4277-32-1

Usage

Uses

Used in Pharmaceutical Synthesis:
(1R,2R)-Cyclooctane-1,2-diol is utilized as a chiral building block for the synthesis of pharmaceuticals, contributing to the production of enantiopure compounds that are essential for ensuring the desired therapeutic effects and minimizing potential side effects.
Used in Agrochemical Production:
In the agrochemical industry, (1R,2R)-Cyclooctane-1,2-diol serves as a chiral building block, aiding in the synthesis of enantiomerically pure agrochemicals to enhance their efficacy and reduce environmental impact.
Used in Fine Chemicals Synthesis:
(1R,2R)-Cyclooctane-1,2-diol is employed as a chiral building block in the synthesis of various fine chemicals, leveraging its unique structure to create high-quality specialty products.
Used as a Chiral Resolving Agent:
(1R,2R)-Cyclooctane-1,2-diol has potential applications as a chiral resolving agent, playing a crucial role in the separation of enantiomers, which is vital for the development of pure enantiomer compounds in various industries.
Used in the Development of Chiral Catalysts:
As a precursor, (1R,2R)-Cyclooctane-1,2-diol contributes to the development of new chiral catalysts for asymmetric synthesis reactions, facilitating the creation of enantiomerically pure products with high selectivity and efficiency.

Upstream product

• 931-88-4 cis-Cyclooctene 
• 931-88-4 1,2-cyclooctene 
• 42565-22-0 trans-1,2-cyclooctanediol 
• 108-24-7 acetic anhydride 
• 286-62-4 Cyclooctene oxide 
• 19740-90-0 (Z)-9-oxabicyclo[6.1.0]non-4-ene 
• 1552-12-1 1,5-cis,cis-cyclooctadiene 
• 69926-50-7 (1S,2S)-(Z)-cyclooct-5-ene-1,2-diol 
• 931-87-3 (R)-(-)-(E)-cyclooctene 
• 931-89-5 (E)-cyclooctene 
• 292-64-8 Cyclooctan 
• 75-91-2 tert.-butylhydroperoxide 
• 80937-33-3 oxygen 
• 78823-36-6 p-nitrobenzoic-propionic anhydride 

Downstream Products

• 284-20-8 9-oxa-bicyclo[4.2.1]nonane 
• 502-49-8 cycloactanone 
• 3806-59-5 1,3-cyclooctadiene 
• 505-48-6 octane-1,8-dioic acid 
• 3008-37-5 cyclooctane-1,2-dione 
• 307965-14-6 2-hydroxycyclooctyl p-toluenesulfonate 
• 496-82-2 2-hydroxycylooctanone 
• 638-54-0 1,8-octanedial 

Relevant academic research and scientific papers

Catalytic oxygen atom transfer promoted by tethered Mo(VI) dioxido complexes onto silica-coated magnetic nanoparticles

The preparation of three novel active and stable magnetic nanocatalysts for the selective liquid-phase oxidation of several olefins, has been reported. The heterogeneous systems are based on the coordination of cis-MoO2 moiety onto three different SCMNP@Si-(L1-L3) magnetically active supports, functionalized with silylated acylpyrazolonate ligands L1, L2 and L3. Nanocatalysts thoroughly characterized by ATR-IR spectroscopy, TGA and ICP-MS analyses, showed excellent catalytic performances in the oxidation of conjugated or unconjugated olefins either in organic or in aqueous solvents. The good magnetic properties of these catalytic systems allow their easy recyclability, from the reaction mixture, and reuse over five runs without significant decrease in the activity, either in organic or water solvent, demonstrating their versatility and robustness.

Liquid-phase oxidation of olefins with rare hydronium ion salt of dinuclear dioxido-vanadium(V) complexes and comparative catalytic studies with analogous copper complexes

Homogeneous liquid-phase oxidation of a number of aromatic and aliphatic olefins was examined using dinuclear anionic vanadium dioxido complexes [(VO2)2(salLH)]? (1) and [(VO2)2(NsalLH)]? (2) and dinuclear copper complexes [(CuCl)2(salLH)]? (3) and [(CuCl)2(NsalLH)]? (4) (reaction of carbohydrazide with salicylaldehyde and 4-diethylamino salicylaldehyde afforded Schiff-base ligands [salLH4] and [NsalLH4], respectively). Anionic vanadium and copper complexes 1, 2, 3, and 4 were isolated in the form of their hydronium ion salt, which is rare. The molecular structure of the hydronium ion salt of anionic dinuclear vanadium dioxido complex [(VO2)2(salLH)]? (1) was established through single-crystal X-ray analysis. The chemical and structural properties were studied using Fourier transform infrared (FT-IR), ultraviolet–visible (UV–Vis), 1H and 13C nuclear magnetic resonance (NMR), electrospray ionization mass spectrometry (ESI-MS), electron paramagnetic resonance (EPR) spectroscopy, and thermogravimetric analysis (TGA). In the presence of hydrogen peroxide, both dinuclear vanadium dioxido complexes were applied for the oxidation of a series of aromatic and aliphatic alkenes. High catalytic activity and efficiency were achieved using catalysts 1 and 2 in the oxidation of olefins. Alkenes with electron-donating groups make the oxidation processes easy. Thus, in general, aromatic olefins show better substrate conversion in comparison to the aliphatic olefins. Under optimized reaction conditions, both copper catalysts 3 and 4 fail to compete with the activity shown by their vanadium counterparts. Irrespective of olefins, metal (vanadium or copper) complexes of the ligand [salLH4] (I) show better substrate conversion(%) compared with the metal complexes of the ligand [NsalLH4] (II).

A stand-alone cobalt bis(dicarbollide) photoredox catalyst epoxidates alkenes in water at extremely low catalyst load

The cobalt bis(dicarbollide) complex, Na[3,3′-Co(η5-1,2-C2B9H11) (Na[1]), is an effective photoredox catalyst for the oxidation of alkenes to epoxides in water. Advantageous features of Na[1] include its lack of photoluminescence, high solubility and surfactant behavior in aqueous media, as well as the donor ability of the carborane ligand and high oxidizing power of the Co4+/3+ couple. These features differentiate it from the well-known and widely used photosensitizer tris (2,2′-bipyridine) ruthenium(ii) ([Ru(bpy)3]2+), which also participates in electron transfer through an outer sphere mechanism. A comparison of the catalytic performance of [Ru(bpy)3]2+ with Na[1] for alkene photo-oxidation is fully in favor of Na[1], as the former shows very low or null efficiency. With a catalyst loading of 0.1 mol% conversions between 65-97% have been obtained in short reaction times, 15 minutes, with moderate selectivity for the corresponding epoxide, due to the formation of side products as diols. But when the catalyst loading is reduced to 0.01 mol%, the selectivity for the corresponding epoxide increased considerably, being the only compound formed after 15 minutes of reaction (selectivity >99%). High TON values have been obtained (TON = 8500) for the epoxidation of aromatic and aliphatic alkenes in water. We have verified that Na[3,3′-Co(η5-1,2-C2B9H11)2] acts as a photocatalyst in both the epoxidation of alkenes and in their hydroxylation in aqueous medium with a higher rate for epoxidation than for hydroxylation. Preliminary photooxidation tests using methyl oleate as the substrate led to the selective epoxidation of the double bond. These results represent a promising starting point for the development of practical methods for the processing of unsaturated fatty acids, such as the valorisation of animal fat waste using this sustainable photoredox catalyst. This journal is

Double end-on azido derivative of a tridentate (NNO) Schiff base dimeric copper(II) complex: synthesis, X-ray structure, magnetic property and catalytic effectiveness

A dimeric copper(II) complex, bis{(2-[1-(aminoethylimino)ethyl]-phenoxo}-di-μ1,1-azido-dicopper(II), [Cu2(L)2(μ2-1,1-N3)2] (1) [L = 2-[1-(aminoethylimino)ethyl]-phenoxo ion], has been isolated using a self-assembly reaction using a 1:1:1 molar ratio of Cu(NO3)2·3H2O, HL and NaN3 in methanol at room temperature and characterized through X-ray diffraction analysis and spectroscopic studies. X-ray structural analysis reveals that 1 consists of two distinct dinuclear molecular units, where each copper(II) center in the individual dinuclear unit adopts a distorted square pyramidal geometry with a CuN4O chromophore ligated through a tridentate (NNO) Schiff base and two N atoms of two different bridging azides in μ1,1-mode. Two Cu(II) centers are linked through double μ2-1,1-N3 bridges to form the dinuclear unit [Cu2(L)2(μ2-1,1-N3)2]. In the crystalline state, the dinuclear units in 1 are associated through weak intermolecular N-H?O hydrogen bonds to afford a 2-D sheet structure viewed along the crystallographic a-axis. The small magnitude of the antiferromagnetic interaction (J = –0.45 cm?1) is a result of the long Cu···Cu separation (3.205(2) ?). The catalytic efficacy of 1 was studied in a series of solvents for the epoxidation of alkenes using tert-butyl-hydroperoxide (TBHP) as an efficient oxidant under mild conditions.

Rare earth Ce- and Nd-doped spinel nickel ferrites as effective heterogeneous catalysts in the (ep)oxidation of alkenes

Cerium (Ce)- and neodymium (Nd)-doped spinel nickel ferrites catalysts system were synthesized using a cost-effective sol–gel route. The as-prepared nickel ferrites and its doped Ce and Nd nanomaterials were characterized in terms of Fourier transform infrared spectrophotometry, X-ray diffraction, field emission scanning electron microscopy, energy-dispersive X-ray spectroscopy, transmission electron microscopy, selected area diffraction pattern, zeta potential and magnetism techniques. Their catalytic potential was examined in the (ep)oxidation of 1,2-cyclooctene by using hydrogen peroxide (H2O2) or tert-butylhydroperoxide (t-BuOOH). Optimization of various parameters, including solvent, oxidant and catalyst type revealed that chloroform (CHCl3) or 1,2-dichloroethane as a solvent and t-BuOOH as an oxidant were found to be the best choice for this catalytic system. The catalytic efficiency was found as Nd–NiFe2O4 > Ce–NiFe2O4 > NiFe2O4. Further, the applied nanocatalysts could be easily renovated and exhibited high catalytic reactivity for 5 times of recycling experiments with long-time durability. A reasonable discussion of the mechanism reaction reinforced the action of these spinel catalysts.

Polymer-anchored mononuclear and binuclear CuII Schiff-base complexes: Impact of heterogenization on liquid phase catalytic oxidation of a series of alkenes

Liquid phase catalytic oxidation of a number of alkenes, for example, cyclohexene, cis-cyclooctene, styrene, 1-methyl cyclohexene and 1-hexene, was performed using polymer-anchored copper (II) complexes PS-[Cu (sal-sch)Cl] (5), PS-[Cu (sal-tch)Cl] (6), PS-[CH2{Cu (sal-sch)Cl}2] (7) and PS-[CH2{Cu (sal-tch)Cl}2] (8). Neat complexes [Cu (sal-sch)Cl] (1), [Cu (sal-tch)Cl] (2), [CH2{Cu (sal-sch)Cl}2] (3) and [CH2{Cu (sal-tch)Cl}2] (4) were isolated by reacting CuCl2·2H2O with [Hsal-sch] (I), [Hsal-tch] (II), [H2bissal-sch] (III) and [H2bissal-tch] (IV), respectively, in refluxing methanol. Complexes 1–4 have been covalently anchored in Merrifield resin through the amine nitrogen of the semicarbazide or thiosemicarbazide moiety. A number of analytical, spectroscopic and thermal techniques, such as CHNS analysis, Fourier transform-infrared, UV–Vis, PMR, 13C-NMR, electron paramagnetic resonance, scanning electron microscopy, energy-dispersive X-ray analysis, thermogravimetric analysis, atomic force microscopy, atomic absorption spectroscopy, and electrospray ionization-mass spectrometry, were used to analyze and establish the molecular structure of the ligands (I)–(IV) and complexes (1)–(8) in solid state as well as in solution state. Grafted complexes 5–8 were employed as active catalysts for the oxidation of a series of alkenes in the presence of hydrogen peroxide. Copper hydroperoxo species ([CuIII (sal-sch)-O-O-H]), which is believed to be the active intermediate, generated during the catalytic oxidation of alkenes, are identified. It was found that supported catalysts are very economical, green and efficient in contrast to their neat complexes as well as most of the recently reported heterogeneous catalysts.

Synthesis, characterization, and catalytic oxidation of styrene, cyclohexene, allylbenzene, and cis-cyclooctene by recyclable polymer-grafted Schiff base complexes of vanadium(IV)

Schiff base-functionalized chloromethylated polystyrenes, PS-[Ae-Eol] (I), PS-[Hy-Eda] (II) and PS-[HyP-Eda] (III), were synthesized by reacting 2-(2-aminoethoxy)ethanol (Ae-Eol), N-(2-hydroxyethyl)ethylenediamine (Hy-Eda), and N-(2-hydroxpropyl)ethylened

Synthesis of a pair of homochiral manganese-based coordination polymers as stable catalyst for the selective oxidation of cis-cyclooctene

A pair of homochiral manganese-based coordination polymers [Mn(H2O)2(bpy)(L-DBTA)] (L-1) and [Mn(H2O)2(bpy)(D-DBTA)](D-1): Syntheses, crystal structures and catalytic properties for the selective oxidation of cis-cyclooctene. The homochiral manganese-based 3D supermolecule framework exhibits high catalytic activity (38.85% conversion based on cis-cyclooctene and 76.13% selectivity for epoxycyclooctane) and stability for selective oxidation of cis-cyclooctene in the absence of solvent using TBHP as radical initiator and oxygen (in the air) as oxidant at 80 °C.

Molybdenum(II) Complexes with α-Diimines: Catalytic Activity in Organic and Ionic Liquid Solvents

The new [MoX(η3-C3H5)(CO)2(α-diimine)] complexes with: (i) X = Br or triflate and α-diimine = 1,10-phenanthroline (phen) and dipyridophenazine (dppz); and (ii) X = Br and α-diimine = phen and dppz, with several substituents, are synthesized and characterized. The structures of [MoBr(η3-C3H5)(CO)2(Cl-phen)] and [Mo(CF3SO3)(η3-C3H5)(CO)2(dppz)] are determined by using single-crystal X-ray diffraction. These and three complexes of 2,2′-bipyridyl (bpy), and its two derivatives with Me and tBu substituents, are tested in the homogeneous catalytic epoxidation of several olefins in dichloromethane, exhibiting, in general, a good selectivity towards the respective epoxide and relatively low TOFs. For the first time, the oxidation of cis-cyclooctene with some of these catalysts is also conducted in a variety of room-temperature ionic liquids (RTILs). In the presence of [MoBr(η3-C3H5)(CO)2(phen)], the conversions, in general, increase, compared with the reactions in organic solvents. Interestingly, different chemoselectivity is found when [C6mim][Ntf2] and [C2mim][FAP] are used with diol (24–26 %). On the other hand, [MoBr(η3-C3H5)(CO)2(L)] (L = Me-phen or dppz) exhibits much lower conversions in the RTILs tested than in common organic solvents.

Two kinds of cobalt–based coordination polymers with excellent catalytic ability for the selective oxidation of cis-cyclooctene

Two kinds of cobalt–based coordination polymers {[Co(dsd)(H2O)4]·4,4′-bpy}(1) and {[Co(dsd)(H2O)4]·H2O} (2) with the chain structure possess excellent catalytic ability for the selective oxidation of