19079-29-9

Usage

Chemical Description

(+)-3-carene is a terpene derivative that serves as the starting material for the synthesis of the rigidified amino acids.

Upstream product

• 4497-92-1 2-carene 
• 201230-82-2 carbon monoxide 
• 82470-87-9 α-terpinylphenylsulphide 
• 917-54-4 methyllithium 
• 94806-25-4 (E)-4-(Tri-n-butylstannyl)-3-buten-2-one 
• 78-79-5 isoprene 
• 936-91-4 3-carene epoxide 
• 116872-39-0 (+/-)-10-phenylsulfonylcar-3-ene 
• 3479-89-8 3,7,7-trimethyl-cyclohepta-1,3,5-triene 
• 15103-32-9 4-hydroxymethyl-2-carene 
• 936-91-4 α-3,4-Epoxycarane 
• 554-61-0 2-carene 
• 80-56-8 Pinene 
• 108-24-7 acetic anhydride 

Downstream Products

• 17092-80-7 m-mentha-1,3(8)-diene 
• 4017-83-8 (-)-(1R,3R,6S)-4-methylene-7,7-dimethylbicyclo[4.1.0]heptan-3-ol 
• 499-03-6 (3R)-(+)-Sylvestren 
• 13837-95-1 1(7),8-m-Menthadien, β-Silvestren 
• 5208-37-7 8-hydroxy-m-cymene 
• 5208-31-1 (5S)-(-)-5β-(1-Hydroxy-1-methylethyl)-1-methyl-1,3-cyclohexadien 
• 65221-02-5 3-caren-9-ol 
• 498-12-4 3-carene-10-carboxylic acid 
• 74496-72-3 3-carene-9-carboxylic acid 
• 74496-73-4 (-)-3-carene-9-carboxylic acid 
• 38462-38-3 (1R,3R,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-4-en-3-ylmethyl acetate 
• 21558-57-6 Acetic acid (1R,2R,5R)-5-isopropenyl-2-methyl-cyclohex-3-enylmethyl ester 
• 57400-90-5 (+)-8-Acetoxy-p-mentha-1,5-dion 
• 43124-74-9 p-Menth-4-en-1,2-diol 

Relevant academic research and scientific papers

SYNTHESIS OF FUSED CYCLOPROPANES FROM γ-STANNYL ALCOHOLS

Fused cyclopropanes including 3-carene and isosequicarene have been prepared by treatment of γ-stannyl alcohols with thionyl chloride.

Regioselective and Stereospecific Copper-Catalyzed Deoxygenation of Epoxides to Alkenes

Two copper salts (Cu(CF3CO2)2 and IMesCuCl) were identified as earth-abundant, inexpensive, but effective metal catalysts together with diazo malonate for chemo-/regioselective and stereospecific deoxygenation of various epoxides with tolerance of common functional groups (alkene, ketone, ester, p-methoxybenzyl, benzyl, tert-butyldimethylsilyl, and triisopropylsilyl). In particular, the unprecedented regioselectivity allowed for the first time monodeoxygenation of diepoxides to alkenyl epoxides. Density functional theory mechanistic studies showed that the deoxygenation occurred by collapsing the free ylide, unfavoring the possible intuitive pathway via cycloreversion of possible oxetane.

Unusual reactions of (+)-Car-2-ene and (+)-Car-3-ene with aldehydes on K10 clay

The reactions of (+)-car-2-ene (1) and (+)-car-3-ene (2) with aldehydes in the presence of montmorillonite clay were studied for the first time (Schemes 3 and 5). The major products of these reactions are optically active, substituted hexahydroisobenzofurans, probably formed as a result of an attack of the protonated aldehyde at the cyclopropane ring. Quite unexpectedly, the products are cis-configured at the ring-fusion site; the fact was established by means of quantum-chemical calculations and NMR data. It appeared that the behavior of the 2 : 3 mixture 1/2 in reactions with aldehydes in the presence of K10 clay differed substantially from the reactivities of the corresponding individual monoterpenes. Copyright 2010 Verlag Helvetica Chimica Acta AG, Zuerich, Switzerland.

Thermal transformation of monoterpenes within thionin-supported zeolite Na-Y. Acid-catalyzed or electron transfer-induced?

Several monoterpenes (monocyclic, bicyclic or acyclic) isomerize and finally transform to p-cymene in the dark upon loading within thionin-supported zeolite Na-Y. The same reactions occur in Na-Y dried under the same conditions as thionin/Na-Y. It is postulated that the thermal treatment of Na-Y generates 'electron holes' (probably acidic sites). The transformation of monoterpenes occurs more likely via an electron transfer-induced reaction subordinated to the occurrence of the acidic sites. The radical cation of the more thermodynamically stable monoterpene, α-terpinene, eventually dehydrogenates to p-cymene. For comparison, the same reactions were performed within methyl viologen-supported Na-Y. Copyright

Reactions of some terpenes and their derivatives with acylating agents in the presence of aluminosilicate catalysts

Reactions of camphene, α-fenchene, limonene, caryophyllene, α- and β-pinenes, verbenol, walterol, and verbenone with acylating agents in the presence of clay K-10 and wide-porous β-zeolite were studied. Presumable schemes and rules of the occurring proces

Fine particle and gaseous emission rates from residential wood combustion

Residential wood combustion emissions were analyzed to determine emission rates and to develop chemical emissions profiles that represent the appliances and woods typically used in wood-burning-communities. Over 350 elements, inorganic compounds, and organic compounds were quantified. A range of 4-9 g/kg dry fuel of particulate matter(a dilution stack sampler equipped with a 2.5-μm particle selective cyclone. Emissions were diluted 20-70 times, cooled to ambient temperature, and allowed 80 s for condensation prior to collection. Wood type, wood moisture, burn rate, and fuel load were varied for different experiments. Fine particle and se mivolatile organic compounds were collected on filter/PUF/XAD/PUF cartridges. Inorganic samples and mass were collected on Teflon and quartz filters. Volatile organic carbon compounds were trapped with Tenax (C8- C20), canister (C2-C12), and 2,4-dinitrophenylhydrazine impregnated cartridges (carbonyl compounds). Analysis of particle and semivolatile organic species was conducted by gas chromatography/mass spectrometry. Teflon filters were analyzed for mass by gravimetry, trace elements were analyzed by X-ray fluorescence and ammonium was analyzed by automated colorimetry. Quartz filters were analyzed for organic and elemental carbon by thermal/optical reflectance, and forts were analyzed by ion chromatography. Select quartz filters were analyzed by accelerator mass spectrometry for carbon-12 and carbon-14 abundance. Canister and Tenax samples were analyzed by gas chromatography with a flame ionization detector, and carbonyl compounds were analyzed by high-performance liquid chromatography. Residential wood combustion emissions were analyzed to determine emission rates and to develop chemical emissions profiles that represent the appliances and woods typically used in wood-burning communities. Over 350 elements, inorganic compounds, and organic compounds were quantified. A range of 4-9 g/kg dry fuel of particulate matter (a dilution stack sampler equipped with a 2.5-μm particle selective cyclone. Emissions were diluted 20-70 times, cooled to ambient temperature, and allowed 80 s for condensation prior to collection. Wood type, wood moisture, burn rate, and fuel load were varied for different experiments. Fine particle and semivolatile organic compounds were collected on filter/PUF/XAD/PUF cartridges. Inorganic samples and mass were collected on Teflon and quartz filters. Volatile organic carbon compounds were trapped with Tenax (C8-C20), canister (C2-C12), and 2,4-dinitrophenylhydrazine impregnated cartridges (carbonyl compounds). Analysis of particle and semivolatile organic species was conducted by gas chromatography/mass spectrometry. Teflon filters were analyzed for mass by gravimetry, trace elements were analyzed by X-ray fluorescence, and ammonium was analyzed by automated colorimetry. Quartz filters were analyzed for organic and elemental carbon by thermal/optical reflectance, and ions were analyzed by ion chromatography. Select quartz filters were analyzed by accelerator mass spectrometry for carbon-12 and carbon-14 abundance. Canister and Tenax samples were analyzed by gas chromatography with a flame ionization detector, and carbonyl compounds were analyzed by high-performance liquid chromatography.

Syntheses with organoboranes - VIII. Transformation of (1S,6R)-(+)-2- carene into (1S,6R)-(+)-3(10)-carene and (1R,5R)-(-)-α-thujene into (1R,5R)- (+)-sabinene

The transformation of (1S,6R)-(+)-2-carene and (1R,5R)-(-)-α-thujene into (1S,6R)-(+)-3(10)-carene and (1R,5R)-(+)-sabinene, respectively, by metallation-transmetallation-hydrolysis via the corresponding allylic organoborane intermediates is described.

Chiral Synthesis via Organoboranes. 35. Simple Procedures for the Efficient Recycling of the Terpenyl Chiral Auxiliaries and Convenient Isolation of the Homoallylic Alcohols in Asymmetric Allyl- and Crotylboration of Aldehydes

Asymmetric allyl- and crotylboration of aldehydes, RCHO, with terpenyl-based allyl- and crotylborane reagents Ter2*BAll (1), Ter2*BCrtZ (2), and Ter2*BCrtE (3, Ter* = Ipc, 4-Icr and 2-Icr; All = allyl and Crt = crotyl), afford Ter2*BOCH*(R)C*(1R)(2R)CH=CH2 intermediates 4.In these reactions, the isolation of homoallylic alcohols, HOCH*(R)C*(1R)(2R)CH=CH2 (5), can be accomplished via oxidation of 4 with alkaline hydrogen peroxide.Unfortunately, oxidative workup destroys the chiral auxiliary and produces a large amount of nonrecyclable byproduct, terpenol (Ter*OH).Further, isolation of the pure homoallylic alcohol by distillation can be difficult if it boils in the range of the abundant byproduct.Therefore, in order to recycle the chiral auxiliaries and isolate the product homoallylic alcohols in an efficient manner, we have developed the following procedures: (1) elimination workup, in which enantiomerically pure α-pinene and Δ2- and Δ3-carenes are liberated from terpenylborinates 4 by treatment with isobutyraldehyde and 1 mol percent BF3*OEt2; (2) ethanolamine workup involving treatment of 4 with ethanolamine (EA) to achieve the precipitation of the ethanolamine adducts (EA-BTer2*, Ter* = Ipc and 2-Icr, 11 and 12) from which the Ter2*BOMe can be easily regenerated; and (3) 8-hydroxyquinoline workup, involving treatment of 4 with 8-hydroxyquinoline (8-HQ) to precipitate the 8-HQ adducts (8-HQ-BTer2*, Ter* = Ipc, 4-Icr and 2-Icr, 13-15), from which the various Ter2*BOMe intermediates can be conveniently liberated.It is hoped that these procedures will significantly enhance the scope of asymmetric allyl-/crotylboration of aldehydes with Ter2*BAll (1), Ter2*BCrtZ (2), and Ter2*BCrtE (3) and serve as excellent alternatives for any catalytic versions yet to be discovered.

Stereospecific Conversions of (+)-2- and (+)-3-Carenes into Optically active Seven-Membered Ring Systems

The reactions of (+)-2-carene (6b) and (+)-3-carene (15) with iron carbonyls are studied under various conditions.Besides double bond isomerization and interconversion of the two isomeric hydrocarbons, at least two different modes of ring opening leading to six- and seven-membered ring products are observed.Under mild conditions the primary ring opening complex 7b is isolated without loss of sterical information.Carbonylation of 7b under various conditions yields optically active cycloheptene systems 18, 19, and 20 or the bicyclic systems 9b and 10b.

Transformations of 3-carene oxide at rhenium-containing catalysts

The transformations of 3-carene oxide at rhenium-containing catalysts were studied.The introduction of rhenium into the catalytic system significantly increases the reaction rate and leads to the formation of compounds not previously encountered in the products from the isomerization of 3-carene oxide, i.e., 3-carene, 3(10),4-caradiene, 3,3,6-trimethylcycloheptanone, and 3-caren-10-ol.