Month: November 2022

Feng, Minghao published the artcileDeployment of Sulfinimines in Charge-Accelerated Sulfonium Rearrangement Enables a Surrogate Asymmetric Mannich Reaction, Recommanded Product: 3-Acetylthiophene, the main research area is polysubstituted amino amide preparation chemoselective diastereoselective enantioselective; carboxamide sulfinimine Mannich reaction.

β-Amino acid derivatives are key structural elements in synthetic and biol. chem. Despite being a hallmark method for their preparation, the direct Mannich reaction encounters significant challenges when carboxylic acid derivatives are employed. Indeed, not only is chemoselective enolate formation a pitfall (particularly with carboxamides), but most importantly the inability to reliably access α-tertiary amines through an enolate/ketimine coupling is an unsolved problem of this century-old reaction. Herein, authors report a strategy enabling the first direct coupling of carboxamides with ketimines for the diastereo- and enantioselective synthesis of β-amino amides. This conceptually novel approach hinges on the innovative deployment of enantiopure sulfinimines in sulfonium rearrangements, and at once solves the problems of chemoselectivity, reactivity, and (relative and absolute) stereoselectivity of the Mannich process. In-depth computational studies explain the observed, unexpected (dia)stereoselectivity and showcase the key role of intramol. interactions, including London dispersion, for the accurate description of the reaction mechanism.

Journal of the American Chemical Society published new progress about Amines Role: RCT (Reactant), RACT (Reactant or Reagent). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Burckhardt, Birgitta Christina published the artcileElectrophysiologic characterization of an organic anion transporter cloned from winter flounder kidney (fROAT), Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, the main research area is flounder kidney anion transporter; sequence Pseudopleuronectes anion transporter.

The 2-electrode voltage clamp technique was used to demonstrate translocation of p-aminohippurate (PAH) and related compounds such as loop diuretics in Xenopus laevis oocytes expressing the renal organic anion transporter from winter flounder kidney (fROAT). In fROAT-expressing oocytes, PAH (0.1 mM) induced a depolarization of 4.2 mV and at a holding potential of -60 mV an inward current of -22.6 nA. PAH-induced current and the current calculated from [3H]PAH uptake were of similar magnitude. Depolarization, inward current, and current-to-uptake relation indicated exchange of the monovalent PAH with a divalent anion, possibly α-ketoglutarate (α-KG), causing net efflux of 1 neg. charge. The kinetic anal. of PAH-induced currents revealed that translocation is dependent on membrane potential, saturable with an apparent Km of 58 μM, and sensitive to probenecid and furosemide. In contrast to probenecid and furosemide, the loop diuretics bumetanide, ethacrynic acid, and tienilic acid and the nephrotoxic mycotoxin ochratoxin A elicited inward currents indicating translocation through fROAT. Substrate-dependent currents provide a tool to elucidate the structure/function relationship of the renal organic anion transporter.

Journal of the American Society of Nephrology published new progress about Anion transporters Role: BAC (Biological Activity or Effector, Except Adverse), BSU (Biological Study, Unclassified), PRP (Properties), BIOL (Biological Study). 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Recommanded Product: 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Chen, Nancy published the artcileIn vitro drug-drug interactions of budesonide: inhibition and induction of transporters and cytochrome P450 enzymes, Quality Control of 40180-04-9, the main research area is budesonide drug interaction transporter cytochrome enzyme inhibition; Budesonide; cytochrome P450 enzymes; drug metabolism; drug transporters; drug–drug interactions; glucocorticoid; human hepatocytes; human liver microsomes.

1. Budesonide is a glucocorticoid used in the treatment of several respiratory and gastrointestinal inflammatory diseases. Glucocorticoids have been demonstrated to induce cytochrome P 450 (CYP) 3A and the efflux transporter P-glycoprotein (P-gp). This study aimed to evaluate the potential of budesonide to act as a perpetrator or a victim of transporter- or CYP-mediated drug-drug interactions (DDIs).2. In vitro studies were conducted for P-gp, breast cancer resistance protein and organic anion and cation transporters (OATP1B1, OATP1B3, OAT1, OAT3, OCT2) in transporter-transfected cells. Changes in mRNA expression in human hepatocytes and enzyme activity in human liver microsomes by budesonide were determined for CYP1A2, CYP2B6, CYP2C8, CYP2C9, CYP2C19, CYP2D6 and CYP3A.3. The data indicated that budesonide is a substrate of P-gp but is not a substrate or an inhibitor of the other transporters investigated. Budesonide is neither an inducer nor an inhibitor of major CYP enzymes. The effect of P-gp on budesonide disposition is anticipated to be low owing to CYP3A-mediated clearance.4. Collectively, our data indicate there is a low risk of budesonide perpetrating clin. DDIs mediated by the transporters or CYPs studied.

Xenobiotica published new progress about Cation transporters Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 40180-04-9 belongs to class benzothiophene, name is 2-(2,3-Dichloro-4-(thiophene-2-carbonyl)phenoxy)acetic acid, and the molecular formula is C13H8Cl2O4S, Quality Control of 40180-04-9.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Gong, Fei-Yuan published the artcileRhodium-Catalyzed Decarboxylative Hydroacylation of Vinylethylene Carbonates for Regioselective Ester Synthesis, Name: 3-Acetylthiophene, the main research area is salicylaldehyde aryl vinylethylene carbonate rhodium catalyst decarboxylative hydroacylation; aryl butenyl hydroxybenzoate preparation regioselective diastereoselective.

A rhodium(I)-catalyzed decarboxylative hydroacylation of readily available vinylethylene carbonates with salicylaldehydes for regioselective preparation of esters was developed. Reaction optimization revealed that methacrylamide might promote the hydroacylation by bidentate chelation assistance to the cationic rhodium. Mechanistic findings suggested that this one-pot coupling reaction proceeds via Markovnikov hydrorhodation-initiated site-selective β-C-O bond cleavage with concurrent release of CO2.

Advanced Synthesis & Catalysis published new progress about Aromatic esters Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Name: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Shen, Cong published the artcileAccess to axially chiral aryl 1,3-dienes by transient group directed asymmetric C-H alkenylations, Category: benzothiophene, the main research area is axially chiral aryl diene preparation; styrene olefin palladium catalyst asym CH alkenylation.

Herein presented, a Pd-catalyzed atroposelective preparation of aryl 1,3-dienes from readily available styrenes and olefins through an aldehyde derived transient chiral auxiliary, proceeding by enantioselective olefinic C-H alkenylation of styrenes via seven-membered endo-cyclometallation. The generality of the protocol was demonstrated by the smooth conversion of a wide range of 2-vinyl benzaldehyde derivatives to afford up to 99% yields and high to excellent enantioselectivities (up to >99% ee). The derived axially chiral carboxylic acid was demonstrated to be a more efficient ligand in the Cp*Co(III)-catalyzed asym. C(sp3)-H alkylation.

Organic Chemistry Frontiers published new progress about Alkenes Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Category: benzothiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Huang, Mouxin published the artcileDeracemization through photochemical E/Z isomerization of enamines, Recommanded Product: 3-Acetylthiophene, the main research area is aldehyde enamine deracemization; photosensitizer aminocatalyst isomerization.

Catalytic deracemization of α-branched aldehydes is a direct strategy to construct enantiopure α-tertiary carbonyls, which are essential to pharmaceutical applications. Here, authors report a photochem. E/Z isomerization strategy for the deracemization of α-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. A variety of racemic α-branched aldehydes could be directly transformed into either enantiomer with high selectivity. Rapid photodynamic E/Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the enantioenrichment. This study presents a distinctive photochem. E/Z isomerization strategy for externally tuning enamine catalysis.

Science (Washington, DC, United States) published new progress about Diastereoselective synthesis. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Shen, Jiabin published the artcileCopper-catalyzed selective oxidation of hydrazones through C(sp3)-H functionalization, Product Details of C6H6OS, the main research area is acetophenone hydrazone selective oxidation copper catalyst.

A simple and mild protocol for copper-catalyzed oxidation of hydrazones at the α-position has been reported. Various substrates are compatible, providing the corresponding products in moderate to good yields. This strategy provides an efficient and convenient solution for the synthesis of carbonyl hydrazone. A free radical pathway mechanism is suggested for the transformation.

Organic & Biomolecular Chemistry published new progress about Morpholines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Product Details of C6H6OS.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Xu, Jun published the artcileOxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis, COA of Formula: C6H6OS, the main research area is ketosulfone acylsulfonamide preparation; hydrazone sulfinate oxidative sulfonylation copper silver catalyst.

A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones with sodium sulfinates was demonstrated. A wide range of β-ketosulfones RC(O)CH(R1)SO2R2 [R = c-hexyl, Ph, 4-FC6H4, etc.; R1 = H, Me, Et, etc.; R2 = Et, Ph, 2-thienyl, etc.] and N-acylsulfonamides R3C(O)N(R4)(SO2Ph) [R3 = c-hexyl, Ph, 2-FC6H4, etc; R4 = morpholino] were directly synthesized in moderate to good yields. This work provided a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.

Journal of Organic Chemistry published new progress about Ketones Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, COA of Formula: C6H6OS.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Oe, Yuno published the artcileAn N-Fluorinated Imide for Practical Catalytic Imidations, Recommanded Product: 3-Acetylthiophene, the main research area is fluorosulfonyl aryl carbamate preparation; arene neopentyl fluoro fluorosulfonyl carbamate imidation copper catalyst.

Hherein the development of a novel N-fluorinated imide, N-fluoro-N-(fluorosulfonyl)carbamate (NFC), by which the attached imide moiety acted as a modular synthetic handle for one-step derivatization to amines, sulfonamides, and sulfamides was reported. Furthermore, this study revealed the superior reactivity of NFC as showcased in a copper-catalyzed imidation of benzene derivatives and imidocyanation of aliphatic alkenes, overcoming the limitation of NFSI-mediated reactions.

Journal of the American Chemical Society published new progress about Imidation. 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Recommanded Product: 3-Acetylthiophene.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Li, DingXi published the artcileAsymmetric Synthesis of 1-Benzazepine Derivatives via Copper-Catalyzed Intramolecular Reductive Cyclization, Application In Synthesis of 1468-83-3, the main research area is benzazepine preparation diastereoselective enantioselective; dienyl arene ketimine reductive intramol cyclization copper catalyst.

An asym. construction of enantioenriched 2,3-substituted-1-benzazepine derivatives containing a cyclic tertiary amine moiety was developed by copper-catalyzed reductive intramol. cyclization of (E)-dienyl arenes with a tethered ketimine. This protocol involves tandem chemo-, regio-, and enantioselective hydrocupration and asym. cyclization in the presence of a chiral bisphosphine-copper catalyst. Under mild conditions, a broad range of 1-benzazepine derivatives I (R1 = H, 6-Me, 7-F, etc.; RL = C6H5, 4-BrC6H4, 4-MeOC6H4, etc.; RS = H, Me, Et, etc.) was obtained in good to high yields with high degrees of diastereoselectivity and enantioselectivity.

Organic Letters published new progress about Benzazepines Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 1468-83-3 belongs to class benzothiophene, name is 3-Acetylthiophene, and the molecular formula is C6H6OS, Application In Synthesis of 1468-83-3.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem