7298-89-7Relevant academic research and scientific papers
Crystal, spectral characterization, molecular docking, Hirshfeld computational studies and 3D-energy framework analysis of a novel puckered compound (C14H15Cl O): 2-Chloro-3-phenyl-5,5-dimethylcyclohex-2-en-1-one
Ganesha, D. P.,Hariprasad, S.,Jeevan Chakravarthy, A. S.,Lakshminarayana, B. N.,Sreenatha, N. R.,Suchithra, B.
, (2020)
A novel compound, 2-chloro-3-phenyl-5,5-dimethylcyclohex-2-en-1-one, was synthesized and characterized by FT-IR, GC-Mass spectroscopy and NMR techniques. The single crystal XRD data of the compound, obtained by slow evaporation technique, revealed that the compound crystallized in a monoclinic lattice system, with the space group P21/n . Its asymmetric unit comprises of two molecules A and B, both adopting a non-planar structure. The Cg1A and Cg1B rings are puckered and adopt nearly envelope E1 and E1 conformations in A and B, respectively. The anionic and cationic entities in the crystal are interconnected by very weak intermolecular C–H?O interactions. The three dimensional Hirshfeld surfaces and associated two dimensional fingerprint plots have been performed to gain insight into these interactions. The interaction energies play a major role in the supramolecular architecture of molecular units in a crystal. These were calculated and analyzed using the energy density wave function of B3LYP/6-31G(d,p), which revealed the domination of dispersion energies over classical electrostatic energy frameworks. In addition, molecular docking studies were performed over several proteins out of which good binding results were observed for secreted aspartic protease from Candida albicans and nicotinic acetyl choline receptor.
Structural characterization, computational, charge density studies of 2-chloro-3-(2’-methoxy)-5,5-dimethyl-2-cyclohexenone
Hariprasad, S.,Jeevan Chakravarthy, A. S.,Lakshminarayana, B. N.,Sreenatha, N. R.
, (2021)
The title compound (C15H17ClO2), was crystallized in monoclinic system with P21/c space group. The Cg1 ring in the compound was puckered and displayed a half-chair conformation. In the crystalline solid of title compound the molecules are held together through cationic and anionic synthons of the type C-H…O. The qualitative evaluation of these interactions were performed by Hirshfeld and its related fingerprint plots. The propensity of the crystal packing was determined by enrichment ratios. Three dimensional architecture of the crystal packing was stabilized by interaction energies hence, it was carried out by using the accurate energy density model of B3LYP/6-311G(d,p). The electron density ρ(r) studies was also carried out to describe the nature of chemical bonding between the critical bond points. Laplacian of the electron densities ?2ρ(r) were calculated to identify the points where the charges are appearing to be concentrated in the title compound.
Chemistry of diazocarbonyl compounds: XX. Chemoselective O-alkylation of 3(2H)-oxoisothiazole-1,1-dioxides
Schulze,Nikolaev,Hennig,Rodina,Sieler,Nikolaev
, p. 740 - 746 (2004)
Catalytic decomposition of diazoacetylacetone, ethyl diazoacetate, and diethyl diazomalonate effected by dirhodium tetraacetate in the presence of 3(2H)-oxoisothiazole-1,1-dioxides resulted in O-alkylation of amide carbonyl of the heterocycle affording th
Synthesis of some novel chloro-/aryl-substituted-5,5-dimethyl-2-cyclohexenones
HariPrasad, S.,Jeevan Chakravarthy, A. S.,Pavan, K. P.,Venkatesh, G. B.
, (2020/02/15)
Two novel structural isomers: the dihalo-5,5-dimethyl-2-cyclohexenones were synthesized. Regioselective Suzuki-Miyaura cross coupling reaction of the isomers with nine different aryl boronic acids afforded eighteen novel compounds: the 2-aryl-3-chloro-5,5-dimethyl-2-cyclohexenones and the 3-aryl-2-chloro-5,5-dimethyl-2-cyclohexenones in 90–95% yields, which were characterized spectroscopically by IR, NMR and MS. The single crystal X-Ray diffraction ORTEP views of four representative compounds unambiguously confirm the formation of substituted cyclohexenones.
A green approach for efficient α-halogenation of β-dicarbonyl compounds and cyclic ketones using N-halosuccinimides in ionic liquids
Meshram,Reddy,Vishnu,Sadashiv,Yadav
, p. 991 - 995 (2007/10/03)
Room temperature ionic liquids (ILs) are used as a green recyclable reaction media for the α-monohalogenation of 1,3-diketones, β-keto-esters and cyclic ketones with N-halosuccinimides in excellent yields in the absence of a catalyst. The recovered ionic liquid was reused five to six times with consistent activity.
New Enzyme Models of Chloroperoxidase: Improved Stability and Catalytic Efficiency of Iron Porphyrinates Containing a Thiolato Ligand
Wagenknecht, Hans-Achim,Claude, Cécile,Woggon, Wolf-Dietrich
, p. 1506 - 1520 (2007/10/03)
The heme-thiolate protein chloroperoxidase (CPO) catalyzes the chlorination of activated C-H bonds. A reaction mechanism is proposed for this enzymatic transformation (Scheme 1), and a new iron(III) porphyrinate complex 13 is synthesized containing pentafluorophenyl groups at two meso-positions and a thiophenolato ligand coordinating to the Fe-atom (Schemes 2 and 3). Due to the presence of the electron-withdrawing substituents, the catalyst 13 is appreciably resistant to oxidants (HOCl) and chlorinates, e.g., monochlorodimedone (5), with turnover numbers up to 1530. The redox potential of 13, E0 = - 134 mV, and the Soret band (λmax 448 nm) of the CO adduct of the reduced state of 13 are close to the corresponding values of the enzyme CPO.
A New Reaction of α-Chloro-α-chlorosulfenyl Ketones: Facile Syntheses of 3,3-Dichloro- and 3-Chloro-Chroman-4-ones and Thiochroman-4-ones
Gabbutt, Christopher D.,Hepworth, John D.,Heron, B. Mark
, p. 5245 - 5254 (2007/10/02)
3-Chloro-3-chlorosulfenylchroman-4-ones are efficiently obtained from chroman-4-ones by treatment with thionyl chloride.Direct oxidation affords 3,3-dichlorochroman-4-ones, whilst conversion to the sulfenamides prior to oxidation provides a facile route to 3-chlorochroman-4-ones.
