Month: November 2022

Rosso, Cristian published the artcileUnveiling the Synthetic Potential of Substituted Phenols as Fully Recyclable Organophotoredox Catalysts for the Iodosulfonylation of Olefins, Computed Properties of 111-83-1, the publication is ACS Catalysis (2022), 12(8), 4290-4295, database is CAplus.

An efficient photocatalytic procedure for the direct iodosulfonylation of terminal olefins RCHCH₂ (R = Bu, cyclohexylmethyl, 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butyl, etc.) with α-iodo phenylsulfones R¹S(O)₂CH(R²)I (R¹ = Me, Ph, cyclohexyl, naphthalene-1-yl, etc.; R² = H, Me) was described. Specifically, the process uses the simple, robust, and fully recyclable phenol derivative I as the precatalytic system and occurs with visible-light irradiation (450 nm). Mechanistic investigations proved the key role of the in situ generated photocatalyst, namely phenolate anion, which has shown high catalytic activity and considerable stability toward the operating conditions. Importantly, this photocatalytic transformation provides a wide variety of densely functionalized alkyl iodides RCH(I)CH₂CH(R²)S(O)₂R¹ (23 examples, up to 95% yield). Finally, the synthetic potential of this photochem. transformation was demonstrated by scaling up the process under microfluidic conditions (up to 0.67 mmol h^-1) while accessing a series of relevant product manipulations.

ACS Catalysis published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Computed Properties of 111-83-1.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Page, Brent D. G. published the artcileInhibiting Aberrant Signal Transducer and Activator of Transcription Protein Activation with Tetrapodal, Small Molecule Src Homology 2 Domain Binders: Promising Agents against Multiple Myeloma, Quality Control of 21101-63-3, the publication is Journal of Medicinal Chemistry (2013), 56(18), 7190-7200, database is CAplus and MEDLINE.

[(Arylsulfonyl)glycinyl](cyclohexylbenzyl)aminosalicylic acids such as I (R = 4-MeC₆H₄, F₅C₆; R¹ = 2-F₃CC₆H₄) were prepared as inhibitors of the signal transducer and activator of transcription (STAT) protein Stat3 for potential use as treatments for multiple myeloma. The hydrophobicities of I and their inhibition of Stat3 were determined; mol. docking of selected compounds to the SH2 domain of Stat3 and inhibition of Stat3 phosphorylation under various conditions were determined for selected compounds, and the activity of I (R = 4-MeC₆H₄; R¹ = 2-F₃CC₆H₄) against human multiple myeloma cells and human hematopoietic cells and its induction of apoptosis in multiple myeloma cells was determined

Journal of Medicinal Chemistry published new progress about 21101-63-3. 21101-63-3 belongs to bromides-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Bromide,sulfides,Benzyl bromide,Benzene, name is (4-(Bromomethyl)phenyl)(trifluoromethyl)sulfane, and the molecular formula is C8H6BrF3S, Quality Control of 21101-63-3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Kropp, Paul J. published the artcileSurface-Mediated Reactions. 4. Hydrohalogenation of Alkynes, COA of Formula: C6H12Br2, the publication is Journal of Organic Chemistry (1994), 59(11), 3102-12, database is CAplus.

The use of appropriately prepared silica gel and alumina has been found to mediate the addition of hydrogen halides to alkynes. The technique has been rendered even more convenient by the use of various organic and inorganic acid halides that react in the presence of silica gel or alumina to generate hydrogen halides in situ. Treatment in this fashion of 1-propynylbenzene (1), which underwent no reaction in CH₂Cl₂ solution saturated with HCl, readily afforded the syn addition product alkenyl chloride (E)-PhCX:CHMe, [(E)-4, X = Cl]. On extended treatment (E)-4 (X = Cl) underwent subsequent isomerization to the thermodynamically more stable Z isomer. In a similar way bromides (E)- and (Z)-4 (X = Br) were obtained without competing formation of the radical products (E)- and (Z)-PhCH:CMeBr, which occurred in solution In contrast with slow solution-phase hydriodination of alkyne 1, surface-mediated addition readily afforded (E)-4 (X = I), followed by isomerization to the Z isomer. Equilibration E ⇌ Z of the alkenyl halides 4 was shown to involve, at least in part, addition-elimination via the gem-dihalides PhCX₂Et. Analogous behavior was exhibited by the phenylalkynes PhCCPh and PhCCCMe₃ on surface-mediated hydrohalogenation. Surface-mediated addition of HBr and HI to the internal alkylalkyne PrCCPr afforded principally the anti addition products (Z)-PrCX:CHPr. Treatment of the terminal alkynes BuCH₂CCH and Me₃CCCH with (COBr)₂ over alumina gave the dibromides, whereas use of acetyl bromide as the HBr precursor afforded the alkenyl bromides.

Journal of Organic Chemistry published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, COA of Formula: C6H12Br2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Bricaud, Quentin published the artcileTerthiophene-cyanovinylene π-conjugated polymers as donor material for organic solar cells, HPLC of Formula: 303734-52-3, the publication is Synthetic Metals (2009), 159(23-24), 2534-2538, database is CAplus.

Conjugated polymers of hybrid structure containing cyanovinylene linkages have been synthesized by Knoevenagel condensation of diformyl terthienyls with para-dicyanomethylbenzene. UV-vis and cyclic voltammetric data show that these polymers combine reduced band gap, improved light-harvesting properties and low lying HOMO level. Whereas the very low solubility of the polymers did not allow the fabrication of bulk heterojunction solar cells, bilayer heterojunction solar cells have been realized using thermally evaporated films of fullerene C₆₀ as acceptor material. The best devices show a maximum external quantum efficiency of ∼20% and a power conversion efficiency of 0.40% under simulated AM 1.5 solar illumination.

Synthetic Metals published new progress about 303734-52-3. 303734-52-3 belongs to bromides-buliding-blocks, auxiliary class Thiophene,Bromide, name is 2-Bromo-3-(2-ethylhexyl)thiophene, and the molecular formula is C12H19BrS, HPLC of Formula: 303734-52-3.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Mathew, Sanyo published the artcileEnhanced Helical Folding of ortho-Phenylenes through the Control of Aromatic Stacking Interactions, Recommanded Product: 2-Bromo-5-methoxybenzene boronic acid, the publication is Journal of the American Chemical Society (2014), 136(47), 16666-16675, database is CAplus and MEDLINE.

The ortho-phenylenes are a simple class of foldamers, with the formation of helixes driven by offset aromatic stacking interactions parallel to the helical axis. For the majority of reported o-phenylene oligomers, the perfectly folded conformer comprises perhaps 50-75% of the total population. Given the hundreds or thousands of possible conformers for even short oligomers, this distribution represents a substantial bias toward the folded state. However, “next-generation” o-phenylenes with better folding properties are needed if these structures are to be exploited as functional units within more complex architectures. Here, we report several new series of o-phenylene oligomers, varying both the nature and orientation of the substituents on every repeat unit. The conformational behavior was probed using a combination of NMR spectroscopy, DFT calculations, and X-ray crystallog. We find that increasing the electron-withdrawing character of the substituents gives oligomers with substantially improved folding properties. With moderately electron-withdrawing groups (acetoxy), we observe >90% of the perfectly folded conformer, and stronger electron withdrawing groups (triflate, cyano) give oligomers for which misfolded states are undetectable by NMR. The folding of these oligomers is only weakly solvent-dependent. General guidelines for the assessment of o-phenylene folding by NMR and UV-vis spectroscopy are also discussed.

Journal of the American Chemical Society published new progress about 89694-44-0. 89694-44-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is 2-Bromo-5-methoxybenzene boronic acid, and the molecular formula is C7H8BBrO3, Recommanded Product: 2-Bromo-5-methoxybenzene boronic acid.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Booker-Milburn, Kevin I. published the artcileFe(III)/Cu(II) mediated 5- and 6-exo oxidative ring-expansion/cyclisation of cyclopropyl ethers: studies towards dictyol C and α-eudesmol, COA of Formula: C7H13BrSi, the publication is Tetrahedron Letters (2000), 41(23), 4651-4655, database is CAplus.

The outcome of oxidative ring-expansion/cyclization of cyclopropanes with a mixed Fe(III)/Cu(II) system was found to be dependent on the mode of cyclization. When 6-exo cyclization was attempted, unusual products resulting from oxidation of ring-opened primary radicals were obtained.

Tetrahedron Letters published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C7H13BrSi, COA of Formula: C7H13BrSi.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Chretien, Jacques R. published the artcileSolvation and steric effects on electrophilic reactivity of ethylenic compounds. 3. Stereo-, regio-, and chemoselectivity of alkene bromination in methanol, Formula: C6H12Br2, the publication is Journal of Organic Chemistry (1993), 58(7), 1917-21, database is CAplus.

The stereo-, regio- and chemoselectivities of the bromination of 30 alkenes bearing 1-3 alkyl groups (Me, Et, Pr, iso-Pr, tert-Bu, neopentyl) were investigated in methanol containing 0.2 M NaBr at 25° under kinetic conditions. The reaction of cis– and trans-alkenes, RC_αH:C_βHR’, with R more electron-donating than R’, is stereospecific, in agreement with the occurrence of a bromonium ion intermediate. Methanol and bromide ion trap the bridged ion anti with respect to the bridging bromine atom, independently of the crowding of the double bond. In contrast to the usual belief, the anti-Markovnikov regioselectivity of attack by methanol is always favored, even in the absence of bulky substituents; the better a donor R is, the more the nucleophile attacks C_β. The chemoselectivity dependence on the double-bond substituents is also unexpected; dibromide formation increases with respect to that of methoxy bromide as electron-donation by R and R’ increases, although the increasing carbocationic character of the carbon atoms of the bridged ion should favor trapping of the intermediate by methanol. Analogous trends for the regio- and chemoselectivity dependence on the substituents are observed in the bromination of monosubstituted alkenes, RCH:CH₂, via bromonium ions. These results are attributed to a decrease in the pos. charge densities on the carbon atoms of the bridged ions when the ability of the donor substituents to delocalize charge increases. gem-Disubstituted alkenes, RR’C:CH₂, and trimethylethylene behave differently as regards the regio- and chemoselectivity. They react 100% Markovnikov and chemoselectively (about 80%) in favor of attack by methanol. It is shown that these selectivities agree fairly well with highly dissym. bromonium ions as intermediates in the bromination of these alkenes.

Journal of Organic Chemistry published new progress about 594-81-0. 594-81-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 2,3-Dibromo-2,3-dimethylbutane, and the molecular formula is C6H12Br2, Formula: C6H12Br2.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Ghirardello, Mattia published the artcileSynthesis of Chiral Ionic Liquids from Natural Monosaccharides, Safety of 1-Bromooctane, the publication is European Journal of Organic Chemistry (2022), 2022(21), e202200100, database is CAplus.

Three series of new ionic liquids (ILs), namely imidazolium-, pyrazolium-, and bis-benzimidazolium-containing ILs, were prepared from low-cost, unprotected carbohydrates. Information on anion-cation interactions and solvation shell were obtained via diffusion NMR and heteronuclear Overhauser correlation maps (HOESY), resp.

European Journal of Organic Chemistry published new progress about 111-83-1. 111-83-1 belongs to bromides-buliding-blocks, auxiliary class Bromide,Aliphatic hydrocarbon chain, name is 1-Bromooctane, and the molecular formula is C8H17Br, Safety of 1-Bromooctane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Sartini, Stefania published the artcileBenzofuroxane Derivatives as Multi-Effective Agents for the Treatment of Cardiovascular Diabetic Complications. Synthesis, Functional Evaluation, and Molecular Modeling Studies, Synthetic Route of 76283-09-5, the publication is Journal of Medicinal Chemistry (2012), 55(23), 10523-10531, database is CAplus and MEDLINE.

Diabetes mellitus is the major risk factor for cardiovascular disorders. Aldose reductase, the rate-limiting enzyme of the polyol pathway, plays a key role in the pathogenesis of diabetic complications. Accordingly, inhibition of this enzyme is emerging as a major therapeutic strategy for the treatment of hyperglycemia-induced cardiovascular pathologies. In this study, the authors describe a series of 5(6)-substituted benzofuroxane derivatives, synthesized as aldose reductase inhibitors. Besides inhibiting efficiently the target enzyme, these benzofuroxane derivatives showed addnl. NO donor and antioxidant properties, thus emerging as novel multi-effective compounds The benzyloxy derivative (I), the most promising of the whole series, showed a well-balanced, multifunctional profile consisting of submicromolar ALR2 inhibitory efficacy (IC₅₀ = 0.99±0.02 μM), significant and spontaneous NO generation properties, and excellent hydroxyl radical scavenging activity. Computational studies of the novel compounds clarified the aldose reductase inhibitory profile observed, thus rationalizing structure-activity relationships of the whole series.

Journal of Medicinal Chemistry published new progress about 76283-09-5. 76283-09-5 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Benzyl bromide,Benzene, name is 4-Bromo-1-(bromomethyl)-2-fluorobenzene, and the molecular formula is C7H5Br2F, Synthetic Route of 76283-09-5.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary

Steward, Kimberly M. published the artcileAsymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters [Erratum to document cited in CA158:36961], Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the American Chemical Society (2015), 137(11), 3991, database is CAplus and MEDLINE.

In follow up experiments the authors discovered errors in analyzing the unpurified ¹H NMR spectra, which led to incorrect reporting of the crude diastereomer ratios for the lactone products; the correct ratios are given and an alternative exptl. procedure is presented that generally results in improved stereoselectivity.

Journal of the American Chemical Society published new progress about 69361-41-7. 69361-41-7 belongs to bromides-buliding-blocks, auxiliary class PROTAC Linker,Aliphatic Linker, name is (4-Bromobut-1-yn-1-yl)trimethylsilane, and the molecular formula is C16H20N2, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane.

Referemce:
https://en.wikipedia.org/wiki/Bromide,
bromide – Wiktionary