68546-28-1

Upstream product

• 124-76-5 isoborneol 
• 576-26-1 2.6-dimethylphenol 
• 18501-53-6 2,2-ethanediyldioxy-bornane 
• 75-77-4 chloro-trimethyl-silane 
• 76-29-9 3-bromocamphor 
• 13559-66-5 (+/-)-camphor oxime 
• 464-15-3 bornane 
• 507-70-0 1,7,7-trimethyl bicyclo[2.2.1]heptan-2-ol 
• 33081-41-3 1,7,7-Trimethyl-2-nitrobicyclo<2.2.1>heptane 
• 7519-74-6 thiocamphor 
• 17697-12-0 benzeneseleninic anhydride 
• 3751-96-0 8-bromonorbornan-2-one 
• 50882-17-2 d,l-methyl-3-camphorcarboxylate 
• 6627-72-1 rac-endo-borneol 

Downstream Products

• 2513-91-9 (1R)-bornan-2-one-phenylhydrazone 
• 464-43-7 d-borneol 
• 24393-70-2 isoborneol 
• 25611-66-9 4,7,7,4',7',7'-hexamethyl-[2,2']binorbornyl-3,3'-dione 
• 24797-59-9 3-benzyl-1,7,7-trimethyl-norbornan-2-one 
• 28627-52-3 N-((1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2-ylidene)benzenamine 
• 113157-91-8 (1R)-bornan-2-one-(4-bromo-phenylhydrazone); (d-camphor)-(4-bromo-phenylhydrazone) 
• 7070-29-3 3,3-dimethyl-2-methylene-1-phenyl-norbornane 
• 10226-01-4 3-(α-Phenyl-β-benzoylethyl)-campher 
• 63297-76-7 1,7,7-Trimethyl-2-(methylsulfanyl-phenyl-methyl)-bicyclo[2.2.1]heptan-2-ol 
• 6627-72-1 rac-endo-borneol 
• 5649-82-1 (1S,2S,4S,1'S,2'S,4'S)-1,7,7,1',7',7'-Hexamethyl-[2,2']bi[bicyclo[2.2.1]heptyl]-2,2'-diol 
• 93144-85-5 Phenyl-(1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl)-amine 
• 24268-24-4 1,7,7-trimethyl-3-(phenylimino)bicyclo[2.2.1]heptan-2-one 

Relevant academic research and scientific papers

An efficient approach for the conversion of oximes into carbonyl compounds using dichloramine-T

An efficient approach for the conversion of oximes into the corresponding carbonyl compounds using dichloramine-T is described. The reaction was performed in acetonitrile in the presence of small amount of water. In comparison to reported oxidative deoximating agents, the reaction was rapid and gave good yields of the products. The conversion was found to be chemoselective and during the reaction sensitive groups, like phenolic and C=C bonds, remained intact. Georg Thieme Verlag Stuttgart.

Addition of tris(trimethylsilyl) phosphite to quinuclidin-3-one and its carbocyclic analogs

Convenient methods of synthesis of functionalized phosphonic acids and their trimethylsilyl esters containing quinuclidine, adamantine, and bornane (camphane) moieties, involving reactions of tris(trimethylsilyl) phosphite with quinuclidin-3-one and its c

Reactions of terpene alcohols and diols with chlorine dioxide in dimethylformamide

The system chlorine dioxide–dimethylformamide in combination with or without a catalytic amount of MoCl5, CeCl3, ZrOCl2, or VO(acac)2 induces oxidative chlorination of a number of bicyclic terpene alcohols and v

On the key role of hydroxyl groups in platinum-catalysed alcohol oxidation in aqueous medium

In the aerobic selective oxidation of alcohols in aqueous medium in a batch reactor, it was observed that the addition of water to dioxane solvent (10-50 vol%) substantially increased the activity of a Pt/C catalyst. Periodic density functional theory (DFT) calculations were carried out to compare the reactivity of alcohols on the bare Pt(111) surface and in the presence of adsorbed water or hydroxyl groups, to explain the effect of water. The calculations indicate that the presence of adsorbed hydroxyl groups promotes the catalytic activity by participating directly in the catalytic pathways and reducing the activation barrier. Good agreement was found between the experiments in aqueous phase and these calculations. Further, decarbonylation of the aldehyde may be involved in the deactivation during oxidation of a primary alcohol. The Royal Society of Chemistry 2013.

Chemoselective Electrochemical Oxidation of Secondary Alcohols Using a Recyclable Chloride-Based Mediator

Selective anodic oxidation of alcohols in the presence of other functional groups can be accomplished by using nitroxyl radical mediators. However, the electrochemical chemoselective oxidation of secondary alcohols in the presence of primary alcohols is a

A Structural View on the Stereospecificity of Plant Borneol-Type Dehydrogenases

The development of sustainable processes for the valorization of byproducts and other waste streams remains an ongoing challenge in the field of catalysis. Racemic borneol, isoborneol and camphor are currently produced from α-pinene, a side product from the production of cellulose. The pure enantiomers of these monoterpenoids have numerous applications in cosmetics and act as reagents for asymmetric synthesis, making an enzymatic route for their separation into optically pure enantiomers a desirable goal. Known short-chain borneol-type dehydrogenases (BDHs) from plants and bacteria lack the required specificity, stability or activity for industrial utilization. Prompted by reports on the presence of pure (?)-borneol and (?)-camphor in essential oils from rosemary, we set out to investigate dehydrogenases from the genus Salvia and discovered a dehydrogenase with high specificity (E>120) and high specific activity (>0.02 U mg?1) for borneol and isoborneol. Compared to other specific dehydrogenases, the one reported here shows remarkably higher stability, which was exploited to obtain the first three-dimensional structure of an enantiospecific borneol-type short-chain dehydrogenase. This, together with docking studies, led to the identification of a hydrophobic pocket in the enzyme that plays a crucial role in the stereo discrimination of bornane-type monoterpenoids. The kinetic resolution of borneol and isoborneol can be easily integrated into the existing synthetic route from α-pinene to camphor thereby allowing the facile synthesis of optically pure monoterpenols from an abundant renewable source.

Borneol dehydrogenase from Pseudomonas sp. TCU-HL1 possesses novel quinuclidinone reductase activities

Borneol dehydrogenase (BDH) catalyses the last step of the camphor biosynthetic pathway in plants and the first reaction in the borneol degradation pathway in soil microorganisms. Native or engineered BDH can be used to produce optically pure borneol and camphor. The recently reported apo-form crystal structure of BDH (PDB ID: 6M5N) from Pseudomonas sp. TCU-HL1 superimposes well with that of 3-quinuclidinone reductase (QR) (PDB ID: 3AK4) from Agrobacterium tumefaciens. QR catalyses the conversion of 3-quinuclidinone into (R)-3-(?)-quinuclidinol, an important chiral synthone for several drugs. However, the kinetic parameter, kcat, of QR was not determined in the previous reports even though both BDH and QR have various potential industrial applications. Here, we aimed to further characterise their structural and functional relationship. Recombinant QR with the native sequence was cloned, expressed in E. coli, and purified. We found that 3-quinuclidinone can be used as an alternative substrate for BDH. Only (R)-3-(?)-quinuclidinol was detected in this BDH-catalysed reaction. The results of 3 D molecular docking simulation show that 3-quinuclidinone and (+)-/(-)- borneol were docked to two different parts of the QR active site. In contrast, all three compounds are docked uniformly to the alpha-1 helix of BDH. There results explain why BDH can turnover 3-quinuclidinone, while QR can not act on (+)-/(-)-borneol.

Zwitterion-induced organic-metal hybrid catalysis in aerobic oxidation

In many metal catalyses, the traditional strategy of removing chloride ions is to add silver salts via anion exchange to obtain highly active catalysts. Herein, we reported an alternative strategy of removing chloride anions from ruthenium trichloride using an organic [P+-N-] zwitterionic compound via multiple hydrogen bond interactions. The resultant organic-metal hybrid catalytic system has successfully been applied to the aerobic oxidation of alcohols, tetrahydroquinolines, and indolines under mild conditions. The performance of zwitterion is far superior to that of many other common Lewis bases or Br?nsted bases. Mechanistic studies revealed that the zwitterion triggers the dissociation of chloride from ruthenium trichloride via nonclassical hydrogen bond interaction. Preliminary studies show that the zwitterion is applicable to catalytic transfer semi-hydrogenation.

Dysprosium-doped zinc tungstate nanospheres as highly efficient heterogeneous catalysts in green oxidation of terpenic alcohols with hydrogen peroxide

A green route to oxidize terpenic alcohols (nerol and geraniol) with H2O2over a solid catalyst was developed. The Dy-doped ZnWO4catalyst was synthesized by coprecipitation and microwave-assisted hydrothermal heating, containing different dysprosium loads. All the catalysts were characterized through infrared spectroscopy, powder X-ray diffraction, surface area and porosimetry, transmission electronic microscopy image, andn-butylamine potentiometric titration analyses. The influence of main reaction parameters such as temperature, the stoichiometry of reactants, loads, and catalyst nature was assessed. ZnWO42.0 mol% Dy was the most active catalyst achieving the highest conversion (98%) and epoxide selectivity (78%) in nerol oxidation. The reaction scope was extended to other terpenic alcohols (i.e., geraniol, borneol, and α-terpineol). The highest activity of ZnWO42.0 mol% Dy was assigned to the lower crystallite size, higher surface area and pore volume, higher acidity strength and the greatest dysprosium load.

Ruthenium-on-Carbon-Catalyzed Facile Solvent-Free Oxidation of Alcohols: Efficient Progress under Solid-Solid (Liquid)-Gas Conditions

A protocol for the ruthenium-on-carbon (Ru/C)-catalyzed solvent-free oxidation of alcohols, which proceeds efficiently under solid-solid (liquid)-gas conditions, was developed. Various primary and secondary alcohols were transformed to corresponding aldehydes and ketones in moderate to excellent isolated yields by simply stirring in the presence of 10% Ru/C under air or oxygen conditions. The solvent-free oxidation reactions proceeded efficiently regardless of the solid or liquid state of the substrates and reagents and could be applied to gram-scale synthesis without loss of the reaction efficiency. Furthermore, the catalytic activity of Ru/C was maintained after five reuse cycles.