Heterocyclic Building Blocks-Quinuclidine

DeBergh, J. Robb published the artcileSynthesis of Aryl Sulfonamides via Palladium-Catalyzed Chlorosulfonylation of Arylboronic Acids, Formula: C28H41N2P, the publication is Journal of the American Chemical Society (2013), 135(29), 10638-10641, database is CAplus and MEDLINE.

A palladium-catalyzed method for the preparation of sulfonamides is described. The process exhibits significant functional group tolerance and allows for the preparation of a number of arylsulfonyl chlorides and sulfonamides under mild conditions. E.g., in presence of the Pd catalyst I (L = ligand II), reaction of PhOSO₂Cl with 4-methoxyphenylboronic acid, followed by reaction with morpholine, gave 95% sulfonamide III.

Journal of the American Chemical Society published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C28H41N2P, Formula: C28H41N2P.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Yang, Yang published the artcileHighly Selective Palladium-Catalyzed Cross-Coupling of Secondary Alkylzinc Reagents with Heteroaryl Halides, Synthetic Route of 1160556-64-8, the publication is Organic Letters (2014), 16(17), 4638-4641, database is CAplus and MEDLINE.

The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described [e.g., using a palladacycle precatalyst ligated by CPhos, 3-chlorobenzisothiazole was coupled with i-PrZnBr.LiCl to afford 3-isopropylbenzisothiazole in 78% yield (normal:rearranged ratio = 98:2)]. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.

Organic Letters published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C22H23ClN4, Synthetic Route of 1160556-64-8.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Neunhoeffer, Otto published the artcileTricyclohexylmethane series. II. Cyclohexylphenyl-substituted pinacols and pinacolones, Application of 4-Cyclohexylbenzoic acid, the publication is Justus Liebigs Annalen der Chemie (1936), 47-58, database is CAplus.

cf. C. A. 28, 3385.3. The action of cyclohexylmagnesium chloride (I) upon benzil gives only hydrobenzoin (quant. yield). The reaction of I and (CO₂Et)₂ (22 g.) gives 23 g. cyclohexylglyoxylic acid, b_0.5 90-100° (hydrazide, m. 199°), 22 g. Et dicyclohexylglycolate, b_0.5 123-3.5°, m. 70°, and 1.8 g. of 1,1,2-tricyclohexylethan-1-ol-2-one, m. 154°. Ph₂CHCO₂Et (II) does not react with I. Catalytic reduction of II gives Et dicyclohexylacetate, m. 88°, which also does not react with I. The Na compound of dicyclohexylphenylmethyl (III) and BzCl give only the dimer of III, m. 207°; PhCN gives triphenyltriazine, m. 230°. I and the acid Me ester of benzilic acid give 2-cyclohexyl-1-diphenylethan-1-ol-2-one, m. 112°. Catalytic reduction of benzopinacolone results in the absorption of 6 mol H₂ and the formation of 1,2-dicyclohexyl-1,1-diphenylethan-2-one (IV), m. 130°; oxidation gives Ph₂CO. Reduction of cyclohexyl Ph ketone with Zn and 50% H₂SO₄ gives a mixture of 2 forms of dicyclohexyldiphenylethylene glycol (V), m. 198° and 160°; with concentrated HCl and boiling AcOH there results IV. While IV is not reduced in the usual ways, cyclohexylmagnesium iodide gives dicyclohexyldiphenylethylene, m. 192°; BzO₂H gives the V m. 195-6°.

Justus Liebigs Annalen der Chemie published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, Application of 4-Cyclohexylbenzoic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Baddam, Sudhakar Reddy published the artcileZinc triflate catalyzed synthesis of thioethers, Name: 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid, the publication is Chemistry & Biology Interface (2014), 4(2), 131-136, 6 pp., database is CAplus.

Zinc triflate-catalyzed aralkylation of thiols using various substituted benzylic alcs. was developed for the synthesis of thioether (sulfide) derivatives This procedure presents a greener approach for the synthesis of sulfides.

Chemistry & Biology Interface published new progress about 162515-68-6. 162515-68-6 belongs to quinuclidine, auxiliary class Thiol,Carboxylic acid,Aliphatic cyclic hydrocarbon, name is 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid, and the molecular formula is C6H10O2S, Name: 2-(1-(Mercaptomethyl)cyclopropyl)acetic acid.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Romero-Zuniga, Gabriela Yolotzin published the artcileEnhanced mechanical performance of a DGEBA epoxy resin-based shape memory polymer by introducing graphene oxide via covalent linking, Recommanded Product: 4,4-Diaminodicyclohexyl methane, the publication is Journal of Applied Polymer Science (2022), 139(2), 51467, database is CAplus.

Shape memory polymers (SMP) are prepared, via dual thiol-epoxy/thiol-ene reactions, from diglycidyl ether of bisphenol A (DGEBA), a trithiol (TMP), a tetraallyl amine (TAA), and small amounts (0.1-0.5 weight%) of graphene oxide either pristine (GO) or functionalized with methacrylate groups (GO_M). The incorporation of GO_M to the epoxy resin network permits a good load transfer, which is reflected in improved properties such as Young modulus (from 220 to 519 MPa), tensile strength (from 46.3 to 69.2 MPa), Izod impact strength (from 0.051 to 0.42 J/mm), torque (from 0.008 to 0.031 Nm), and glass transition temperature (from 75 to 105°C). Such improvement in properties is attributed to the incorporation of GO_M via covalent linking, which is a good strategy for improving polymer-particle interaction and particle dispersion. The epoxy-based SMP also show high storage modulus (up to 2.36 GPa) and high deformation capacity, which are reflected in good shape fixity (between 97% and 100%) and thermo-induced shape recovery (between 97% to 99.7%) behaviors in flexion mode tests.

Journal of Applied Polymer Science published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Recommanded Product: 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Park, Byeongyeon published the artcile3,4-Dihydroquinazoline derivatives inhibit the activities of cholinesterase enzymes, HPLC of Formula: 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2017), 27(5), 1179-1185, database is CAplus and MEDLINE.

A series of 3,4-dihydroquinazoline derivatives consisting of the selected compounds from our chem. library on the diversity basis and the new synthetic compounds were in vitro tested for their inhibitory activities for both acetylcholinesterase (AChE, from elec. eel) and butyrylcholinesterase (BChE, from equine serum) enzymes. It was discovered that most of the compounds displayed weak AChE and strong BuChE inhibitory activities. In particular, compound 8b and 8d were the most active compounds in the series against BChE with IC₅₀ values of 45 nM and 62 nM, as well as 146- and 161-fold higher affinity to BChE, resp. To understand the excellent activity of these compounds, mol. docking simulations were performed to get better insights into the mechanism of binding of 3,4-dihydroquinazoline derivatives As expected, compound 8b and 8d bind to both catalytic anionic site (CAS) and peripheral site (PS) of BChE with better interaction energy values than AChE, in agreement with our exptl. data. Furthermore, the non-competitive/mixed-type inhibitions of both compounds further confirmed their dual binding nature in kinetic studies.

Bioorganic & Medicinal Chemistry Letters published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C13H16O2, HPLC of Formula: 20029-52-1.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Shevchenko, V. P. published the artcileInfluence of the nature of activated hydrogen isotope species on the isotope exchange efficiency, with preparation of labeled sodium 4-phenylbenzoate as example, COA of Formula: C13H16O2, the publication is Radiochemistry (Moscow, Russian Federation) (2015), 57(4), 431-438, database is CAplus.

The influence of the nature of activated hydrogen isotope species on the isotope exchange efficiency was studied with preparation of labeled sodium 4-phenylbenzoate as example. The effect of various factors on the deuterium labeling of this compound was examined At temperatures lower than 200 °C, deuterium is mainly incorporated into the Ph moiety, i.e., under these conditions activated hydrogen species are incorporated by the electrophilic mechanism. In the range from 260 to 300 °C, the mean number of deuterium atoms incorporated into 4-phenylbenzoic acid mols. becomes approx. constant (about 8.22 deuterium atoms per mol.). At these temperatures, deuterium is efficiently incorporated both into the Ph fragment and into the benzoic acid residue, which suggests the prevalence of the radical substitution mechanism under these conditions. At temperatures at which the isotope substitution in sodium 4-phenylbenzoate occurs by the electrophilic mechanism, 4-cyclohexylbenzoic acid is formed concurrently, i.e., the maximal yield of 4-cyclohexylbenzoic acid can be reached at temperatures that are most favorable for the isotope exchange by the electrophilic mechanism. At 200 °C, the content of 4-cyclohexylbenzoic acid in the reaction mixture reaches a maximum A sharp increase in the contribution of the radical mechanism of the process at higher temperatures led to a decrease in the yield of 4-cyclohexylbenzoic acid. It was assumed that clusters of activated hydrogen species and electrons, solvated on the support surface, undergo rearrangement with increasing temperature Whereas the major role in labeling by the electrophilic mechanism is played by hydrogen isotope cations, at higher temperatures hydrogen isotope cations interact with electrons to form hydrogen atoms, which become active participants of the exchange process.

Radiochemistry (Moscow, Russian Federation) published new progress about 20029-52-1. 20029-52-1 belongs to quinuclidine, auxiliary class Carboxylic acid,Benzene, name is 4-Cyclohexylbenzoic acid, and the molecular formula is C11H14O4, COA of Formula: C13H16O2.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Doi, Marina published the artcilePhotoluminescence properties of copolyimides containing naphthalene core and analysis of excitation energy transfer between the dianhydride moieties, Name: 4,4-Diaminodicyclohexyl methane, the publication is Journal of Photopolymer Science and Technology (2021), 34(5), 423-430, database is CAplus.

The photoluminescence (PL) properties of semi-aromatic polyimide (PI) films and their model compounds (MCs) prepared from dianhydrides having a rigid naphthalene core were analyzed. The PMMA-dispersed MC and copolymerized PI (CoPI) films derived from 2,3,6,7-naphthalenetetracarboxylic dianhydride (NTDA) exhibited long-lived phosphorescence owing to the suppression of mol. motion by the rigidity of a naphthalene core. Addnl., the PMMA-dispersed MC and the CoPI films derived from 1,5-dibromo derivative of NTDA (DBrNT) exhibited room-temperature phosphorescence due to the enhancement of spin-orbit coupling by bromine atoms. The photophys. processes of the CoPI films prepared from NTDA/DBrNT and 4,4′-oxydiphtalic dianhydride (ODPA) in which the latter absorption band is located at a shorter wavelength than the former were analyzed. After UV irradiation, efficient excitation energy transfer occurs from the ODPA to NTDA/DBrNT moieties, and only the emission from the latter moieties was observed These results demonstrate that the CoPI films derived from two dianhydrides absorbing different UV wavelengths can be used as spectral conversion films that convert a wide range of UV-light into longer wavelength visible light.

Journal of Photopolymer Science and Technology published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Name: 4,4-Diaminodicyclohexyl methane.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Yang, Yang published the artcilePalladium-Catalyzed Completely Linear-Selective Negishi Cross-Coupling of Allylzinc Halides with Aryl and Vinyl Electrophiles, Computed Properties of 1160556-64-8, the publication is Angewandte Chemie, International Edition (2013), 52(52), 14098-14102, database is CAplus and MEDLINE.

A linear-selective Negishi coupling reaction was developed and the synthesis of the target compounds was achieved by a reaction of (allyl)zinc reagents [i.e., (prenyl)zinc bromide, (farnesyl)zinc, etc.] with aryl halides, heteroaryl halides, vinyl halides. The reaction features mild reaction conditions and a broad reactant scope with respect to aryl halides and vinyl halides and (allyl)zinc coupling components. Under optimized reaction conditions [2′-(amino-κN)[1,1′-biphenyl]-2-yl-κC][2′-(dicyclohexylphosphino-κP)-N²,N²,N⁶,N⁶-tetramethyl[1,1′-biphenyl]-2,6-diamine](methanesulfonate-κO)palladium was used as a catalyst. This synthetic approach was applied to the preparation of 6-methyl-3-(3-methyl-2-buten-1-yl)-9H-carbazol-2-ol (siamenol).

Angewandte Chemie, International Edition published new progress about 1160556-64-8. 1160556-64-8 belongs to quinuclidine, auxiliary class Mono-phosphine Ligands, name is 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, and the molecular formula is C18H20N2O12, Computed Properties of 1160556-64-8.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider

Rahimi, AliReza published the artcileAmphiphilic marine coating systems of self-stratified PDMS-PEG surfaces with an epoxy-polyurethane matrix, Computed Properties of 1761-71-3, the publication is Journal of Coatings Technology and Research (2022), 19(3), 795-812, database is CAplus.

Marine coatings protect submerged surfaces from the neg. effects of biofouling. In this work, we demonstrate a new method to prepare self-stratified, amphiphilic glycidyl-carbamate (GC)-based (epoxy urethane-based) coatings (AmpSiGC coatings) that have fouling-release properties making them suitable for marine use. The prepared coating systems are unique and durable in character as the bulk coating takes advantage of both epoxy and urethane functionalities while the surface is comprised of both hydrophilic and hydrophobic domains, granting it an amphiphilic characteristic. The exptl. approach aimed to evaluate several factors that influence coating performance, including mol. weight of poly(ethylene glycol) (PEG) and PDMS moieties, ratio of hydrophobic (PDMS) and hydrophilic (PEG) components in the system, and the effect of different curing agents. The results demonstrated that polymeric chains of 10,000 M_n PDMS and 750 M_n PEG at 10-15 weight% each offer substantially improved or comparable fouling-release performance in comparison to com. marine coatings. This paper reports on the facile synthesis and characterization of the GC resin and GC prepolymers using FTIR and epoxy titrations; surface characterization of the coatings using ATR-FTIR, XPS, and AFM; and fouling-release assessment of the surfaces using laboratory biol. assays with the barnacle Amphibalanus amphitrite, the algae Ulva linza and Navicula incerta, and the bacteria Cellulophaga lytica. Several of the AmpSiGC coatings exhibited promising performance, which were better or comparable to the internal and com. reference coatings. The performance of the systems was dependent on all of the factors considered in this study.

Journal of Coatings Technology and Research published new progress about 1761-71-3. 1761-71-3 belongs to quinuclidine, auxiliary class Ploymers, name is 4,4-Diaminodicyclohexyl methane, and the molecular formula is C13H26N2, Computed Properties of 1761-71-3.

Referemce:
https://en.wikipedia.org/wiki/Quinuclidine,
Quinuclidine | C7H13N | ChemSpider