6705-49-3

Basic information

• Product Name: 7-OXABICYCLO[4.1.0]HEPTAN-2-ONE
• Synonyms: 7-OXABICYCLO[4.1.0]HEPTAN-2-ONE;2,3-Epoxycyclohexanone;7-Oxabicyclo[4.1.0]heptan-2-one(6CI,7CI,8CI,9CI);2,3-Epoxy-1-cyclohexanone;2,3-Epoxycyclohexan-1-one;7-Oxabicyclo[4.1.0]heptan-2-one 98%
• CAS NO: 6705-49-3
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.13
• EINECS: 229-751-4
• Product Categories: EPOXYDE;C3 to C6;Carbonyl Compounds;Ketones
• Mol File: 6705-49-3.mol
• Article Data: 154

Chemical Properties

• Boiling Point: 76-78 °C15 mm Hg(lit.)
• Flash Point: 205 °F
• Appearance: /
• Density: 1.13 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.263mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 7-OXABICYCLO[4.1.0]HEPTAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-OXABICYCLO[4.1.0]HEPTAN-2-ONE(6705-49-3)
• EPA Substance Registry System: 7-OXABICYCLO[4.1.0]HEPTAN-2-ONE(6705-49-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 6705-49-3(Hazardous Substances Data)

Usage

Description

7-Oxabicyclo[4.1.0]heptan-2-one is a chemical compound that is one of the products formed during the oxidation of cyclohexene by dendritic complexes. It has been reported as an anticapsin analog and is known for its unique bicyclic structure with an oxygen atom and a ketone group.

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 
• 2699-13-0 3-methoxycyclohexene 
• 822-67-3 Cyclohex-2-enol 
• 110-83-8 cyclohexene 
• 1192-78-5 2,3-epoxycyclohexanol 
• 72029-31-3 cis-2,3-epoxycyclohexanol 
• 92735-08-5 ((S)-Cyclohex-2-enyloxy)-trimethyl-silane 
• 7553-56-2 iodine 
• 6426-26-2 (S)-cyclohex-2-en-1-ol 
• 89064-04-0 (1S,2S,6R)-7-oxabicyclo[4.1.0]heptan-2-ol 
• 3413-44-3 (R)-2-cyclohexen-1-ol 
• 60464-75-7 Trimethyl-[(S)-(7-oxa-bicyclo[4.1.0]hept-2-yl)oxy]-silane 
• 71055-13-5 ethyl (E)-2-(cyclohex-2-en-1-ylidene)acetate 
• 92841-93-5 (1R,2S,6S)-7-oxabicyclo[4.1.0]heptan-2-ol 

Downstream Products

• 627-93-0 hexanedioic acid dimethyl ester 
• 1119-40-0 Dimethyl glutarate 
• 92735-09-6 (2R,3S)-2-decyl-3-hydroxycyclohexan-1-one 
• 1192-78-5 2,3-epoxycyclohexanol 
• 34737-39-8 2-butylcyclohex-2-en-1-one 
• 70871-45-3 2-hydroxy-3-phenyl-2-cyclohexen-1-one 
• 950585-11-2 (1R,2S)-3-(diethylphenylsilyl)-2-phenylcyclohexane 
• 950585-10-1 (1S,2R)-3-(diethylphenylsilyl)-2-phenylcyclohexane 

Relevant articles and documents

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.

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.

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.

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.

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.]

Tandem Lewis acid catalysis for the conversion of alkenes to 1,2-diols in the confined space of bifunctional TiSn-Beta zeolite

The generation of multifunctional isolated active sites in zeolite supports is an attractive method for integrating multistep sequential reactions into a single-pass tandem catalytic reaction. In this study, bifunctional TiSn-Beta zeolite was prepared by a simple and scalable post-synthesis approach, and it was utilized as an efficient heterogeneous catalyst for the tandem conversion of alkenes to 1,2-diols. The isolated Ti and Sn Lewis acid sites within the TiSn-Beta zeolite can efficiently integrate alkene epoxidation and epoxide hydration in tandem in a zeolite microreactor to achieve one-step conversion of alkenes to 1,2-diols with a high selectivity of >90%. Zeolite confinement effects result in high tandem rates of alkene epoxidation and epoxide hydration as well as high selectivity toward the desired product. Further, the novel method demonstrated herein can be employed to other tandem catalytic reactions for sustainable chemical production.