Catalysis-chemistry

Jilek, Jiri O. published the artcileSynthetic spasmolytics. V. Cyclic analogs of compounds of the 3,3-diphenylpropylamine series, Computed Properties of 1949-41-3, the publication is Chemicke Listy pro Vedu a Prumysl (1952), 292-6, database is CAplus.

cf. C.A. 46, 8004h. Amino ketones obtained by the Mannich reaction with 1-indanone (I), 3,4-dihydro-1(2H)-naphthalenone (II), and 6,7,8,9-tetrahydro-5H-cycloheptabenzen-5-one (III) were treated with PhMgBr (IV), and the corresponding carbinols dehydrated. Attempts to hydrogenate the olefins thus obtained resulted in hydrogenolysis. Some of the products have spasmolytic effects, lower than those of their open-chain analogs. I (17 g.), 40 g. C₅H₁₀NH.HCl (V), 3.9 g. paraformaldehyde (VI), and 100 mL. EtOH were refluxed 8 h., 1 more g. VI was added, the mixture refluxed 2 h., allowed to stand overnight, the EtOH distilled off, the residue dissolved in 300 mL. H₂O, the unreacted I extracted with C₆H₆, the aqueous layer made alk., the bases extracted with C₆H₆, the residue (21 g.) dissolved in 200 mL. ether, and 18 g. (53%) HCl salt, m. 213-15° (from EtOH-Me₂CO), of 2-(1-piperidylmethyl)-1-indanone (VII) precipitated with 10% EtOH solution of HCl. Analogously, 35.5 g. (58%) 3,4-dihydro-2-(1-piperidyl)methyl-l(2H)-naphthalenone (VIII) HCl salt, m. 228-30°, was obtained from 78 g. II (32 g. recovered unchanged), 71 g. V, and 15 + 1 g. VI. 6,7,8,9-Tetrahydro-6-(1-piperidylmethyl)-5H-cycloheptabenzen-5-one (IX) HCl salt, m. 230°, was prepared from 5.5 g. III, 4.8 g. V, and 1.1 g. VI in 37% yield. α-[2-(1-Piperidyl)-ethyl]benzhydrol, m. 109° [HCl salt, m. 238° (from EtOH)] (X), was prepared from BzCH₂CH₂NC₅H₁₀ and PhMgBr. PhMgBr (prepared from 7.8 g. Mg and 49.5 g. PhBr in 30 mL. ether) treated with 35.5 g. VIII and the mixture decomposed with 150 mL. 25% solution of NH₄Cl gave 23 g. (56%) 1,2,4-tetrahydro-1-phenyl-2-(1-piperidylmethyl)-1-naphthol (XI), b_0.5 192-6°, m. 136-7° (from 80% EtOH); HCl salt, m. 23° (decomposition) (from EtOH). 6,7,8,9-Tetrahydro-5-phenyl-6- (1-piperidylmethyl)- 5H-cyclopentabenzen-5-ol (XII), b_0.5 200-5°, m. 144-5°, HCl salt, m. 233-4° (from Me₂CO), was prepared analogously from 3.8 g. Mg, 24 g. PhBr, and 18 g. IX in a 40% yield (8.3 g.). Dehydration of X by boiling with a mixture of HCl and AcOH gave Ph₂C: CHCH₂NC₅H₁₀, b_0.3 158-78°; HCl salt, m. 210-11° (from Me₂CO). VII (29.5 g.) with PhMgBr (prepared from 6.3 g. Mg and 39 g. PhBr in 350 mL. ether) gave directly 14.7 g. (47%) 3-phenyl-2-(1-piperidylmethyl)indene, b_1.2 190-200°, m. 112.5° (from EtOH); HCl salt, m. 233-4° (from EtOH). XI (15 g.) was refluxed 48 h. with 70 mL. HCO₂H at 120-30°, then diluted with 500 mL. H₂O, neutralized with 40% NaOH to pH 5-6, and extracted with ether yielded 11.6 g. (82%) 3,4-dihydro-1-phenyl-2-(1-piperidyl)-methylnaphthalene, b_0.5 178-82°, m. 73.5° (from EtOH); HCl salt (with 1 mol EtOH), m. 188° (from Me₂CO). Similar dehydration of 6.7 g. XII with 35 mL. HCO₂H gave 6.1 g. 8,9-dihydro-5-phenyl-6-(1-piperidyl)methyl-7H-cycloheptabenzene, m. 104.5° (from EtOH); HCl salt, m. 216-18° (from EtOH). Hydrogenation of the unsaturated products was carried out in MeOH solutions over Pd-C catalysts and yielded, resp., Ph₂CHCH₂CH₂NC₅H₁₀ (XlII) (HCl salt, m. 214-16°); 1-phenyl-2-methylindan, b₁ 107-8°; 1,2,3,4-tetra-hydro-2-methyl-1-phenylnaphthalene, b_1.5140 5°, m. 52-3°; and 6,7,8,9-tetrahydro-6-methyl-5-phenyl-5H-cycloheptabenzene, b_0.6 135-8°. XIII was also prepared from NaNH₂ and Ph₂C(CN)CH₂CH₂NC₅H₁₀. 2-Methyl-1(2H)-naphthalenone (XIV), b₂₀ 143-5°, was obtained by cyclization of PhCH₂CH₂CHMeCOCl (XV), with AlCl₃ in a 78% yield. XV was obtained from PhCH₂CH₂CHMeCO₂H, b₂₀ 179-82°, prepared from PhCH₂CH₂CMe(CO₂H)₂, m. 160°, di-Et ester, b_0.4 140-2_° b₃₀ 198-202°. XIV (16 g.) was added to PhMgBr (prepared from 3.2 g. Mg and 20.9 g. PhBr in 100 mL. Et₂O), the mixture decomposed with 30 g. NH₄Cl in 60 mL. H₂O, and extracted with ether; evaporation of the solvent yielded 9 g. (38%) 1,2,3,4-tetrahydro-2-methyl-1-phenyl-1-naphthol (XVI), b_0.9 147-50°, m. 76-7° (from petr. ether). XVI (3 g.) refluxed 48 h. with HCO₂H gave 1.5 g. (54%) 3,4-dihydro-2-methyl-1-phenylnaphthalene, b_0.5 123-4°. The same product, b_0.5 130-5°, was obtained by hydrogenolysis of 3,4-dihyro-1-phenyl-2-(1-piperidylmethyl)naphthalene when the reaction was interrupted after consumption of 2 equivalents

Chemicke Listy pro Vedu a Prumysl published new progress about 1949-41-3. 1949-41-3 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene, name is 2-Methyl-4-phenylbutanoic acid, and the molecular formula is C11H14O2, Computed Properties of 1949-41-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Tan, Jin-Fay published the artcileAlkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C-H Activation-Lossen Rearrangement-Wallach Reaction, Synthetic Route of 1293990-73-4, the publication is ACS Catalysis (2020), 10(6), 3790-3796, database is CAplus.

A highly regioselective synthesis of 4-fluoro-2-pyridones using 1-alkynyl triazenes as a convenient fluoroalkyne surrogates was reported. The protocol comprises an alkenyl C-H annulation with 1-alkynyl triazenes followed by a treatment with HF·pyridine smoothly delivering a broad range of 4-fluoro-2-pyridones in a one-pot fashion in 90 min at 23-60 C. Notably, a rare Lossen rearrangement occurs during the C-H functionalization part of the transformation, allowing selective access to the less-available 4-fluoro-2-pyridone framework. Furthermore, the triazenyl intermediate was elaborated into addnl. fluorine-containing substituents like fluorinated alkoxy and trifluoromethyl groups.

ACS Catalysis published new progress about 1293990-73-4. 1293990-73-4 belongs to catalysis-chemistry, auxiliary class Aliphatic Chain, name is O-Pivaloylhydroxylamine trifluoromethanesulfonate, and the molecular formula is C12H10F2Si, Synthetic Route of 1293990-73-4.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Rahman, Taskia published the artcileSpinel Structured Copper Ferrite Nano Catalyst with Magnetic Recyclability for Oxidative Decarboxylation of Phenyl Acetic Acids, Category: catalysis-chemistry, the publication is Catalysis Letters (2020), 150(8), 2267-2272, database is CAplus.

A simple, efficient and environmentally benign method has been discussed for the synthesis of aldehydes and ketones by the oxidative decarboxylation of phenylacetic acid under ligand free condition using simple, efficient, preparatively easy, magnetically recoverable and low cost spinel CuFe₂O₄ nanoparticles. The catalyst was characterized using powder-XRD, FTIR, FE-SEM, EDX, VSM and HRTEM. The recyclability was examined and the results showed that the catalyst remained almost equally active up to five consecutive cycles. Spinel Structured Copper Ferrite is a very efficient nano catalyst for Oxidative decarboxylation of Ph acetic acids and can be reused up to five cycles without significant loss in catalytic activity.

Catalysis Letters published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Matassini, Camilla published the artcileOn the Virtue of Indium in Reduction Reactions. A Comparison of Reductions Mediated by Indium and Zinc: Is Indium Metal an Effective Catalyst for Zinc Induced Reductions?, HPLC of Formula: 4230-93-7, the publication is European Journal of Inorganic Chemistry (2020), 2020(11-12), 1106-1113, database is CAplus.

Indium(0)-mediated reductions have been reported for the transformation of several functional groups (imines, oximes, nitro groups, isoxazolidines, and conjugated alkenes, among others), prompted by the opportunity of performing the reactions in aqueous media and green conditions. We describe here the comparison of several reactions using indium or the less expensive zinc, carried out in order to evaluate the effective advantages brought about indium metal. We found some reactions for which use of In is mandatory and others where Zn worked equally well or even better. The reduction of hydroxylamines to the corresponding amines was the only reduction for which use of In provided much better results than Zn and was also possible to apply an efficient catalytic version with use of 2-5 mol-% In in the presence of stoichiometric Zn. Applicability of this catalytic reduction to “one-pot” model processes is also demonstrated.

European Journal of Inorganic Chemistry published new progress about 4230-93-7. 4230-93-7 belongs to catalysis-chemistry, auxiliary class Alkenyl,Nitro Compound,Benzene,Ether, name is 1,2-Dimethoxy-4-(2-nitrovinyl)benzene, and the molecular formula is C10H11NO4, HPLC of Formula: 4230-93-7.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Al Temimi, Abbas H. K. published the artcilePeptide-appended permethylated β-cyclodextrins with hydrophilic and hydrophobic spacers, Name: Dbco-maleimide, the publication is Bioconjugate Chemistry (2017), 28(8), 2160-2166, database is CAplus and MEDLINE.

A novel synthetic methodol., employing a combination of the strain-promoted azide-alkyne cycloaddition and maleimide-thiol reactions, for the preparation of permethylated β-cyclodextrin-linker-peptidyl conjugates is reported. Two different bifunctional maleimide crosslinking probes, the polyethylene glycol containing hydrophilic linker bicyclo[6.1.0] nonyne-maleimide and the hydrophobic 5′-dibenzoazacyclooctyne-maleimide, were attached to azide-appended permethylated β-cyclodextrin. The successfully introduced maleimide function was exploited to covalently graft a cysteine-containing peptide (Ac-Tyr-Arg-Cys-Amide) to produce the target conjugates. The final target compounds were isolated in high purity after purification by isocratic preparative reverse-phase high-performance liquid chromatog. This novel synthetic approach is expected to give access to many different cyclodextrin-linker peptides.

Bioconjugate Chemistry published new progress about 1395786-30-7. 1395786-30-7 belongs to catalysis-chemistry, auxiliary class Inhibitor, name is Dbco-maleimide, and the molecular formula is C25H21N3O4, Name: Dbco-maleimide.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Wagner, Patrick published the artcilet-BuXPhos: a highly efficient ligand for Buchwald-Hartwig coupling in water, Application In Synthesis of 1237588-12-3, the publication is Green Chemistry (2014), 16(9), 4170-4178, database is CAplus.

An efficient and versatile ‘green’ catalytic system for the Buchwald-Hartwig cross-coupling reaction in water is reported. In an aqueous micellar medium, the combination of t-BuXPhos with [(cinnamyl)PdCl]₂ showed excellent performance for coupling of aryl bromides or chlorides with a large set of amines, amides, ureas, and carbamates. The method is functional-group tolerant, proceeds smoothly (30 to 50 °C), and provides rapid access to the target compounds in good to excellent isolated yields. When applied to the synthesis of a known NaV1.8 modulator, this method led to a significant improvement of the E-factor in comparison with classical organic synthesis.

Green Chemistry published new progress about 1237588-12-3. 1237588-12-3 belongs to catalysis-chemistry, auxiliary class Mono-phosphine Ligands, name is 4-(2-(Di(adamantan-1-yl)phosphino)phenyl)morpholine, and the molecular formula is C4H6O3, Application In Synthesis of 1237588-12-3.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Pascali, Claudio published the artcileSimple preparation and purification of ethanol-free solutions of 3′-deoxy-3′-[¹⁸F]fluorothymidine by means of disposable solid-phase extraction cartridges, Computed Properties of 17351-62-1, the publication is Nuclear Medicine and Biology (2012), 39(4), 540-550, database is CAplus and MEDLINE.

3′-Deoxy-3′-[¹⁸F]fluorothymidine ([¹⁸F]FLT) shows great potential as a tracer for proliferative studies with PET. However, its regular application is often limited by low radiochem. yields and the use of a troublesome HPLC separation Moreover, a high content of ethanol, at least one-fold higher than the European Pharmacopoeia and US Pharmacopoeia’s established limit, is always present in the final product. The present study reports an optimization of the reaction conditions and a simple and straightforward purification step which affords a solution of [¹⁸F]FLT suitable for human use. Several conditions and materials were tested for both the nucleophilic substitution and purification step. The latter was achieved by means of a series of com. solid-phase extraction cartridges. Very conveniently, the whole one-pot synthesis was carried out on com. automated modules using basically the same setup employed for the synthesis of [¹⁸F]FDG. Under routine conditions, radiochem. yields of 37% [decay-corrected to start of synthesis (SOS)] were achieved in ca. 39 min from SOS, with radiochem. purities >98% (usually >99%). The negligible radiolysis observed could be easily suppressed by adding 0.5% of EtOH. Typical unlabeled chem. impurities detected were thymidine (0.15 ppm), thymine (0.28 ppm) and stavudine (0.05 ppm). A reliable, simple and efficient preparation of [¹⁸F]FLT has been developed, able to afford an ethanol-free solution of the tracer with no need for any HPLC purification Because of its similarity to the [¹⁸F]FDG synthesis, the method can be readily implemented on basically all the com. modules developed for this common radiotracer.

Nuclear Medicine and Biology published new progress about 17351-62-1. 17351-62-1 belongs to catalysis-chemistry, auxiliary class Salt,Amine, name is Tetrabutylammonium hydrogencarbonate, and the molecular formula is C17H37NO3, Computed Properties of 17351-62-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Tanwar, Lalita published the artcileSynthesis of Benzylic Alcohols by C-H Oxidation, Category: catalysis-chemistry, the publication is Journal of the American Chemical Society (2019), 141(45), 17983-17988, database is CAplus and MEDLINE.

Selective methylene C-H oxidation for the synthesis of alcs. with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcs. to ketones. Here, authors report the selective synthesis of benzylic alcs. employing bis(methanesulfonyl) peroxide as an oxidant. Authors attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. Authors envision that our method will be useful for applications in the discovery of drugs and agrochems.

Journal of the American Chemical Society published new progress about 457-68-1. 457-68-1 belongs to catalysis-chemistry, auxiliary class Fluoride,Benzene, name is Bis(4-fluorophenyl)methane, and the molecular formula is C4H5NS2, Category: catalysis-chemistry.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Chen, Qin published the artcileSynthesis and characterization of platinum(II)-thiolate complexes. Crystal and molecular structures of cis-Pt(Ph₃P)₂(SC₆H₂-2,4,6-iPr₃)Cl and cis-Pt(Ph₃P)₂(SC₆H₂-2,4,6-iPr₃)₂, COA of Formula: C15H24S, the publication is Inorganica Chimica Acta (1994), 216(1-2), 83-7, database is CAplus.

The reaction of cis-Pt(Ph₃P)₂Cl₂ with 2,4,6-triisopropylbenzenethiol (HTIPT) in benzene at 65° yields yellow crystals of cis-[Pt(Ph₃P)₂(TIPT)Cl] (1), while the reaction of cis-Pt(Ph₃P)₂Cl₂ and HTIPT in benzene at room temperature yields cis-[Pt(Ph₃P)₂(TIPT)₂] (2). In contrast to the tendency of solutions of [Pt(R₃P)₂(SR’)₂] with sterically innocent thiolates to rearrange into a complex mixture of cis and trans complexes and polynuclear materials upon exposure to air, solutions of both 1 and 2 are stable with respect to isomerization and oligomerization. Crystal data for 1·2H₂O are monoclinic space group P2₁/c, Z = 4, R = 0.074 and for 2 they are monoclinic space group P2₁/n, Z = 4, R = 0.049..

Inorganica Chimica Acta published new progress about 22693-41-0. 22693-41-0 belongs to catalysis-chemistry, auxiliary class Other Functionalization Reagent, name is 2,4,6-Triisopropylbenzenethiol, and the molecular formula is C15H24S, COA of Formula: C15H24S.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Lekkala, Chinnari published the artcileCopper-Catalyzed One-Pot Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from Arylacetic Acids and Hydrazides via Dual Oxidation, Computed Properties of 104-03-0, the publication is ACS Omega (2022), 7(31), 27157-27163, database is CAplus and MEDLINE.

A simple and efficient protocol was developed to access sym. and unsym. 2,5-disubstituted 1,3,4-oxadiazoles from arylacetic acids and hydrazides via copper-catalyzed dual oxidation under an oxygen atm. Oxidative decarboxylation of arylacetic acids and oxidative functionalization of the imine C-H bond were the key steps. This was the first example of the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles through dual oxidation in one-pot. Avoidance of the expensive ligand and high yield of the products were advantageous features of the developed method.

ACS Omega published new progress about 104-03-0. 104-03-0 belongs to catalysis-chemistry, auxiliary class Nitro Compound,Carboxylic acid,Benzene, name is 4-Nitrophenylacetic acid, and the molecular formula is C8H7NO4, Computed Properties of 104-03-0.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia