499-97-8

Usage

Synthesis Reference(s)

Tetrahedron Letters, 21, p. 1767, 1980 DOI: 10.1016/S0040-4039(00)77832-4

InChI:InChI=1/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h10H,1,3-7H2,2H3

Upstream product

• 18479-64-6 1-hydroxymethy-4-isopropenyl-1-cyclohexane 
• 144-62-7 oxalic acid 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 74043-09-7 4-acetyl-1-trimethylsilylmethyl-1-cyclohexene 
• 177698-19-0 Beta-pinene 
• 7299-42-5 δ-terpineol 
• 67-56-1 methanol 
• 5989-27-5 D-limonene 
• 288-32-4 1H-imidazole 
• 5989-54-8 (-)-(S)-limonene 
• 18172-67-3 beta-pinene 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 70901-64-3 trimethyl(2-methylenebut-3-enyl)silane 
• 536-59-4 perillol 

Relevant academic research and scientific papers

PROCESS FOR PREPARING JET FUEL FROM MOLECULES DERIVED FROM BIOMASS

The invention relates to a process for preparing jet fuel or jet fuel precursors which comprises the treatment of a charge derived from biomass, the said charge comprising at least one compound chosen from terpenes of formula [CH2=C(CH3)CH=CH2]n, in which n is an integer of from 2 to 12, the carbon chain of which is linear, cyclic or branched, or cyclic or branched terpenes as defined previously, which have been chemically modified by oxidation and/or rearrangement of the carbon backbone, the said process comprising a cycloaddition step (i) followed by a cracking and hydrogenation step (ii).

Unique catalysis of gold nanoparticles in the chemoselective hydrogenolysis with H2: Cooperative effect between small gold nanoparticles and a basic support

Gold nanoparticles on hydrotalcite act as a heterogeneous catalyst for the chemoselective hydrogenolysis of various allylic carbonates to the corresponding terminal alkenes using H2 as a clean reductant. The combination of gold nanoparticles and basic supports elicited significantly unique and selective catalysis in the hydrogenolysis.

Kinetics of thermal conversions of monoterpenic compounds in supercritical lower alcohols

The most important information concerning thermal conversions of vegetable terpenes (α-pinene, β-pinene, turpentine, and cis-verbenol) in supercritical lower alcohols is systematized. The kinetics of selected reactions is reported and is compared with the kinetics of the same reactions in the gas and liquid phases. Thermodynamic calculations of the phase states and kinetic parameters are presented for a number of multicomponent multiphase systems containing terpenes and lower alcohols. The effect of the supercritical solvent pressure on the rate and selectivity of the selected reactions is reported.

Intermolecular hydroaminations via strained (E)-cycloalkenes

(Chemical Equation Presented) A photoinduced procedure for the intermolecular hydroamination of alkenes using azoles is described. This reaction occurs in modest to good yield for 6- and 7-membered cyclic alkenes. Upon irradiation at 254 nm in the presence of methyl benzoate and a small amount of triflic acid as an additive (20 mol %), imidazoles, pyrazoles, triazoles, and tetrazole can react with the alkene to afford complex Markovnikov adducts. The proposed mechanism involves photoisomerization to generate highly strained (E)-cycloalkene intermediates and (E)-cycloalkene protonation followed by reaction with the azole nucleophile. Alkene isomerization was found to be a competing side reaction under these conditions.

Comparative thermolysis of β-and α-pinenes in supercritical ethanol: The reaction characterization and enantiomeric ratios of products

The thermolysis of β-pinene and the co-thermolysis of an equimolar mixture of β-and α-pinenes in supercritical ethanol were carried out. The reaction of β-pinene affords β-myrcene as the major product (>70%). Considerable differences in the temperature dependence of the reaction rate were revealed for the transformations of β-pinene into β-myrcene and of α-pinene into limonene. The pre-exponential factors and the activation energies were calculated. The enantiomeric ratios of the thermolysis products of β-and α-pinenes and limonene were estimated. The starting monoterpenes do not undergo racemization during thermolysis. The thermolysis of enantiomerically pure α-pinene affords racemic (±)-limonene, whereas (-)-β-pinene gives (-)-limonene. The enantiomeric ratio in the latter remains equal to the enantiomeric purity of the starting β-pinene.

Comprehensive kinetic and mechanistic considerations for the gas-phase behaviour of pinane-type compounds

The thermal behaviour of selected pinane-type compounds, α-pinene (1), β-pinene (2), pinane (3) and nopinone (4), has been investigated. The conversion of the bicyclic starting materials to their acyclic and monocyclic isomers as well as the consecutive reactions of the acyclic main isomerisation products are discussed. The conversion of 1-4 in a reaction network is presented and the experimental evidence for the formation of pyrolysis products by a biradical pathway is discussed. In addition to these results a kinetic model describing the isomerisation of the bicyclic compounds to their acyclic and monocyclic isomers is presented. A good correlation between kinetic simulations and experimental data is revealed. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Thermal behaviour of selected C10H16 monoterpenes

The presented work investigates the thermal behaviour of selected monoterpenes under various reactor temperatures and residence times (carrier gas, reactor inserts). In addition to the analysis of the liquid products by capillary GC and GC-MS, chemical derivatisation techniques (Diels-Alder reaction, hydrogenation) were used to identify the liquid-phase products. A thermal conversion of β-pinene (1), myrcene (2) and limonene (4) in a reaction network is presented and the experimental evidence for the formation of pyrolysis products by a biradical pathway is discussed. The reaction network was modified based on the identification of additional C10H 16 terpene isomers. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

Diastereoselectivity control in photosensitized addition of methanol to (r)-(+)-limonene

Highly diastereodifferentiating bimolecular asymmetric photoreaction was achieved in the photosensitized polar addition of methanol to (R)-(+)-limonene. The diastereomeric excess (de) of the photoadduct could be controlled and fine-tuned by changing the i

Highly diastereoselective photoaddition of methanol to limonene

Extremely high diastereomeric excess was achieved from the photosensitized polar addition of methanol to (R)-(+)-limonene 1. Diastereomeric excess was varied from 28.1 to 96.3% depending on the solvent polarity, reaction temperature, and structure of sens

Halogenated Terpenoids. XXIX the 1-Bromo 1-Bromomethyl Cyclohexyl System

Bromination of methylene groups exocyclic to cyclohexyl systems normally affords two isomeric products; the axial 1-bromo equatorial 1-bromomethyl compound and the axial 1-bromomethyl equatorial 1-bromo derivative. Free energy differences between these two isomers, and the conformations adopted by the axial 1-bromomethyl group, have been explored by n.m.r. spectroscopy, by X-ray crystallography and by MM3 calculations. Evidence is presented to show that the ax-bromomethyl group exists primarily as those rotamers which site the bromine atom synclinal to the vicinal bromine. The A value for a bromomethyl group in this system is then similar to that of an unsubstituted methyl group.