4475-42-7

Usage

InChI:InChI=1/C28H36N4/c1-25(2)17-9-11-19(29-17)26(3,4)21-13-15-23(31-21)28(7,8)24-16-14-22(32-24)27(5,6)20-12-10-18(25)30-20/h9-16,29-32H,1-8H3

Upstream product

• 109-97-7 pyrrole 
• 108-94-1 cyclohexanone 
• 67-64-1 acetone 
• 75-75-2 methanesulfonic acid 
• 99840-54-7 5,5'-dimethyldipyrromethane 

Downstream Products

• 1003-90-3 2,3,4,5-tetramethylpyrrole 
• 541-59-3 maleiimide 
• 7696-51-7 2-isopropylpyrrole 
• 109-97-7 pyrrole 
• 1082760-87-9 C₇H₅O₂^(1-)*C₁₆H₃₆N⁽¹⁺⁾*C₂₈H₃₆N₄ 
• 1404118-54-2 C₃₇H₄₅N₅O 
• 1404118-55-3 C₄₆H₅₄N₆O₂ 

Relevant academic research and scientific papers

Rhodium-calix[4]pyrrole and rhodium-tetraphenyl porphyrin: preparation, surface grafting and their catalytic application in nitro-benzene reduction

Rhodium containing macromolecules calix[4]pyrrole (RhCP) and tetraphenyl porphyrin (RhTPP) were prepared and grafted on the surface of functionalised molecular sieve materials. 1H and 13C NMR, CHNS and mass spectral analyses were used for the structural elucidation of homogeneous organometallic complexes.1H NMR and CHNS analyses confirm the formation of calix[4]pyrrole (CP) and tetraphenyl porphyrin (TPP). The introduction of rhodium ions into the macromolecule is well evident from the disappearance of the 1H NMR signal characteristic of N-H proton (7.1 ppm in CP and ?2.74 ppm in TPP). Furthermore the formation of RhCP and RhTPP complexes is confirmed using CHNS and mass spectral analysis; the data are in line with theoretically calculated values. The grafting of RhCP and RhTPP on a diamino functionalised SBA-15 support was confirmed through low angle XRD, 13C MAS-NMR and SEM-EDAX analysis. Both homogeneous and heterogeneous catalysts were utilized for nitrobenzene reduction. RhCP and RhTPP heterogenized on SBA-15-F showed complete conversion of nitrobenzene with exclusive formation of aniline as a product. The catalytic activities were retained in both the systems even after several runs.

Calix[4]pyrrole Hydridosilicate: The Elusive Planar Tetracoordinate Silicon Imparts Striking Stability to Its Anionic Silicon Hydride

Anionic hydridosilicates are highly reactive and strong hydride donors. In contrast, calix[4]pyrrole hydridosilicate is an entirely water-stable, anionic silicon hydride, which does not show hydridic reactivity. However, it still acts as an electron donor and enables the detection of a single electron transfer process in the reduction chemistry with hydridosilicates. Most important, these unusual properties are imparted by the unique planar structure of its elusive parent neutral silane-substantiating the effect of planar tetracoordinate silicon for the first time.

Synthesis, structure, and complexation properties of partially and completely reduced meso-octamethylporphyrinogens (calix[4]pyrroles)

(Figure Presented) New tricks for an old dog: Calixpyrroles bind anions efficiently and can be transformed into transition-metal complexes only under forcing conditions. Reducing the macrocycle creates a ligand that easily forms classical Werner complexes with copper, nickel, and palladium ions. The metal complexes present an array of four directed hydrogen bonds, which specifically bind the counterions (see picture; blue N, white H, green Cl, red Cu, Ni, or Pd).

The first direct synthesis of β-unsubstituted meso-decamethylcalix[5] pyrrole

The first direct synthesis of ss-unsubstituted meso-decamethylcalix[5] pyrrole from pyrrole and acetone, with moderate yield, is described. The results showed that a bismuth salt was necessary to obtain calix[5]pyrrole, with the best results obtained usingBi(NO3)3.

Synthesis and anion binding properties of the smallest meso-expanded calix[4]pyrrole

Abstract: The smallest core expanded calix[4]pyrrole derivative (5) was synthesized via incorporation of an additional sp3meso-carbon at the periphery of the macrocycle. Anion binding study of the macrocycle reveals clearly the effect of core s

Synthesis of a new calix[n]pyrrole: Meso-pentaspirocyclohexyl calix[5]pyrrole

We describe the first synthesis of the novel meso-pentaspirocyclohexyl calix[5]pyrrole 2b. Anion-guest properties of the new compound were evaluated with respect to fluoride, chloride, and bromide tetrabutylammonium salts by 1H NMR titration techniques in deuterated dichloromethane at 22 °C by following the induced shifts in the NH resonances upon complexation.

Calix[4]pyrrole: A new ion-pair receptor as demonstrated by liquid-liquid extraction

Solvent-extraction studies provide confirming evidence that meso-octamethylcalix[4]pyrrole acts as an ion-pair receptor for cesium chloride and cesium bromide in nitrobenzene solution. The stoichiometry of the interaction under extraction conditions from water to nitrobenzene was determined from plots of the cesium distribution ratios vs cesium salt and receptor concentration, indicating the formation of an ion-paired 1:1:1 cesium:calix[4]pyrrole:halide complex. The extraction results were modeled to evaluate the equilibria inherent to the solvent-extraction system, with either chloride or bromide. The binding energy between the halide anion and the calix[4]pyrrole was found to be about 7 kJ/mol larger for cesium chloride than for the cesium bromide. The ion-pairing free energies between the calix[4]pyrrole-halide complex and the cesium cation are nearly the same within experimental uncertainty for either halide, consistent with a structural model in which the Cs+ cation resides in the calix bowl. These results are unexpected since nitrobenzene is a polar solvent that generally leads to dissociated complexes in the organic phase when used as a diluent in extraction studies of univalent ions. Control studies involving nitrate revealed no evidence of ion pairing for CsNO3 under conditions identical to those where it is observed for CsCl and CsBr.

Calix[3]pyrrole: A Missing Link in Porphyrin-Related Chemistry

A long-standing question in porphyrin chemistry is why pyrrole monomers selectively form tetrapyrrolic macrocycles, whereas the corresponding tripyrrolic macrocycles are never observed. Calix[3]pyrrole, a tripyrrolic porphyrinogen-like macrocycle bearing three sp3-carbon linkages, is a missing link molecule that might hold the key to this enigma; however, it has remained elusive. Here we report the synthesis and strain-induced transformations of calix[3]pyrrole and its furan analogue, calix[3]furan. These macrocycles are readily accessed from cyclic oligoketones. Crystallographic and theoretical analyses reveal that these three-subunit systems possess the largest strain energy among known calix[n]-type macrocycles. The ring-strain triggers transformation of calix[3]pyrrole into first calix[6]pyrrole and then calix[4]pyrrole under porphyrin cyclization conditions. The present results help explain the absence of naturally occurring three-pyrrole macrocycles and the fact that they are not observed as products or intermediate during classic porphyrin syntheses.

The elusive β-unsubstituted calix[5]pyrrole finally captured

Themeso-decamethyl-calix[5]pyrrole2bwassynthesizedfromthefuran- basedanalogue1bviathehomologationofthefuranringstopyrrole,anditssolid- statestructurewasdeterminedbyX-raycrystallography:surprisingly, thebindingconstantof2btowardchlorideisfoundtobelowerthan

Dioxygen Activation and Pyrrole α-Cleavage with Calix[4]pyrrolato Aluminates: Enzyme Model by Structural Constraint

The present work describes the reaction of triplet dioxygen with the porphyrinogenic calix[4]pyrrolato aluminates to alkylperoxido aluminates in high selectivity. Multiconfigurational quantum chemical computations disclose the mechanism for this spin-forb