6705-49-3

Usage

Uses

Used in Pharmaceutical Research:
7-Oxabicyclo[4.1.0]heptan-2-one is used as a substrate for investigating the substrate specificity of purified recombinant NADPH-dependent 3-quinuclidinone reductases from Microbacterium luteolum JCM 9174. This application is significant for understanding the reductive reaction of ketones, which can contribute to the development of new drugs and therapies.
Used in Chemical Synthesis:
7-Oxabicyclo[4.1.0]heptan-2-one, due to its unique structure, can be used as a building block or intermediate in the synthesis of various organic compounds. Its presence as an analog of anticapsin suggests potential applications in the development of new pharmaceuticals or chemical products with specific biological activities.
Used in Analytical Chemistry:
7-Oxabicyclo[4.1.0]heptan-2-one can be employed as a reference material or standard in analytical chemistry for the calibration of instruments and methods used in the identification and quantification of similar compounds. Its unique properties make it a valuable tool for researchers in this field.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 4931, 1983 DOI: 10.1021/jo00173a029

InChI:InChI=1/C6H8O2/c7-4-2-1-3-5-6(4)8-5/h5-6H,1-3H2/t5-,6+/m1/s1

Upstream product

• 930-68-7 cyclohexenone 
• 822-67-3 Cyclohex-2-enol 
• 2699-13-0 3-methoxycyclohexene 
• 110-83-8 cyclohexene 
• 1192-78-5 2,3-epoxycyclohexanol 
• 64-19-7 acetic acid 
• 75-05-8 acetonitrile 
• 67-56-1 methanol 
• 64-17-5 ethanol 
• 4845-05-0 cyclohex-2-enyl hydroperoxide 
• 72029-31-3 cis-2,3-epoxycyclohexanol 
• 92841-93-5 (1R,2S,6S)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 71055-13-5 ethyl (E)-2-(cyclohex-2-en-1-ylidene)acetate 
• 6426-26-2 (S)-cyclohex-2-en-1-ol 

Downstream Products

• 23740-67-2 3-hydroxy-2-morpholin-4-yl-cyclohexanone 
• 29329-03-1 5-hexynal 
• 627-93-0 hexanedioic acid dimethyl ester 
• 1119-40-0 Dimethyl glutarate 
• 23740-37-6 2-methoxycyclohex-2-en-1-one 
• 92208-13-4 2,2-Dimethoxy-7-oxa-bicyclo[4.1.0]heptane 
• 137934-96-4 2,2,6-Trimethoxy-cyclohexanol 
• 137934-95-3 2-hydroxy-3-methoxycyclohexanone 
• 103560-51-6 6-phenylselenenyl-2,3-epoxycyclohexenone 
• 42466-33-1 2-(3-methoxybenzylthio)cyclohex-2-en-1-one 
• 1121-18-2 2-methyl-2-cyclohexen-1-one 
• 6610-21-5 6-methylcyclohex-2-en-1-one 
• 89782-52-5 3t-bromo-1-ethyl-1c,2r-cyclohexanediol 
• 89697-38-1 1-vinyl-2-(1-hydroxyprop-2-enyl)-cyclopentanol 

Relevant academic research and scientific papers

Isocyano Enones: Addition-Cyclization Cascade to Oxazoles

Copper iodide catalyzes the conjugate addition of organometallic and heteroatom nucleophiles to isocyano enones to afford oxazoles. A range of enolates, metalated nitriles, amines, and thiols undergo catalyzed conjugate addition to cyclic and acyclic oxoalkene isocyanides. Mechanistic studies suggest that copper complexation facilitates the nucleophilic attack on the isocyano enone to generate an enolate that cyclizes onto the isocyanide leading to a variety of substituted acyclic or ring-fused oxazoles.

Monodisperse iron oxide nanoparticles embedded in Mg-Al hydrotalcite as a highly active, magnetically separable, and recyclable solid base catalyst

Magnetically separable Mg-Al hydrotalcite was prepared by titration method in various molar ratios of (Mg + Al) to Fe, and we compared their catalytic behavior for epoxidation of 2-cyclohexen-1-one using hydrogen peroxide. The catalyst was characterized using X-ray diffraction (XRD), transmission electron microscopy (TEM), superconducting quantum interference device (SQUID), and inductively coupled plasma (ICP). The FeHT100 (ratio of (Mg + Al) to Fe = 100) showed high activity and selectivity in epoxidation of 2-cyclohexen-1-one with hydrogen peroxide. After magnetic separation, FeHT100 kept superior properties and could be reused for four reactions without loss of activity.

Trinuclear Dioxidomolybdenum(VI) Complexes of Tritopic Phloroglucinol-Based Ligands and Their Catalytic Applications for the Selective Epoxidation of Olefins

Four trinuclear dioxidomolybdenum(VI) complexes, [{MoVIO2(H2O)}3ptk(bhz)3] (1), [{MoVIO2(H2O)}3ptk(fah)3] (2), [{MoVIO2(H2O)}3ptk(inh)3] (3), and [{MoVIO2(H2O)}3ptk(nah)3] (4), based on the tritopic central 2,4,6-triacetylphloroglucinol (H3ptk) ligands H6ptk(bhz)3 (I), H6ptk(fah)3 (II), H6ptk(inh)3 (III) and H6ptk(nah)3 (IV) (Hbhz = benzoylhydrazide, Hfah = 2-furanoylhydrazide, Hinh = isonicotinoylhydrazide and Hnah = nicotinoylhydrazide), respectively, are presented. All of the synthesized ligands, as well as their complexes, have been characterized by elemental, thermal, and electrochemical analyses, spectroscopic techniques (FTIR, UV/Vis, 1H and 13C NMR), and single-crystal X-ray studies of [{MoVIO2(H2O)}{MoVIO2(MeOH)}2ptk(bhz)3]·2H2O·1.25MeOH (1a) and [{MoVIO2(EtOH)}3ptk(fah)3]·3EtOH (2a). Each pocket of the ligands coordinates in a dibasic tridentate fashion through two oxygen atoms and one nitrogen atom to each metal center. Due to the presence of tridentate binding pockets in the ligands, each metal center conserves its octahedral structure by coordinating with water molecules in the synthesized complexes or by other solvent(s) in the crystal structures. These complexes were evaluated for the epoxidation of terminal and internal alkenes in the presence of H2O2 using NaHCO3 as a promoter. Under the optimized reaction conditions, all alkenes were converted to the corresponding epoxides selectively in good yield and high turnover number.

Isotope effects and the mechanism of epoxidation of cyclohexenone with tert-butyl hydroperoxide

(Chemical Equation Presented) The mechanism of the epoxidation of 2-cyclohexen-1-one with tert-butyl hydroperoxide mediated by DBU was studied by a combination of experimental kinetic isotope effects (KIEs) and theoretical calculations. A large 12C/13C (k12C/k 13C) isotope effect of ≈1.032 was observed at the C3 (β) position of cyclohexenone, while a much smaller 12C/ 13C isotope effect of 1.010 was observed at the C2 (α) position. Qualitatively, these results are indicative of nucleophilic addition to the enone being the rate-limiting step. Theoretical calculations support this interpretation. Transition structures for the addition step lead to predicted isotope effects that approximate the experimental values, while the predicted isotope effects for the ring-closure step are not consistent with the experimental values. The calculations correctly favor a rate-limiting addition step but suggest that the barriers for the addition and ring-closure steps are crudely similar in energy. The stereochemistry of these epoxidations is predicted to be governed by a preference for an initial axial addition, and the role of this preference in experimental diastereoselectivity observations is discussed.

The catalytic epoxidation of 2-cyclohexen-1-one over uncalcined layered double hydroxides using various solvents

The epoxidation reaction of an α,β-unsaturated ketone (2-cyclohexen-1-one), that is, an electron deficient C=C bond was performed over as-prepared and calcined layered double hydroxides (LDHs) of both the hydrotalcite- and the hydrocalumite type. It was found that the as-prepared LDHs always performed better than the calcined derivatives. Among them, the CaFe-LDH was the most active. The optimum reaction temperature and the most suitable solvent were also found after performing several set of reactions.

Synthesis of a 1,3-Bridged Macrobicyclic Enyne via Chemoselective Cycloisomerization Using Palladium-Catalyzed Alkyne-Alkyne Coupling

A unique intramolecular Pd-catalyzed alkyne-alkyne coupling is presented. This transformation generates a strained, 1,3-bridged, macrocyclic enyne. The process was readily executed on gram scale, and the structure of the product was elucidated via X-ray c

Epoxidation of conjugated C=C-bonds and sulfur-oxidation of thioethers mediated by NADH:FMN-dependent oxidoreductases

Three FMN-dependent oxidoreductases, YcnD and YhdA from Bacillus subtilis and Lot6p from Saccharomyces cerevisiae, oxidised α,β-unsaturated carbonyl compounds and a thioether, respectively, to furnish the corresponding racemic epoxides or sulfoxide, respectively. The mechanism of this enzyme-mediated (rather than enzyme-catalysed) oxidation was shown to proceed via the NADH-dependent reduction of O2, forming H2O 2, which acted as oxidant in a spontaneous (non-enzymatic) fashion. The Royal Society of Chemistry 2009.

Iron-Catalyzed Epoxidation of Linear α-Olefins with Hydrogen Peroxide

The combination of Fe(OTf)2 with N-methyl bis(picolylamine) (Me-bpa) L7 enables epoxidation of linear olefins including terminal, internal, and cyclic ones, using hydrogen peroxide as terminal oxidant under mild conditions. In the presence of picolinic acid as additive improved yields of epoxides up to 75 % have been achieved.

Effect of Support Nature on Ruthenium-Catalyzed Allylic Oxidation of Cycloalkenes

Allylic oxidation of cycloalkenes is a promising route to generate α,β-unsaturated ketones but encounters difficulties in selectivity control. Here, it is demonstrated that ruthenium nanoparticles (1–2?nm sized) decorated on TiO2 nanomaterials with different morphologies (nanoparticles, nanotubes and nanofibers) are demonstrated highly efficiency and selectivity for the selective aerobic oxidation of cyclohexene and indane. The as-prepared Ru/TiO2 nanofibers (NFs) represents higher activity for the allylic oxidation of cyclohexene (conv. 95%) with 78% selectivity toward 2-cyclohexen-1-one at 75?°C under 4?bar O2. Whereas, Ru/TiO2 nanoparticles (NPs) and Ru/TiO2 nanotubes (NTs) show 92 and 84% conversion, respectively. Upon switching to Al2O3 support, catalytic activity with Ru/Al2O3 is decreased significantly to 27%. Very high activity for indane (conv. 70%) toward 2,3-dihydro-1H-inden-1-one (selectivity 85%) has also been observed by using Ru/TiO2 NFs. Ru/TiO2 nanomaterials possess higher catalytic efficiency as compared to Ru NPs and TiO2 nanomaterials individually, representing a positive synergetic effect. Moreover, these reported results suggest that the higher activities of Ru/TiO2 NPs and Ru/TiO2 NFs are related to the crystalline structure, pore volume and surface area of the supports. Graphical Abstract: [Figure not available: see fulltext.]

Asymmetric Epoxidation of Enones Promoted by Dinuclear Magnesium Catalyst

Asymmetric synthesis with cheaper and non-toxic alkaline earth metal catalysts is becoming an important and sustainable alternative to conventional catalytic methodologies mostly relying on precious metals. In spite of some sustainable methods for enantioselective epoxidation of enones, the development of a well-defined and efficient catalyst based on magnesium complexes for these reactions is still a challenging task. In this perspective, we present the application of chiral dinuclear magnesium complexes for asymmetric epoxidation of a broad range of electron-deficient enones. We demonstrate that the in situ generated magnesium-ProPhenol complex affords enantioenriched oxiranes in high yields and with excellent enantioselectivities (up to 99% ee). Our extensive study verifies the literature data in this area and provides a step forward to better understand the factors controlling the oxygenation process. Elaborated catalyst offers mild reaction conditions and a truly wide substrate scope. (Figure presented.).