4436-58-2

Basic information

• Product Name: Cycloheptanone,2-hydroxy-
• Synonyms: 2-hydroxycyloheptanone;2-hydroxycycloheptanone;(+/-)-2-Hydroxy-cycloheptanon;(+/-)-1-hydroxycycloheptanone
• CAS NO: 4436-58-2
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• Mol File: 4436-58-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Cycloheptanone,2-hydroxy- (CAS DataBase Reference)
• NIST Chemistry Reference: Cycloheptanone,2-hydroxy- (4436-58-2)
• EPA Substance Registry System: Cycloheptanone,2-hydroxy- (4436-58-2)

Safety Data

• Hazardous Substances Data: 4436-58-2(Hazardous Substances Data)

Upstream product

• 56-23-5 tetrachloromethane 
• 2050-20-6 diethyl pimelate 
• 143-19-1 sodium Oleate 
• 52329-71-2 1-hydroxycyclohexanecarboxaldehyde 
• 77256-26-9 2-Iodocycloheptanone 
• 1056246-49-1 2-bromocycloheptanone 
• 13553-19-0 trans-cycloheptane-1,2-diol 
• 22081-48-7 (cyclohept-1-en-1-yloxy)(trimethyl)silane 
• 502-42-1 cycloheptanone 

Downstream Products

• 35376-00-2 methyl 7-oxoheptanoate 
• 2050-20-6 diethyl pimelate 
• 55956-38-2 Δ¹⁽⁷⁾-8,11-dioxabicyclo<5.4.0>undecene 
• 73682-15-2 cis-1,2-bis-(4-nitro-benzoyloxy)-cycloheptane 
• 533-75-5 2-hydroxy-2,4,6-cycloheptatrien-1-one 

Relevant articles and documents

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

A new class of poly-N-vinylpyrrolidinones containing an asymmetric center at C5 of the pyrrolidinone ring were synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1,3- and 1,2-trans-cycloalkanediols and desymmetrization of meso cis-diols took place with 0.15 mol % Pd/Au (3:1)-17 under oxygen atmosphere in water to give excellent chemical and optical yields of (S)-hydroxy ketones. Various alkenes were oxidized with 0.5 mol % Pd/Au (3:1)-17 under 30 psi of oxygen in water to give the dihydroxylated products in >93% ee. Oxidation of (R)-limonene at 25 °C occurred at the C-1,2-cyclic alkene function yielding (1S,2R,4R)-dihydroxylimonene 49 in 92% yield. Importantly, cycloalkanes were oxidized with 1 mol % Cu/Au (3:1)-17 and 30% H2O2 in acetonitrile to afford chiral ketones in very good to excellent chemical and optical yields. Alkene function was not oxidized under the reaction conditions. Mechanisms were proposed for the oxidation reactions, and observed stereo- and regio-chemistry were summarized.

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.

Oxidation reactions catalysed by titanium- and chromium-containing silicalites

While the titanium silicalite-1 (TS-1)-tert-butyl hydroperoxide (TBHP) combination exhibits remarkable activity and selectivity in the oxidative cleavage of the C-C double bond of silyl enol ethers to produce dicarboxylic acids, the chemoselective oxidation of thioethers to sulfoxides without generation of sulfones is achieved using chromium silicalite-2 (CrS-2)-H2O2.