Category: quinuclidine

Habicht, J. published the artcileInhibition of prostaglandin E₂ release by salicylates, benzoates and phenols: a quantitative structure-activity study, SDS of cas: 20029-52-1, the publication is Journal of Pharmacy and Pharmacology (1983), 35(11), 718-23, database is CAplus and MEDLINE.

Concentrations inhibiting 50% of PGE₂  [363-24-6] release from phorbol ester-stimulated mouse peritoneal macrophages in vitro were determined for monosubstituted congeners of salicylic acid, benzoic acid, and phenol. Other compounds, mainly benzoic acids, were inactive. An attempt was made to establish QSAR from the exptl. data using literature or calculated values for the logarithmic octanol-water partition coefficients of the compounds, molar refractivity and sigma values of substituents as well as structural indicator variables. The equations had moderate predictive power and should be considered as a 1st step in the investigation of factors determining the biog. activity of salicylates, benzoates, and phenols.

Journal of Pharmacy and Pharmacology 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, SDS of cas: 20029-52-1.

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

Arrechea, Pedro Luis published the artcileBiaryl Phosphine Based Pd(II) Amido Complexes: The Effect of Ligand Structure on Reductive Elimination, COA of Formula: C28H41N2P, the publication is Journal of the American Chemical Society (2016), 138(38), 12486-12493, database is CAplus and MEDLINE.

Kinetic studies conducted under both catalytic and stoichiometric conditions were employed to investigate the reductive elimination of RuPhos (2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl) based palladium amido complexes. These complexes were found to be the resting state in Pd-catalyzed cross-coupling reactions for a range of aryl halides and diarylamines. Hammett plots demonstrated that Pd(II) amido complexes derived from electron-deficient aryl halides or electron-rich diarylamines undergo faster rates of reductive elimination. A Hammett study employing SPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) and analogs of SPhos demonstrated that electron donation of the “lower” aryl group is key to the stability of the amido complex with respect to reductive elimination. The rate of reductive elimination of an amido complex based on a BrettPhos-RuPhos hybrid ligand (2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,6′-diisopropoxybiphenyl) demonstrated that the presence of the 3-methoxy substituent on the “upper” ring of the ligand slows the rate of reductive elimination. These studies indicate that reductive elimination occurs readily for more nucleophilic amines such as N-alkyl anilines, N,N-dialkyl amines, and primary aliphatic amines using this class of ligands.

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, COA of Formula: C28H41N2P.

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

Han, Chong published the artcileNegishi Coupling of Secondary Alkylzinc Halides with Aryl Bromides and Chlorides, SDS of cas: 1160556-64-8, the publication is Journal of the American Chemical Society (2009), 131(22), 7532-7533, database is CAplus and MEDLINE.

An efficient palladium-catalyzed process has been developed for Negishi coupling of secondary alkylzinc halides with a wide range of aryl bromides and activated aryl chlorides. A palladium catalyst composed of a new biaryldialkylphosphine ligand, CPhos, effectively promotes the rate of the reductive elimination step relative to the rate of the undesired β-hydride elimination. The broad substrate scope and excellent ratio of the desired secondary to the undesired primary coupling product make this method a powerful and reliable tool for C(sp³)-C(sp²) bond formation.

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, SDS of cas: 1160556-64-8.

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

Zhang, Hu published the artcilePalladium-Catalyzed Negishi Coupling of α-CF₃ Oxiranyl Zincate: Access to Chiral CF₃-Substituted Benzylic Tertiary Alcohols, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine, the publication is Journal of the American Chemical Society (2017), 139(33), 11590-11594, database is CAplus and MEDLINE.

We report a Pd-catalyzed stereospecific α-arylation of optically pure 2,3-epoxy-1,1,1-trifluoropropane (TFPO). This method allows for the direct and reliable preparation of optically pure 2-CF₃-2-(hetero)aryloxiranes, which are precursors to many CF₃-substituted tertiary alcs. The use of continuous-flow methods has allowed the deprotonation of TFPO and subsequent zincation at higher temperature compared to that under traditional batch 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 C8H5F3N4, Recommanded Product: 2′-(Dicyclohexylphosphino)-N2,N2,N6,N6-tetramethyl-[1,1′-biphenyl]-2,6-diamine.

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

Yan, Lin published the artcile2-Aryl(pyrrolidin-4-yl)acetic acids are potent agonists of sphingosine-1-phosphate (S1P) receptors, Application In Synthesis of 20029-52-1, the publication is Bioorganic & Medicinal Chemistry Letters (2006), 16(13), 3564-3568, database is CAplus and MEDLINE.

2-Aryl(pyrrolidin-4-yl)acetic acids I [R = i-Bu, cyclopentyl, cyclohexyl, F₃C(CH₂)₂, 3,3-difluoro-1-cyclopentyl, 4,4-difluoro-1-cyclohexyl] and II were synthesized and their biol. activities as agonists of S1P receptors were evaluated. These analogs were able to induce lowering of lymphocyte counts in the peripheral blood of mice and were found to have good overall pharmacokinetic properties in rats.

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 C8H6ClNO, Application In Synthesis of 20029-52-1.

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

Buu-Hoi published the artcileChemistry of cyclohexylbenzene, COA of Formula: C13H16O2, the publication is Bulletin de la Societe Chimique de France (1944), 127-36, database is CAplus.

Cyclohexylbenzene (I) is an excellent starting material for organic syntheses; its derivatives crystallize readily, are soluble in most organic solvents; they are often cleaved by AlCl₃ (II), forming cyclohexyl radicals. Condensation of 15 g. I with 10 g. phthalic anhydride in 150 cc. of benzene (III), wi h 20 g. of II under cooling, yields after decomposition with HCl 2-(p-cyclohexylbenzoyl)benzoic acid (IV), m. 179-80° (from petr. ether). Reduction of IV with Zn and NH₄OH gives 2-(p-cyclohexylbenzyl)benzoic acid, m. 137° (from III). I condensed with succinic anhydride in PhNO₂, with II, gives β-(p-cyclohexylbenzoyl)propionic acid (V), m. 134° (from III). Clemmensen-Martin reduction of V gives γ-(p-cyclohexylphenyl)butyric acid (VI), b₁₈ 240°, m. 47° (from III + petr. ether); its acid chloride (VII), b_3-4 185-90°, treated with NH₃ yields the acid amide of VI, m. 128° (from III). Reaction of 6 g. of VII with 5 g. of II in III yields 3 g. of 7-cyclohexyl-1-tetralone (VIII), b₂₁ 222-4° (semicarbazone, m. 270-1°) (decomposition), some α-tetralone, and I, the latter being formed from cyclohexyl radicals and III. Clemmensen-Martin reduction of VIII yields 7-cyclohexyl-1,2,3,4-tetrahydronaphthalene (IX), b₂₀ 192-5°. Dehydrogenation of IX with Se at 335-40° for 15 h. is a good method for preparing 2-C₁₀H₇Ph. Heating equimolar amounts of VIII and isatin with 3 mols. of KOH for 24 h. on the steam cone in a min. of alc. gives 2-cyclohexyl-12-aza-7-benzanthracenecarboxylic acid (decomposition on heating). The Grignard reagent prepared from 145 g. p-bromocyclohexylbenzene yields with 30 g. of (CH₂)₂O at -10° 50 g. of 2-(p-cyclohexylphenyl)ethanol (X), b₁₄ 190-5°; phenylurethane, m. 100°. Treating 50 g. of X in CHCl₃ with 28 g. PBr₃ yields 30 g. of 2-(p-cyclohexylphenyl)-1-bromoethane (XI), b₁₄ 188-90°. Addition of 27 g. of XI to 18 g. of Et malonate (XII) in 25 cc. of absolute alc. containing 2.3 g. of Na yields 20 g. of Et [2-(p-cyclohexylphenyl)ethyl]malonate (XIII), b₁₅ 245-8°, saponified to VI. Addition of 10 g. of XI to a solution of 10 g. of PhCH(CO₂Et)₂ in 50 cc. of xylene and 1 g. of Na yields Et (phenyl(2-p-cyclohexylphenyl)malonate, b_3-4 245-55°, saponified to α-phenyl-γ-(p-cyclohexylphenyl)butyric acid (XIV), b_2.5 260°, m. 134° (from III). The acid chloride (XV) of XIV treated with NH₃ yields the amide of XIV m. 106-7°. Reaction of XV with II and III gives 2-phenyl-7-cyclohexyl-1-tetralone (XVI), b_2.7 240-50°, some I, and 2-phenyltetralone. Clemmensen reduction of XVI gives 2-phenyl-7-cyclohexyl-1,2,3,4-tetrahydronaphthalene, b_0.7 190-200°, dehydrogenated by Se to 2,7-diphenylnaphthalene, m. 142-3° (from alc.). KCN with p-(chloromethyl)cyclohexylbenzene (XVII) in EtOH results in a mixture of p-cyclohexylbenzyl Et ether, b₁₃ 175-7°, and (p-cyclohexylphenyl)acetonitrile (XVIII), b₁₂ 189-92°, m. 38°. Condensation of XVIII with p-ONC₆H₄NMe₂ by KOH gives p-C₆H₁₁C₆H₄ C(CN):NC₆H₄NMe₂ (XIX), m. 124-5°, and C₆H₁₁C₆H₄C(CN):̈ONC₆H₄NMe₂, m. 197-8° (from AcOH). Acid hydrolysis of XIX gives some C₆H₁₁C₆H₄COCN, m. 50° (petr. ether), and alk. hydrolysis leads to p-cyclohexylbenzoic acid, m. 197° (from AcOH). Condensation of 5 g. of XVIII with 2.8 g. of BzH (EtONa) gives α-(p-cyclohexylphenyl)cinnamonitrile (XX), m. 117° (alc.), and with 2.5 g. of furfural yields α-(p-cyclohexylphenyl)-2-furanacrylonitrile, m. 64°. These nitriles could not be hydrolyzed. Condensation of XX with III and II yields I and a mixture of PhCH(CN)CHPh₂ and Ph₂C(CN)CH₂Ph, not further purified. Saponification of XVIII with KOH gives (p-cyclohexylphenyl)acetic acid; its acid chloride (XXI), b₃ 165-6°, upon treatment with NH₃ gives (p-cyclohexylphenyl)acetamide, m. 163° (from III). XXI in III treated with II yields I, desoxybenzoin, and some p-cyclohexyldesoxybenzoin, b₁₆ 260-70°, m. 103° (from alc.). If the condensation is carried out in PhNO₂, 45 g. p,p’-dicyclohexyldesoxybenzoin, b_1.6 250-60°, m. 146°, is obtained and no cleavage of the cyclohexyl radical occurs. Condensation of XVII (45 g.) with 32 g. iso-PrCOPh previously treated with 8.9 g. NaNH₂ (XXII) in 200 cc. of III yields 47 g. of p-C₆H₁₁C₆H₄CH₂CMe₂Bz (XXIII), b₂ 223-6°. By treatment with XXII cleavage of XXIII to C₆H₁₁C₆H₄CH₂CMe₂CONH₂ (XXIV), m. 125°, is effected. NaOBr degradation of XXIV leads to the isocyanate, b₂ 145-50°, which upon treatment with HCl gives C₆H₁₁C₆H₄CH₂CMe₂NH₂.HCl; free base, b₃ 157-9°, m. 45° (from petr. ether); picrate, m. 175°; Bz derivative, m. 135°. To 90 g. of XII in 120 g. absolute alc. and 11 g. of Na, 100 g. of XVII was added, yielding 100 g. of Et (p-cyclohexylphenylmethyl) malonate, b₁₃ 230-2°; saponification yields the substituted malonic acid, m. 163° (with loss of CO₂). On distilling the acid, β-(p-cyclohexylphenyl)propionic acid (XXV), b_15-16 225-30°, m. 125° (from III), is obtained; its acid chloride (XXVI), b_2.5 170-2°, treated with NH₃ yields the amide of XXV, m. 167°. Reaction of 15 g. of XXVI with 50 cc. of III, with II catalyst, yields 7 g. of 6-cyclohexyl-1-indanone (XXVII), b_13-14 203-5°, m. 87° (semicarbazone, m. 230°), and some I and 1-indanone. XXVII condensed with isatin, with KOH, gives 3-cyclohexyl-5-aza-6,7-benzofluorene-8-carboxylic acid, decarboxylating on heating to 3-cyclohexyl-5-aza-6,7-benzofluorene, b₂ 240-50°, m. 129° (from alc.); picrate, decompose below 200°. Clemmensen reduction of XXVII yields 6-cyclohexylindan, b₁₆ 174-6°. Cyclohexyl p-nitrobenzoate, b₂ 180°, m. 52° (from alc.), prepared by treating p-O₂NC₆H₄COCl with excess of cyclohexanol, shows remarkable properties against pneumococci and tubercle bacilli.

Bulletin de la Societe Chimique de France 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, COA of Formula: C13H16O2.

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

Xiao, Xueyang published the artcilePolymeric dual-modal imaging nanoprobe with two-photon aggregation-induced emission for fluorescence imaging and gadolinium-chelation for magnetic resonance imaging, Computed Properties of 1353016-70-2, the publication is Bioactive Materials (2023), 538-549, database is CAplus and MEDLINE.

Nanoprobes that offer both fluorescence imaging (FI) and magnetic resonance imaging (MRI) can provide supplementary information and hold synergistic advantages. However, synthesis of such dual-modality imaging probes that simultaneously exhibit tunability of functional groups, high stability, great biocompatibility and desired dual-modality imaging results remains challenging. In this study, we used an amphiphilic block polymer from (ethylene glycol) Me ether methacrylate (OEGMA) and N-(2-hydroxypropyl) methacrylamide (HPMA) derivatives as a carrier to conjugate a MR contrast agent, Gd-DOTA, and a two-photon fluorophore with an aggregation-induced emission (AIE) effect, TPBP, to construct a MR/two-photon fluorescence dual-modality contrast agent, Gd-DOTA-TPBP. Incorporation of gadolinium in the hydrophilic chain segment of the OEGMA-based carrier resulted in a high r¹ value for Gd-DOTA-TPBP, revealing a great MR imaging resolution The contrast agent specifically accumulated in the tumor region, allowing a long enhancement duration for vascular and tumor contrast-enhanced MR imaging. Meanwhile, coupling TPBP with AIE properties to the hydrophobic chain segment of the carrier not only improved its water solubility and reduced its cytotoxicity, but also significantly enhanced its imaging performance in an aqueous phase. Gd-DOTA-TPBP was also demonstrated to act as an excellent fluorescence probe for two-photon-excited bioimaging with higher resolution and greater sensitivity than MRI. Since high-resolution, complementary MRI/FI dual-modal images were acquired at both cellular and tissue levels in tumor-bearing mice after application of Gd-DOTA-TPBP, it has great potential in the early phase of disease diagnosis.

Bioactive Materials 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 C14H31NO2, Computed Properties of 1353016-70-2.

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

Rao, K. V. Raghavendra published the artcileTheoretical Study, Synthesis, and Reactivity of Five-Membered-Ring Acyl Sulfonium Cations, HPLC of Formula: 162515-68-6, the publication is European Journal of Organic Chemistry (2015), 2015(28), 6125-6129, database is CAplus.

The feasibility of the cyclization of γ-alkylthiobutyric acid derivatives to form previously unknown five-membered-ring acyl sulfonium cations was studied. Exptl. results were in good agreement with our DFT calculations that predicted such cyclizations to be easy if starting with acyl iodides and mixed anhydrides of triflic acid. Particularly efficient were the reactions of γ-alkylthiobutyryl fluorides with trimethylsilyl triflate in CDCl₃ solution, which led to cyclic acyl sulfonium triflates. In some cases, the observed acyl sulfonium salts were stable enough to be characterized by NMR spectroscopy. They were found to be both alkyl-transfer reagents and acylating agents. They react with amines to form amides. These findings lend some weight to our hypothesis that the acyl sulfonium derived from methionine may have played a major role in the prebiotic synthesis of the first peptides on the primitive Earth.

European Journal of Organic Chemistry 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, HPLC of Formula: 162515-68-6.

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

Kinaci, Emre published the artcileEpoxidation of cardanol’s terminal double bond, Quality Control of 1761-71-3, the publication is Polymers (Basel, Switzerland) (2020), 12(9), 2104, database is CAplus and MEDLINE.

In this investigation, the terminal double bonds of the side chain epoxidized cardanol glycidyl ether (SCECGE) mol. were further epoxidized in the presence of Oxone (potassium peroxomonosulfate) and fluorinated acetone. Regular methods for the double bond epoxidation are not effective on the terminal double bonds because of their reduced electronegativity with respect to internal double bonds. The terminal double bond functionality of the SCECGE was epoxidized to nearly 70%, increasing the epoxy functionality of SCECGE from 2.45 to 2.65 epoxies/mol. as measured using proton magnetic nuclear resonance (¹H-NMR). This modified material-side chain epoxidized cardanol glycidyl ether with terminal epoxies (TE-SCECGE)-was thermally cured with cycloaliphatic curing agent 4,4′-methylene bis(cyclohexanamine) (PACM) at stoichiometry, and the cured polymer properties, such as glass transition temperature (T_g) and tensile modulus, were compared with SCECGE resin cured with PACM. The T_g of the material was increased from 52 to 69°C as obtained via a dynamic mech. anal. (DMA) while the tensile modulus of the material increased from 0.88 to 1.24 GPa as a result of terminal double bond epoxidation In addition to highlighting the effects of dangling side groups in an epoxy network, this modest increase in T_g and modulus could be sufficient to significantly expand the potential uses of amine-cured cardanol-based epoxies for fiber reinforced composite applications.

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 C13H26N2, Quality Control of 1761-71-3.

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

Kinaci, Emre published the artcileInfluence of epoxidized cardanol functionality and reactivity on network formation and properties, Computed Properties of 1761-71-3, the publication is Polymers (Basel, Switzerland) (2020), 12(9), 1956, database is CAplus and MEDLINE.

Cardanol is a renewable resource based on cashew nut shell liquid (CNSL), which consists of a phenol ring with a C15 long aliphatic side chain in the meta position with varying degrees of unsaturation Cardanol glycidyl ether was chem. modified to form side-chain epoxidized cardanol glycidyl ether (SCECGE) with an average epoxy functionality of 2.45 per mol. and was cured with petroleum-based epoxy hardeners, 4-4′-methylenebis(cyclohexanamine) and diethylenetriamine, and a cardanol-based amine hardener. For comparison, cardanol-based diphenol diepoxy resin, NC514 (Cardolite), and a petroleum-based epoxy resin, diglycidyl ether of bisphenol-A (DGEBA) were also evaluated. Chem. and thermomech. analyzes showed that for SCECGE resins, incomplete cure of the secondary epoxides led to reduced cross-link d., reduced thermal stability, and reduced elongation at break when compared with difunctional resins containing only primary epoxides. However, because of functionality greater than two, amine-cured SCECGE produced a T_g very similar to that of NC514 and thus could be useful in formulating epoxy with renewable cardanol content.

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 C13H26N2, Computed Properties of 1761-71-3.

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