Month: December 2022

Depre, Dominique published the artcileOrigin of the E/Z Selectivity in the Synthesis of Tetrasubstituted Olefins by Wittig Reaction of α-Fluorophosphonium Ylides: An Explanation for the Low Stereoselectivity Observed in Reactions of α-Alkoxy Aldehydes, Application In Synthesis of 401-55-8, the publication is Organic Letters (2017), 19(6), 1414-1417, database is CAplus and MEDLINE.

A series of tetrasubstituted fluoroalkenes were synthesized in good yield and high E/Z selectivity (up to 96/4) by Wittig reaction between α-heterosubstituted ketones and α-fluorophosphonium ylides. A detailed study of factors that control stereoselectivity in these reactions shows that stereoselectivity is the result of stabilizing CH···F and N···C=O interactions in the addition TS leading to the E isomer. This anal. provides a rationale for the observed decrease in selectivity for reactions of stabilized ylides with α-alkoxy aldehydes.

Organic Letters 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, Application In Synthesis of 401-55-8.

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

Slegel, P. published the artcileEnantiomeric separation of chiral carboxylic acids, as their diastereomeric carboxamides, by thin-layer chromatography, Product Details of C4H7BrO2, the publication is Journal of Pharmaceutical and Biomedical Analysis (1987), 5(7), 665-73, database is CAplus and MEDLINE.

A thin-layer chromatog. (TLC) method is described for the enantiomeric separation of chiral carboxylic acids using chiral derivatization and nonchiral TLC conditions (ordinary plates and mobile phases) to sep. the diastereomeric carboxamides obtained. New chiral derivatizing agents, “levobase” (1R, 2R)-(-)-1-(4-nitrophenyl)-2-amino-1,3-propanediol, and “dextrobase” (the enantiomer of levobase) are used for carboxamide formation in the presence of dicyclohexylcabodiimide as coupling agent. The procedure is very simple and convenient to carry out. Good resolution is obtained for a wide range of carboxylic acid enantiomeric pairs containing 1 to 2 chiral centers.

Journal of Pharmaceutical and Biomedical Analysis published new progress about 56970-78-6. 56970-78-6 belongs to bromides-buliding-blocks, auxiliary class Bromide,Carboxylic acid,Aliphatic hydrocarbon chain,Inhibitor, name is 3-Bromo-2-methylpropanoic acid, and the molecular formula is Al2H32O28S3, Product Details of C4H7BrO2.

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

Van Allen, Derek published the artcileCopper-Catalyzed Synthesis of Unsymmetrical Triarylphosphines, Application In Synthesis of 25753-84-8, the publication is Journal of Organic Chemistry (2003), 68(11), 4590-4593, database is CAplus and MEDLINE.

Various triarylphosphines were prepared in good yields by coupling diphenylphosphine and aryl iodides with catalytic amounts of CuI in the presence of either K₂CO₃ or Cs₂CO₃. CuI was chosen after screening various copper salts, such as CuBr and CuCl, and complexes, i.e., Cu(PPh₃)₃Br (1), Cu(neocup)PPh₃Br (neocup = neocuproine) (2), Cu(phen)PPh₃Br (phen = phenanthroline) (3), and Cu(neocup)₂Br·H₂O (4). Catalysts 1–4 were prepared and identified by comparison with previously published x-ray crystallog. data. In an example cross-coupling reaction, 1-naphthyldiphenylphosphine was prepared via reaction of diphenylphosphine and 1-iodonaphthalene in the presence of CuI and Cs₂CO₃, and analyzed by x-ray crystallog. This method tolerates a variety of functional groups, such as ketones and esters, and does not require the use of expensive additives or harsh reaction conditions, and is palladium free.

Journal of Organic Chemistry published new progress about 25753-84-8. 25753-84-8 belongs to bromides-buliding-blocks, auxiliary class Copper, name is Bromo(1,10-phenanthroline)(triphenylphosphine)copper(I), and the molecular formula is C24H12, Application In Synthesis of 25753-84-8.

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

Goel, Shruti published the artcileKinetics and mechanism of the oxidation of organic sulfides by benzyltrimethylammonium tribromide, Name: Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, the publication is Journal of Chemical Research, Synopses (1996), 510-511, database is CAplus.

The oxidation of organic sulfides by benzyltrimethylammonium tribromide involves formation of a halo sulfonium cation in the slow step and its subsequent decomposition in the fast step to give sulfoxides.

Journal of Chemical Research, Synopses published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, Name: Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide.

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

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

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

Ghiringhelli, Francesca published the artcileDirect β- and γ-C(sp³)-H Alkynylation of Free Carboxylic Acids, Computed Properties of 21101-63-3, the publication is Angewandte Chemie, International Edition (2020), 59(51), 23127-23131, database is CAplus and MEDLINE.

The authors report the identification of a novel class of ligands for palladium-catalyzed C(sp³)-H activation that enables the direct alkynylation of free carboxylic acid substrates. In contrast to previous synthetic methods, no introduction/removal of an exogenous directing group is required. A broad scope of acids including both α-quaternary and challenging α-non-quaternary can be used as substrates. Addnl., the alkynylation in the distal γ-position is reported. Finally, this study encompasses preliminary findings on an enantioselective variant of the title transformation as well as synthetic applications of the products obtained.

Angewandte Chemie, International Edition 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, Computed Properties of 21101-63-3.

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

Ito, Akihiro published the artcileA spiro-fused triarylaminium radical cation with a triplet ground state. [Erratum to document cited in CA139:036205], Application In Synthesis of 111865-47-5, the publication is Angewandte Chemie, International Edition (2009), 48(32), 5785, database is CAplus.

On page 923, Equation 2 is incorrect; the correct version of the equation is given. In this article, in the right-hand column on page 923, the optimized value for the exchange coupling J should be corrected to J=11.2cm^-1 (=16.0 K), and Reference [3] cited in this paragraph should be Reference [6].

Angewandte Chemie, International Edition published new progress about 111865-47-5. 111865-47-5 belongs to bromides-buliding-blocks, auxiliary class Benzenes, name is Mono(N,N,N-trimethyl-1-phenylmethanaminium) tribromide, and the molecular formula is C10H16Br3N, Application In Synthesis of 111865-47-5.

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