696-71-9

Usage

Uses

Used in Chemical Synthesis:
Cyclooctanol is used as a key starting material for the synthesis of cyclooctanone, which is an important intermediate in the production of various chemicals and pharmaceuticals.
Used in Pharmaceutical Industry:
Cyclooctanol is utilized as a precursor in the synthesis of pharmaceutical compounds, contributing to the development of new drugs and therapeutic agents.
Used in Industrial Chemical Production:
Cyclooctanol plays a significant role in the production of industrial chemicals, as it can be converted into cyclooctanone, which is further used to manufacture other valuable compounds.

InChI:InChI=1/C8H16O/c9-8-6-4-2-1-3-5-7-8/h8-9H,1-7H2

Upstream product

• 502-49-8 cycloactanone 
• 286-62-4 Cyclooctene oxide 
• 98-85-1 1-Phenylethanol 
• 292-64-8 Cyclooctan 
• 931-89-5 (E)-cyclooctene 
• 6597-09-7 toluene-4-sulfonic acid cyclooctyl ester 
• 69126-54-1 benzyl cyclooctyl ether 
• 42463-67-2 Cyclooctyl-phenylacetat 
• 79734-96-6 <1-2H1>cyclooctanol 
• 58378-54-4 (Z)-cyclooctanol-5-d 
• 71024-53-8 cyclooctyl nitrate 
• 88773-85-7 2-Cyclooctyloxy-tetrahydro-pyran 
• 79263-67-5 (2-Methoxy-phenoxymethoxy)-cyclooctane 
• 4925-71-7 cis-1,2-epoxycyclooctane 

Downstream Products

• 931-88-4 cis-Cyclooctene 
• 58906-69-7 Chlorameisensaeure-cyclooctylester 
• 772-60-1 cyclooctyl acetate 
• 1556-08-7 cyclooctyl chloride 
• 79263-67-5 (2-Methoxy-phenoxymethoxy)-cyclooctane 
• 107164-76-1 Boc-Asp(OCoc)-OBzl 
• 121487-59-0 5-thiocyanopentanal 
• 120-92-3 cyclopentanone 
• 502-49-8 cycloactanone 
• 107164-85-2 Boc-Asp(OCoc)-Gly-OBzl 
• 284-20-8 9-oxa-bicyclo[4.2.1]nonane 
• 72359-96-7 8-chloro-1-octanal 
• 21573-31-9 oct-7-enal 
• 91712-76-4 6-iodo-1,4-epoxycyclooctane 

Relevant academic research and scientific papers

Catalytic oxyfunctionalization of saturated hydrocarbons by non-heme oxo-bridged diiron(III) complexes: role of acetic acid on oxidation reaction

Oxo-bridged diiron(III) complexes [Fe2O(L1)2(H2O)2](ClO4)4 (1) and [Fe2O(L2)2(H2O)2](ClO4)4 (2), where L1 and L2 are tetradentate N-donor N,N′-bis(2-pyridylmethyl)-1,2-cyclohexanediamine and N,N′-bis(2-pyridylmethyl)ethane-1,2-diamine respectively, have been isolated as synthetic models of non-heme iron oxygenases and characterized by physicochemical and spectroscopic methods. Both the complexes have been studied as catalysts for the oxyfunctionalization of saturated hydrocarbons using green hydrogen peroxide (H2O2) as oxidant under mild conditions. The selectivity (A/K) and regioselectivity (3°/2°) in oxidative C–H functionalization of alkanes suggests the involvement of metal-based intermediate in the oxygenation reaction. The catalytic efficiency is found to be strongly dependent on the presence of acetic acid. Remarkable increase in conversion and selectivity favoring the formation of alcohols in the oxidation of cyclohexane and cyclooctane and exclusive hydroxylation of adamantane with drastic enhancement of regioselectivity has been achieved by the addition of acetic acid in the presence of H2O2.

Pyridazine N-Oxides as Photoactivatable Surrogates for Reactive Oxygen Species

A method for the photoinduced evolution of atomic oxygen from pyridazine N-oxides was developed. This underexplored oxygen allotrope mediates arene C-H oxidation within complex, polyfunctional molecules. A water-soluble pyridazine N-oxide was also developed and shown to promote photoinduced DNA cleavage in aqueous solution. Taken together, these studies highlight the utility of pyridazine N-oxides as photoactivatable O(3P) precursors for applications in organic synthesis and chemical biology.

Efficient and selective oxidation of hydrocarbons with tert-butyl hydroperoxide catalyzed by oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles

The catalytic activity of an oxidovanadium(IV) unsymmetrical Schiff base complex supported on γ-Fe2O3 magnetic nanoparticles, γ-Fe2O3@[VO(salenac-OH)] in which salenac-OH = [9-(2′,4′-dihydroxyphenyl)-5,8-diaza-4

Primary Alcohols via Nickel Pentacarboxycyclopentadienyl Diamide Catalyzed Hydrosilylation of Terminal Epoxides

The efficient and regioselective hydrosilylation of epoxides co-catalyzed by a pentacarboxycyclopentadienyl (PCCP) diamide nickel complex and Lewis acid is reported. This method allows for the reductive opening of terminal, monosubstituted epoxides to form unbranched, primary alcohols. A range of substrates including both terminal and nonterminal epoxides are shown to work, and a mechanistic rationale is provided. This work represents the first use of a PCCP derivative as a ligand for transition-metal catalysis.

Efficient oxidation of cycloalkanes with simultaneously increased conversion and selectivity using O2 catalyzed by metalloporphyrins and boosted by Zn(AcO)2: A practical strategy to inhibit the formation of aliphatic diacids

The direct sources of aliphatic acids in cycloalkanes oxidation were investigated, and a strategy to suppress the formation of aliphatic acids was adopted through enhancing the catalytic transformation of oxidation intermediates cycloalkyl hydroperoxides to cycloalkanols by Zn(II) and delaying the emergence of cycloalkanones. Benefitted from the delayed formation of cycloalkanones and suppressed non-selective thermal decomposition of cycloalkyl hydroperoxides, the conversion of cycloalkanes and selectivity towards cycloalkanols and cycloalkanones were increased simultaneously with satisfying tolerance to both of metalloporphyrins and substrates. For cyclohexane, the selectivity towards KA-oil was increased from 80.1% to 96.9% meanwhile the conversion was increased from 3.83 % to 6.53 %, a very competitive conversion level with higher selectivity compared with current industrial process. This protocol is not only a valuable strategy to overcome the problems of low conversion and low selectivity lying in front of current cyclohexane oxidation in industry, but also an important reference to other alkanes oxidation.

Three metal centers (Co _AOMARKENCODEAMPX0AOA) Cu _AOMARKENCODEAMPX0AOA Method using Zn) 2D MOFs/ultraviolet light to catalyze oxidation of cycloalkane

The invention relates to a three-metal center (Co _AOMARKENCODEAMPX0AOA). Cu _AOMARKENCODEAMPX0AOA The method comprises Zn) 2D MOFs/ultraviolet light catalytic oxidation of cycloalkane to synthesize cycloalkyl alcohol and cycloalkanone, and belongs to the field of industrial catalysis and fine organic synthesis. To the application method, metalloporphyrin three-metal center (Co _AOMARKENCODEAMPX0AOA) is used. Cu _AOMARKENCODEAMPX0AOA Zn) 2D MOFs dispersed in cycloalkane, wherein metalloporphyrin three-metal center (Co _AOMARKENCODEAMPX0AOA) Cu _AOMARKENCODEAMPX0AOA Zn) 2D MOFs mass is 0.01% - 20%, g / mol of the substance of the cycloalkane, and the reaction system is sealed. An oxidant is introduced, the ultraviolet lamp is a light source, and the reaction liquid of the stirring reaction 2.0-24 . 0h. is subjected to post-treatment to obtain the product cycloalkyl alcohol and cycloalkyl ketone. The method provided by the invention has the advantages of low reaction temperature, mild reaction conditions, high reaction efficiency, high selectivity of cycloalkyl alcohol and cycloalkyl ketone, less byproducts and small environmental impact. The invention provides a high efficiency. Available, safe cycloalkanes selectively catalyze the oxidative synthesis of cycloalkyl alcohols and cycloalkyl ketones.

Hydroxylation of Unactivated C(sp3)-H Bonds with m-Chloroperbenzoic Acid Catalyzed by an Iron(III) Complex Supported by a Trianionic Planar Tetradentate Ligand

Hydroxylation of cyclohexane with m-chloroperbenzoic acid was examined in the presence of an iron(III) complex supported by a trianionic planar tetradentate ligand. The present reaction system shows a high turnover number of 2750 with a high product selectivity of alcohol (93%). The turnover frequency was 0.51 s-1, and the second-order rate constant (k) for the C-H bond activation of cyclohexane was 1.08 M-1 s-1, which is one of the highest values among the iron complexes in the oxidation of cyclohexane so far reported. The present catalytic system can be adapted to the hydroxylation of substrates having only primary C-H bonds such as 2,2,3,3-tetramethylbutane as well as gaseous alkanes such as butane, propane, and ethane. The involvement of an iron(III) acyl peroxido complex as the reactive species was suggested by spectroscopic measurements of the reaction solution.

Revisiting Alkane Hydroxylation with m-CPBA (m-Chloroperbenzoic Acid) Catalyzed by Nickel(II) Complexes

Mechanistic studies are performed on the alkane hydroxylation with m-CPBA (m-chloroperbenzoic acid) catalyzed by nickel(II) complexes, NiII(L). In the oxidation of cycloalkanes, NiII(TPA) acts as an efficient catalyst with a high yield and a high alcohol selectivity. In the oxidation of adamantane, the tertiary carbon is predominantly oxidized. The reaction rate shows first-order dependence on [substrate] and [NiII(L)] but is independent on [m-CPBA]; vobs=k2[substrate][NiII(L)]. The reaction exhibited a relatively large kinetic deuterium isotope effect (KIE) of 6.7, demonstrating that the hydrogen atom abstraction is involved in the rate-limiting step of the catalytic cycle. Furthermore, NiII(L) supported by related tetradentate ligands exhibit apparently different catalytic activity, suggesting contribution of the NiII(L) in the catalytic cycle. Based on the kinetic analysis and the significant effects of O2 and CCl4 on the product distribution pattern, possible contributions of (L)NiII?O. and the aroyloxyl radical as the reactive oxidants are discussed.

Synthesis of new rhodium(III) complex by benzylic C[sbnd]S bond cleavage of thioether containing NNS donor Schiff base ligand: Investigation of catalytic activity towards transfer hydrogenation of ketones

A new rhodium(III)-triphenylphosphine mixed ligand complex, [Rh(PPh3)(L)Cl2] (1) is synthesized by benzylic C[sbnd]S bond cleavage of L-CH2Ph ligand (where, L-CH2Ph = 2-(benzylthio)-N-(pyridin-2-ylmethylene)aniline). The complex is thoroughly characterized by several spectroscopic techniques. Geometry of the complex is confirmed by single crystal X-ray crystallography. Electronic structure, redox properties, absorption and emission properties of the complex were studied. DFT and TDDFT calculations were carried out to interpret the electronic structure and absorption properties of the complex respectively. The synthesized Rh(III) complex was tested as catalyst towards transfer hydrogenation reaction of ketones in iPrOH and an excellent catalytic conversion was observed under mild conditions.

Chemoselective Cleavage of Si-C(sp3) Bonds in Unactivated Tetraalkylsilanes Using Iodine Tris(trifluoroacetate)

Organosilanes are synthetically useful reagents and precursors in organic chemistry. However, the typical inertness of unactivated Si-C(sp3) bonds under conventional reaction conditions has hampered the application of simple tetraalkylsilanes in organic synthesis. Herein we report the chemoselective cleavage of Si-C(sp3) bonds of unactivated tetraalkylsilanes using iodine tris(trifluoroacetate). The reaction proceeds smoothly under mild conditions (-50 °C to room temperature) and tolerates various polar functional groups, thus enabling subsequent Tamao-Fleming oxidation to provide the corresponding alcohols. NMR experiments and density functional theory calculations on the reaction indicate that the transfer of alkyl groups from Si to the I(III) center and the formation of the Si-O bond proceed concertedly to afford an alkyl-λ3-iodane and silyl trifluoroacetate. The developed method enables the use of unactivated tetraalkylsilanes as highly stable synthetic precursors.