67210-36-0

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-1,2-EPOXYDECANE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its versatility in undergoing regioselective ring-opening reactions allows for the creation of complex organic molecules, contributing to the development of new drugs and therapies.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-(+)-1,2-EPOXYDECANE serves as a key intermediate in the production of various agrochemicals. Its unique properties facilitate the synthesis of compounds used in the development of pesticides, herbicides, and other agricultural products.
Used in Specialty Chemicals:
(R)-(+)-1,2-EPOXYDECANE is utilized as a chemical intermediate in the synthesis of specialty chemicals, which are tailored for specific applications and industries. Its unique structure and reactivity enable the production of high-value compounds for use in various markets.
Used in Adhesives, Coatings, and Composites:
(R)-(+)-1,2-EPOXYDECANE is used as a monomer in the preparation of epoxy resins, which are widely used in the formulation of adhesives, coatings, and composites. These materials are essential in various industries, including construction, automotive, and aerospace, due to their high strength, durability, and resistance to environmental factors.

InChI:InChI=1/C10H20O/c1-2-3-4-5-6-7-8-10-9-11-10/h10H,2-9H2,1H3/t10-/m1/s1

Upstream product

• 1119-86-4 1,2-decanediol 
• 104898-05-7 (R)-2-bromodecanol 
• 1262435-12-0 1-p-Tolylsulfanyl-decan-2-ol 
• 152517-50-5 (R)-1-tert-Butylsulfanyl-decan-2-ol 
• 155721-05-4 (2R)-1-(Tosyloxy)decan-2-ol 
• 71271-24-4 2-Hydroxycaprinsaeure-methylester 
• 872-05-9 1-Decene 
• 2404-44-6 1,2-Epoxydecane 
• 261160-96-7 (R)-1-chloro-2-decanol 
• 13125-66-1 n-heptylmagnesium bromide 
• 155721-03-2 (2R,3R)-1-(Tosyloxy)-2,3-epoxydecane 
• 155721-04-3 (2S,3R)-1-(Tosyloxy)-3-iododecan-2-ol 
• 99745-00-3 (2S,3S)-2,3-epoxydecan-1-ol 
• 152398-26-0 1-tert-Butylsulfanyl-decan-2-ol 

Downstream Products

• 130594-21-7 1,1-Diphenyl-undecane-1,3-diol 
• 130594-12-6 2-Octyl-1,1-diphenyl-propane-1,3-diol 
• 69830-91-7 (R)-4-dodecanolide 
• 132131-36-3 (R)-5-Octyl-tetrahydro-furan-2-ol 
• 158663-79-7 (R)-1-{2-[2-(4-Decyloxy-phenyl)-pyrimidin-5-yl]-[1,3]dithian-2-yl}-decan-2-ol 
• 152291-72-0 (R)-1-[4-(5-Octyl-pyrimidin-2-yl)-phenyl]-undecan-3-ol 

Relevant academic research and scientific papers

Stereoselective synthesis of 10,11-dihydro-leukotriene B4 and related metabolites

Nickel-catalyzed coupling reaction of cis bromide 6 and the borates 5a and 5b, prepared from the boronate esters 4a and 4b, proceeded stereospecifically to furnish 7a and 7b, which upon treatment with Bu4NF in THF afforded 10,11-dihydro-leukotriene B4 (1) and the B3 (2), respectively. In a similar way, EE ether 19 and rac-4a gave 20 and the subsequent functional group transformation afforded 10,11-dihydro-12-oxo-LTB4 (3).

The Configuration of Distaminolyne A is S: Quantitative Evaluation of Exciton Coupling Circular Dichroism of N, O- Bis-arenoyl-1-amino-2-alkanols

The 2S configuration of the marine natural product distaminolyne A was recently disputed based upon total synthesis, yet paradoxically supported by a second independent total synthesis from a different research group. We now verify the 2S configuration of

Construction of an Asymmetric Porphyrinic Zirconium Metal-Organic Framework through Ionic Postchiral Modification

Herein, one kind of neutral chiral zirconium metal-organic framework (Zr-MOF) was reported from the porphyrinic MOF (PMOF) family with a metallolinker (MnIII-porphyrin) as the achiral polytopic linker [free base tetrakis(4-carboxyphenyl)porphyrin] and chiral anions. Achiral Zr-MOF was chiralized through the exchange of primitive anions with new chiral organic anions (postsynthetic exchange). This chiral functional porphyrinic MOF (CPMOF) was characterized by several techniques such as powder X-ray diffraction, Fourier transform infrared spectroscopy, ultraviolet-visible spectroscopy, 1H NMR, energy-dispersive X-ray spectroscopy, scanning electron microscopy, and Brunauer-Emmett-Teller measurements. In the resulting structure, there are two active metal sites as Lewis acid centers (Zr and Mn) and chiral species as Br?nsted acid sites along with their cooperation as nucleophiles. This CPMOF shows considerable bimodal porosity with high surface area and stability. Additionally, its ability was investigated in asymmetric catalyses of prochiral substrates. Interactions between framework chiral species and prochiral substrates have large impacts on the catalytic ability and chirality induction. This chiral catalyst proceeded asymmetric epoxidation and CO2 fixation reactions at lower pressure with high enantioselectivity due to Lewis acids and chiral auxiliary nucleophiles without significant loss of activity up to the sixth step of consecutive cycles of reusability. Observations revealed that chiralization of Zr-MOF could happen by a succinct strategy that can be a convenient method to design chiral MOFs.

Chirally-Modified Graphite Oxide as Chirality Inducing Support for Asymmetric Epoxidation of Olefins with Grafted Manganese Porphyrin

Abstract: A chirality inducer was prepared by graphite oxide (GO) functionalization with enantiopure l-tartrate (GO*) and used as asymmetric support for a covalently-linked manganese porphyrine complex [Mn(TPyP)OAc]. The thereby obtained heterogeneous catalyst, GO*-[Mn(TPyP)OAc], showed excellent performance and ee-values of 92–99% for the asymmetric epoxidation of prochiral olefins with O2 as oxidant and isobutyraldehyde as co-reductant in acetonitrile; linear terminal olefins with 54–76% conversion and quantitative conversion of aromatic olefins. The GO*-[Mn(TPyP)OAc] catalyst is highly active, recyclable, and at the same time simple and inexpensive to prepare with a chiral inducer from the chiral pool. The structure of the catalyst was elucidated by scanning electron microscopy (SEM), transmission electron microscopy (TEM), BET analysis,?FT-IR, Raman, and photoluminescence spectroscopic methods. Graphic Abstract: Graphite oxide functionalized with an enantiopure group was used as a chirality inducer and asymmetric support for a Mn-porphyrine complex. The thereby obtained heterogeneous catalyst is an excellent enantioselective catalyst for the epoxidation of prochiral olefins.[Figure not available: see fulltext.].

Enantioselective organocatalysis-based synthesis of 3-hydroxy fatty acids and fatty γ-lactones

3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.

An effective strategy for creating asymmetric MOFs for chirality induction: A chiral Zr-based MOF for enantioselective epoxidation

Recently the construction of chiral MOFs (CMOFs) has been very challenging and complex. For the first time, we synthesized a chiral Zr-based MOF with l-tartaric acid by solvent-assisted ligand incorporation (SALI). We show that a CMOF can be postsynthetically generated by a simple method: incorporating chiral carboxylic groups on the achiral NU-1000. The post-synthesized chiral NU-1000 was used as an asymmetric support for producing a chiral catalyst with molybdenum catalytic active centers as Lewis acid sites. Enantioselective epoxidation of various prochiral alkens to epoxids by using [C-NU-1000-Mo] is comparable to that using other asymmetric homogeneous and heterogeneous catalysts, along with high enantiomeric excess and selectivity to epoxide (up to 100%). The CMOF could be reused in the styrene oxidation after five cycles without substantial deterioration in the CMOF crystallinity or catalytic performance.

Dual activity of durable chiral hydroxyl-rich MOF for asymmetric catalytic reactions

The quest to prepare of asymmetric heterogeneous catalysts with both effective Br?nsted acid sites (BASs) and Lewis acid sites is very significant challenge. Herein, we report the construction of a chiral metal-organic framework with two kinds of catalytic active sites (Lewis acid/Br?nsted acid). It contains coordinative unsaturation metal centers and chiral functional groups that have cooperation in the catalytic activity. In the synthesized CMOF, the chiral decoration of metal node was performed through the practical method: anions exchange hypothesis (post-synthetic exchange). For this aim, the elimination of framework fluorides happened by using the enantiopure auxiliary anions (L-(+)-tartrate anion (tart?)) that led to a chiral cationic MOF with eventual chemical formula [Cr3tart(H2O)2O(bdc)3]. XRD, BET, 1H NMR, SEM and EDX were employed to characterize of the present CMIL. Despite the chiral tartrate anions generate a chiral environment, they have main role in the activating of epoxide ring due to hydrogen-bonding interaction. Experiments show that the enantiopure tartrate-functionalized MIL-101(Cr) as a green asymmetric catalyst has the considerable performance in the enantioselective reactions due to chiral modified surface without remarkable loss in activity.

Collaborative effect of Mn-porphyrin and mesoporous SBA-15 in the enantioselective epoxidation of olefins with oxygen

The rational design of heterogeneous, low cost transition metal complexes that can catalyze olefin with high enantioselectivity and activity has been a challenging goal for the synthetic chemist. In this study a chiral ion pair strategy was used for the synthesis of a biomimetic efficient manganese-tetrapyridylporphyrin (H2TPyP) catalyst for the asymmetric epoxidation of olefins with O2. Complex Mn-TPyP was covalently linked to mesoporous SBA-15 in heme-type environments and its counter ion was replaced by L-tartrate anion (SBA15-[Mn(TPyP)TA]). Chiral and achiral homogeneous analogous of Mn-TPyP were also prepared. The Mn-porphyrin confined in nanoreactors of SBA-15 exhibited enhanced activity (TOF = 652 h?1) and enantiomeric excess (ee 93%) compared with the value obtained when the same chiral catalyst functioned in homogeneous solution (TOF 97 h?1 and ee 83%) in the oxidation of 1-decene with O2/isobutyraldehyde. The high specific surface area, uniformly sized pore channels and site isolated active centers of the catalyst may contribute to the high activity and enantioselectivity. SBA15-[Mn(TPyP)TA] was structurally stable and could be recycled for repeated use. Total turnover number in the oxidation of styrene after five cycles was 47,400 with 86% epoxide selectivity and ee 86%.

Enhanced enantioselective oxidation of olefins catalyzed by Mn-porphyrin immobilized on graphene oxide

An efficient enantioselective heterogeneous catalyst, GO-[Mn(TPyP)tart], was prepared by covalent attachment of Mn(III) complex of H2TPyP via the propyl linkage to graphene oxide (GO) nanosheet and using chiral tartrate counter ion. The catalyst was characterized by Fourier transform infrared (FT-IR), diffuse reflectance ultraviolet–visible (DR UV–Vis) spectroscopy, powder X-ray diffraction (XRD), scanning electron microscopy (SEM), Raman and thermogravimetric analysis (TGA). The graphene-supported Mn-porphyrin showed higher activity for the enantioselective epoxidation of unfunctionalized olefins with molecular oxygen in the presence of isobutyraldehyde. It could be recovered easily and reused in asymmetric oxidation of styrene precursor in a five-step sequence without any considerable loss of its catalytic activity and selectivity. The obtained optically epoxide selectivities were achieved in 86% to 100%.

A heterogenized chiral imino indanol complex of manganese as an efficient catalyst for aerobic epoxidation of olefins

Herein, a new heterogenized chiral catalyst, GFC-[Mn(L)(OH)], was synthesized by grafting the complex [Mn(L)(OH)] on carbon-coated magnetic Fe3O4 nanoparticle-decorated reduced graphene oxide sheets (GFC) through an amine linkage (L = (1R,2S)-1-(N-salicylideneamino)-2-indanol). The catalyst was characterized via FT-IR, UV/vis, XRD, SEM, and vibrating sample magnetometer (VSM) techniques. It exhibited excellent activity and selectivity in the epoxidation of olefins with oxygen in the presence of isobutyraldehyde under mild conditions (conversion 38-98%; selectivity 65-98%; and enantioselectivity 58-100%, except for alpha-methylstyrene). Furthermore, the synergistic effect of the reduced graphene oxide support was observed on the increasing activity, epoxide selectivity, and enantioselectivity. The catalyst can be recovered via magnetic separation from the reaction mixture and recycled five times without any significant loss in its activity. The advantage of this development is the use of both the synergic effect of reduced graphene oxide and the magnetite nanoparticles to obtain an easily recyclable heterogeneous green catalyst. In addition, high asymmetric induction of a rigid indanol-based unit of the ligand results in high enantioselectivity.