514-99-8

Usage

InChI:InChI=1S/C10H18O/c1-10(2)8-4-3-7(6-11)9(10)5-8/h7-9,11H,3-6H2,1-2H3

Upstream product

• 177698-19-0 Beta-pinene 
• 18172-67-3 (?)-β-pinene 
• 109002-21-3 2-<6,6-dimethylbicyclo<3.1.1>hept-2-yl>-5,5-ethylenedioxypentanal N,N-dimethylhydrazone 
• 515-00-4 myrtenol 
• 108-95-2 phenol 
• 62-53-3 aniline 
• 23727-16-4 myrtenal 
• 6712-78-3 myrtenol 
• 1118071-19-4 2-chloromethyl-6,6-dimethylbicyclo[3.1.1]heptane 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 18172-67-3 beta-pinene 
• 33741-30-9 methyl (1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-carboxylate 
• 64-19-7 acetic acid 
• 64-17-5 ethanol 

Downstream Products

• 127-92-4 6,6-Dimethyl-bicyclo<3.1.1>heptan 
• 4764-14-1 6,6-dimethylbicyclo<3.3.1>heptane-2-carboxaldehyde 
• 81510-28-3 (1R,2R,5R)-2-[2-(Diphenyl-phosphinoyl)-ethoxymethyl]-6,6-dimethyl-bicyclo[3.1.1]heptane 
• 4764-14-1 (-)-cis-myrtanal 
• 590410-99-4 (1R,2R,5R)-trans-myrtanyl tosylate 
• 29021-36-1 (1R)-10-Acetoxy-cis-pinan 
• 4764-14-1 cis-myrtanal 
• 16750-96-2 trans-Myrtanyl-tosylat 
• 4764-14-1 (+/-)-Myrtanal 
• 4764-14-1 (+/-)-Isomyrtanal 
• 81510-31-8 [2-((1R,2R,5R)-6,6-Dimethyl-bicyclo[3.1.1]hept-2-ylmethoxy)-ethyl]-diphenyl-phosphane 

Relevant academic research and scientific papers

Biomass- And calcium carbide-based recyclable polymers

Biomass is a renewable source of valuable feedstock for the chemical industry of the future. A promising approach to the utilization of valuable components of biomass is the synthesis of monomers and polymers, if the overall technology is designed for a clean cycle without pollution of the environment with newly created polymers. In this work, we have developed a methodology for the recycling of polymers based on biomass and calcium carbide. First, we modified a series of biomass-derived terpene alcohols with calcium carbide followed by polymerization of the isolated vinyl ethers. Then, to study the recycling potential, the obtained polymers were subjected to pyrolysis at moderate temperatures (200-450 °C). The pyrolysis products were analyzed using TGA-MS, GC-MS, and NMR, and it was found that the polymers can be transformed quite easily. The products of the pyrolysis consisted of the starting terpenols, as well as the corresponding non-toxic ketones or aldehydes: up to 87% of the starting alcohol or up to 100% of the total sum of alcohol + aldehyde or alcohol + ketone (GC-yields). Then, the reaction mixture was hydrogenated and resulted in the formation of starting alcohol only. According to the studied pathway of polymers re-building, a terpene fragment attached to the main polyethylene chain through an oxygen atom promotes the transformation of the obtained polymers. Thus, the products of pyrolysis are environmentally friendly and can be reused in the further synthesis of monomers. The developed system has shown a unique assembling/disassembling ability and advances the concept of reusable bio-derived high value-added materials.

One-Pot Myrtenol Amination over Au, Au–Pd and Pd Nanoparticles Supported on Alumina

Abstract: One-pot bio-based myrtenol amination was studied in the presence of alumina supported Au, Au–Pd and Pd nanoparticles subjected to the thermal treatment under oxidizing or reducing atmosphere. Myrtenol amination with aniline was carried out under nitrogen atmosphere (9?bar) at 453?K using toluene as a solvent. The effect of the active metal along with the influence of redox pre-treatment on the catalytic behavior in the hydrogen borrowing reaction was explored. The catalyst characterization was done by transmission electron microscopy, X-ray photoelectron spectroscopy, inductively coupled plasma optical emission spectroscopy, nitrogen adsorption. The active metal and the catalysts redox pretreatment affected more noticeably selectivity to the reaction products rather than myrtenol conversion. Monometallic Au/Al2O3 catalyst promoted predominantly formation of the target secondary amine and the corresponding imine without a significant impact of the side reaction of C=C bond hydrogenation in myrtenol, whereas monometallic Pd catalyst activated C=C bond resulting in its hydrogenation. At the same time in the presence of Au–Pd simultaneous hydrogenation of both C=C and C=N bond occurred. Au–Pd catalysts activated in oxygen and hydrogen showed different catalytic activity determined by the composition of surface active sites. Monometallic gold catalyst was more effective in the hydrogen transfer in the case of substrates with competitive unsaturated functional groups. Graphic Abstract: [Figure not available: see fulltext.].

Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide

A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.

A preparation method of Myrtle myristic aldehyde

The invention discloses a preparation method of myrtanal. The method sequentially comprises the following steps: 1, carrying out a hydroboration-oxidation reaction on beta-pinene to generate myrtanol; and 2, carrying out a selective oxidation reaction on myrtanol and active dimethyl sulphoxide to generate myrtanal. Myrtanol is synthesized in a high efficiency manner through hydroboration-oxidation of beta-pinene as a raw material, and the yield is greater than 90%; myrtanal is prepared through selective oxidation of the active dimethyl sulphoxide at room temperature, and the yield is greater than 80%, so the total yield of conversion from the initial raw material beta-pinene to myrtanal is greater than 72%. Compared with present methods, the method disclosed in the invention has the advantages of cheap and easily available reaction raw materials, mild reaction conditions, high purity and high yield of the above obtained product, and great reduction of the preparation cost of myrtanal.

Development of a flow method for the hydroboration/oxidation of olefins

A method for the continuous preparation of alcohols by hydroboration/oxidation of olefins using flow techniques is described. The process allows the isolation of up to 120 mmol h-1 of the desired alcohol in a very rapid manner with good functional group tolerance. The flow setup can be modified to perform a continuous extraction of the desired alcohol from the biphasic mixture produced by the reaction. This journal is

Alkylation of phenol by myrtenol

Alkylation of phenol by myrtenol in the presence of aluminum phenoxide and aluminum isopropoxide was studied in the temperature range 120-160°C. The reaction occurred with the formation of an array of alkylated phenols. Isomerization of the terpene substituent as a result of rearrangements of the bicyclic myrtenol structure was observed. The side reaction of myrtenol reduction occurred during the alkylation in the presence of aluminum isopropoxide. A significant number of compounds with two aromatic moieties was formed in the presence of aluminum phenoxide.

PS-COD and PS-9-BBN: Polymer-supported reagents for solution-phase parallel synthesis

(Chemical Equation Presented) 1,5-Cyclooctadiene was deprotonated under LICKOR conditions and reacted with Merrifield resin to afford an immobilized cyclooctadiene in high yield. This polymer is effective as a halogen scavenger, while hydroboration leads to a supported 9-BBN analogue. The latter exhibits similar regioselectivity to 9-BBN in olefin hydroboration.

HYDRONOPOL DERIVATIVES AS AGONISTS ON HUMAN ORL1 RECEPTORS

The invention relates to a group of hydronopol derivatives which are agonists on human ORL1 (nociceptin) receptors. The invention also relates to the preparation of these compounds, to pharmaceutical compositions containing a pharmacologically active amount of at least one of these novel hydronopol derivatives as an active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of disorders in which ORL1 receptors are involved. The invention relates to compounds of the general formula (1) wherein the symbols have the meanings as given in the description.

METHOD OF HYDROBORATING ALCOHOLS AND REDUCING FUNCTIONAL GROUPS USING A RECYCLABLE FLUOROUS BORANE-SULFIDE

A method of hydroborating an alkene or alkyne, or reducing an organic functionality, oxidizing primary and secondary alcohols using a fluorous borane-sulfide is disclosed. The method includes regeneration and recycling the fluorous borane-sulfide.

Dod-S-Me and methyl 6-morpholinohexyl sulfide (MMS) as new odorless borane carriers

Odorless Dod-S-Me (1) and MMS (3) are developed as efficient borane carriers. The yields of hydroborations and reductions with borane complex 2 of 1 are very high and the recovery of 1 after the reaction is quantitative. The borane complexes 4 and 5 of 3 are also useful. In the latter case chromatographic separation is unnecessary when excess oxidizing agent (alkaline H2O2) is used after hydroboration.