497-38-1Relevant articles and documents
Marshall
, p. 753 (1971)
Synthetic Methods and Reactions; 77. Dimethyl Sulfoxide/Chlorosulfonyl Isocyanate: An Extremely Mild Reagent for Oxidation of Alcohols to Carbonyl Compounds
Olah, George A.,Vankar, Yashwant D.,Arvanaghi, Massoud
, p. 141 - 142 (1980)
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Acid-catalyzed hydrolysis of bridged bi- and tricyclic compounds. XXXVIII - Kinetics and mechanisms of 1- and 3-nortricyclanols
Lajunen, Martti,Lahti, Veli
, p. 854 - 858 (2001)
The disappearance of 1- and 3-nortricyclanols (1-OH and 2-OH) in aqueous perchloric acid was followed by capillary GC at different temperatures and acid concentrations. 1-OH is ca 1000 times more reactive than 2-OH. The activation parameters, solvent deut
Supported rhenium nanoparticle catalysts for acceptorless dehydrogenation of alcohols: Structure-activity relationship and mechanistic studies
Kon, Kenichi,Onodera, Wataru,Toyao, Takashi,Shimizu, Ken-Ichi
, p. 5864 - 5870 (2016)
Al2O3-supported Re with different oxidation states and Re0 metal nanoparticles on various supports are prepared, characterized and tested for the dehydrogenation of 2-octanol. The activity of Re/Al2O3 increases with the fraction of metallic Re. The activity of metallic Re depends on the support oxides, and the support with moderate electronegativity (Al2O3) gives the highest turnover frequency (TOF) per surface Re0 site. Re/Al2O3 is effective for acceptorless dehydrogenation of various aliphatic secondary alcohols to ketones. The kinetic isotope effects on the dehydrogenation of 2-propanol show that dissociation of the α-C-H bond of 2-propanol is the rate-limiting step. The IR study of the reaction of gas phase 2-propanol over the Re/Al2O3 surface shows that the acid-base pair site of Al2O3 is responsible for the O-H dissociation of 2-propanol. The structural requirements are discussed on the basis of the mechanistic results.
Hart,H.,Martin,R.A.
, p. 6362 - 6366 (1960)
Aerobic oxidation and oxidative esterification of alcohols through cooperative catalysis under metal-free conditions
Karimi, Babak,Ghahremani, Mina,Vali, Hojatollah,Ciriminna, Rosaria,Pagliaro, Mario
supporting information, p. 8897 - 8900 (2021/09/10)
The ABNO@PMO-IL-Br material obtained by anchoring 9-azabicyclo[3.3.1]nonane-3-oneN-oxyl (keto-ABNO) within the mesopores of periodic mesoporous organosilica with bridged imidazolium groups is a robust bifunctional catalyst for the metal-free aerobic oxidation of numerous primary and secondary alcohols under oxygen balloon reaction conditions. The catalyst, furthermore, can be successfully employed in the first metal-free self-esterification of primary aliphatic alcohols affording valued esters.
A Structural View on the Stereospecificity of Plant Borneol-Type Dehydrogenases
Chánique, Andrea M.,Dimos, Nicole,Drienovská, Ivana,Calderini, Elia,Pantín, Mónica P.,Helmer, Carl P. O.,Hofer, Michael,Sieber, Volker,Parra, Loreto P.,Loll, Bernhard,Kourist, Robert
, p. 2262 - 2277 (2021/03/16)
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.
