1073-76-3

Usage

Structure

Cyclic enone with a cyclooctadiene ring and a ketone functional group

Applications

a. Building block in organic synthesis
b. Preparation of pharmaceuticals, agrochemicals, and materials
c. Ligand in organometallic chemistry
d. Starting material for the synthesis of natural products and complex molecules

Versatility

Wide range of applications in the field of chemistry

Upstream product

• 72708-69-1 cis,cis-Cycloocta-2,7-dienone Ethylene Ketal 
• 502-49-8 cycloactanone 
• 35242-04-7 cis,cis-2,7-cyclooctadienone 
• 292-64-8 Cyclooctan 
• 696-71-9 cyclooctanol 

Downstream Products

• 37758-99-9 9anti-phenyl-9-phospha-bicyclo[3.3.1]nonan-3-one 
• 57458-75-0 9syn-oxo-9anti-phenyl-9λ⁵-phospha-bicyclo[3.3.1]nonan-3-one 
• 84002-78-8 (Z)-7-Pentyl-8-phenylselanyl-cyclooct-2-enone 
• 51113-06-5 cis,trans-2,7-cyclooctadienone 
• 887278-76-4 5-[8-(tert-butyldiphenylsilanyloxy)-(3R,7S)-3,7-dimethyloctane-1-sulfonyl]-1-phenyl-1H-tetrazole 
• 200121-99-9 8-(tert-butyldiphenylsilanyloxy)-(3R,7S)-3,7-dimethyloctan-ol 
• 200122-06-1 8-(tert-butyldiphenylsilanyloxy)-(3R,7S)-3,7-dimethyloctanoic acid methyl ester 
• 887278-75-3 5-[8-(tert-butyldiphenylsilanyloxy)-(3R,7S)-3,7-dimethyloctylsulfanyl]-1-phenyl-1H-tetrazole 
• 1428645-45-7 C₃₇H₅₈O₃Si 
• 1428645-53-7 C₃₇H₅₈O₃Si 
• 37759-00-5 9syn-methyl-3-oxo-9anti-phenyl-9-phospha-bicyclo[3.3.1]nonanium; iodide 
• 15486-23-4 euphococcinine 
• 682811-45-6 2-(2,2-dimethylpropyl)-1,3a,4,5,6,6a-hexahydropentalen-1-ol 
• 682811-45-6 2-(2,2-dimethylpropyl)-1,3a,4,5,6,6a-hexahydropentalen-1-ol 

Relevant academic research and scientific papers

Modulation of the reactivity profile of IBX by ligand complexation: Ambient temperature dehydrogenation of aldehydes and ketones to α,β-unsaturated carbonyl compounds

The reactivity profile of IBX can be altered by complexation with various ligands (e. g. 1-4). A new complex, IBX·MPO, is a remarkably effective oxidant and allows the room-temperature dehydrogenation of carbonyl compounds, for example, the formation of cyclooctenones 6 and 7 from cyclooctanone 5. IBX = iodoxybenzoic acid; MPO = 4-methoxypyridine-N-oxide.

Expedient synthesis of bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes via the double Michael addition to cyclic dienones

We report the expedient synthesis of 8-disubstituted bicyclo[3.2.1]octane- 3-ones and 9-disubstituted bicyclo[3.3.1]octane-3-ones through the double Michael addition (DMA) of carbon nucleophiles to 7 and 8-membered ring dienones. The reaction proceeds in 42-96% yield with an interesting control of the stereochemistry of the bridged secondary, tertiary or quaternary centre.

CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones

Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.

Asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol

An efficient asymmetric synthesis of cyclo-archaeol and β-glucosyl cyclo-archaeol is presented employing catalytic asymmetric conjugate addition and catalytic epoxide ring opening as the key steps. Their occurrence in deep sea hydrothermal vents has been

Synthesis and analysis of the all-(S) side chain of phosphomycoketides: A test of NMR predictions for saturated oligoisoprenoid stereoisomers

(4S,8S,12S,16S,20S)-Pentamethylheptacosan-1-ol has been synthesized and analyzed by resolution-enhanced NMR spectroscopy with the aid of a recent set predicted spectra of all its stereoisomers. The configuration was confirmed, but isomer purity of the sample (～70%) was lower than expected. A truncated analogue, (2S,6S,10S,14S)-2,6,10,14-tetramethylhenicosan-1-ol TBDPS ether, was prepared from a late stage synthetic intermediate. Analysis of its spectra confirmed the configuration and showed that the sample was isomerically pure. The results suggest that a late-stage epimerization, not a failure of an asymmetric synthesis step, caused the formation of minor stereoisomers in the sample of pentamethylheptacosan-1-ol. The study shows the value of the predicted set of oligoisoprenoid spectra and further extends the predictive model to a new subclass of compounds.

Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones

α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.

Effective oxidation of benzylic and alkane C-H bonds catalyzed by sodium o-iodobenzenesulfonate with Oxone as a terminal oxidant under phase-transfer conditions

Catalytic oxidation of benzylic C-H bonds could be efficiently realized using IBS as a catalyst which was generated in situ from the oxidation of sodium 2-iodobenzenesulfonate (1b) by Oxone in the presence of a phase-transfer catalyst, tetra-n-butylammonium hydrogen sulfate, in anhydrous acetonitrile at 60 °C. Various alkylbenzenes, including toluenes and ethylbenzenes, several oxygen-containing functionalities substituted alkylbenzenes, and a cyclic benzyl ether could be efficiently oxidized. And, the same reagent system of cat. 1b/Oxone/cat. n-Bu4NHSO4 could be applied to the effective oxidation of alkanes as well.

Iodine(V) reagents in organic synthesis. Part 4. o-Iodoxybenzoic acid as a chemospecific tool for single electron transfer-based oxidation processes

o-Iodoxybenzoic acid (IBX), a readily available hypervalent iodine(V) reagent, was found to be highly effective in carrying out oxidations adjacent to carbonyl functionalities (to form α, β-unsaturated carbonyl compounds) and at benzylic and related carbon centers (to form conjugated aromatic carbonyl systems). Mechanistic investigations led to the conclusion that these new reactions are initiated by single electron transfer (SET) from the substrate to IBX to form a radical cation which reacts further to give the final products. Fine-tuning of the reaction conditions allowed remarkably selective transformations within multifunctional substrates, elevating the status of this reagent to that of a highly useful and chemoselective oxidant.

First example of an enone-alkene [2 + 2 + 2] photocycloaddition: 1,3-photocycloaddition of tetramethylethylene across 2,7-cyclooctadienone

(equation presented) Irradiation of cyclooctadienone (1) in the presence of tetramethylethylene (TME) produces 9,10,10-tetramethyl-11-oxatricyclo[6.3.0.01,7]undec-2-ene (7) in 33% yield. This reaction is the first example of a 1,3-cycloaddition of an alkene across an enone system. This novel cycloaddition suggests that there is substantial interaction between the carbonyl carbon and the β-enone carbon in the triplet excited state of 1.