Author: Jessica.F

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

Steward, Kimberly M. published the artcileAsymmetric Synthesis of Diverse Glycolic Acid Scaffolds via Dynamic Kinetic Resolution of α-Keto Esters, Synthetic Route of 69361-41-7, the publication is Journal of the American Chemical Society (2012), 134(49), 20197-20206, database is CAplus and MEDLINE.

The dynamic kinetic resolution of α-keto esters via asym. transfer hydrogenation has been developed as a technique for the highly stereoselective construction of structurally diverse β-substituted-α-hydroxy carboxylic acid derivatives Through the development of a privileged m-terphenylsulfonamide for (arene)RuCl(monosulfonamide) complexes with a high affinity for selective α-keto ester reduction, excellent levels of chemo-, diastereo-, and enantiocontrol can be realized in the reduction of β-aryl- and β-chloro-α-keto esters.

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 C6H8O6, Synthetic Route of 69361-41-7.

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

Ashley, Andrew E. published the artcileHomoleptic Permethylpentalene Complexes: “Double Metallocenes” of the First-Row Transition Metals, Formula: C4H10Br2CoO2, the publication is Journal of the American Chemical Society (2008), 130(46), 15662-15677, database is CAplus and MEDLINE.

The synthesis of the bimetallic permethylpentalene complexes Pn^*₂M₂ (M = V, Cr, Mn, Co, Ni; Pn^* = C₈Me₆) was accomplished, and all of the complexes were structurally characterized in the solid state by single-crystal x-ray diffraction. Pn^*₂V₂ (1) and Pn^*₂Mn₂ (3) show very short intermetallic distances that are consistent with metal-metal bonding, while the Co centers in Pn^*₂Co₂ (4) exhibit differential bonding to each side of the Pn^* ligand that is consistent with an η⁵:η³ formulation. The Pn^* ligands in Pn^*₂Ni₂ (5) are best described as η³:η³-bonded to the metal centers. ¹H NMR studies indicate that all of the Pn^*₂M₂ species exhibit D_2h mol. symmetry in the solution phase; the temperature variation of the chem. shifts for the resonances of Pn^*₂Cr₂ (2) indicates that the mol. has an S = 0 ground state and a thermally populated S = 1 excited state and can be successfully modeled using a Boltzmann distribution (ΔH° = 14.9 kJ mol^-1 and ΔS° = 26.5 J K^-1 mol^-1). The solid-state molar magnetic susceptibility of 3 obeys the Curie-Weiss law with μ_eff = 2.78 μB and θ = -1.0 K; the complex is best described as having an S = 1 electronic ground state over the temperature range 4-300 K. Paradoxically, attempts to isolate the double ferrocene equivalent, Pn^*₂Fe₂, led only to the isolation of the permethylpentalene dimer Pn^*₂ (6). Solution electrochem. studies were performed on all of the organometallic compounds; 2-5 exhibit multiple quasi-reversible redox processes. D. functional theory calculations were performed on this series of complexes to rationalize the observed structural and spectroscopic data and provide estimates of the M-M bond order.

Journal of the American Chemical Society published new progress about 18346-57-1. 18346-57-1 belongs to bromides-buliding-blocks, auxiliary class Cobalt, name is Cobalt(II) dibromo(1,2-dimethoxyethane), and the molecular formula is C4H10Br2CoO2, Formula: C4H10Br2CoO2.

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

Fujii, Akira published the artcileProbiotics. Antistaphylococcal and antifibrinolytic activities of ω-amino- and ω-guanidinoalkanesulfonic acids, HPLC of Formula: 55788-44-8, the publication is Journal of Medicinal Chemistry (1975), 18(5), 502-5, database is CAplus and MEDLINE.

A series of 5 H2N(CH2)nSO3H (I, n = 1-5) was prepared by reacting the dibromoalkane with Na2SO3 followed by NH4OH, while the guanidino analogs (II, n = 2-5) were prepared from the corresponding I by reaction with S-ethylisothiourea sulfate [22722-03-8]. All 9 compounds significantly protected mice against Staphylococcus aureus, but did not inhibit growth of S. aureus in vitro, while most of I had antifibrinolytic activity. δ-Aminobutanesulfonic acid (I, n = 4) [14064-34-7] had significantly greater antistaphylococcal activity than γ-aminobutyryl-L-histidine [3650-73-5], and had antifibrinolytic activity equal to ε-aminohexanoic acid [60-32-2]. None of II had antifibrinolytic activity. Structure-activity relations are discussed.

Journal of Medicinal Chemistry published new progress about 55788-44-8. 55788-44-8 belongs to bromides-buliding-blocks, auxiliary class Bromide,Salt,Aliphatic hydrocarbon chain,Aliphatic hydrocarbon chain, name is Sodium 3-bromopropane-1-sulfonate, and the molecular formula is C3H6BrNaO3S, HPLC of Formula: 55788-44-8.

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

Durand-Reville, Thomas F. published the artcileDiscovery of an Orally Available Diazabicyclooctane Inhibitor (ETX0282) of Class A, C, and D Serine β-Lactamases, Formula: C4H6BrFO2, the publication is Journal of Medicinal Chemistry (2020), 63(21), 12511-12525, database is CAplus and MEDLINE.

Multidrug resistant Gram-neg. bacterial infections are an increasing public health threat due to rapidly rising resistance toward β-lactam antibiotics. The hydrolytic enzymes called β-lactamases are responsible for a large proportion of the resistance phenotype. β-Lactamase inhibitors (BLIs) can be administered in combination with β-lactam antibiotics to negate the action of the β-lactamases, thereby restoring activity of the β-lactam. Newly developed BLIs offer some advantage over older BLIs in terms of enzymic spectrum but are limited to the i.v. route of administration. Reported here is a novel, orally bioavailable diazabicyclooctane (DBO) β-lactamase inhibitor. This new DBO, ETX1317(I), contains an endocyclic carbon-carbon double bond and a fluoroacetate activating group and exhibits broad spectrum activity against class A, C, and D serine β-lactamases. The ester prodrug of ETX1317, ETX0282(II), is orally bioavailable and, in combination with cefpodoxime proxetil, is currently in development as an oral therapy for multidrug resistant and carbapenem-resistant Enterobacterales infections.

Journal of Medicinal Chemistry published new progress about 401-55-8. 401-55-8 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Aliphatic hydrocarbon chain,Ester, name is Ethylbromofluoroacetate, and the molecular formula is C4H6BrFO2, Formula: C4H6BrFO2.

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

Gotchev, Dimitar B. published the artcileSynthetic Studies Toward (-)-FR901483 Using a Conjugate Allylation To Install the C-1 Quaternary Carbon, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of Organic Chemistry (2006), 71(25), 9393-9402, database is CAplus and MEDLINE.

Two approaches to the aza-tricyclo dodecane skeleton of (-)-FR901483 are reported. Both routes utilized a Grignard addition to an N-acylpyridinium salt, e.g. from 4-methoxypyridine and PhOCOCl, to establish the absolute stereochem. at C-6 and a highly diastereoselective conjugate allylation reaction to form the quaternary center at C-1 of the natural product in an excellent yield. Although the desired polysubstituted piperidine intermediates, e.g. I, were prepared regio- and stereoselectively, the construction of the C-8/C-9 bond connectivity could not be achieved. All attempts at a pinacol cyclization or an intramol. 6-exo-tet epoxide opening were unsuccessful because of an unfavorable A^(1,3) strain inherent in the mol.

Journal of Organic Chemistry 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, Safety of (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Clive, Derrick L. J. published the artcileRadical cyclizations of geminal radical precursors, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) (1991), 3263-70, database is CAplus.

Polycyclic structures, e.g., I (R = SiMe₃, SiPh₂Me), can be generated by double radical cyclization, using compounds, e.g., (RCCCH₂CH₂)₂C(OH)CHCl₂, having two groups, capable of being homolyzed, attached to a single carbon that is suitably located with respect to two unsaturated pendants.

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) 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, Recommanded Product: (4-Bromobut-1-yn-1-yl)trimethylsilane.

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