592-98-3

Usage

InChI:InChI=1S/C8H16/c1-3-5-7-8-6-4-2/h5,7H,3-4,6,8H2,1-2H3

Upstream product

• 729593-69-5 4-ethoxy-3-bromo-octane 
• 589-62-8 octan-4-ol 
• 693-03-8 n-butyl magnesium bromide 
• 28832-55-5 2-Chlorobutanal 
• 111-65-9 octane 
• 111-87-5 octanol 
• 589-98-0 rac-3-octanol 
• 7642-04-8 cis-2-octene 
• 111-66-0 oct-1-ene 
• 110-82-7 cyclohexane 
• 76200-37-8 trimethyl(1-(phenylthio)pentyl)silane 
• 123-38-6 propionaldehyde 
• 109-65-9 1-bromo-butane 
• 7623-11-2 2-chlorobutyryl chloride 

Downstream Products

• 1731-84-6 nonanoic acid methyl ester 
• 124-19-6 nonan-1-al 
• 27649-40-7 2-ethylheptanal 
• 49642-49-1 2-methyl-1-octanal 
• 140238-46-6 2-n-propylhexanal 
• 90482-62-5 3,4-Epoxyoctane 
• 2177-86-8 methyl 2-methyloctanoate 
• 28180-71-4 rac-trans-2-butyl-3-ethyloxirane 
• 28180-71-4 (+/-)-erythro-3,4-epoxy-octane 
• 2243-27-8 nonanonitrile 
• 111-65-9 octane 
• 111-66-0 oct-1-ene 

Relevant academic research and scientific papers

Continuous flow hydrogenation with Pd complexes of pyridine-benzotriazole ligands

The use of continuous flow systems in chemical synthesis provides great advantages in terms of sustainability, efficiency, and safety. The ability to control reaction parameters such as temperature, pressure, and catalyst exposure in flow system enables rapid optimization of reaction conditions. In the present study, palladium complexes of 1-(piridin-2-il)-1H-benzo[d][1,2,3]triazol, N-((1H-benzo[d][1,2,3]triazol-1-il)metil)piridin-2-amin, and (1H-benzo[d][1,2,3]triazol-1-yl)(pyridin-2-yl)methanone ligands were synthesized and characterized. The catalytic activities of complexes are investigated in the hydrogenation of various alkenes such as styrene, cyclohexene, and 1-octene under continuous flow conditions. The complexes showed very high activity at 10-bar H2 pressure and 50°C for short periods of 5–10?min. The catalysts reused for 10 cycles with no significant loss of catalytic activity.

Photocatalytic-controlled olefin isomerization over WO3–x using low-energy photons up to 625 nm

WO3–x (W-1) was used to achieve controllable photoisomerization of linear olefins without substituents under 625 nm light irradiation. Thermodynamic and kinetic isomers were obtained by regulating the carbon chain length of the olefins. Terminal olefins were converted into isomerized products, and the internal olefin mixtures present in petroleum derivatives were transformed into valuable pure olefin products. Oxygen vacancies (OVs) in W-1 altered the electronic structure of W-1 to improve its light-harvesting ability, which accounted for the high activity of olefin isomerization under light irradiation up to 625 nm. Additionally, OVs on the W-1 surface generated unsaturated W5+ sites that coordinated with olefins for the efficient adsorption and activation of olefins. Mechanistic studies reveal that the in situ formation of surface π-complexes and π-allylic W intermediates originating from the coordination of coordinated unsaturated W5+ sites and olefins ensure high photocatalytic activity and selectivity of W-1 for the photocatalytic isomerization of olefins via a radical mechanism.

Graphdiyne-based Pd single-Atom catalyst for semihydrogenation of alkynes to alkenes with high selectivity and conversion under mild conditions

The development of efficient heterogeneous catalysts for alkyne hydrogenation with high activity and selectivity is highly desirable and yet remains a great challenge. Herein, a Pd single-Atom catalyst (Pds-GDY) is prepared using graphdiyne as support, and used in the semihydrogenation of alkynes. As a proof of concept, the Pds-GDY exhibits a high activity for the semihydrogenation of phenylacetylene under mild reaction conditions, with a TOF of 6290 h-1, and a selectivity of 99.3% at 100% conversion, both much higher than those of the counterparts comprising Pd nanoparticles (NPs), namely, PdNP1-GDY (with 2 nm Pd NPs) and PdNP2-GDY (with 12 nm Pd NPs). In addition, after the full conversion of phenylacetylene, Pds-GDY could still maintain a selectivity as high as 98.9% towards styrene, with almost no phenylethane produced even with a prolonged reaction time; in contrast, for PdNP1-GDY and PdNP2-GDY, within the same reaction time, the selectivity decreases dramatically to 66.6% and 8.5%, respectively. Infrared spectroscopy reveals that Pds-GDY features the weakest adsorption to styrene, which is responsible for its high performance. This work provides an effective strategy to rationally design Pd catalysts for semihydrogenation of alkynes to alkenes with desirable activity and selectivity. This journal is

Regioselective Isomerization of Terminal Alkenes Catalyzed by a PC(sp3)Pincer Complex with a Hemilabile Pendant Arm

We describe an efficient protocol for the regioselective isomerization of terminal alkenes employing a previously described bifunctional Ir-based PC(sp3)complex (4) possessing a hemilabile sidearm. The isomerization, catalyzed by 4, results in a one-step shift of the double bond in good to excellent selectivity, and good yield. Our mechanistic studies revealed that the reaction is driven by the stepwise migratory insertion of Ir?H species into the terminal double bond/β-H elimination events. However, the selectivity of the reaction is controlled by dissociation of the hemilabile sidearm, which acts as a selector, favoring less sterically hindered substrates such as terminal alkenes; importantly, it prevents recombination and further isomerization of the internal ones.

Gem-Dialkyl Effect in Diphosphine Ligands: Synthesis, Coordination Behavior, and Application in Pd-Catalyzed Hydroformylation

A series of palladium complexes with C3-bridged bidentate bis(diphenylphosphino)propane ligands with substituents of varying steric bulk at the central carbon have been synthesized. The size of the gem-dialkyl substituents affects the C-C-C bond angles within the ligands and consequently the P-M-P ligand bite angles. A combination of solid-state X-ray diffraction (XRD) and density functional theory (DFT) studies has shown that an increase in substituent size results in a distortion of the 6-membered metal-ligand chair conformation toward a boat conformation, to avoid bond angle strain. The influence of the gem-dialkyl effect on the catalytic performance of the complexes in palladium-catalyzed hydroformylation of 1-octene has been investigated. While hydroformylation activity to nonanal decreases with increasing size of the gem-dialkyl substituents, a change in chemoselectivity toward nonanol via reductive hydroformylation is observed.

POCN Ni(ii) pincer complexes: Synthesis, characterization and evaluation of catalytic hydrosilylation and hydroboration activities

A series of iminophosphinite POCN pincer Ni(ii) complexes, (POCN)NiMe and (POCN)NiLn(BX4) (L = CH3CN, n = 0, 1; X = F, Ph, C6F5), have been developed and subjected to catalytic hydrosilylation of alkenes, aldehydes and ketones and hydroboration of carbonyl compounds. The stoichiometric reactivity of (POCN)NiMe and (POCN)Ni(BF4) with PhSiH3 and HBPin suggests that catalytic reactions proceed via the hydride intermediate (POCN)NiH. With regard to reactions with HBPin, efficient and mild hydroboration of a variety of carbonyl compounds, including highly chemoselective hydroboration of benzaldehyde in the presence of other common potent reductive functional groups, such as alkenes, alkynes, esters, amides, nitriles, nitro compounds and even ketones, and the first example of base metal catalyzed hydroboration of amides, including mild direct hydroborative reduction of primary and secondary amides to borylated amines were demonstrated for (POCN)NiMe.

Dimerization of Linear Butenes on Zeolite-Supported Ni2+

Nickel- and alkali-earth-modified LTA based zeolites catalyze the dimerization of 1-butene in the absence of Br?nsted acid sites. The catalyst reaches over 95% selectivity to n-octenes and methylheptenes. The ratio of these two dimers is markedly influenced by the parallel isomerization of 1-butene to 2-butene, shifting the methylheptene/octene ratio from 0.7 to 1.4 as the conversion increases to 35%. At this conversion, the thermodynamic equilibrium of 90% cis- and trans-2-butenes is reached. Conversion of 2-butene results in methylheptene and dimethylhexene with rates that are 1 order of magnitude lower than those with 1-butene. The catalyst is deactivated rapidly by strongly adsorbed products in the presence of 2-butene. The presence of π-allyl-bound butene and Ni-alkyl intermediates was observed by IR spectroscopy, suggesting both to be reaction intermediates in isomerization and dimerization. Product distribution and apparent activation barriers suggest 1-butene dimerization to occur via a 1′-adsorption of the first butene molecule and a subsequent 1′- or 2′-insertion of the second butene to form octene and methylheptene, respectively. The reaction order of 2 for 1-butene and its high surface coverage suggest that the rate-determining step involves two weakly adsorbed butene molecules in addition to the more strongly held butene.

Mechanistic Study of a Re-Catalyzed Monoalkylation of Phenols

A mechanistic study of a rhenium catalyzed monoalkylation of phenols is described. Reaction kinetics reveals a zero-order dependence on both alkene and phenol and a half order dependence on catalyst. Isotopic labeling studies, competition experiments, kinetic isotope effects, and Hammett analysis together afford experimental data consistent with a reversible C-H activation step and an irreversible hydrometalation process. The turnover-limiting step is identified as catalyst deaggregation. NMR studies of binary mixtures of catalyst and a single substrate (alkene or phenol) as well as those of reaction mixtures identify potential intermediates and off-cycle species. Despite the numerous Re complexes formed in these mixtures, the overall reaction is both high yielding and highly selective for monoalkylation of phenols.

NCP ligand, [...] complex, synthesis method, intermediate and application

The invention discloses an NCP ligand, iridium complex, synthetic method, intermediate and application thereof. The invention provides an NCP ligand and an NCP ligand iridium complex, wherein R1, R2, R3, R4, R5, R6 and R7 separately represent hydrogen atom or C1-C30 alkyl, R' and R'' independently represent C1-C30 alkyl. The invention provides the application of the NCP ligand iridium complex to the catalysis of alkane dehydrogenation reaction, olefin isomerization reaction, alcohol dehydrogenation reaction, ester alpha alkylation reaction, and amide alpha alkylation reaction. The NCP ligand provided by the invention contains dialkyl substituted phosphine, which has strong electron donating ability and can form a NCP ligand iridium complex by complexing with iridium. The NCP ligand iridium complex uses pyridine to replace a conventional alkyl phosphate electron donor, and has the advantages of good stability, high selectivity on alkane dehydrogenation reaction, mild reaction conditions, good catalytic effect, and industrial production prospect.

Alkene Isomerization-Hydroboration Catalyzed by First-Row Transition-Metal (Mn, Fe, Co, and Ni) N-Phosphinoamidinate Complexes: Origin of Reactivity and Selectivity

We describe the results of our combined experimental and computational investigation of structurally analogous (N-phosphinoamidinate)metal(N(SiMe3)2) precatalysts ((PN)M; M = Mn2+, Fe2+, Co2+, and Ni2+ d5-d8) in the isomerization-hydroboration of 1-octene, cis-4-octene, or trans-4-octene (1a-c) with HBPin. As part of this investigation, the synthesis and crystallographic characterization of diamagnetic (PN)Ni, ((PN)NiH)2, (PN)NiH(L) (L = pyridine or DMAP), and (PN)Ni(NHdipp) (dipp = 2,6-iPr2C6H3) are reported. Divergent catalytic reactivity and selectivity was noted for members of the (PN)M series; (PN)Mn and (PN)Ni afforded poor hydroboration yields, whereas the use of (PN)Fe or (PN)Co afforded high conversion and selectivity for the terminal borylation product, (n-octyl)BPin (2a). DFT calculations involving (PN)M as well as stoichiometric reactivity studies featuring (PN)Ni confirmed that (PN)MH intermediates generated upon reaction of (PN)M with HBPin represent viable catalytic species whereby formation of putative (PN)Ni(H2BPin) is reversible. Conversely, poor catalytic performance was noted for ((PN)NiH)2 and (PN)NiH(L) (L = pyridine or DMAP). Using DFT calculations, the relative reactivity of (PN)M precatalysts was found to be a function of their spin-state energy gaps. For reaction of (PN)MnH with trans-4-octene (1c) there is no viable spin crossover mechanism and migratory insertion is slow, resulting in poor reaction yields. In contrast, (PN)FeH can access a lower barrier through spin crossover, whereas (PN)CoH has a very low migratory insertion barrier from its low spin state. While (PN)NiH has a reasonable migratory insertion barrier, it is plausible that off-catalytic cycle intermediates are responsible for the diminished reaction rate and product yields that are observed experimentally. On the basis of the computed isomerization and borylation energy landscapes, a Curtin-Hammett-type scenario with fast isomerization through β-hydride elimination and migratory insertion steps is proposed, giving rise to a catalytic equilibrium of isomeric (PN)M(octyl) resting states, followed by slow product-forming borylation. The significantly lower barriers calculated for borylation of terminal (PN)M(n-octyl) species versus isomeric internal (PN)M(CHR2) intermediates provides a rationale for the experimentally observed terminal isomerization-hydroboration selectivity.