1-Phenyl-3,3-di(1H-pyrazol-1-yl)propan-1-one

Abstract

The title compound, 1-phenyl-3,3-di(1H-pyrazol-1-yl)propan-1-one, was synthesized in a 52% yield for the first time by a one-step reaction between 1H-pyrazole and 1-phenylprop-2-yn-1-one (their ratio being 2:1) in solid Al2O3 at room temperature. The product was characterized by 1H-NMR, 13C-NMR, IR spectroscopy, X-Ray diffraction and elemental analysis.

New Copper Complexes with N,O-Donor Ligands Based on Pyrazole Moieties Supported by 3-Substituted Acetylacetone Scaffolds

“…In particular, the C=O bonds (mean length of 1.199 Å) have clear double bond character and the bonds made by the C1 atom (mean length of 1.526 Å) have single-bond character. Likewise, the distribution of the average bond lengths about the pyrazolyl rings (1.356, 1.332, 1.384, 1.368 and 1.465 Å for, respectively, N1-N2, N1-C2, C2-C3, C3-C4, N2-C4 distances) matches those found in reported [107][108][109] compounds (1.366, 1.334, 1.394, 1.367, 1.357 and 1.462 Å), thus suggesting that there is not conjugation outside the ring and that N1-C2 and C3-C4 distances have the greater double-bond character. As for the above compounds, the exploration of the CCDC database reveals only one bis-triphenylphosphine copper(I) complex having some similarity with the one presented here [111].…”

“…As for the above compounds, the exploration of the CCDC database reveals only one bis-triphenylphosphine copper(I) complex having some similarity with the one presented here [111]. matches those found in reported [107][108][109] compounds (1.366, 1.334, 1.394, 1.367, 1.357 and 1.462 Å), thus suggesting that there is not conjugation outside the ring and that N1-C2 and C3-C4 distances have the greater double-bond character. As for the above compounds, the exploration of the CCDC database reveals only one bistriphenylphosphine copper(I) complex having some similarity with the one presented here [111].…”

“…In the latter, the propan-2-one chain bound to C1 is also planar and makes angles of 87.7 and 54.1 • , respectively, with the mean planes of the pyrazolyl and phenyl moieties. A comparison (Tables 2-5) of the selected structural parameters in the common fragments of the three molecules indicate that the distribution of the bond lengths in the pyrazolyl rings and in the 2,4-pentanedione/propan-2-one chains is comparable, and it is also comparable with those reported for the few molecules [106][107][108][109] sharing some similarities with the compounds described here. In particular, the C=O bonds (mean length of 1.199 Å) have clear double bond character and the bonds made by the C1 atom (mean length of 1.526 Å) have single-bond character.…”

“…An examination of the CCDC repository [104,105] shows that the above fragment has not yet been documented, so, to the best of our knowledge, these molecules and complex 3 below are the first examples of structures containing this rather unusual synthon, while only few compounds show only some degree of similarity with those described here. Among these, ethyl N-(2-acetyl-3-oxo-1-phenylbutyl)carbamate [106] incorporates the 3-phenylmethyl-2,4-pentanedione moiety bound to a sp 2 nitrogen that is also present in the 1 and 2 ligands, while few [107][108][109] bis-pyrazolyl derivatives show the pyrazole ring bound to a short alkyl-carbonyl chain. 1, 2 and 8 are optically active molecules, because the C1 atom of all compounds shows four different substituent groups.…”