Month: April 2022

Application of 894086-00-1. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 5-(di-tert-Butylphosphino)-1′,3′,5′-triphenyl-1’H-1,4′-bipyrazole, is researched, Molecular C32H35N4P, CAS is 894086-00-1, about Univariate classification of phosphine ligation state and reactivity in cross-coupling catalysis.

Minimal buried volume of the phosphine ligands was correlated with the stoichiometry of nickel and palladium complexes and catalytic activity in Suzuki, Heck and Buchwald amination reactions. Chemists often use statistical anal. of reaction data with mol. descriptors to identify structure-reactivity relationships, which can enable prediction and mechanistic understanding. In this study, we developed a broadly applicable and quant. classification workflow that identifies reactivity cliffs in 11 Ni- and Pd-catalyzed cross-coupling datasets using monodentate phosphine ligands. A distinctive ligand steric descriptor, min. percent buried volume [%Vbur (min)], is found to divide these datasets into active and inactive regions at a similar threshold value. Organometallic studies demonstrate that this threshold corresponds to the binary outcome of bisligated vs. monoligated metal and that %Vbur (min) is a phys. meaningful and predictive representation of ligand structure in catalysis.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Spiroazetidine-piperidine bromoindane as a key modular template to access a variety of compounds via C-C and C-N bond-forming reactions, published in 2012-11-21, which mentions a compound: 894086-00-1, mainly applied to palladium catalyst borylation Suzuki coupling spiroazetidine piperidine bromoindan, Electric Literature of C32H35N4P.

In the context of our ghrelin inverse agonist program, a functionalized bromoindane I provided a versatile intermediate for structure-activity relationship studies. After developing operationally simple cross-coupling reactions, a broad spectrum of chem. space was successfully explored. Optimization of a one-pot borylation/Suzuki sequence provided the desired products in high yield with low loading of the palladium catalyst. High yields of N-linked heterocyclic analogs were obtained through palladium catalyzed C-N bond formation. In addition, carboxylation of the bromoindane provided an indane carboxylic acid for further diversification.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 1H-Pyrazole-5-carbaldehyde( cas:948552-36-1 ) is researched.Safety of 1H-Pyrazole-5-carbaldehyde.Matyuska, Ferenc; May, Nora V.; Benyei, Attila; Gajda, Tamas published the article 《Control of structure, stability and catechol oxidase activity of copper(II) complexes by the denticity of tripodal platforms》 about this compound( cas:948552-36-1 ) in New Journal of Chemistry. Keywords: copper pyrazolylmethylaminoethylamine complex preparation ESR formation constant; crystal structure copper pyrazolylmethylaminoethylamine. Let’s learn more about this compound (cas:948552-36-1).

Copper(II) complexes of a new polydentate tripodal ligand trenpyz (L, tris[2-(5-pyrazolylmethyl)aminoethyl]amine) were characterized in both solution and solid states. A combined evaluation of potentiometric UV-Vis and EPR data provided both thermodn. and structural information on the complexes formed in solution In equimolar solution the highly stable square pyramidal CuHL and trigonal bipyramidal CuL are the dominant species at around pH 3 and 5-8, resp. Above pH 8 further deprotonation was observed (pK = 9.56), which is related to the formation of a copper(II)-bound pyrazolate anion. This creates the possibility for the formation of oligonuclear complexes, through pyrazolate bridges, and at a 3/2 Cu(II)/L ratio three trinuclear complexes were identified, similar to the copper(II)-tachpyz (N,N’,N”-tris(5-pyrazolylmethyl)-1,3,5-cis,cis-triamino-cyclohexane) system studied earlier. The trinuclear complexes of the two ligands have considerably different speciations, due to the different denticities of tripodal platforms. At the optimal pH the catechol oxidase activities of the triply deprotonated trinuclear complexes of trenpyz and tachpyz are similar, but the pH-rate constant profiles are significantly different, as a consequence of the deviations in their speciation. Consequently, the H2dtbc oxidation promoted by these trinuclear complexes can be easily controlled by the denticity of the tripodal ligands, since it affects the coordination environment of the central metal ion, which is proposed to be the main actor during the reaction.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2,4-Dimethyl-1H-pyrrole, is researched, Molecular C6H9N, CAS is 625-82-1, about A BODIPY-based fluorescent sensor for the detection of Pt2+ and Pt drugs.HPLC of Formula: 625-82-1.

A boron-dipyrromethene (BODIPY) -based fluorescent sensor PS with an NO4S2 podand ligand was studied for the selective detection of Pt2+ over 21 cations as well as selected platinum drugs in aqueous medium. The platinum sensor PS shows 28-fold, 22-fold and 14-fold fluorescence turn-on enhancements to Pt2+, cisplatin and nedaplatin, and was thereby employed to detect platinum drugs in A-549 human lung cancer cells.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 1H-Pyrazole-5-carbaldehyde, is researched, Molecular C4H4N2O, CAS is 948552-36-1, about Improving iodine adsorption performance of porous organic polymers by rational decoration with nitrogen heterocycle.Formula: C4H4N2O.

Four kinds of porous aminal-linked organic polymers (PAOPs) were synthesized via one-step condensation between cheap melamine and resp. aldehydes decorated with different nitrogen heterocycle, to evaluate the influence of nitrogen heterocycle on the adsorption performance of target polymer toward iodine. Though having the smallest surface area of 209.9 m2/g, PAOP-4 decorated with pyridine group exhibits an adsorption capacity of 108 wt% (iodine/adsorbent weight%), surpassing other three PAOPs with Brunauer-Emmett-Teller area varying from 305.8 to 533.0 m2/g. Based on Raman spectral analyses, the characteristic band of I3- and I5- was used to evaluate the electronic interaction between iodine and the nitrogen heterocycle, giving an order of pyridine > tetrazole > pyrazole > imidazole. This manifests the vital role of chem. interaction playing in the iodine adsorption by PAOP-4, which is much helpful for designing high-performance organic adsorbent toward iodine.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Palladium(II) acetate, is researched, Molecular C4H6O4Pd, CAS is 3375-31-3, about The role of hydrogen bronzes in the hydrogenation of polyfunctional reagents: cinnamaldehyde, furfural and 5-hydroxymethylfurfural over Pd/HxWO3 and Pd/HxMoO3 catalysts, the main research direction is cinnamaldehyde hydroxymethyl furfural hydrogen bronze hydrogenation palladium catalyst.Computed Properties of C4H6O4Pd.

Differences in the activity of Pd/WO3 and Pd/MoO3 (Pd loading 0.4-4 weight%) catalysts in competitive hydrogenations of the C=C and C=O groups in polyfunctional reagents have been studied as a function of two effects: (1) the in situ formation of hydrogen bronzes, HxWO3 and HxMoO3, and (2) the electronic interaction between the supports and the metallic Pd. The cinnamaldehyde (CAL), furfural (FU) and 5-hydroxymethylfurfural (HMF) were hydrogenated under mild reaction conditions. The formation of hydrogen bronzes in Pd/WO3 and phys. mixture of Pd/WO3 with supporting WO3 oxide upon exposure to H2 was also studied using the gas flow-through microcalorimetry. In both Pd/MoO3 and Pd/WO3 catalysts, the electronic interactions contributed to the promotion of selectivity toward the C=O hydrogenation in CAL and FU, yet in Pd/MoO3 this effect was much more pronounced. On the other hand, apart from increasing the overall reaction rate, the formation of hydrogen bronzes remarkably enhances the C=C hydrogenation in CAL, as well as the decarbonylation of FU to furan and hydrogenolysis of C-OH in HMF to 5-methylfurfural. The bronze effects are significantly stronger in HxWO3, compared to HxMoO3, which may be related to higher H-species mobility and weaker H-bonding in the W-O-H (54 kJ/mol H2) than in the Mo-O-H (100 kJ/mol H2). This may also explain very high tendency of Pd/WO3 to furan ring hydrogenation in FU and HMF as well as almost selective (>98%) hydrogenation of furfuryl alc. to tetrahydrofurfuryl alc.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C32H35N4P. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: 5-(di-tert-Butylphosphino)-1′,3′,5′-triphenyl-1’H-1,4′-bipyrazole, is researched, Molecular C32H35N4P, CAS is 894086-00-1, about Palladium-Catalyzed Coupling of Hydroxylamines with Aryl Bromides, Chlorides, and Iodides. Author is Porzelle, Achim; Woodrow, Michael D.; Tomkinson, Nicholas C. O..

The bis-pyrazole phosphine ligand BippyPhos is effective for the palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides, chlorides, and iodides. Reactions proceed smoothly at 80 °C in toluene in the presence of Cs2CO3 to give synthetically versatile N-arylhydroxylamine products in good to excellent yield.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthetic Route of C8H17BrO. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 8-Bromooctan-1-ol, is researched, Molecular C8H17BrO, CAS is 50816-19-8, about Synthesis of N-Aryl- and N-alkyl-Substituted Imidazolium Silver Complexes: Cytotoxic Screening by Using Human Cell Lines Modelling Acute Myeloid Leukaemia. Author is Alme, Eirin; Toernroos, Karl Wilhelm; Gjertsen, Bjoern Tore; Bjoersvik, Hans-Rene.

A series of N-aryl- and N-alkyl substituted imidazoles has been synthesized and complexed with Ag+ to obtain silver-NHC complexes of the form [Ag(NHC)2]X. These silver-NHC complexes were tested in vitro against the human cell lines HL-60 and MOLM-13, which both model acute myeloid leukemia (AML). A substantial difference in cytotoxicity was revealed varying in the range 13-4 μM and 22-9 μM for HL-60 and MOLM-13, resp. Furthermore, this study revealed that when an alkyl group is installed on the imidazole scaffold, its position substantially influences the cytotoxicity of the corresponding silver NHC complex.

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Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Syntheses in the heterocyclic series. IV. Syntheses of heterocyclic aldehydes. 4-Pyrimidinecarboxaldehyde》. Authors are Bredereck, Hellmut; Sell, Ruediger; Effenberger, Franz.The article about the compound:1H-Pyrazole-5-carbaldehydecas:948552-36-1,SMILESS:O=CC1=CC=NN1).Safety of 1H-Pyrazole-5-carbaldehyde. Through the article, more information about this compound (cas:948552-36-1) is conveyed.

cf. CA 59, 10054b. A series of heterocyclic aldehyde acetals and aldehydes was prepared from the appropriate bifunctional compounds with an aldehyde acetal group. Me2NCH:CHCOCH(OEt)2 (I) and HN:CHNH2.AcOH (II) yielded 4-pyrimidinecarboxaldehyde di-Et acetal (III) and from this the free 4-pyrimidinecarboxaldehyde (IV). AcCH2COCH(OEt)2 (V), b10 101-3°, b0.001 48-50°, was prepared in 65% yield by the method of Panizzi (CA 38, 35003). AcCH(OAc)CH(OMe)2 (8.0 g.), b10 98-104°, in 50 cc. absolute MeOH refluxed 45 min. with 2 cc. 2% NaOMeMeOH yielded 5.0 g. AcCH(OH)CH(OMe)2 (VI), b8 87°, n20D 1.4302. AcCH(OMe)2 (29.2 g.) and 29.4 g. Me2NCH(OEt)2 heated 20 h. at 80° gave 32 g. I, b0.001 115-20°, n20D 1.5210, m. 25-30°. N2H4.H2SO4 (16.3 g.) in 100 cc. 10% aqueous NaOH treated dropwise at ∼15° with stirring with 23.5 g. V and the mixture stirred 1 h. at 15° yielded 20.5 g. (crude) 5(3)-methylpyrazole-3(5)-carboxaldehyde di-Et acetal (VII), b0.001 94-6°, n20D 1.4744. VII (4.0 g.), 0.85 cc. concentrated HCl, and 31 cc. H2O kept 10 h. at room temperature yielded 2.25 g. 5(3)-methylpyrazole-3(5)-carboxaldehyde (VIII), m. 188-9° (decomposition); oxime m. 171° (H2O); semicarbazone m. 193-8° (decomposition) (H2O); phenylhydrazone m. 184° (50% aqueous EtOH). VIII (0.5 g.) in 50 cc. concentrated NH4OH yielded during 3 days 0.4 g. 3(5)-methyl-5(3)-aminomethylenepyrazole, decomposed 170-3°. VIII (1.1 g.) and 2 cc. dry piperidine heated 3 h. at 80-90° gave 1.15 g. 3(5)-methyl-5(3)-piperidinomethylenepyrazole, m. 228-9° (decomposition). VIII (0.5 g.) in 30 cc. N2H4.H2O kept 3 days gave 0.3 g. 5(3)-methylpyrazole-3(5)-aldehyde azine, pale yellow. N2H4.H2SO4 (6.5 g.) in 40 cc. 10% aqueous NaOH treated dropwise with stirring at room temperature with 10 g. I, and the mixture stirred 2 h. and kept overnight gave 7.1 g. pyrazole-3-carboxaldehyde di-Et acetal (IX), b0.001 86°, n20D 1.4746; phenylhydrazone m. 199-201°. IX (4.0 g.) in 1% HCl kept several hrs. at room temperature gave 1.8 g. pyrazole-3-carboxaldehyde, m. 146-7° (H2O). HN:C(NH2)2 carbonate (3.1 g.) in 1 cc. concentrated H2SO4 and 5 cc. H2O treated with 5.67 g. Ba(OH)2 in 50 cc. H2O, the mixture filtered, concentrated to 10 cc., and treated 3 days with 5.0 g. VI, and the crude product (5.5 g.) treated in MeOH with picric acid in MeOH gave 5.5 g. (crude) picrate of 2-amino-4(5)-methylimidazole-5(4)-carboxaldehyde di-Me acetal (X), m. 229-30° (MeOH). VI (7.4 g.), 6.3 g. MeSC(:NH)NH2.HCl (XI.HCl), and 25 cc. absolute EtOH treated during 1 h. at room temperature with 1.15 g. Na in 25 cc. absolute EtOH, kept 3 days, and the oily product (2.0 g.) treated with saturated picric acid in MeOH gave 0.1 g. picrate, decomposed 163-5°, of the 2-MeS analog of X. VI (7.4 g.) and 7.8g. PhC(:NH)NH2.HCl gave 3.7 g. (crude) 2-Ph analog of X, m. 144-5° (AcOBu); picrate m. 239-40° (decomposition) (MeOH). V (75.2 g.), 72.4 g. XI, and 160 cc. H2O treated dropwise with stirring at room temperature during 0.5 h. with 29.2 g. KOH in 40 cc. H2O gave 49 g. di-Et acetal (XII) of 2-methylthio-6-methyl-4-pyrimidinecarboxaldehyde (XIII), yellowish oil, b0.001, 100-3°, n20D 1.5229; oxime m. 218-19° (decomposition)(EtOH); semicarbazone, light yellow, m. 215-20° (EtOH); phenylhydrazone, yellow, m. 182° (EtOH). XII (10.0 g.), 100 cc. 50% EtOH, and 1 cc. concentrated HCl refluxed 1 h. gave 5.7 g. XIII, m. 87° (petr. ether), b0.001 93-7°. XII (22.4 g.) in 400 cc. EtOH refluxed 2 h. with ∼100 g. Raney Ni gave 11.8 g. di-Et acetal (XIV) of 6-methylpyrimidine-4-carboxaldehyde (XV), b0.001 61-5°, n20D 1.4655; oxime m. 150° (H2O); semicarbazone m. 217° (EtOH); phenylhydrazone, yellow, m. 120-1° (50% EtOH). XIV (50 g.) in 50 cc. 50% EtOH and 0.5 cc. concentrated HCl refluxed 1 h. gave 3.4 g. XV, m. 53° (petr. ether). V (19 g.), 18.8 g. MeC(:NH)NH2.HCl, and 42 g. K2CO2 in 150 cc. H2O kept 3 days yielded 9.9 g. 2,6-dimethylpyrimidine-4-carboxaldehyde di-Et acetal (XVI), b0.001 50-9°, n20D 1.4712-1.4737; oxime m. 213° (1:3 EtOH-H2O). I (15 g.) and 15.6 g. PhC(:NH)NH2.HCl in 40 cc. H2O treated dropwise with stirring at 30° with 5.6 g. KOH in 20 cc. H2O and kept 2 days yielded 5.0 g. 2-Ph analog of XVI, viscous, yellow oil, b0.001 110-19°; oxime m. 165-6°(50% EtOH). I (20.5 g.), 18.3 g. XI, and 60 cc. H2O treated dropwise during 0.5 h. at room temperature with 7.3 g. KOH in 25 cc. H2O, stirred 1 h. at 50°, and kept several days yielded 14.3 g. pale yellow di-Et acetal (XVII) of 2-methylthiopyrimidine-4-carboxaldehyde (XVIII), b0.001, 112-16°, n20D 1.5190; oxime m. 165° (50% EtOH); semicarbazone, yellowish, m. 224° (50% EtOH); phenylhydrazone, yellow, m. 192-4° (EtOH). XVII (6.0 g.) in 60 cc. 50% EtOH refluxed 40 min. with 0.9 cc. concentrated HCl gave 2.8 g. XVIII, m. 68° (petr. ether), b0.001 110-12°. I (31.2 g.) and 40.2 g. II heated 2.5 h. at 115° gave 27 g. III, b0.001 63-5°, n20D 1.4683. XVII (20 g.) in 400 cc. EtOH refluxed 2 h. with ∼90 g. Raney Ni gave 5.7 g. III, b0.001 65-7°, n20D 1.4683. III gave in air III.H2O, m. 93° (sublimed at 70-80°/8 mm.); oxime m. 153-4°; semicarbazone m. 212° (decomposition); phenylhydrazone, yellow, m. 168-9° (50% EtOH). I (15 g.), 10.8 g. MeC(:NH)NH2.HCl, and 20 cc. absolute EtOH treated with stirring at 40° with 2.6 g. Na in 40 cc. EtOH, and the mixture stirred 2 h. at 40° and refluxed 15 min. gave 10.8 g. 2-Me derivative (XIX) of III, b7 104°, n20D 1.4719, phenylhydrazone m. 172° (50% EtOH). XIX (5.8 g.), 80 cc. H2O, and 0.35 cc. concentrated H2SO4 heated 3 h. at 60° and 1 h. at 70° yielded 5.5 g. 2-Me derivative of IV.H2O, m. 66° (sublimed in vacuo at 30°). PhC(:NH)NH2.HCl (15.5 g.), 20 g. I, and 20 cc. absolute EtOH treated dropwise at room temperature with 2.3 g. Na in 60 cc. absolute EtOH, and the mixture stirred 1 h. and kept overnight gave 15.7 g. 2-Ph derivative (XX) of III, b0.002 123°, n20D 1.5506; oxime m. 138°; phenylhydrazone m. 211° (EtOH). XX (5.2 g.), 30 cc. 50% EtOH, and 0.45 g. concentrated HCl refluxed 40 min. yielded 1.2 g. 2-Ph derivative of IV, m. 118° (cyclohexane). I (8.6 g.), 2.6 g. urea, and 0.99 g. Na in 40 cc. absolute EtOH refluxed 6 h. gave 1.4 g. 2-OH derivative of III, m. 143-4° (EtOH). HN:C(NH2)2 carbonate (1.12 g.) in the min. amount 1:5 H2SO4-H2O, treated with aqueous Ba(OH)2, filtered, concentrated to 10 cc., and treated 24 h. with 2.5 g. I yielded 0.80 g. 2-NH2 derivative of III, m. 137-8° (EtOH). IV (1.0 g.) in 5 cc. absolute EtOH treated with a few drops aqueous KCN yielded 0.60 g. pyrimidoin, orange-yellow, decomposed ∼239° (1:1 EtOH-Me2SO).

After consulting a lot of data, we found that this compound(948552-36-1)Safety of 1H-Pyrazole-5-carbaldehyde can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Category: pyridine-derivatives. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 8-Bromooctan-1-ol, is researched, Molecular C8H17BrO, CAS is 50816-19-8, about Synthesis and glycosidase inhibition of N-substituted derivatives of 1,4-dideoxy-1,4-imino-D-mannitol (DIM). Author is Yang, Lin-Feng; Shimadate, Yuna; Kato, Atsushi; Li, Yi-Xian; Jia, Yue-Mei; Fleet, George W. J.; Yu, Chu-Yi.

N-Substituted derivatives of 1,4-dideoxy-1,4-imino-D-mannitol (DIM), the pyrrolidine core of swainsonine, have been synthesized efficiently and stereoselectively from D-mannose with 2,3:5,6-di-O-isopropylidene DIM I as a key intermediate. These N-substituted derivatives include N-alkylated, N-alkenylated, N-hydroxyalkylated and N-aralkylated DIMs with the carbon number of the alkyl chain ranging from one to nine. The obtained 33 N-substituted DIM derivatives were assayed against various glycosidases, which allowed a systematic evaluation of their glycosidase inhibition profiles. Though N-substitution of DIM decreased their α-mannosidase inhibitory activities, some of the derivatives showed significant inhibition of other glycosidases.

After consulting a lot of data, we found that this compound(50816-19-8)Category: pyridine-derivatives can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem