1674-08-4

Usage

Definition

ChEBI: The (1S,3R,5S)-stereoisomer of pinocarveol.

Upstream product

• 17004-05-6 3-amino-β-pinene 
• 515-00-4 myrtenol 
• 58434-29-0 myrtenyl hydroperoxide 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 177698-19-0 Beta-pinene 
• 1686-14-2 α-pinene epoxide 
• 16812-40-1 pinocarvone 
• 80-56-8 Pinene 
• 111827-60-2 10-dimethylmethoxysilyl-α-pinene 
• 51131-99-8 (1S,3R,5S)-3-hydroperoxy-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane 
• 19890-00-7 (1S)-pinocarvone 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 14575-92-9 2,3-epoxy-cis-pinane 

Downstream Products

• 18172-67-3 (?)-β-pinene 
• 7785-26-4 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 16812-40-1 pinocarvone 
• 4080-46-0 2⁽¹⁰⁾,3-pinadiene 
• 99-87-6 4-methylisopropylbenzene 
• 21195-59-5 2-methyl-5-(1-methylethenyl)-1,3-cyclohexadiene 
• 18358-53-7 pinocamphone 
• 1196-00-5 (-)-isopinocampheol 
• 10446-49-8 4-nitro-benzoic acid-((1S,3R)-pin-2⁽¹⁰⁾-en-3-yl ester) 
• 18680-27-8 pinanediol 
• 20536-52-1 2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol 
• 52363-24-3 β-<2,2,3-Trimethyl-cyclopentyl>-aethanol 
• 1727-66-8 (-)-(1S)-(2,2,3-trimethylcyclopent-3-en-1-yl)acetic acid 
• 1741-36-2 3.5-Dinitro-benzoesaeure-(+)-neoisopinocampheyl-ester 

Relevant academic research and scientific papers

Application of an indenyl molybdenum dicarbonyl complex in the isomerisation of α-pinene oxide to campholenic aldehyde

The complex [{(η5-Ind)Mo(CO)2(μ-Cl)} 2] (1) has been tested for the industrially relevant catalytic isomerisation of α-pinene oxide (PinOx) to campholenic aldehyde (CPA) in the liquid phase. PinOx conversion and CPA selectivity are strongly influenced by the solvent employed. Complete conversion of PinOx was achieved within 1 min at 55 °C or 30 min at 35 °C using 1,2-dichloroethane as solvent, giving CPA in 68% yield. Other products included trans-carveol, iso-pinocamphone and trans-pinocarveol. The stability of 1 under the reaction conditions used was investigated by using FT-IR spectroscopy and electrospray ionisation mass spectrometry (ESI-MS) to characterise recovered solids. In the presence of air/moisture 1 undergoes oxidative decarbonylation upon dissolution to give oxomolybdenum species that are proposed to include a tetranuclear oxomolybdenum(v) complex. Conversely, ESI-MS studies of 1 dissolved in dry acetonitrile show mononuclear species of the type [IndMo(CO)2(CH 3CN)n]+. The crystal structure of the ring-slipped dicarbonyl complex [(η3-Ind)Mo(CO) 2Cl(CH3CN)2] (2) (obtained after dissolution of 1 in acetonitrile) is reported. the Partner Organisations 2014.

Rearrangement of α-pinene oxide to campholenic aldehyde over the trimesate metal-organic frameworks MIL-100, MIL-110 and MIL-96

The catalytic performance of porous metal-benzenetricarboxylates, such as MIL-100(Al, Fe and Cr), MIL-110(Al) and MIL-96(Al), was investigated with a combination of physicochemical and catalytic approaches in the rearrangement of α-pinene oxide to campholenic aldehyde (CA). The investigation of Lewis acidity was done by EPR and IR spectroscopy using 2,2′,6,6′- tetramethyl-1-piperidinyoxyl radical and benzonitrile as the probe molecules, respectively. For Al-BTCs, both these methods showed a decrease in the amount of Lewis acid sites as follows: MIL-100 > MIL-110 > MIL-96. The reaction rate and selectivity toward CA also decreased in the same order. A relatively good correlation between selectivity toward CA and the electronegativity of the metal ion was found for isostructural MIL-100(Al, Fe and Cr). The selectivity toward CA decreased in the order: MIL-100(Al) > MIL-100(Fe) > MIL-100(Cr). The high selectivity toward CA in the presence of MIL-100 has been suggested to originate from the unique structure of this material, which favors shape selectivity.

Acid/vanadium-containing saponite for the conversion of propene into coke: Potential flame-retardant filler for nanocomposite materials

Vanadium-containing saponite samples were synthesized in a one-pot synthetic procedure with the aim of preparing samples for potential application as fillers for polymeric composites. These vanadium-modified materials were prepared from an acid support by adopting a synthetic strategy that allowed us to introduce isolated structural V species (H/V-SAP). The physicochemical properties of these materials were investigated by XRD analysis and by DR-UV/Vis and FTIR spectroscopy of CO that was adsorbed at 100 K; these data were compared to those of a V-modified saponite material that did not contain any Bronsted acid sites (Na/V-SAP). The surface-acid properties of both samples (together with the fully acidic H-SAP material and the Na-SAP solid) were studied in the catalytic isomerization of α-pinene oxide. The V-containing solids were tested in the oxidative dehydrogenation reaction of propene to evaluate their potential use as flame-retardant fillers for polymer composites. The effect of tuning the presence of Lewis/Bronsted acid sites was carefully studied. The V-containing saponite sample that contained a marked presence of Bronsted acid sites showed the most interesting performance in the oxidative dehydrogenation (ODH) reactions because they produced coke, even at 773 K. The catalytic data presented herein indicate that the H/V-SAP material is potentially active as a flame-retardant filler. In questo lavoro e stato sintetizzata tramite metodologia one-pot una saponite contenente in struttura vanadio, di interesse come additivo per compositi polimerici. La metodologia di sintesi adottata ha permesso di ottenere un solido acido contenente siti di vanadio strutturale isolati (H/V-SAP). Le proprieta chimico-fisiche di tale materiale sono state studiate tramite XRD, DR-UV-Vis e FT-IR di CO adsorbito a 100 K e confrontate con quelle di una V-saponite priva di acidita di Bronsted (Na/V-SAP). Le proprieta acide di entrambi i materiali (e di saponiti acidi H-SAP e sodica Na-SAP) sono state investigate sottoponendo i campioni ad un test catalitico di isomerizzazione dell' ossido di α-pinene. I campioni contenenti vanadio sono stati infine testati come catalizzatori per la reazione di deidrogenazione ossidativa del propene, con l'obiettivo di valutarne i loro potenziale uso come additivi ritardanti di fiamma per compositi polimerici. La saponite contenente vanadio strutturale e caratterizzata da una marcata acidita di Bronsted ha mostrato le migliori prestazioni catalitiche, producendo prodotti carboniosi anche ad alte temperature di esercizio (773 K). I dati catalitici qui mostrati indicano che il campione H/V-SAP e potenzialmente attivo come ritardante di fiamma per compositi polimerici. A hard day's saponite: An acid/vanadium-containing saponite (H/V-SAP) was synthesized and its physicochemical properties were compared to those of a V-modified saponite material that did not contain acid sites. Both samples were tested in the oxidative dehydrogenation (ODH) reaction of propene to study the capability of the samples to form coke species. H/V-SAP was the most interesting catalyst for the production of coke. Copyright

Ascaridole as a pharmacologically active principle of 'Paico,' a medicinal Peruvian plant

'Paico,' Chenopodium ambrosioides L., is a traditional Peruvian medicine which is considered to be nervine, antirheumatic, anthelmintic, etc. An attempt was made to isolate the component having sedative and/or analgesic properties from 'Paico' and 'Aritasou' (the Japanese name for C. ambrosioides). Ascaridole was identified as the active principle in both materials.

Homo- and heterogeneous α-pinene photooxidation using a protoporphyrin-derived amide

6,7-Bis[3-(NIμ-tert-butyloxycarbonyllysine methyl ester)]-1,3,5,8-tetramethyl-2,4-divinylporphyrin (3) was synthesized and successfully immobilized in a silica matrix by a sol-gel method. Protoporphyrin (PP)-derived amide 3 showed much higher photostability than its parent PP-IX. Its UV/Vis absorption, excitation, and fluorescence spectra as well as its ability to generate 1O2 were measured both in solution and in the matrix. Subsequently, free and immobilized porphyrins 3 were used as sensitizers in the photooxidation of α-pinene, and their photocatalytic properties were compared. Newly synthesized protoporphyrin (PP)-derived amide 3 is more photostable than PP-IX. Because it is able to generate 1O2, it could be used as a biomimetic catalyst for the oxidation of α-pinene under visible light. After successful immobilization in a silica matrix, a transparent organic-inorganic hybrid was obtained that shows intensive luminescence. Copyright

THE ALLYLIC REARRANGEMENT OF HYDROPEROXIDES : THE ALLYLPEROXYL RADICAL

The free-radical rearrangement of pinocarveyl hydroperoxide (1) or myrtenyl hydroperoxide (2) in hexane produces an equilibrium mixture of both hydroperoxides.The absence of carbon skeletal rearrangement suggests that the intermediate radical involved in hydroperoxide isomerization has its unpaired electron localized elsewhere than the α-carbon atom.The failure of oxygen to react with pinocarveyl, myrtenyl, and acyclic hydroperoxides (8) and (9) during the allylic rearrangement supports this suggestion.The kinetics of the rearrangement of 1-isopropyl-2-methylallyl hydroperoxide (8) is compatible with a mechanism in wich the intermediate is a common allylperoxyl radical produced directly from either allylic isomer.

Palladium catalyzed oxidation of monoterpenes: NMR study of palladium(II)-monoterpene interactions

Reactions of the monoterpenes β-pinene, limonene and myrcene with Pd(II) complexes in acetic acid solutions were studied by 1H NMR spectroscopy. Various π-allyl palladium complexes were detected in situ and their interaction with CuCl2 has been investigated. The results clarify the mechanism of allylic oxidation of these substrates mediated by Pd(II)/Cu(II)-based catalytic systems. Originally introduced to regenerate reduced palladium species, CuCl2 has been shown to play an important role in the formation and/or decomposition of key reaction intermediates - π-allyl palladium complexes. β-Pinene and myrcene readily react with Pd(OAc)2 giving corresponding π-allyls, with two complexes acyclic and cyclic being formed from myrcene. On the other hand, the formation of π-allyl complexes from limonene occurs at a significant rate only in the presence of CuCl2. NMR observations, including selective paramagnetic enhancement of spin-lattice relaxation, indicate that π-allyl palladium intermediates specifically interact with Cu(II) ions in the reaction solutions. Such interaction probably involves Cu(II) bonding to Pd(II) via bridging ligands, and seems to be responsible for the accelerative effect of CuCl 2 in the palladium catalyzed oxidation of the monoterpenes. Indeed, most of these reactions do not occur at all in the absence of CuCl2.

TERPENOIDS FROM THE FRENCH LIVERWORT TARGIONIA HYPOPHYLLA

Key Word Index - Targionia hypophylla; Targioniaceae; Hepaticae; cis- and trans-pinocarveyl acetates; mono-, sesqui- and diterpenoids.Two monoterpene acetates, cis- and trans-pinocarveyl acetates, which make up the characteristic aroma of the thalloid liverwort Targionia hypophylla were isolated, together with the previously known sesquiterpene alcohol, drimenol.

Carbon-Carbon Bond Scission during the Reactions of Allylic Hydroperoxides with some Transition Metal Compounds. Result Relevant to a Recent Proposal

The proposal that 4-exo closure of an allylic peroxyl radical can account for the titled reactions of pinocarveyl hydroperoxide has been considered in the light of literature data, along with the results of reactions carried out with a range of alternative copper and iron reagents and with the previously examinated reagents in the presence or absence of suitable traps: an acid-catalysed pathway is proposed to account for the observed scission reaction.

Catalytic isomerisation of α-pinene oxide in the presence of ETS-10 supported ferrocenium ions

Ferrocenium ions, [Fc]+, have been immobilised in the microporous titanosilicate ETS-10 by ion exchange of Na+/K+ ions under hydrothermal conditions. The resultant hybrid inorganic-organometallic (ETS-10/[Fc]+) material was characterised by elemental analysis, diffuse reflectance UV-Vis spectroscopy, FT-IR spectroscopy, powder X-ray diffraction, scanning electron microscopy, and thermogravimetric analysis. The ETS-10/[Fc]+ sample was tested as a catalyst for the isomerisation of α-pinene oxide (PinOx) at 35 C. With α, α, α-trifluorotoluene (TFT) as solvent, campholenic aldehyde (CPA) was the main product formed in 38% yield at 100% conversion and 30 min reaction. Other reaction products included trans-carveol, iso-pinocamphone and trans-pinocarveol. The same PinOx conversion and CPA yield could be reached within 1 min reaction time by increasing the reaction temperature (to 55 °C) and the Fe:PinOx molar ratio. Other solvents (hexane, CH3CN, toluene) led to poorer results than TFT. Characterisation of the used catalyst, together with an analysis of the catalytic activity of the liquid phase obtained after contact of ETS-10/[Fc]+ with TFT, indicated that the ETS-10/[Fc]+ sample was resistant toward leaching of iron-containing active species. When the recovered solid was reused in a second batch run, catalytic activity was lower than in the first run, while selectivity to CPA was higher.