Tag: M.W=200-250

Gorsline, Bradley J. published the artcileC-H Alkenylation of Heteroarenes: Mechanism, Rate, and Selectivity Changes Enabled by Thioether Ligands, SDS of cas: 55788-44-8, the publication is Journal of the American Chemical Society (2017), 139(28), 9605-9614, database is CAplus and MEDLINE.

Thioether ancillary ligands have been identified that can greatly accelerate the C-H alkenylation of O-, S-, and N-heteroarenes. Kinetic data suggest thioether-Pd-catalyzed reactions can be as much as 800× faster than classic ligandless systems. Furthermore, mechanistic studies revealed C-H bond cleavage as the turnover-limiting step, and that rate acceleration upon thioether coordination is correlated to a change from a neutral to a cationic pathway for this key step. The formation of a cationic, low-coordinate catalytic intermediate in these reactions may also account for unusual catalyst-controlled site selectivity wherein C-H alkenylation of five-atom heteroarenes can occur under electronic control with thioether ligands even when this necessarily involves reaction at a more hindered C-H bond. The thioether effect also enables short reaction times under mild conditions for many O-, S-, and N-heteroarenes (55 examples), including examples of late-stage drug derivatization.

Journal of the American Chemical Society 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, SDS of cas: 55788-44-8.

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

Ruan, Zhuwei published the artcileTotal Synthesis of (+)-Hinckdentine A: Harnessing Noncovalent Interactions for Organocatalytic Bromination, Recommanded Product: 2-Bromo-5-methoxybenzene boronic acid, the publication is JACS Au (2022), 2(4), 793-800, database is CAplus and MEDLINE.

Synthesis of hinckdentine A, a marine-sponge-derived tribrominated indole alkaloid bearing a unique indolo[1,2-c]quinazoline skeleton, was completed in 12 steps featuring the construction of the α-quaternary carbon center by asym. azo-ene cyclization. A novel organocatalyst, e.g., 1-(3,5-bis-trifluoromethyl-phenyl)-3-[2-(diphenyl-phosphinothioyl)-phenyl]-thiourea was developed to promote high-yielding tribromination, which represents a challenging process encountered in previous syntheses. D. functional theory calculations scrutinized viable substrates and deciphered the origin of the enhancement of C8 electrophilic bromination with a bifunctional organocatalyst. Moreover, the application of organocatalyst-enabled bromination on various substrates such as 1H-indazole, 1-isothiocyanato-2,4-dimethoxybenzene, (2H-1,3-benzodioxol-5-yl)methanol, etc. was demonstrated to highlight future late functionalizations of biol. intriguing targets.

JACS Au 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

Guerrero, Miguel published the artcileDesign and Synthesis of a Novel and Selective Kappa Opioid Receptor (KOR) Antagonist (BTRX-335140), Name: 2-Amino-5-bromo-3-fluorobenzaldehyde, the publication is Journal of Medicinal Chemistry (2019), 62(4), 1761-1780, database is CAplus and MEDLINE.

κ Opioid receptor (KOR) antagonists are potential pharmacotherapies for the treatment of migraine and stress-related mood disorders including depression, anxiety, and drug abuse, thus the development of novel KOR antagonists with an improved potency/selectivity profile and medication-like duration of action has attracted the interest of the medicinal chem. community. In this paper, we describe the discovery of 1-(6-ethyl-8-fluoro-4-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)quinolin-2-yl)-N-(tetrahydro-2H-pyran-4-yl)piperidin-4 amine (CYM-53093, BTRX-335140) as a potent and selective KOR antagonist, endowed with favorable in vitro ADMET and in vivo pharmacokinetic profiles and medication-like duration of action in rat pharmacodynamic experiments Orally administered CYM-53093 showed robust efficacy in antagonizing KOR agonist-induced prolactin secretion and in tail-flick analgesia in mice. CYM-53093 exhibited a broad selectivity over a panel of off-target proteins. This compound is in phase 1 clin. trials for the treatment of neuropsychiatric disorders wherein dynorphin is thought to contribute to the underlying pathophysiol.

Journal of Medicinal Chemistry published new progress about 906811-51-6. 906811-51-6 belongs to bromides-buliding-blocks, auxiliary class Fluoride,Bromide,Amine,Benzene,Aldehyde, name is 2-Amino-5-bromo-3-fluorobenzaldehyde, and the molecular formula is C7H5BrFNO, Name: 2-Amino-5-bromo-3-fluorobenzaldehyde.

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

Lange, Stefanie C. published the artcileEfficient and Tunable Three-Dimensional Functionalization of Fully Zwitterionic Antifouling Surface Coatings, SDS of cas: 55788-44-8, the publication is Langmuir (2016), 32(40), 10199-10205, database is CAplus and MEDLINE.

In order to enhance the sensitivity and selectivity of surface-based (bio)sensors, it is of crucial importance to diminish background signals that arise from the nonspecific binding of biomols., so-called biofouling. Zwitterionic polymer brushes have been shown to be excellent antifouling materials. However, for sensing purposes, antifouling does no suffice, but need to be combined with the possibility to efficiently modify the brush with recognition units. So far this has only been achieved at the expense of either antifouling properties or binding capacity. Herein the authors present a conceptually new approach by integrating both characteristics into a single, tailor-made monomer: a novel sulfobetaine-based zwitterionic monomer equipped with a clickable azide moiety. Copolymerization of this monomer with a well-established standard sulfobetaine monomer, results in highly antifouling surface coatings with a high, yet tunable amount of clickable groups present throughout the entire brush. Subsequent functionalization of the azido-brushes, via e.g. widely used strain-promoted alkyne azide click reactions yields fully zwitterionic 3D-functionalized coatings with a recognition unit of choice that can be tailored for any specific application. Here the authors show a proof-of-principle with biotin-functionalized brushes on Si₃N₄ that combine excellent antifouling properties with specific avidin binding from a protein mixture The signal-to-noise ratio is significantly improved over traditional chain end modification of sulfobetaine polymer brushes, even if the azide content is lowered to 1%, thus offering a viable approach for the development of significantly improved performance of biosensors on any surface.

Langmuir 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, SDS of cas: 55788-44-8.

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

Bian, Jianwei published the artcileEnantioselective Total Synthesis of (+)- and (-)-Nigellamine A₂, Product Details of C7H13BrSi, the publication is Journal of the American Chemical Society (2006), 128(23), 7428-7429, database is CAplus and MEDLINE.

The nigellamine alkaloids are dolabellane diterpenes displaying potent lipid metabolism-promoting activity. Total synthesis of (+)- and (-)-nigellamine A₂ has been accomplished. Absolute stereochem. of synthetic nigellamine A₂ was established through an intramol. asym. allylic alkylation using a Pd(phosphinooxazoline) catalyst. Other notable transformations include a radical alkynylation, a diastereoselective Nozaki-Hiyama-Kishi cyclization, and a regio- and stereoselective catalytic epoxidation On the basis of X-ray crystallog. anal. of an optically active intermediate, we have confirmed the assigned absolute stereochem. of the natural product. Minor modifications of the synthetic sequence outlined here should provide access to the other nigellamine alkaloids.

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 C7H13BrSi, Product Details of C7H13BrSi.

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

Muir, Calum W. published the artcileOne-Pot Homologation of Boronic Acids: A Platform for Diversity-Oriented Synthesis, Application In Synthesis of 849062-12-0, the publication is Organic Letters (2015), 17(24), 6030-6033, database is CAplus and MEDLINE.

Formal homologation of sp²-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chem. is demonstrated in the context of the synthesis of a series of analogs of a BET bromodomain inhibitor.

Organic Letters published new progress about 849062-12-0. 849062-12-0 belongs to bromides-buliding-blocks, auxiliary class Bromide,Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Bromo-5-methoxyphenyl)boronic acid, and the molecular formula is C7H8BBrO3, Application In Synthesis of 849062-12-0.

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

Donkervoort, Johannes G. published the artcileNovel tridentate diamino organomanganese(II) complexes as homogeneous catalysts in manganese(II)/copper(I) catalyzed carbon-carbon bond forming reactions, Name: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Journal of Organometallic Chemistry (1998), 558(1-2), 61-69, database is CAplus.

The new, paramagnetic arylmanganese(II) complex Li[MnCl₂(NCN)] (2, NCN = [C₆H₃(CH₂NMe₂)₂-2,6]^–) was obtained in high yield from the reaction of MnCl₂ and [Li(NCN)]₂ in a 2:1 molar ratio. In THF solution, 2 is likely an ionic species [Li(THF)_n][MnCl₂(NCN)] (mol. weight determination and conductivity measurements), while magnetic measurements indicate that a high spin d⁵ Mn(II) center is present. Subsequent reaction of 2 with RLi afforded [MnR(NCN)] (R = Me, Bu). Complex 2, using CuCl as a co-catalyst, is an effective catalyst system for cross-coupling of Grignard reagents with alkyl bromides and the 1,4-addition of organomagnesium halides to α,β-unsaturated ketones. No further additives or co-solvents are necessary. For both reactions a dramatic decrease in reaction times is observed when compared to standard Mn/Cu systems. Alkyl bromides with unsaturated or heteroatom functionalities can be cross-coupled. Also, excellent reactivity towards normally unreactive β,β-disubstituted ketones was observed in the 1,4-addition reaction.

Journal of Organometallic 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, Name: (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Donkervoort, Johannes G. published the artcileNovel organomanganese(II) complexes active as homogeneous catalysts in manganese(II)/copper(I) catalyzed carbon-carbon bond formation reactions, Name: (4-Bromobut-1-yn-1-yl)trimethylsilane, the publication is Recueil des Travaux Chimiques des Pays-Bas (1996), 115(11/12), 547-548, database is CAplus.

Novel organomanganese complexes 2,6-(Me₂NCH₂)₂C₆H₂X (I; X = MnLiCl₂), prepared from I (X = Li) and MnCl₂, reacted with RLi (R = Me, Bu, Ph) to give the corresponding I (X = R). These new complexes are active catalysts with CuCl for cross-coupling reactions of R¹Br [R¹ = n-C₈H₁₇, BuCO(CH₂)₁₀, EtO₂CCH₂CH₂, CH₂:CHCH₂CH₂. Me₃SiCCCH₂CH₂] with R²MgCl (R² = Me₂CH, Bu, EtCHMe, Me₃C, n-C₁₄H₂₉) to give 8 corresponding R¹R² in 75-92% yield.

Recueil des Travaux Chimiques des Pays-Bas 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, Name: (4-Bromobut-1-yn-1-yl)trimethylsilane.

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

Dower, William V. published the artcileThermal conversion of 1,5,9-triynes. [2 + 2 + 2] Cycloadditions or [3.3]sigmatropic shifts?, Product Details of C7H13BrSi, the publication is Tetrahedron (1986), 42(6), 1873-81, database is CAplus.

The gas phase pyrolysis products [labeled and unlabeled naphthalene and [1,2:4,5]dicyclobutabenzene or hexaradialene] of RCC(CH₂)₂CC(CH₂)₂CCR [R = H, D (I)] and HCC(CH₂)₂¹³C¹³C(CH₂)₂CCH (II) or 1,5,9-cyclododecatriyne (III) and III–1,10–¹³C₂ (IV), examined at 400-600°/10^-4-40 tor with ∼1 ms-15 s contact times, show that the mechanism involves a series of [3.3] sigmatropic shifts; [2 + 2 + 3] cycloadditions of the alkyne units do not occur. The preparation of I, II, III, and IV are discussed.

Tetrahedron 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, Product Details of C7H13BrSi.

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

Vereshchagin, A. N. published the artcileAnisotropy of polarizability and dipole moments of some 1,2-dibromoethane derivatives, Quality Control of 594-81-0, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1973), 163-5, database is CAplus.

Kerr constants and dipole moments of BrRR1CCR2R3Br (I, R-R3 = H, Me, Ph) were reported. The trans conformers of such compounds had effective dipole moments that could not be described by the simple moment-additive scheme. The Me-substituted I in solution were mainly in transform whereas Ph shifted the conformational equilibriumsubstantially by destabilizing the trans location of the 2 Br atoms probably by gauche interaction of Ph and Br components. This interaction was ∼1.2 cal/mole.

Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya 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 C38H24F4O4P2, Quality Control of 594-81-0.

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