Day: November 28, 2022

Arias, Leire published the artcileRegioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones, Related Products of benzofurans, the publication is Journal of Organic Chemistry (2012), 77(1), 266-275, database is CAplus and MEDLINE.

A fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogs can be obtained from com. sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.

Journal of Organic Chemistry published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4, Related Products of benzofurans.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Naka, Hiroshi published the artcileAn Aluminum Ate Base: Its Design, Structure, Function, and Reaction Mechanism, HPLC of Formula: 69626-75-1, the publication is Journal of the American Chemical Society (2007), 129(7), 1921-1930, database is CAplus and MEDLINE.

An Al ate base, i-Bu₃Al(TMP)Li, was designed and developed for regio- and chemoselective direct generation of functionalized aromatic Al compounds Direct alumination followed by electrophilic trapping with I₂, Cu/Pd-catalyzed C-C bond formation, or direct oxidation with mol. O₂ proved to be a powerful tool for the preparation of 1,2-di- or 1,2,3-trisubstituted aromatic compounds This deprotonative alumination using i-Bu₃Al(TMP)Li is effective in aliphatic chem. as well, enabling regio- and chemoselective addition of functionalized allylic ethers and carbamates to aliphatic and aromatic aldehydes. A combined multinuclear NMR spectroscopy, x-ray crystallog., and theor. study showed that the Al ate base is a Li/Al bimetallic complex bridged by the N atom of TMP and the α-C of an i-Bu ligand and that the Li exclusively serves as a recognition point for electroneg. functional groups or coordinative solvents. The mechanism of directed ortho alumination reaction of functionalized aromatic compounds was studied by NMR and in situ FTIR spectroscopy, x-ray anal., and DFT calculation The reaction proceeds with facile formation of an initial adduct of the base and aromatic, followed by deprotonative formation of the functionalized aromatic Al compound Deprotonation by the TMP ligand rather than the iso-Bu ligand was suggested and reasoned by spectroscopic and theor. study. The remarkable regioselectivity of the ortho alumination reaction was explained by a coordinative approximation effect between the functional groups and the counter Li⁺ ion, enabling stable initial complex formation and creation of a less strained transition state structure.

Journal of the American Chemical Society published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, HPLC of Formula: 69626-75-1.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Xu, Bin published the artcilePhotocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes, Formula: C8H5IO, the publication is Journal of the American Chemical Society (2020), 142(13), 6206-6215, database is CAplus and MEDLINE.

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. A photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes is reported. Quantum mech. calculations (uM06-2X and DLPNO), including TD-DFT calculations, and exptl. studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cl^• radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. The use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity is anticipated.

Journal of the American Chemical Society published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C15H12O6, Formula: C8H5IO.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Gawlik, Maciej published the artcileIdentification and characterization of citalopram new metabolites with the use of UHPLC-Q-TOF technique: In silico toxicity assessment of the identified transformation products, Product Details of C20H19FN2O2, the publication is Journal of Pharmaceutical and Biomedical Analysis (2020), 113299, database is CAplus and MEDLINE.

In this study the metabolite profiling of citalopram with the use of human liver microsomes as well as the complementary photocatalytic method were established. This strategy allowed the detection of five metabolites of citalopram including 3-hydroxycitalopram and 3-oxocitalopram which were found as a new and not previously described metabolites of this drug The photocatalytic simulation of metabolism was carried out using tungsten (VI) oxide nanopowders with the different particle sizes, which allowed to examine the effect of this photocatalyst parameter on the mapping of metabolic processes. The accurate characterization of all observed structures was possible due to the use of ultra-high-pressure liquid chromatog. and high-resolution mass spectrometry combined system as a highly useful technique in drug metabolism studies. In order to perform the toxicity prediction of citalopram and its metabolites, the acute toxicity to rodents, as well as genotoxicity, carcinogenicity, developmental toxicity and receptor-mediated toxicity was calculated basing on the in silico tools.

Journal of Pharmaceutical and Biomedical Analysis published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Product Details of C20H19FN2O2.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Varga, Balint published the artcileSynthesis and Photochemical Application of Hydrofluoroolefin (HFO) Based Fluoroalkyl Building Block, COA of Formula: C8H5IO, the publication is Organic Letters (2021), 23(12), 4925-4929, database is CAplus and MEDLINE.

A novel fluoroalkyl iodide, 3-chloro-1,1,1,2-tetrafluoro-2-iodopropane was synthesized on multigram scale from refrigerant gas HFO-1234yf as cheap industrial starting material in a simple, solvent-free, and easily scalable process. Here, its applicability in a metal-free photocatalytic ATRA reaction demonstrated to synthesize valuable fluoroalkylated vinyl iodides RCH(I)=CHC(F)(CF₃)CH₂Cl (R = n-Bu, Ph, pyridin-3-yl, etc.) and proved the straightforward transformability of the products in cross-coupling chem. to obtain conjugated systems R¹C(CCR²)=CHC(F)(CF₃)CH₂Cl (R¹ = Ph, n-Bu, 1-naphthyl, etc.; R² = n-Bu, TMS, Ph, 2-thienyl, etc.); R¹C(Ar)=CHC(F)(CF₃)CH₂Cl (Ar = Ph, furan-3-yl, 3-methyl-3H-imidazo[4,5-b]pyridine-6-yl, etc.).

Organic Letters published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C7H5Br2F, COA of Formula: C8H5IO.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Zhang, De-Wu published the artcileNew 2-arylbenzofuran metabolite from cell cultures of Morus alba, SDS of cas: 56317-21-6, the publication is Journal of Asian Natural Products Research (2015), 17(6), 683-688, database is CAplus and MEDLINE.

A new 2-arylbenzofuran compound, 5-dehydroxy-moracin U (1), along with 10 known compounds (2-11), were isolated from cell cultures of Morus alba. Their structures were elucidated on the basis of extensive spectroscopic analyses. The anti-inflammatory activity assay of – showed that and exhibited significant inhibitory effect on LPS-induced NO production with the values of 76.4% and 98.7% at 10^– 5 M, resp.

Journal of Asian Natural Products Research published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C18H34N4O5S, SDS of cas: 56317-21-6.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Zhang, Long published the artcileCharacterization of a new flavone and tyrosinase inhibition constituents from the twigs of Morus Alba L, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Molecules (2016), 21(9), 1130/1-1130/9, database is CAplus and MEDLINE.

The twigs of Morus alba.L were found to show strong tyrosinase inhibition activity, and the responsible active components in the extract were further investigated in this study. A flavone, named morusone (1), and sixteen known compounds 2-17 were isolated from M. alba twigs and their structures were identified by interpretation of the corresponding ESI-MS and NMR spectral data. In the tyrosinase inhibitory test, the compounds steppogenin (IC50 0.98 ± 0.01 μM), 2,4,2′,4′-tetrahydroxychalcone (IC50 0.07 ± 0.02 μM), morachalcone A (IC50 0.08 ± 0.02 μM), oxyresveratrol (IC50 0.10 ± 0.01 μM), and moracin M (8.00 ± 0.22 μM) exhibited significant tyrosinase inhibition activities, much stronger than that of the pos. control kojic acid. These results suggest that M. alba twig extract should served as a good source of natural tyrosinase inhibitors for use in foods as antibrowning agents or in cosmetics as skin-whitening agents.

Molecules published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C24H12, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Zhang, Dejiang published the artcileNickel- and Palladium-Catalyzed Cross-Coupling of Stibines with Organic Halides: Site-Selective Sequential Reactions with Polyhalogenated Arenes, SDS of cas: 69626-75-1, the publication is ACS Catalysis (2022), 12(2), 854-867, database is CAplus.

Herein, the authors disclose a general and efficient method for the synthesis of Sb-aryl and Sb-alkyl stibines by the Ni-catalyzed cross-coupling of halostibines with organic halides. The synthesized Sb-aryl stibines couple with aryl halides to give biaryls efficiently via Pd catalysis. Sequential reactions of stibines with polyhalogenated arenes bearing active C-I/C-Br sites and inactive C-Cl sites successfully proceeded, giving a variety of complex mols. with good site selectivity. Drugs such as diflunisal and fenbufen, as well as a fenofibrate derivative, were synthesized on gram scales in good yields, together with the high recovery of chlorostibine. Also, catalytic mechanisms are proposed based on the results of control experiments

ACS Catalysis published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C6H13NO2, SDS of cas: 69626-75-1.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Haraguchi, Ryosuke published the artcilePalladium-Catalyzed Formylation of Arylzinc Reagents with S-Phenyl Thioformate, Safety of 2-Iodobenzofuran, the publication is Organic Letters (2017), 19(7), 1646-1649, database is CAplus and MEDLINE.

In the presence of Pd(OAc)₂ and tri(2-furyl)phosphine in toluene/THF, arylzinc reagents derived from aryl iodides and an alkenylzinc reagent were chemoselectively formylated with S-Ph thioformate PhSCHO to yield aryl aldehydes ArCHO (Ar = 4-NCC₆H₄, 4-EtO₂CC₆H₄, 4-i-Pr₂NCOC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 3-ClC₆H₄, 3-BrC₆H₄, 4-MeOC₆H₄, 1,3-benzodioxol-5-yl, 4-HOC₆H₄, 4-Me₂NC₆H₄, 2-MeC₆H₄, 2-MeOC₆H₄, 2,4,6-Me₃C₆H₂, 2-naphthyl, 1-naphthyl, 2-thienyl, 2-benzofuranyl, 1-Me-5-indolyl) and trans-cinnamaldehyde in 56-97% yields. Using deuterated and ¹³C-labeled deuterated and ¹³C-labeled S-Ph thioformate, 4-DCOC₆H₄CN and 4-BrC₆H₄¹³CH:CH₂ were prepared in high isotopic purities by this method.

Organic Letters published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Safety of 2-Iodobenzofuran.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Zheng, Zong-Ping published the artcileTyrosinase inhibition constituents from the roots of Morus australis, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Fitoterapia (2012), 83(6), 1008-1013, database is CAplus and MEDLINE.

The phytochem. profiles of Morus australis roots, stems and twigs were firstly compared by HPLC anal. It was found that Morus australis stem extract mainly contained one known tyrosinase inhibitor, oxyresveratrol, while its root and twig extract might contain some unknown potential tyrosinase inhibitors. The root extract of Morus australis was further investigated in this study. One new compound, austraone A, together with 21 known compounds, was isolated and their structures were identified by interpretation of MS and NMR data. In the tyrosinase inhibitory testing, some of them, such as oxyresveratrol, moracenin D, sanggenon T, and kuwanon O, exhibited stronger tyrosinase inhibitory activities than that of kojic acid. These results suggested the Morus australis root extract as a good source of natural tyrosinase inhibitors with a great potential to be used in foods as anti-browning agents and in cosmetics as skin-whitening agents.

Fitoterapia published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C18H28B2O4, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem