1196-31-2Relevant articles and documents
Synthesis, structural characterization and alcohol oxidation activity of a new mononuclear manganese(II) complex
Najafpour, Mohammad Mahdi,Amini, Mojtaba,Bagherzadeh, Mojtaba,Boghaei, Davar M.,McKee, Vickie
, p. 297 - 303 (2010)
A manganese(II) complex of 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz) has been synthesized and characterized by single-crystal X-ray diffraction, elemental analyses, IR, and UV-Vis spectroscopic techniques. Oxidation of alcohols to their corresponding aldehydes and ketones was conducted by this catalyst using oxone (2KHSO5KH-SO4K2SO4) as an oxidant under biphasic reaction conditions (CH2Cl2/H 2O) and tetra-n-butylammonium bromide as phase transfer agent under air at room temperature. Easy preparation, mild reaction conditions, high yields of the products, short reaction times, no further oxidation to the corresponding carboxylic acids, high selectivity and inexpensive reagents make this catalytic system a useful oxidation method for aliphatic and benzylic alcohols. Springer Science+Business Media B.V. 2010.
Characterization of two enone reductases from Nicotiana tabacum cell cultures
Tang, Yi-xiong,Suga, Takayuki
, p. 2599 - 2603 (1992)
Two enone reductases, designated Reductase-I and -II, were isolated from Nicotiana tabacum cell cultures. These two reductases have different Mrs, pH optimum, coenzyme requirement and substrate specificity. Reductase-I catalyses the reduction of the endocyclic CC double bond of enones which bear a hydrogen-substituent at the position β to the carbonyl, while Reductase-II catalyses the reduction of the exocyclic CC double bond of enones.
A new vanadium Schiff base complex as catalyst for oxidation of alcohols
Bagherzadeh, Mojtaba,Amini, Mojtaba
, p. 3849 - 3858 (2010)
The monoanionic bidentate Schiff base, N-(phenolyl)-benzaldimine (HL), has been employed to synthesize a new vanadium(IV) complex of general composition [VO(L)2] (where L = O, N donor of Schiff base). The ligand and complex have been fully characterized by elemental analyses, molar conductance data, FT-IR, 1H- and 13C-NMR, and UV-Vis spectroscopies. Oxidation of alcohols to their corresponding aldehydes and ketones was conducted by this complex catalyst using Oxone as oxidant under biphasic reaction conditions (CH2Cl2/H2O) and tetra-n-butylammonium bromide as phase transfer agent under air at room temperature.
Stereoselectivity in Oxidative and Reductive Transformations of p-Menthane Derivatives with the Cultured Cells of Nicotiana tabacum
Suga, Takayuki,Hamada, Hiroki,Hirata, Toshifumi,Izumi, Shunsuke
, p. 903 - 906 (1987)
The biotransformation of the enantiomeric pairs of 2- and 3-oxygenated p-methane derivatives with the cultured cells of Nicotiana tabacum was investigated.It was found that (I) the cultured cells transform only 2-oxygenated p-menthane derivatives to a great extent, (ii) the cultured cells cause the highly stereospecific reduction for (1R,4R)-2-oxo-p-menthane, whereas this is not the case for its enantiomer, and (iii) the cultured cells enantioselectively oxidize the hydroxyl group of 2-hydroxyl-p-methanes.
Oxidation of secondary terpene alcohols by chlorine dioxide
Frolova,Popov,Rubtsova,Kuchin
, p. 724 - 727 (2008)
Secondary terpene alcohols cis- and trans-verbenol, neo-iso-verbanol, borneol, iso-borneol, and menthol were oxidized by chlorine dioxide into the corresponding ketones. It was shown that the nature of the solvent and catalyst and the structure of the starting compound, including the stereochemistry of the hydroxyl, influenced the oxidation process.
Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates
Lavinda, Olga,Witt, Collin H.,Woerpel, K. A.
, (2022/02/19)
Unlike many reactions of their six-membered-ring counterparts, the reactions of chiral seven-membered-ring enolates are highly diastereoselective. Diastereoselectivity was observed for a range of substrates, including lactam, lactone, and cyclic ketone derivatives. The stereoselectivity arises from torsional and steric interactions that develop when electrophiles approach the diastereotopic π-faces of the enolates, which are distinguished by subtle differences in the orientation of nearby atoms of the ring.
Rapid, chemoselective and mild oxidation protocol for alcohols and ethers with recyclable N-chloro-N-(phenylsulfonyl)benzenesulfonamide
Badani, Purav,Chaturbhuj, Ganesh,Ganwir, Prerna,Misal, Balu,Palav, Amey
supporting information, (2021/06/03)
Chlorine is the 20th most abundant element on the earth compared to bromine, iodine, and fluorine, a sulfonimide reagent, N-chloro-N-(phenylsulfonyl)benzenesulfonamide (NCBSI) was identified as a mild and selective oxidant. Without activation, the reagent was proved to oxidize primary and secondary alcohols as well as their symmetrical and mixed ethers to corresponding aldehydes and ketones. With recoverable PS-TEMPO catalyst, selective oxidation over chlorination of primary and secondary alcohols and their ethers with electron-donating substituents was achieved. The reagent precursor of NCBSI was recovered quantitatively and can be reused for synthesizing NCBSI.
Menthylamine synthesis via gold-catalyzed hydrogenation of menthone oxime
Demidova, Yu. S.,Mozhaitsev, E. S.,Murzin, D. Yu.,Nefedov, A. A.,Salakhutdinov, N. F.,Saraev, A. A.,Simakov, A.,Simakova, I. L.,Suslov, E. V.,Volcho, K. P.
, (2020/09/03)
In the current work gold nanoparticles supported on oxides (MgO, Al2O3, ZrO2, TiO2) were used for menthylamine synthesis via menthone oxime hydrogenation. An increase of the gold nanoparticles size and application of metal oxides with a strong basic character such as magnesia favored deoximation to menthone. Au/Al2O3 catalyst with the gold nanoparticles size of 2.0 nm afforded high catalytic activity and selectivity to menthylamine. The reaction kinetics including stereoselectivity to the reaction products and recyclability of the catalyst was studied using Au/Al2O3 in the temperature range 90?110 °C under hydrogen pressure of 5.5–7.5 bar. The catalytic behavior was influenced by the solvent nature, with higher selectivity to desired amine achieved using methanol. The reaction rate was pressure independent, while has first order with respect to menthone oxime concentration. Stereoselectivity to menthylamines and menthones was independent on the reaction temperature and the hydrogen pressure.
Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water
Song, Tao,Ma, Zhiming,Yang, Yong
, p. 1313 - 1319 (2019/01/25)
Herein, we report highly chemoselective hydrogenation of α,β-unsaturated carbonyls to saturated carbonyls catalyzed by cobalt nanoparticles supported on the biomass-derived carbon from bamboo shoots with molecular hydrogen in water, which is the first prototype using a heterogeneous non-noble metal catalyst for such organic transformation as far as we know. The optimal cobalt nanocatalyst, CoOx@NC-800, manifested remarkable activity and selectivity for hydrogenation of C=C in α,β-unsaturated carbonyls under mild conditions. A broad set of α,β-aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one-pot cascade synthesis of saturated carbonyls was realized with high activity and selectivity via the cross-aldol condensation of ketones with aldehydes followed by selective hydrogenation. More importantly, this one-pot strategy is applicable for the expedient synthesis of Loureirin A, a versatile bioactive and medicinal molecule, from readily available starting materials, further highlighting the practical utility of the catalyst. In addition, the catalyst can be easily separated for successive reuses without significant loss in both activity and selectivity.
Method for preparing high-purity L-menthone
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Paragraph 0071-0074; 0075-0078; 0079-0082; 0083-0096, (2019/04/06)
The invention discloses a method for preparing high-purity L-menthone. The method includes: under action of a solid base loaded ruthenium catalyst, subjecting raw material L-isopulegol for heterogeneous catalytic reaction to obtain a product-high-purity L-menthone. In mild reaction conditions, the ruthenium catalyst loaded on solid base is utilized to heterogeneously catalyze L-isopulegol to prepare L-menthone with high yield, the catalyst can be recycled conveniently and quickly, and the method is simpler in reaction process, low in reaction cost and high in environment friendliness; througha hydrogenation transfer process, hydrogen is not needed, so that the method has better process safety and industrial prospect.
