is meaningful to understand the secondary structure-associated solution behaviors of the synthetic polypeptides.

Langmuir published new progress about Biomimetics. 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Application of C4H8O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Thane, Taylor A.; Jarvo, Elizabeth R. published the artcile< Ligand-Based Control of Nickel Catalysts: Switching Chemoselectivity from One-Electron to Two-Electron Pathways in Competing Reactions of 4-Halotetrahydropyrans>, Formula: C4H8O, the main research area is cyclopropylethanol preparation chemoselective; halotetrahydropyran cross electrophile coupling nickel phosphine catalyst; alkyl tetrahydropyran preparation chemoselective; halo tetrahydropyran reduction nickel amine catalyst.

A ligand-based modulation of catalyst preference for one- or two-electron pathways employing 4-halotetrahydropyrans I (Ar = 2-naphthyl, 4-phenylphenyl) as model substrates that can undergo divergent reaction pathways was evaluated. Chemoselectivity for one- or two-electron oxidative addition is predicted by ligand class. Phosphine-ligated nickel catalysts favor closed-shell oxidative addition In contrast, nitrogen-ligated nickel catalysts prefer the one-electron pathway, initiating with halogen atom transfer.

Organic Letters published new progress about Bond activation catalysts (C-O, C-X). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Formula: C4H8O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhang, Xinyu; Li, Linxuan; Zanoni, Giuseppe; Han, Xinyue; Bi, Xihe published the artcile< Direct gem-Difluoroalkenylation of X-H Bonds with Trifluoromethyl Ketone N-Triftosylhydrazones for Synthesis of Tetrasubstituted Heteroatomic gem-Difluoroalkenes>, Quality Control of 627-27-0, the main research area is heteroatomic gem difluoroalkene preparation DFT; trifluoromethyl ketone triftosylhydrazone amine difluoroalkenylation silver catalyst; alc trifluoromethyl ketone triftosylhydrazone difluoroalkenylation silver catalyst; carbene; difluoroalkene; difluoroalkenylation; rhodium catalysis; silver catalysis.

Here, the first direct X-H bond gem-difluoroalkenylation of amines, e.g., N-methylaniline and alcs., e.g., methanol with trifluoromethyl ketone N-triftosylhydrazones, e.g., benzenesulfonic acid, 2-(trifluoromethyl)-, 2-(2,2,2-trifluoro-1-phenylethylidene)hydrazide under silver (for (hetero)aryl hydrazones) or rhodium (for alkyl hydrazones) was reported, thereby providing a most powerful method for the synthesis of tetrasubstituted heteroat. gem-difluoroalkenes, e.g., (2,2-difluoro-1-phenyl-vinyl)-methyl-phenyl-amine/1,1-difluoro-2-methoxy-2-phenylethene. This method features a broad substrate scope, high product yield, excellent functional group tolerance, and operational simplicity (open air conditions). Moreover, the site-specific replacement of the carbonyl group with a gem-difluorovinyl ether bioisostere in drug Trimebutine and the post-modification of bioactive mols. demonstrates potential use in medicinal research. Finally, the reaction mechanism was investigated by combining experiments and DFT calculations, and disclosed that the key step of HF elimination occurred via five-membered ring transition state, and the difference in the electrophilicity of Ag- and Rh-carbenes as well as the multiple intermol. interactions rendered the effectiveness of Rh catalyst selectively for alkyl hydrazones.

Chemistry – A European Journal published new progress about Alkenylation (difluoro-). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Quality Control of 627-27-0.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ying, Hanglu; Yao, Jie; Wu, Fan; Zhao, Yufen; Ni, Feng published the artcile< A mild and concise synthesis of aryloxy phosphoramidate prodrug of alcohols via transesterification reaction>, Recommanded Product: But-3-en-1-ol, the main research area is aryloxy phosphoramidate prodrug alc transesterification reaction.

A synthesis of aryloxy phosphoramidate prodrug of alcs. enabled by a transesterification strategy is described here. This reaction operates under mild conditions and thus has excellent functional group tolerance. This method provides an efficient and practical solution to the rapid construction of the aryloxy phosphoramidate prodrugs library for potential SAR studies.

RSC Advances published new progress about Alcohols Role: BUU (Biological Use, Unclassified), BIOL (Biological Study), USES (Uses). 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

Yamaguchi, Eiji; Inagawa, Hisamori; Itoh, Akichika published the artcile< Selenonium ylides: Synthesis, characterization, and applications to photo-induced cyclopropanation reactions>, Formula: C4H8O, the main research area is cyclopropane preparation photochem; selenonium ylide preparation cyclopropanation alkene; diazomalonate dibenzoselenophene addition reaction rhodium catalyst; Carbene; Cyclopropanation; Photoreaction; Selenonium ylide.

Carbenes are important and highly reactive intermediates for the synthesis of various complex mols. They are now an indispensable chem. species in organic chem. and are used frequently to synthesize complex compounds in drug discovery chem. In general, carbenes are synthesized by a combination of transition metal catalysts and diazo compounds or by the decomposition reactions of diazo compounds This paper reports the development of visible light-initiated photochem. generation of carbenes from novel C,Se-selenonium ylides I (R = Me, Bn, R1 = H, R2 = H, OMe, NO2, R1R2 = -CH:CH-CH:CH-). Overall, this photochem. carbene generation method using C,Se-selenonium ylides does not require a catalyst, is simple to perform, and enables highly efficient cyclopropanation reactions with alkenes, e.g., H2C=CHR3 (R3 = Ph, 2-naphthyl, COMe, etc.).

Photochemical & Photobiological Sciences published new progress about Addition reaction. 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Formula: C4H8O.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Yang, Yifei; Wang, Yonghai; Zuo, Aixia; Li, Chunmei; Wang, Wenyan; Jiang, Wanglin; Zhang, Xiaochen; Che, Xin; Zhang, Yang; Wu, Wentao; Cen, Xiaobo; Wang, Hongbo; Tian, Jingwei published the artcile< Synthesis, biological, and structural explorations of a series of μ-opioid receptor (MOR) agonists with high G protein signaling bias>, Synthetic Route of 627-27-0, the main research area is mu opioid receptor agonist G protein signaling pharmacokinetics antinociceptive; Analgesia; Biased agonism; Respiratory repression; μ-opioid receptor.

Biased agonism refers to the ability of compounds to drive preferred signaling pathways and avoid adverse signaling pathways in a ligand-dependent manner for some G-protein-coupled receptors. It is thought that the separation of therapeutic efficacy (e.g., analgesia) from adverse effects (e.g., respiration depression) can be achieved through the design of biased MOR agonists and one example is the recently approved MOR biased agonist oliceridine (TRV130). However, oliceridine only demonstrates modest beneficial effects as compared to other opioids in terms of therapeutic/adverse effect balance. One possibility attributable to the modest success of oliceridine is its limited bias, and as such developing MOR ligands with a more biased agonism profile could in theory further improve the beneficial effects of the ligands. Here, we rationally designed and synthesized a series of derivatives as potent highly biased MOR agonists (19a-v) through the modification and structure-activity relationship study of TRV130. This novel synthetic mol., LPM3480392 (19m), demonstrated improved in vitro biased agonism (EC50 = 0.35 nM, Emax = 91.4%) with no measured β-arrestin recruitment (EC50 > 30000 nM, Emax = 1.6%), good brain penetration (B/P ratio = 4.61, 0.25 h post-IV dosing 2.0 mg/kg), a favorable pharmacokinetic profile (distribution volume = 10766 mL/kg, t1/2 = 1.9 h) and produced potent antinociceptive effect with reduced respiratory suppression (sO2(%) = 92.17, 0.32 mg/kg, SC) as compared to TRV130. LPM3480392 has completed preclin. studies and is currently under clin. development (CTR20210370) as an analgesic for the treatment of moderate to severe pain.

European Journal of Medicinal Chemistry published new progress about Affinity (binding). 627-27-0 belongs to class alcohols-buliding-blocks, and the molecular formula is C4H8O, Synthetic Route of 627-27-0.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts