4795-86-2

Usage

Uses

Used in Fragrance and Flavor Industry:
(1R)-(+)-CIS-PINANE is utilized as a key ingredient in the production of fragrances and flavors, capitalizing on its natural pine scent to enhance the sensory experience of various consumer products.
Used in Organic Synthesis:
(1R)-(+)-CIS-PINANE serves as a chiral building block in organic synthesis, contributing to the creation of complex molecules with specific stereochemistry, which is crucial for the development of pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, (1R)-(+)-CIS-PINANE is employed as a chiral auxiliary in asymmetric synthesis, facilitating the production of enantiomerically pure compounds. Its unique structure aids in the development of new drugs with improved efficacy and reduced side effects.
Used in Agrochemical Industry:
(1R)-(+)-CIS-PINANE also finds applications in the agrochemical industry, where it is used as a chiral resolving agent in enantiomeric separations, ensuring the production of biologically active compounds for use in crop protection and pest management.
Used in Chiral Auxiliary and Resolving Agent Applications:
(1R)-(+)-CIS-PINANE is used as a chiral auxiliary in asymmetric synthesis for its ability to induce specific stereochemistry in the resulting molecules, which is essential for the biological activity and selectivity of pharmaceuticals and agrochemicals. Additionally, it is used as a chiral resolving agent in enantiomeric separations to obtain pure enantiomers, which is vital for the development of effective and safe chiral drugs and agrochemicals.

InChI:InChI=1/C10H18/c1-7-4-5-8-6-9(7)10(8,2)3/h7-9H,4-6H2,1-3H3/t7?,8?,9-/m1/s1

Upstream product

• 18172-67-3 beta-pinene 
• 7785-70-8 (+)-α-pinene 
• 473-62-1 (1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 
• 177698-19-0 Beta-pinene 
• 80-56-8 Pinene 
• 80-56-8 rac-α-pinene 
• 24031-98-9 (1S,4S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 117227-80-2 (-)(1R)-3ξ-chloro-cis-pinane 
• 1118071-19-4 2-chloromethyl-6,6-dimethylbicyclo[3.1.1]heptane 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 473-64-3 (1R,2S,4R,5R)-(+)-neoisoverbanol 

Downstream Products

• 6783-92-2 1,1,2,3-tetramethylcyclohexane 
• 527-84-4 2-methylisopropylbenzene 
• 99-87-6 4-methylisopropylbenzene 
• 95-93-2 1,2,4,5-tetramethylbenzene 
• 54497-05-1 1,1,2,5-tetramethylcyclohexane 
• 95-63-6 1,2,4-Trimethylbenzene 
• 526-73-8 1,2,3-trimethylbenzene 
• 22571-78-4 (+)-cis-pinononoic acid 
• 16580-23-7 1-isopropyl-2-methylcyclohexane 
• 99-82-1 Menthane 
• 79-91-4 terebic acid 
• 100-21-0 terephthalic acid 
• 91-20-3 naphthalene 
• 2436-90-0 (S)-(+)-dihydromyrcene 

Relevant academic research and scientific papers

Crabtree's catalyst revisited; Ligand effects on stability and durability

The extent of time-dependent deactivation of monophosphine monoamine iridium hydrogenation catalysts by trimer formation is strongly dependent on ligand structure; attempts to counter this process lead to the observation of an oligomerisation resistant catalyst. The Royal Society of Chemistry.

New clay-supported chiral rhodium complexes: Interlayer modification with structural tuning guests and asymmetric hydrogenation

The novel host-guest catalysts, in which a chiral rhodium complex was intercalated into structural tuning guests modified smectites, were synthesized, and drastic change in catalysis was observed depending on the orientation of guest molecules.

The Exploration of Sensitive Factors for the Selective Hydrogenation of α-Pinene Over Recyclable Ni-B/KIT-6 Catalyst

The supported Ni-B/KIT-6 amorphous alloy catalyst was prepared by chemical reduction method for the hydrogenation reaction of α-pinene. The catalyst was characterized by XRD, BET, SEM–EDS, TEM, XPS, ICP and DLS, the influences of single factor of catalyst on its structure, morphology and performance were investigated and analyzed. It was found that the amount of Ni loading, preparation pH and B/Ni molar ratio had great effects on the reduction amount, dispersion and specific surface area of the catalyst, resulted in affecting the catalytic performance of the catalyst. The optimum synthesis conditions were at m(Ni2+)/m(KIT-6) = 1:3, pH 13 and n(B)/n(Ni) = 1.5, obtaining a 90.62% conversion of α-pinene and 97.67% selectivity of cis-pinane. In addition, the catalysts also exhibited better repeatability and stability. Graphic Abstract: [Figure not available: see fulltext.]

A General Approach to Deboronative Radical Chain Reactions with Pinacol Alkylboronic Esters

The generation of carbon-centered radicals from air-sensitive organoboron compounds through nucleohomolytic substitution at boron is a general method to generate non-functionalized and functionalized radicals. Due to their reduced Lewis acidity, alkylboronic pinacol esters are not suitable substrates. We report their in situ conversion into alkylboronic catechol esters by boron-transesterification with a substoichiometric amount of catechol methyl borate combined with an array of radical chain processes. This simple one-pot radical-chain deboronative method enables the conversion of pinacol boronic esters into iodides, bromides, chlorides, and thioethers. The process is also suitable the formation of nitriles and allylated compounds through C?C bond formation using sulfonyl radical traps. The power of combining radical and classical boron chemistry is illustrated with a modular 5-membered ring formation using a combination of three-component coupling and protodeboronative cyclization.

Colloid and Nanosized Catalysts in Organic Synthesis: XXII. Hydrogenation of Cycloolefins Catalyzed by Immobilized Transition Metals Nanoparticles in a Three-Phase System

The processes of unsaturated cyclic hydrocarbons hydrogenation in a three-phase gas-liquid-solid catalyst system in the presence of nanostructured nickel, cobalt, or iron catalysts in a flow reactor at 130°C and atmospheric pressure have studied. RX3Extra activated carbon, γ-Al2O3, NaX zeolite, and Purolite CT-175 cation-exchange resin have been used as supports; NaBH4 and NH2NH2·H2O were used as reducing agents. The catalytic activity of supported nanoparticles and their selectivity with respect to the product of exhaustive hydrogenation have been investigated.

Amine-Borane Dehydrogenation and Transfer Hydrogenation Catalyzed by α-Diimine Cobaltates

Anionic α-diimine cobalt complexes, such as [K(thf)1.5{(DippBIAN)Co(η4-cod)}] (1; Dipp=2,6-diisopropylphenyl, cod=1,5-cyclooctadiene), catalyze the dehydrogenation of several amine-boranes. Based on the excellent catalytic properties, an especially effective transfer hydrogenation protocol for challenging olefins, imines, and N-heteroarenes was developed. NH3BH3 was used as a dihydrogen surrogate, which transferred up to two equivalents of H2 per NH3BH3. Detailed spectroscopic and mechanistic studies are presented, which document the rate determination by acidic protons in the amine-borane.

Highly selective and recyclable hydrogenation of α-pinene catalyzed by ruthenium nanoparticles loaded on amphiphilic core–shell magnetic nanomaterials

A multifunctional nanomaterial (Fe3O4@SiO2@CX@NH2) comprising a magnetic core, a silicon protective interlayer, and an amphiphilic silica shell is successfully prepared. Ru nanoparticles catalyst loaded on Fe3O4@SiO2@CX@NH2 is used in hydrogenation of α-pinene for the first time. The novel nanomaterial with amphipathy can be used as a solid foaming agent to increase gas–liquid–solid three-phase contact and accelerate the reaction. Under the mild conditions (40?°C, 1?MPa H2, 3?h), 99.9% α-pinene conversion and 98.9% cis-pinane selectivity are obtained, which is by far the best results reported. Furthermore, the magnetic nanocomposite catalyst can be easily separated by an external magnet and reused nine times with high selectivity maintaining.

Room Temperature Iron-Catalyzed Transfer Hydrogenation and Regioselective Deuteration of Carbon-Carbon Double Bonds

An iron catalyst has been developed for the transfer hydrogenation of carbon-carbon multiple bonds. Using a well-defined β-diketiminate iron(II) precatalyst, a sacrificial amine and a borane, even simple, unactivated alkenes such as 1-hexene undergo hydrogenation within 1 h at room temperature. Tuning the reagent stoichiometry allows for semi- and complete hydrogenation of terminal alkynes. It is also possible to hydrogenate aminoalkenes and aminoalkynes without poisoning the catalyst through competitive amine ligation. Furthermore, by exploiting the separate protic and hydridic nature of the reagents, it is possible to regioselectively prepare monoisotopically labeled products. DFT calculations define a mechanism for the transfer hydrogenation of propene with nBuNH2 and HBpin that involves the initial formation of an iron(II)-hydride active species, 1,2-insertion of propene, and rate-limiting protonolysis of the resultant alkyl by the amine N-H bond. This mechanism is fully consistent with the selective deuteration studies, although the calculations also highlight alkene hydroboration and amine-borane dehydrocoupling as competitive processes. This was resolved by reassessing the nature of the active transfer hydrogenation agent: experimentally, a gel is observed in catalysis, and calculations suggest this can be formulated as an oligomeric species comprising H-bonded amine-borane adducts. Gel formation serves to reduce the effective concentrations of free HBpin and nBuNH2 and so disfavors both hydroboration and dehydrocoupling while allowing alkene migratory insertion (and hence transfer hydrogenation) to dominate.

Hydrogenation of hydrophobic substrates catalyzed by gold nanoparticles embedded in Tetronic/cyclodextrin-based hydrogels

Hydrogenation of alkenes, alkynes and aldehydes was investigated under biphasic conditions using Au nanoparticles (AuNP) embedded into combinations of α-cyclodextrin (α-CD) and a poloxamine (Tetronic90R4). Thermo-responsive AuNP-containing α-CD/Tetronic90R4 hydrogels are formed under well-defined conditions of concentration. The AuNP displayed an average size of ca. 7 nm and a narrow distribution, as determined by TEM. The AuNP/α-CD/Tetronic90R4 system proved to be stable over time. Upon heating above the gel-to-sol transition temperature, the studied catalytic system allowed hydrogenation of a wide range of substrates such as alkenes, alkynes and aldehydes under biphasic conditions. Upon repeated heating/cooling cycles, the Au NP/α-CD/Tetronic90R4 catalytic system could be recycled several times without a significant decline in catalytic activity.

Efficient and selective reduction of α-pinene to cis-pinane by NaBH4 using NiCl2?6H2O/PEG-800/ethanol as the catalytic system

The reduction of α-pinene by NaBH4 was achieved using NiCl2?6H2O in PEG-800/ethanol system under room temperature. Under the optimized conditions, the conversion of α-pinene and the selectivity of cis-pinane reached 97% and 98%, respectively. On the basis of TEM and a series of poisoning experiments, the nature of the active catalytic species for the reaction was discussed.