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The bitopic ligand 1,1?-bis(dipyrazol-1-ylmethyl)ferrocene, Fe[C 5H4CH(pz)2]2 (1; pz = pyrazolyl ring), has been prepared by the reaction of 1,1?-ferrocenedicarbaldehyde and 1,1?-carbonyldipyrazole. In the solid state, the bis(pyrazolyl) methane moieties are in an antiperiplanar eclipsed orientation. The molecules are organized into a three-dimensional array by pi…pi, weak C-H-…N hydrogen bonding, and C-H…pi interactions. The reactions between 1 and AgBF4, AgPF6, AgSO3CF 3, or AgSbF6 yield {Fe[C5H 4CH(pz)2]2AgBF4}n (2), {Fe[C5H4CH(pz)2]2AgPF 6}n (3), {Fe[C5H4CH(Pz) 2]2AgSO3CF3}n (4), and {Fe[C5H4CH(pz2]2AgSbF 6}n (5), respectively. The solid-state structures consist of coordination polymers with compounds 2 and 3 arranged in helical chains, while the chains in 3·1/2Et2O, 4·1.5C6H 6,5·1/2Et2Et2O, and 5·1/2C 6H6 are nonhelical. In these structures, the ferrocenyl groups adopt a similar orientation, where the angle between CH(pz)2 groups is confined to the range of 85-99 and the silver pyrazolyl coordination spheres are also in very similar distorted-tetrahedral arrangements. Both structural types form three-dimensional supramolecular structures organized by weak hydrogen bonds, pi…pi stacking, and CH…pi interactions. In the helical form, the anions reside in the pockets formed by the close-packed chains, whereas in the nonhelical form, sizable channels, which contain the solvent molecules and the anions, are located between the chains.

Synthesis and Structural Characterization of a Bitopic Ferrocenyl-Linked Bis(pyrazolyl)methane Ligand and Its Silver(I) Coordination Polymers

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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The series of aminophosphonates bearing the 1,1? -bis-substituted ferrocenyl moiety was obtained by the addition of dialkyl phosphites to an azomethine bond of Schiff bases derived from 1,1?-ferrocene-bis-carboxaldehyde. This addition led to both diastereoisomeric forms demonstrating its behaviour to be contrary to the addition to terephthalic Schiff bases, which led exclusively to a meso -form.

First synthesis of 1,1?-ferrocene bis-aminophosphonic esters

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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A simple chromatography-free method for desymmetrizing ferrocene is described starting from the readily available dialdehyde. Oxidation of 1,1?-ferrocenedicarboxaldehyde in a water/acetonitrile mixture with KMnO4 produced 1?-formyl-ferrocenecarboxylic acid. The same reaction carried out in a water/acetone mixture produced 1?-[(E)-3-oxo- but-1-enyl]-ferrocenecarboxylic acid.

A simple method for desymmetrizing 1,1?-ferrocenedicarboxaldehyde

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Further advances in understanding the mechanism of action of resveratrol and its application require new analogs to identify the structural determinants for the cell proliferation inhibition potency. Therefore, we synthesized new trans-resveratrol derivatives by using the Wittig and Heck methods, thus modifying the hydroxylation and methoxylation patterns of the parent molecule. Moreover, we also synthesized new ferrocenylstilbene analogs by using an original protective group in the Wittig procedure. By performing cell proliferation assays we observed that the resveratrol derivatives show inhibition on the human colorectal tumor SW480 cell line. On the other hand, cell viability/cytotoxicity assays showed a weaker effects on the human hepatoblastoma HepG2 cell line. Importantly, the lack of effect on non-tumor cells (IEC18 intestinal epithelium cells) demonstrates the selectivity of these molecules for cancer cells. Here, we show that the numbers and positions of hydroxy and methoxy groups are crucial for the inhibition efficacy. In addition, the presence of at least one phenolic group is essential for the antitumoral activity. Moreover, in the series of ferrocenylstilbene analogs, the presence of a hidden phenolic function allows for a better solubilization in the cellular environment and significantly increases the antitumoral activity.

Inhibition of cancer derived cell lines proliferation by synthesized hydroxylated stilbenes and new ferrocenyl-stilbene analogs. Comparison with resveratrol

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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A series of bismacrocyclic ligands with two ferrocenyl groups, exolendo-1,1?1?1?-[l,2,4,5-tetrakis(5-aza-2-thiahexa-5-enyl) benzene]bisferrocene(exolendo-FeBeFe), 1,1?1?1?-[1,2:1?,2?-tetrakis(5-aza-2-thiahexa-5- enyl)-ethene]bisferrocene(1,2-FeEnFe), 1,1?1?1?-[1,1?:2,2?-tetrakis(5-aza-2-thiahexa-5- enyl)ethene]bisferrocene (1,1-FeEnFe), 1,1?1?1?-[tetrakis(5-aza-2-thiahexa-5-enyl)methane] bisferrocene (FeMeFe), and their dicopper(I) compounds have been synthesized and characterized (electrochemistry, IR, NMR and Moessbauer spectroscopy). The molecular structure of endo-FeBeFe has been determined by X-ray structure analysis and the copper(I)-induced discrimination of the exo- and endo-isomers of FeBeFe has been investigated by 1H NMR spectroscopy. The interaction between copper and iron in the tetranuclear compounds is discussed on the basis of the electrochemical and spectroscopic data.

Bis-macrocyclic ligands with two ferrocenyl end groups, and their tetranuclear dicopper(I) compounds

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Reference of 1271-48-3, Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction by binding to a specific portion of an enzyme and thus slowing or preventing a reaction from occurring. 1271-48-3, Name is 1,1′-Ferrocenedicarboxaldehyde, molecular weight is 242.0516. molecular formula is C12H10FeO2. In an Article,once mentioned of 1271-48-3

Unsymmetrical 1,1?-disubstituted ferrocenes bearing an amino acid moiety and a conjugated electron density controlling substituent were synthesized conveniently starting from 1,1?-ferrocenedicarbaldehyde. The novel ferrocene amino acid derivatives were completely characterized from their MS, 1H NMR and 13C NMR spectra. Their electrochemical behavior was studied by cyclic voltammetry. Their formal redox potentials Ef were slightly influenced by the nature of the amino acid and mainly by the kind of the ethenyl substituent. Furthermore all the (Z)-isomers exhibited a slight anodic shift compared with the corresponding (E)-isomers.

Synthesis, structural characterization and electrochemical study of 1,1?-ferrocenylene labeled amino acids

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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The result showed that such a combination of chemo- and biocatalysis improved the catalytic yield more than two times compared with that of sole metal catalysis. We will look forword to the important role of 1271-48-3, and how the biochemistry of the body works.Computed Properties of C12H10FeO2

The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction. Computed Properties of C12H10FeO2. In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. Introducing a new discovery about 1271-48-3, Name is 1,1′-Ferrocenedicarboxaldehyde

A family of rigid ferrocenyl-terminated redox stars has been synthesizedsby Negishi coupling, including hexa(ferrocenethynyl)benzene complexes, a dodecaferrocenyl star, and stars with extended rigid tetherssand fully characterized. Cyclic voltammetry (CV) studies of the parent complex hexa(ferrocenylethynyl) benzene, 1, show a single wave for the six-electron oxidation of 1 using Nn-Bu4PF6 as the supporting electrolyte on a Pt anode in CH2Cl2, whereas three distinct two-electron reversible CV waves are observed using Nn-Bu 4BArF4 (ArF = 3,5-C 6H3-(CF3)2,). The CV of 1,3,5-tris(ferrocenylethynyl)benzene, 11, also shows only one wave for the three-electron transfer with Nn-Bu4PF6 and three one-electron waves using Nn-Bu4BArF4. This confirms the lack of electronic communication between the ferrocenyl groups and a significant electrostatic effect among the oxidized ferrocenyl groups. This effect is not significant between paraferrocenyl groups in 1,4- bis(ferrocenylethynyl)benzene for which only a single wave is observed even with Nn-Bu4BArF4 as the supporting electrolyte. The para-ferrocenyl substituents are quite independent, which explains that two para-ferrocenyl groups are oxidized at about the same potential in a single CV wave of 1. With the additional steric bulk introduced with a methyl substituent on the ferrocenyl group, however, even the para-methylferrocenyl groups are submitted to a small electrostatic effect splitting the six-electron transfer into six single-electron waves, probably because of the overall steroelectronic constraints. Contrary to 11, 1,3-bis(ferrocenylethynyl)benzene and related complexes with a third, different substituent in the remaining meta position different from a ferrocenylethynyl only show a single two-electron wave using Nn-Bu4BArF4, which is attributed to the transoid conformation of the ferricinium groups minimizing the electrostatic effect. This shows that, in 11, it is the steric frustration that is responsible for the electrostatic effect, and the same occurs in 1. In several cases, DeltaEp is much larger than the expected 60 mV value, characterizing a quasi-reversible (i.e., relatively slow) redox process. It is suggested that this slower electron transfer be attributed to conformational rearrangement of the ferrocenyl groups toward the transoid position in the course of electron transfer. Thus both the thermodynamic and kinetic aspects of the electrostatic factor (isolated from the electronic factor), including the frustration effect, are characterized. The distinction between the electronic communication and through-space electrostatic effect was made possible in all of these complexes in which the absence of wave splitting using a strongly ion-pairing electrolyte shows the absence of significant electronic communication, and was confirmed by the new frustration phenomenon.

Ferrocenyl-terminated redox stars: Synthesis and electrostatic effects in mixed-valence stabilization

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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By means of base-catalysed condensation of 1-acyl-/1,1?- diacylferrocenes (acylformyl or acetyl) with 3-formyl- and 3,7- diacetylphenothiazines a series of novel mono- and bis-chalcones were prepared. The enhanced reactivity of the enolate anions of the mono-chalcone intermediates relative to that of the enolates of the corresponding diacetyl-substituted precursor was interpreted by the electron-releasing effect of the ferrocenyl- or phenothiazinyl group present in the beta position of the enone subunit. The structures of the novel products were evidenced by IR, 1H and 13C NMR spectroscopy including 2D-COSY, 2D-HSQC and 2D-HMBC measurements.

Structure elucidation and DFT-study on substrate-selective formation of chalcones containing ferrocene and phenothiazine units. Study on ferrocenes, Part 17

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Synthesis, structure determination and in vitro antiproliferative assay of a series of novel ferrocenenyl hydrazones containing 4-halopyridazin-3(2H)-one fragment(s) and three representative N-arylsubstituted (Sp)-ferroceno[d] pyridazinones are presented. The model compounds can be considered as different assemblies of the potential binding sites capable of establishing interactions including hydrogen bonds and pi-pi interactions with the relevant residues of biomolecules. Their in vitro antiproliferative effect was investigated against four tumorous cell lines by the 3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide (MTT)-assay. Our data indicate that bis-hydrazone of 1,1?-diformylferrocene carrying N-benzyl substituents and a chloropyridazinyl-substituted ferroceno[d]pyridazinone display significant activity on each cell lines investigated. The efficiency of the latter drug candidate and one N-benzyl mono-hydrazone on A2870 cell line is comparable to that of cisplatin. The constitution and relative configuration of the model compounds were established by 1H, 13C and 15N NMR methods. The structures of a mono- and bis-ferrocenylhydrazone containing 4-bromopyridazinone unit(s) were confirmed by single crystal X-ray diffraction.

Synthesis, spectroscopy, X-ray analysis and in vitro antiproliferative effect of ferrocenylmethylene-hydrazinylpyridazin-3(2H)-ones and related ferroceno[d]pyridazin-1(2H)-ones

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion

 

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Synthetic Route of 1271-48-3, hemistry, like all the natural sciences, begins with the direct observation of nature— in this case, of matter. In a document type is Article, molecular formula is C12H10FeO2, molecular weight is 242.0516, and a compound is mentioned, 1271-48-3, 1,1′-Ferrocenedicarboxaldehyde, introducing its new discovery.

A tetraazamacrocycle containing ferrocene moieties has been synthesized and characterized. The tetraprotonated form of this compound was evaluated as a receptor (R) for anion recognition of several substrates (S), Cl-, PF6-, HSO4-, H2PO 4- and carboxylates, such as p-nitrobenzoate (p-nbz -), phthalate (ph2-), isophthalate (iph2-) and dipicolinate (dipic2-). 1H NMR titrations in CD 3OD indicated that this receptor is not suitable for recognizing HSO4- and H2PO4-, but weakly binds p-nbz-, and strongly interacts with ph2-, dipic2-, and iph2- anions forming 1 : 2 assembled species. The largest beta2 binding constant was determined for ph 2-, followed by dipic2- and finally iph2-. The effect of the anionic substrates on the electron-transfer process of the ferrocene units of R was evaluated using cyclic voltammetry (CV) and square wave voltammetry (SWV) in methanol solution and 0.1 mol dm-3 (CH 3)4NCl as the supporting electrolyte. Titrations of the receptor were undertaken by addition of anion solutions in their tetrabutylammonium or tetramethylammonium forms. The protonated ligand exhibits a reversible voltammogram, which shifts cathodically in the presence of the substrates. The data revealed kinetic constraints in the formation of the receptor/substrate entity for dipic2-, ph2- and iph 2- anions, but not for p-nbz-. In spite of the slow kinetics of assembled species formation with the ph2- substrate, this anion provides the largest redox-response when the supramolecular entity is formed, followed by dipic2-, iph2- and finally p-nbz – anions. This trend is in agreement with the 1H NMR results and the values of the binding constants. Single crystal X-ray structures of the receptor with PF6-, ph2-, iph 2- and p-nbz- were carried out and showed that supermolecules with a RS2 stoichiometry are formed with the first three anions, but RS4 with p-nbz-. In all cases the binding occurs outside the macrocyclic cavity via N-H … O=C hydrogen bonds for carboxylate anions and N-H … F hydrogen bonds for the PF 6- anion, which is in agreement with the solution results. The macrocyclic framework adopts different conformations in order to interact with each substrate having Fe … Fe intramolecular distances ranging from 10.125(14) to 12.783(15) A. The Royal Society of Chemistry 2005.

Carboxylate anions binding and sensing by a novel tetraazamacrocycle containing ferrocene as receptort

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Reference:
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion