Category: quinuclidine

Ponzano, Stefano published the artcileSynthesis, Biological Evaluation, and 3D QSAR Study of 2-Methyl-4-oxo-3-oxetanylcarbamic Acid Esters as N-Acylethanolamine Acid Amidase (NAAA) Inhibitors, Application of 4-Cyclohexylbenzoic acid, the publication is Journal of Medicinal Chemistry (2014), 57(23), 10101-10111, database is CAplus and MEDLINE.

N-(2-Oxo-3-oxetanyl)carbamic acid esters e. g., I, have recently been reported to be noncompetitive inhibitors of the N-acylethanolamine acid amidase (NAAA) potentially useful for the treatment of pain and inflammation. In the present study, we further explored the structure-activity relationships of the carbamic acid ester side chain of 2-methyl-4-oxo-3-oxetanylcarbamic acid ester derivatives Addnl. favorable features in the design of potent NAAA inhibitors have been found together with the identification of a single digit nanomolar inhibitor. In addition, we devised a 3D QSAR using the at. property field method. The model turned out to be able to account for the structural variability and was prospectively validated by designing, synthesizing, and testing novel inhibitors. The fairly good agreement between predictions and exptl. potency values points to this 3D QSAR model as the first example of quant. structure-activity relationships in the field of NAAA inhibitors .

Journal of Medicinal Chemistry 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

Yu, Peng published the artcileIridium-Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis, Related Products of quinuclidine, the publication is Angewandte Chemie, International Edition (2020), 59(7), 2904-2910, database is CAplus and MEDLINE.

Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-Bu halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group tolerance and safety profile of these reactions compared to the state-of-the-art. This method has granted access to alkenyl halide compounds containing acid-sensitive groups, such as tertiary alcs., silyl ethers, and acetals. The synthetic value of those methodologies has been demonstrated by gram-scale synthesis where low catalyst loading was achieved.

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 C18H10, Related Products of quinuclidine.

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

Borrajo-Calleja, Gustavo M. published the artcileMechanistic Investigation of the Pd-Catalyzed Intermolecular Carboetherification and Carboamination of 2,3-Dihydrofuran: Similarities, Differences, and Evidence for Unusual Reaction Intermediates, Related Products of quinuclidine, the publication is Organometallics (2017), 36(18), 3553-3563, database is CAplus.

The mechanism of the Pd-catalyzed intermol. syn carboetherification and syn carboamination of 2,3-dihydrofuran was studied exptl. Crystallog., spectroscopic, and spectrometric methods have shed light on the nature of a number of catalytically competent Pd complexes. Several oxidative addition complexes as well as their cationic derivatives were characterized by x-ray diffraction analyses. In the latter, the complexes derived from 2-bromophenol displayed an unorthodox η⁶ binding mode of the privileged Buchwald-type dialkylbiarylphosphine ligands. The hemilabile character of this interaction was found to facilitate coordination of the polarized olefinic substrate, as evidenced by NMR spectroscopy. In contrast, coordination of the pendant sulfonyl group in the cationic complexes derived from 2-bromo-N-sulfonylated anilines prevented direct binding of 2,3-dihydrofuran. Deprotonation of these species induced aggregation of monomeric units through various weak noncovalent interactions to generate trinuclear Pd clusters. The reversibility of this process was probed by conducting crossover experiments The nature of the alkali ion strongly influences the selectivity of the assembly phenomenon. Examination of the importance of the nucleophilicity in these intermol. reactions revealed that the switch between syn carbofunctionalization and Heck arylation of 2,3-dihydrofuran certainly arose from a zwitterionic intermediate common to both catalytic manifolds. The understanding of these reactions gained through this study should certainly favor the design of novel Pd-catalyzed transformations for related systems.

Organometallics 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, Related Products of quinuclidine.

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

Ruiz-Castillo, Paula published the artcileRational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis, Application of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Journal of the American Chemical Society (2015), 137(8), 3085-3092, database is CAplus and MEDLINE.

The authors report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic anal. and rational design led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The process was effective in coupling a wide range of functionalized aryl and heteroaryl halides under mild conditions.

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, Application of 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

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

Sutton, James C. published the artcileSolid-phase synthesis and SAR of 4-carboxy-2-azetidinone mechanism-based tryptase inhibitors, Application of 4-Cyclohexylbenzoic acid, the publication is Bioorganic & Medicinal Chemistry Letters (2004), 14(9), 2233-2239, database is CAplus and MEDLINE.

A series of non-guanidine N1-activated C4-carboxy azetidinone tryptase inhibitors, e.g. I, was prepared by solid-phase methodol. to quickly assess the SAR associated with distal functionality on the N1-activating group. From these studies, potent inhibitors with improved specificity were discovered.

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 C5H9IO2, Application of 4-Cyclohexylbenzoic acid.

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