96-01-5

Usage

Synthesis Reference(s)

Journal of Medicinal Chemistry, 16, p. 869, 1973 DOI: 10.1021/jm00266a001Organic Syntheses, Coll. Vol. 4, p. 838, 1963

InChI:InChI=1/C10H16O2/c11-9-7-5-3-1-2-4-6-8-10(9)12/h1-8H2

Upstream product

• 96-00-4 2-hydroxycyclodecanone 
• 52190-38-2 2-(methylthio)cyclododecanone 
• 100703-65-9 2-(methylthio)cyclodecanone 
• 100703-66-0 2-(methylthio)cycloundecanone 
• 1502-06-3 cyclodecanone 
• 830-13-7 cyclododecanone 
• 110-40-7 diethyl sebacate 
• 6838-68-2 C₁₆H₃₄O₂Si₂ 
• 106-79-6 dimethyl sebacate 
• 878-13-7 cycloundecanone 

Downstream Products

• 102749-07-5 3,10-dibenzylidene-cyclodecane-1,2-dione 
• 103264-80-8 3,10-bis-(α-piperidino-benzyl)-cyclodecane-1,2-dione 
• 116030-71-8 3,10-bis-(4-methyl-benzylidene)-cyclodecane-1,2-dione 
• 101747-32-4 3-benzylidene-cyclodecane-1,2-dione 
• 103267-81-8 3,10-bis-(4-isopropyl-benzylidene)-cyclodecane-1,2-dione 
• 116031-37-9 3,10-bis-(3-methyl-benzylidene)-cyclodecane-1,2-dione 
• 140237-55-4 2-(2-Oxoethyl)cyclooctanone 
• 111-20-6 1,10-decanedioic acid 
• 103047-56-9 3,10-dibenzyl-cyclodecane-1,2-dione 
• 115293-74-8 3,10-bis-(4-methoxy-benzylidene)-cyclodecane-1,2-dione 
• 30572-96-4 cis-cyclodecane-1,2-diol 

Relevant academic research and scientific papers

A rapid and convenient synthesis of α-diketones

A novel and simple synthetic method for the preparation of series of α-diketones is reported. Α-Ditrimethylsiloxyenes were obtained from the readily available materials diacids or diesters through acyloin condensation, which was oxidized to α-diketones using bromine as the oxidation reagent in presence of water. The structures of α-diketones were confirmed by IR, MS, 1H NMR.

Study on the synthesis of 1,2-diketones

A novel method is discussed for preparation of 1,2-diketones: Esters 1 was used as starting material, the intermediate enol 2 was obtained from sodium and trimethylsilyl chloride via acyloin condensation reaction, while bromine water was used in the further experiment as the oxidation reagent to oxidize compound 2 in the mixed solvent THF/H2O. Four kinds of 1,2-diketones have been synthesized in the new way, one is straight chain compound 3a, 3b and the other is ring compound 3c, 3d. The target compounds were confirmed by IR and 1HNMR. Copyright Taylor & Francis Group, LLC.

Photo-irradiation of α-halo carbonyl compounds: A novel synthesis of α-hydroxy- and α,α′-dihydroxyketones

The reaction of α-halo ketones (α-iodocycloalkanones, α-bromocycloalkanones, α-iodo-β-alkoxy esters, and α-iodoacyclicketones) with irradiation under a high-pressure mercury lamp gave the corresponding α-hydroxyketones in good yields. For α-bromoketones, it was found that α-hydroxylation does not occur. However, α-bromoketones were converted into α-hydroxyketones in the presence of KI. In the case of α,α′-diiodo ketones, α,α′-dihydroxyketones, which up to now have scarcely been reported, were obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxy- and α,α′- dihydroxyketones.

A practical and user-friendly method for the selenium-free one-step preparation of 1,2-diketones and their monoxime analogs

Treatment of α-methylene ketones with excess sodium nitrite and aqueous HCl in THF at reduced temperatures provides an effective tool for the preparation of a variety of 1,2-diketones. The diastereoselective synthesis of the corresponding (Z)-1,2-dione monoximes could be accomplished under similar conditions, but by using only one equivalent of nitrosating reagent.

A novel synthesis of α-hydroxy- and α,α′- dihydroxyketone from α-iodo and α,α′-diiodo ketone using photoirradiation

A novel reaction of α-iodo ketone (α-iodocycloalkanone, α-iodo-β-alkoxy ester, and α-iodoacyclicketone) with irradiation under a high-pressure mercury lamp gave the corresponding α-hydroxyketone in good yields. In the case of α,α′- diiodo ketone, α,α′-dihydroxyketone which little has been reported until now was obtained. This reaction affords a new, clean and convenient synthetic method for α-hydroxy- and α,α′- dihydroxyketone.

Arynic Condensatiopn of Ketone Enolates. 17. New General Access to Benzocyclobutene Derivatives

Arynic condensation of 1,2-diketone monoketal enolates appeared to be a very simple way to synthesize benzocyclobutene derivatives.X-ray diffraction and 1H NMR spectra allowed us to determine the structure of the new compounds and to propose a mechanism concerning these condensations.Finally, during this work we devised a new and easily performed two-step synthesis of 1,2-diketones.

A VERY EFFICIENT PREPARATION OF 1,2-DIKETONES

Treatment of α-thiomethylketones with CuCl2-CuO in aqueous acetone affords the corresponding 1,2-dicarbonyl compounds.