Heterocyclic Building Blocks-Quinuclidine

Barzic, A. I. published the artcileInterlayer dielectrics based on copolyimides containing non-coplanar alicyclic-units for multilevel high-speed electronics, Name: 4,4-Diaminodicyclohexyl methane, the publication is Polymer Testing (2020), 106704, database is CAplus.

A series of copolyimides (CPIs) containing non-coplanar alicyclic units combined with fluorinated or rigid aromatic monomer segments is synthesized. The solid film samples display an elevated heat resistance as their degradation started at temperatures around 415°C. Introduction into CPI backbone of bicyclic units, aromatic/aliphatic rings, angular bonds and/or low polarizable groups, determine the variation of the dielec. constant in the range 2.44-3.04 at 100 Hz. When using these CPIs as interlayer dielecs. (ILDs), it is revealed that resistance-capacitance delay is minimized (∼10-11 s) determining faster response of the device. Atomic force microscopy scans of CPI samples show distinct macromol. architectures, all containing nanopores with features depending on the chem. structure. Interfacial adhesion of investigated ILDs with copper wiring is highest for the samples lacking fluorine groups.

Polymer Testing 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

Wezeman, Tim published the artcileSynthesis of Non-Symmetrical and Atropisomeric Dibenzo[1,3]diazepines: Pd/CPhos-Catalyzed Direct Arylation of Bis-Aryl Aminals, Related Products of quinuclidine, the publication is Australian Journal of Chemistry (2015), 68(12), 1859-1865, database is CAplus.

Pd/CPhos-catalysis provides direct arylation/cyclization of methylene-linked bis[anilines] to dibenzo[1,3]diazepines which are both non-(C2)-sym. and axially chiral. Synthesis of the direct arylation substrates commences with substitution of (N-acyl)anilines to methylene Me sulfide derivatives, followed by halogenation/de-thiomethylation to N-(chloromethyl)anilines. These are substituted with a second aniline derivative, allowing modular preparation of (ortho-halo)aryl-aminal-linked arenes. The C-H functionalizing direct arylation conditions were adapted from Fagnou and others: substrates and potassium carbonate were heated in dimethylacetamide in the presence of palladium acetate and an electron-rich and sterically hindered biarylphosphine ligand, here CPhos. These conditions delivered the C1-(a)sym. dibenzo[1,3]diazepine targets, which, due to torsion around the axis of the newly formed biaryl bond, are also intrinsically atropisomeric. The axially twisted scaffold is known to impart special properties to ligands/catalysts when the products are further converted into the corresponding seven-membered ring-containing N-heterocyclic carbenes. Under optimized conditions the synthesis of the target compounds was achieved using 2′-(dicyclohexylphosphino)-N²,N²,N⁶,N⁶-tetramethyl[1,1′-biphenyl]-2,6-diamine (i.e., CPhos) and palladium acetate as ligand and catalyst combination. Key intermediates included N,N’-(methylene)-N,N’-bis(phenyl)acetamide derivatives (i.e., the above-mentioned aminals).

Australian Journal of Chemistry 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 C5H12O2, Related Products of quinuclidine.

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

David, Tomas published the artcileImproved Conjugation, 64-Cu Radiolabeling, in Vivo Stability, and Imaging Using Nonprotected Bifunctional Macrocyclic Ligands: Bis(Phosphinate) Cyclam (BPC) Chelators, Application In Synthesis of 1353016-70-2, the publication is Journal of Medicinal Chemistry (2018), 61(19), 8774-8796, database is CAplus and MEDLINE.

Bifunctional derivatives of Bis(Phosphinate)-bearing Cyclam (BPC) chelators bearing carboxylate, amine, isothiocyanate, azide or cyclooctyne in BP-side chain were synthesized. Conjugations required no protection of phosphinate or ring secondary amine groups. The ring amines were not reactive (proton protected) at pH < ∼8. For isothiocyanate coupling, oligopeptide N-terminal α-amines were more suitable than alkyl amines, e.g. Lys ω-amine (pKa ∼7.5-8.5 and ∼10-11, resp.) due to lower basicity. The Cu-64 labeling was efficient at room temperature (specific activity ∼100 GBq/μmol; 25°C, pH 6.2, ∼100 ligand equivalent, 10 min). A representative Cu-64-BPC was tested in-vivo showing fast clearance and no non-specific radioactivity deposition. The monoclonal anti-PSCA antibody 7F5 conjugates with thiocyanate BPC derivative or NODAGA were radiolabeled and studied in PC-3-PSCA tumor bearing mice by PET. The radiolabeled BPC conjugate was accumulated in the prostate tumor with low off-target uptake, unlike Cu-64-labeled NODAGA-antibody conjugate. The BPC chelators have a great potential for theranostic applications of Cu-64/Cu-67 matched pair.

Journal of Medicinal Chemistry published new progress about 1353016-70-2. 1353016-70-2 belongs to quinuclidine, auxiliary class Other Aromatic Heterocyclic,Carboxylic acid,Amide,Inhibitor,Inhibitor, name is Dbco-acid, and the molecular formula is C19H15NO3, Application In Synthesis of 1353016-70-2.

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

Heilbron, I. M. published the artcileUnion of aryl nuclei. II. Chloro-, bromo- and nitrofluorenones, Category: quinuclidine, the publication is Journal of the Chemical Society (1938), 113-16, database is CAplus.

By means of the Gomberg reaction, diazotized Me anthranilate (or a derivative) and a neutral aromatic liquid being used, nuclear-substituted biphenyl-2-carboxylic acids become readily available, from which the corresponding substituted fluorenones may be obtained quant. on ring closure. Me 4-chloroanthranilate and C₆H₆ thus give 25% of the Me ester, b₂₀ 180-90°, of 5-chlorodiphenyl-2-carboxylic acid (I), m. 152°; ring closure with H₂SO₄ gives 3-chlorofluorenone (II), yellow, m. 157°; 4-Cl isomer of I, m. 157°; 2-Cl isomer of II, m. 123°; 5-Br analog of I, m. 172°; 3-Br analog of II, m. 161°; the 4-isomers, m. 164°, and 150°, were likewise prepared 4-NO₂ analog of I, m. 173°; ring closure gives the 4-NO₂ analog of II, m. 219°. PhCl and PhBr give mixtures of the 2′- and 4′-Cl and Br derivatives, the separation of which was only partly successful. p-ClC₆H₄N₂Cl and PhMe give 4′-chloro-2-methylbiphenyl, b. 288-90°; oxidation gives 4′-chloro-biphenyl-2-carboxylic acid, m. 161°; ring closure gives the 2-Cl isomer of II.

Journal of the Chemical Society 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, Category: quinuclidine.

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

Kang, Houng published the artcileEnantioselective Vanadium-Catalyzed Oxidative Coupling: Development and Mechanistic Insights, Formula: C28H41N2P, the publication is Journal of Organic Chemistry (2018), 83(23), 14362-14384, database is CAplus and MEDLINE.

The evolution of a more reactive chiral vanadium catalyst for enantioselective oxidative coupling of phenols is reported, ultimately resulting in a simple monomeric vanadium species combined with a Bronsted or Lewis acid additive. The resultant vanadium complex is found to effect the asym. oxidative ortho-ortho coupling of simple phenols and 2-hydroxycarbazoles with good to excellent levels of enantioselectivity. Exptl. and quantum mech. studies of the mechanism indicate that the additives aggregate the vanadium monomers. In addition, a singlet to triplet crossover is implicated prior to carbon-carbon bond formation. The two lowest energy diastereomeric transition states leading to the enantiomeric products differ substantially with the path to the minor enantiomer involving greater torsional strain between the two phenol moieties.

Journal of Organic Chemistry 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

Liu, Yu published the artcileGO-CNTs hybrids reinforced epoxy composites with porous structure as microwave absorbers, Related Products of quinuclidine, the publication is Composites Science and Technology (2020), 108450, database is CAplus.

Foam structures with epoxy as the matrix and both carbon nanotubes (CNTs) and their hybrids with graphene oxide (GO-CNTs) as absorbers were fabricated, and their microwave absorbing and electromagnetic properties were investigated in the frequency range of 1-18 GHz. The fillers and bubbles were uniformly distributed in the composites. The complex permittivity and elec. conductivity of the composites increased as the fillers’ content increasing. The best performance of the reflection loss (RL) can be obtained for a foam structure with 0.5 wt% GO-CNTs, which had a RL peak value of -20dB with a -10 dB range of 5.3 GHz (10.8-16.1 GHz). Multi-layered structures were also discussed in this work, a RL peak value of -40dB with a -10dB range of 7.1 GHz (9.9-17 GHz) had been obtained by combining two foam structures, which are 2 mm thick 0.5 wt% GO-CNTs/epoxy and 1 mm thick 2.0 wt% GO-CNTs/epoxy. Furthermore, the -10dB range can reach 11.5 GHz (6.5-18 GHz) when combining 2.6 mm thick 0.5 wt% GO-CNTs/epoxy and 1.3 mm thick 2.0 wt% GO-CNTs/epoxy.

Composites 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, Related Products of quinuclidine.

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

Tabuchi, Atsuko published the artcileSynthesis and Characterization of White-Light Luminescent End-Capped Polyimides Based on FRET and Excited State Intramolecular Proton Transfer, Application of 4,4-Diaminodicyclohexyl methane, the publication is Polymers (Basel, Switzerland) (2021), 13(22), 4050, database is CAplus and MEDLINE.

N-cyclohexylphthalimide-substituted trifluoroacetylamino (CF₃CONH-) group (3TfAPI), which forms an intramol. hydrogen bond, was synthesized, and it exhibited a bright yellow fluorescence owing to the excited-state intramol. proton transfer (ESIPT) in the solution and crystalline states. In addition, CF₃CONH-substituted phthalic anhydride (3TfAPA) was synthesized, which was attached to the termini of a blue-fluorescent semi-aromatic polyimide (PI) chain. Owing to the efficient Forster resonance energy transfer (FRET) occurring from the main chain to the termini and the suppression of deprotonation (anion formation) at the 3TfAPA moiety by H₂SO₄ doping, the resulting PI films display bright white fluorescence. Moreover, the enhancement of the chain rigidity by substituting the diamine moiety results in an increase in the quantum yield of white fluorescence (Φ) by a factor of 1.7, due to the suppression of local mol. motion. This material design strategy is promising for preparing thermally stable white-light fluorescent PIs applicable to solar spectral converters, displays, and ICT devices.

Polymers (Basel, Switzerland) 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 C9H7NO2, Application of 4,4-Diaminodicyclohexyl methane.

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

Giuntoli, Andrea published the artcileSystematic coarse-graining of epoxy resins with machine learning-informed energy renormalization, COA of Formula: C13H26N2, the publication is npj Computational Materials (2021), 7(1), 168, database is CAplus and MEDLINE.

Abstract: A persistent challenge in mol. modeling of thermoset polymers is capturing the effects of chem. composition and degree of crosslinking (DC) on dynamical and mech. properties with high computational efficiency. We established a coarse-graining (CG) approach combining the energy renormalization method with Gaussian process surrogate models of mol. dynamics simulations. This allows a machine-learning informed functional calibration of DC-dependent CG force field parameters. Taking versatile epoxy resins consisting of Bisphenol A diglycidyl ether combined with curing agent of either 4,4-Diaminodicyclohexylmethane or polyoxypropylene diamines, we demonstrated excellent agreement between all-atom and CG predictions for d., Debye-Waller factor, Young’s modulus, and yield stress at any DC. We further introduced a surrogate model-enabled simplification of the functional forms of 14 non-bonded calibration parameters by quantifying the uncertainty of a candidate set of calibration functions. The framework established provides an efficient methodol. for chem.-specific, large-scale investigations of the dynamics and mechanics of epoxy resins.

npj Computational Materials 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, COA of Formula: C13H26N2.

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

Luo, Qiang published the artcileThe thiolated chitosan: Synthesis, gelling and antibacterial capability, Quality Control of 162515-68-6, the publication is International Journal of Biological Macromolecules (2019), 521-530, database is CAplus and MEDLINE.

Chitosan-1-(mercaptomethyl)-cyclopropane acetic acid (CS-MCA) copolymer was synthesized by amino linkage. The obtained copolymer was characterized by FTIR, ¹H NMR, XRD, TGA and SEM. Porous and reticulate morphologies were found on the CS-MCA surface. The effects of pH on the rheol. properties of CS-MCA were investigated. On the one hand, the apparent viscosity of CS-MCA indicated a shear-thinning behavior. The graft of MCA enhanced the moduli and the maximum elastic properties were observed at pH = 7.00. The addition of dithiothreitol reduced the viscosity and modulus of CS-MCA hydrogel, and the gelation time, temperature and frequency were obtained in dynamic oscillatory tests. The antibacterial effect of CS-MCA against E. coli was investigated for the inhibition zone and bacterial growth curve. These results showed that CS-MCA had better antibacterial ability than chitosan without modification. Therefore, the rheol. behavior and functional activities can be applied for the hydrocolloid gels in food and pharmaceutical applications.

International Journal of Biological Macromolecules 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, Quality Control of 162515-68-6.

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

Cao, Junya published the artcileRu/g-C₃N₄ as an efficient catalyst for selective hydrogenation of aromatic diamines to alicyclic diamines, Synthetic Route of 1761-71-3, the publication is RSC Advances (2020), 10(28), 16515-16525, database is CAplus and MEDLINE.

A series of Ru/g-C₃N₄ materials with highly dispersed Ru were firstly prepared by an ultrasonic impregnation method using carbon nitride as a support. The catalysts were characterized by various techniques including BET and elemental anal., ICP-AES, XPS, XRD, CO₂-TPD and TEM. The results demonstrated that Ru/g-C₃N₄ materials with a mesoporous structure and highly dispersed Ru were successfully prepared The chemo-selective hydrogenation of p-phenylenediamine (PPDA) to 1,4-cyclohexanediamine (CHDA) over Ru/g-C₃N₄ as a model reaction was investigated in detail. PPDA conversion of 100% with a CHDA selectivity of more than 86% could be achieved under mild conditions. It can be inferred that the carbon nitride support possessed abundant basic sites and the Ru/g-C₃N₄-T catalysts provided suitable basicity for the aromatic ring hydrogenation. Compared to the N-free Ru/C catalyst, the involvement of nitrogen species in Ru/g-C₃N₄ remarkably improved the catalytic performance. In addition, the recyclability of the catalyst demonstrated that the aggregation of Ru nanoparticles was responsible for the decrease of the catalytic activity. Furthermore, this strategy also could be expanded to the selective hydrogenation of other aromatic diamines to alicyclic diamines.

RSC Advances 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, Synthetic Route of 1761-71-3.

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