Category: 20029-52-1

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

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

Ding, Wen published the artcileMolecular-oxygen-promoted Cu-catalyzed oxidative direct amidation of nonactivated carboxylic acids with azoles, Computed Properties of 20029-52-1, the publication is Beilstein Journal of Organic Chemistry (2015), 2158-2165, database is CAplus and MEDLINE.

A copper-catalyzed oxidative direct formation of amides from nonactivated carboxylic acids and azoles with dioxygen as an activating reagent was reported. The azole amides were produced in good to excellent yields with a broad substrate scope. The mechanistic studies revealed that oxygen played an essential role in the success of the amidation reactions with copper peroxycarboxylate as the key intermediate. Transamidation occurs smoothly between azole amide and a variety of amines.

Beilstein Journal of Organic 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, Computed Properties of 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

Yamaoka, Nagahisa published the artcileIdentification of novel plasminogen activator inhibitor-1 inhibitors with improved oral bioavailability: Structure optimization of N-acylanthranilic acid derivatives, Product Details of C13H16O2, the publication is Bioorganic & Medicinal Chemistry Letters (2018), 28(4), 809-813, database is CAplus and MEDLINE.

Novel plasminogen activator inhibitor-1 (PAI-1) inhibitors with highly improved oral bioavailability were discovered by structure-activity relationship studies on N-acyl-5-chloroanthranilic acid derivatives Because lipophilic N-acyl groups seemed to be important for the anthranilic acid derivatives to strongly inhibit PAI-1, synthesis of compounds in which 5-chloroanthranilic acid was bound to a variety of highly lipophilic moieties with appropriate linkers was investigated. As the result it appeared that some of the derivatives possessing aryl- or heteroaryl-substituted Ph groups in the acyl chain had potent in vitro PAI-1 inhibitory activity. Oral absorbability of typical compounds was also evaluated in rats, and three compounds which have diverse chem. structure with each other, e.g., I, were selected for further pharmacol. evaluation.

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 C2H3N3, Product Details of C13H16O2.

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

Pasha, Farhan Ahmad published the artcileDFT-based de novo QSAR of phenoloxidase inhibitors, Recommanded Product: 4-Cyclohexylbenzoic acid, the publication is Chemical Biology & Drug Design (2008), 71(5), 483-493, database is CAplus and MEDLINE.

The phenoloxidase or tyrosinase is a key enzyme in insects, which is responsible for hydroxylation of tyrosine into o-quinones via o-diphenols. A series of benzaldehyde thiosemicarbazone, benzaldehyde and benzoic acid families were taken with their pragmatic pIC₅₀ values against phenoloxidase from pieris rapae (Lepidoptera) larvae. D. functional theory-based quant. structure-activity relation (QSAR) analyses were performed to speculate the key interaction. The most fitted four different QSAR models were identified and discussed. The softness, electrophilicity index, molar refractivity and log P were identified as best descriptors; however, the at. values of softness and philicity obtained from Fukui function are more significant than global values. The study reveals that electrostatic and steric fields jointly contribute to activity. To gain further insight, the three-dimensional quant. structure-activity relation (3D-QSAR) analyses were performed using two mol. field techniques: comparative mol. field anal. (CoMFA) and comparative mol. similarity indexes anal. (CoMSIA). The successful 3D-QSAR models were obtained from CoMFA (q² = 0.94, r² = 0.99, r²_pred = 0.92) and CoMSIA (q² = 0.94, r² = 0.98, r²_pred = 0/95). The CoMFA and CoMSIA results indicate that, a bulky and neg. group around sulfur atom but a small and pos. group around nitrogen atom might have good effects on activity. The ortho and meta positions of ring are favorable for small group. These QSAR models might be helpful to design the novel and potent inhibitors.

Chemical Biology & Drug Design 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, Recommanded Product: 4-Cyclohexylbenzoic acid.

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

Santiago, Celine B. published the artcileDeveloping a Modern Approach To Account for Steric Effects in Hammett-Type Correlations, Synthetic Route of 20029-52-1, the publication is Journal of the American Chemical Society (2016), 138(40), 13424-13430, database is CAplus and MEDLINE.

The effects of aryl ring ortho-, meta-, and para-substitution on site selectivity and enantioselectivity were investigated in the following reactions: (1) enantioselective Pd-catalyzed redox-relay Heck reaction of arylboronic acids, (2) Pd-catalyzed β-aryl elimination of triarylmethanols, and (3) benzoylformate decarboxylase-catalyzed enantioselective benzoin condensation of benzaldehydes. Through these studies, it is demonstrated that the electronic and steric effects of various substituents on selectivities obtained in these reactions can be described by NBO charges, the IR carbonyl stretching frequency, and Sterimol values of various substituted benzoic acids. An extended compilation of NBO charges and IR carbonyl stretching frequencies of various substituted benzoic acids was used as an alternative to Hammett values. These parameters provide a correlative tool that allows for the anal. of a much greater range of substituent effects because they can also account for proximal and remote steric effects.

Journal of the American 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, Synthetic Route of 20029-52-1.

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

Charrier, Jean-Damien published the artcileDiscovery and Structure-Activity Relationship of 3-Aminopyrid-2-ones as Potent and Selective Interleukin-2 Inducible T-Cell Kinase (Itk) Inhibitors, Synthetic Route of 20029-52-1, the publication is Journal of Medicinal Chemistry (2011), 54(7), 2341-2350, database is CAplus and MEDLINE.

Interleukin-2 inducible T-cell kinase (Itk) plays a role in T-cell functions, and its inhibition potentially represents an attractive intervention point to treat autoimmune and allergic diseases. Herein we describe the discovery of a series of potent and selective novel inhibitors of Itk. These inhibitors were identified by structure-based design, starting from a fragment generated de novo, the 3-aminopyrid-2-one motif. Functionalization of the 3-amino group enabled rapid enhancement of the inhibitory activity against Itk, while introduction of a substituted heteroaromatic ring in position 5 of the pyridone fragment was key to achieving optimal selectivity over related kinases. A careful anal. of the hydration patterns in the kinase active site was necessary to fully explain the observed selectivity profile. The best mol. prepared in this optimization campaign, 7v, inhibits Itk with a K_i of 7 nM and has a good selectivity profile across kinases.

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, Synthetic Route of 20029-52-1.

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

Pacut, Ryszard published the artcileReduction of polyaromatic carboxylic acids with lithium in ethylenediamine and tetrahydrofuran, Quality Control of 20029-52-1, the publication is Polish Journal of Chemistry (1985), 59(4), 447-51, database is CAplus.

The use of large amounts of Li in the title reduction led to ring reduction without affecting the CO₂H group. Thus, treatment of 5 mmole 1-naphthoic acid with 50 mmole Li in H₂NCH₂CH₂NH₂-THF gave reduced naphthoic acid I. Reduction of 2-naphthoic acid with Li (1:5 molar ratio) gave hydronaphthoic acid II, whereas using (1:15 molar ratio) gave III (R = CO₂H, CHO). Five mmole 4-PhC₆H₄CO₂H reduced with 50 mmole Li gave benzoic acid IV.

Polish Journal of 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, Quality Control of 20029-52-1.

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