625-65-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 3860, 1980 DOI: 10.1021/jo01307a025

InChI:InChI=1/C7H14/c1-6(2)5-7(3)4/h5-6H,1-4H3

Upstream product

• 110-86-1 pyridine 
• 68573-19-3 2-bromo-2,4-dimethyl-pentane 
• 109-06-8 α-picoline 
• 108-48-5 2,6-dimethylpyridine 
• 1000-86-8 2,4-Dimethyl-1,3-pentadiene 
• 102-71-6 triethanolamine 
• 111-76-2 2-Butoxyethanol 
• 64-17-5 ethanol 
• 917-58-8 potassium ethoxide 
• 52912-56-8 2,4-dimethylpentan-3-yl iodide 
• 600-36-2 2,4-dimethyl-3-pentanol 
• 625-06-9 2,4-dimethyl-2-pentanol 
• 84612-74-8 2,4-dimethyl-3-acetoxypentane 
• 5438-17-5 2-hydroxy-2-isopropyl-3-methyl-butyric acid 

Downstream Products

• 66225-53-4 2,4-dimethyl-pentane-2,3-diol 
• 108-08-7 2,4-dimethylpentane 
• 625-06-9 2,4-dimethyl-2-pentanol 
• 49714-52-5 2,2,3-trimethylbutanoic acid 
• 79-31-2 isobutyric Acid 
• 55422-07-6 2,2,4,4-tetramethyl-1-phenyl-phosphetane 1-oxide 
• 82947-39-5 2,2-Bis(trifluoromethyl)ethane-1,1-dicarbonitrile 
• 134539-96-1 2,2,4-Trimethyl-6,6-bis-trifluoromethyl-cyclohex-3-ene-1,1-dicarbonitrile 
• 565-75-3 2,3,4-trimethylpentane 
• 34557-54-5 methane 
• 690-08-4 (E)-4,4-dimethyl-2-pentene 
• 74-84-0 ethane 
• 75-28-5 Isobutane 
• 563-46-2 2-Methyl-1-butene 

Relevant academic research and scientific papers

Kinetics of the thermal isomerization of 1,1,2,2-tetramethylcyclopropane

Reaction rates for the structural isomerization of 1,1,2,2- tetramethylcyclopropane to 2,4-dimethyl-2-pentene have been measured over a wide temperature range, 672-750 K in a static reactor and 1000-1120 K in a single-pulse shock tube. The combined data from the two temperature regions give Arrhenius parameters Ea = 64.7 (±0.5) kcal/mol and log 10(A, s-1) = 15.47 (±0.13). These values lie at the upper end of the ranges of Ea and log A values (62.2-64.7 kcal/mol and 14.82-15.55. respectively) obtained from three previous experimental studies, each of which covered a narrower temperature range. The previously noted trend toward lower Ed values for structural isomerization of methylcyclopropanes as methyl substitution increases extends only through the dimethylcyclopropanes (1,1- and 1,2-); Ea then appears to increase with further methyl substitution. In contrast, the pre-exponential factors for isomerization of cyclopropane and all of the methylcyclopropanes through tetramethylcyclopropane lie within ±0.3 of log10(A,s -1) = 15.2 and show no particular trend with increasing substitution.

Decarbonylative Olefination of Aldehydes to Alkenes

New atom-economical alternatives to Wittig chemistry are needed to construct olefins from carbonyl compounds, but none have been developed to-date. Here we report an atom-economical olefination of carbonyls via aldol-decarbonylative coupling of aldehydes using robust and recyclable supported Pd catalysts, producing only CO and H2O as waste. The reaction affords homocoupling of aliphatic aldehydes, as well as heterocoupling of aliphatic and aromatic ones. Computations provide insight into the selectivity and thermodynamics of the reaction. The tandem aldol-decarbonylation reaction opens the door to exploration of new carbonyl reactivity to construct olefins.

Alkanethiolate-capped palladium nanoparticles for selective catalytic hydrogenation of dienes and trienes

Selective hydrogenation of dienes and trienes is an important process in the pharmaceutical and chemical industries. Our group previously reported that the thiosulfate protocol using a sodium S-alkylthiosulfate ligand could generate catalytically active Pd nanoparticles (PdNP) capped with a lower density of alkanethiolate ligands. This homogeneously soluble PdNP catalyst offers several advantages such as little contamination via Pd leaching and easy separation and recycling. In addition, the high activity of PdNP allows the reactions to be completed under mild conditions, at room temperature and atmospheric pressure. Herein, a PdNP catalyst capped with octanethiolate ligands (C8 PdNP) is investigated for the selective hydrogenation of conjugated dienes into monoenes. The strong influence of the thiolate ligands on the chemical and electronic properties of the Pd surface is confirmed by mechanistic studies and highly selective catalysis results. The studies also suggest two major routes for the conjugated diene hydrogenation: the 1,2-addition and 1,4-addition of hydrogen. The selectivity between two mono-hydrogenation products is controlled by the steric interaction of substrates and the thermodynamic stability of products. The catalytic hydrogenation of trienes also results in the almost quantitative formation of mono-hydrogenation products, the isolated dienes, from both ocimene and myrcene.

DIARYL AMINE ANTIOXIDANTS PREPARED FROM BRANCHED OLEFINS

Diaryl amines are selectively alkylated by reaction with branched olefins, which olefins are capable of forming tertiary carbonium ions and can be conveniently prepared from readily available branched alcohols. The diaryl amine products are effective antioxidants and often comprise a high amount of di-alkylated diaryl amines and a low amount of tri- and tetra-alkylated diaryl amines.

Cross-linked polymer coated Pd nanocatalysts on SiO2 support: Very selective and stable catalysts for hydrogenation in supercritical CO 2

Using greener solvents, enhancing the selectivity and stability of catalysts is an important aspect of green chemistry. In this work, we developed a route to immobilize Pd nanoparticles on the surface of silica particles with cross-linked polystyrene coating by one-step copolymerization, and Pd(0) nanocatalysts supported on the silica particle supports with cross-linked polystyrene coating were successfully prepared. The catalysts were characterized by Fourier transform infrared spectroscopy (FTIR), transmission electron microscopy (TEM), plasma optical emission spectroscopy, and thermogravimetric analysis (TGA), and were used for hydrogenation of 2,4-dimethyl-1,3-pentadiene to produce 2,4-dimethyl-2-pentene and allyl alcohol to produce 1-propanol. It was found that the selectivity of the reaction was enhanced significantly by the polymer coating, and the catalysts were very stable due to the insoluble nature of the cross-linked polymers. Supercritical (sc)CO2 can accelerate the reaction rates of the reactions catalyzed by the specially designed catalysts significantly. The excellent combination of polymer coating and scCO2 has wide potential applications in catalysis.

High yield of liquid range olefins obtained by converting i-propanol over zeolite H-ZSM-5

Methanol, ethanol, and i-propanol were converted under methanol-to-gasoline (MTH)-like conditions (400°C, 1-20 bar) over zeolite H-ZSM-5. For methanol and ethanol, the catalyst lifetimes and conversion capacities are comparable, but when i-propanol is use

Total synthesis of (-)-heptemerone B and (-)-guanacastepene E

A concise, stereoselective, and convergent total synthesis of the unnatural enantiomer of the neodolastane diterpenoid heptemerone B has been completed. Saponification of (-)-heptemerone afforded (-)-guanacastepene E. The absolute stereochemistry of (-)-heptemerone B was thus established as 5-(S), the same as (-)-guanacastepene E. The longest linear sequence of the synthesis comprises 17 (18) steps from simple known starting materials. Our general synthetic approach integrates a diverse set of reactions, including an intramolecular Heck reaction to create one quaternary stereocenter and a cuprate conjugate addition for the establishment of the other. The central seven-membered ring was closed with an uncommon electrochemical oxidation, whereas the five-membered ring was formed through ring-closing metathesis. The absolute configuration of the two key building blocks was established through an asymmetric reduction and an asymmetric ene reaction.

Silica-supported dendrimer-palladium complex-catalyzed selective hydrogenation of dienes to monoolefins

The selective hydrogenation of cyclic and acyclic dienes to monoolefins occurs under very mild conditions, in the presence of silica-supported PAMAM-Pd complexes. The activity and selectivity of this reaction is sensitive to the dendrimer structure. These dendritic complexes display excellent recycle properties, retaining activity for up to eight recycles.

Dilithiated phosphazenes: Scaffolds for the synthesis of olefins through a new class of bicyclic 1,2-oxaphosphetanes

The first examples of the PN-directed dilithiation of (N-methoxycarbonyl)phosphazenes in the Cα and Cortho to the phosphorus, and the use of these dianions in the formation of tri- and tetra-substituted olefins through stereospecific thermolysis of a new type of isolable bicyclic 1,2-oxaphosphetanes are described.

Control of regioselectivity by the lone substituent through steric and electronic effects in the nitrosoarene ene reaction of deuterium-labeled trisubstituted alkenes

For the ene reaction of 4-nitronitrosobenzene (ARNO) with a variety of primary and secondary lone alkyl-substituted substrates, the twix/twin regioselectivity is constant at about 85:15. In contrast, for the lone tert-butyl group and for lone aryl substituents, the twix regioisomer is obtained exclusively. These regioselectivities have been rationalized in terms of steric interactions and coordination between the enophile and the substrates in the transition states of the first reaction step.