705-86-2Relevant articles and documents
Photo-induced radical borylation of hemiacetals via C–C bond cleavage
Liu, Qianyi,Zhang, Jianning,Zhang, Lei,Mo, Fanyang
supporting information, (2021/01/05)
In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.
Synthesis process of natural delta-decalactone
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, (2022/01/10)
The invention relates to a synthesis process of natural delta-decalactone, and belongs to the technical field of food additives, and the natural delta-decalactone is obtained by taking furfural and n-amyl alcohol as raw materials through chlorination, Grignard coupling, Piancatelli rearrangement, hydrogenation and oxidation. The purity of the delta-decalactone prepared in the synthesis process of the natural delta-decalactone can reach 98% or above, the natural degree detected by isotope mass spectrometry C14 is 95% or above, and the problems that the synthesis route of the delta-decalactone is complex and the yield is low are solved; and the experimental method is simple, convenient and feasible, the reaction condition is mild, the experimental condition is easy to realize and control, and the method has the characteristics that the raw materials are easy to obtain and rich in source, the yield is relatively high, the used catalyst can be repeatedly used and the like.
An effective cis-β-octahedral Mn(iii) SALPN catalyst for the Mukaiyama-Isayama hydration of α,β-unsaturated esters
Donnelly, Paul S.,North, Andrea J.,Radjah, Natalia Caren,Ricca, Michael,Robertson, Angus,White, Jonathan M.,Rizzacasa, Mark A.
supporting information, p. 7699 - 7702 (2019/07/09)
Two cis-β-MnIIISALPN catalysts were synthesised and tested in the Mukaiyama-Isayama hydration of α,β-unsaturated esters. The MnIIIEtOSALPN(acac) complex 7 is the most active and catalyses hydration with little or no detectable undesired alkene reduction. This catalyst is superior for alkene hydration compared to the originally reported Mn(dpm)3 catalyst.
Regio- and Enantio-selective Chemo-enzymatic C?H-Lactonization of Decanoic Acid to (S)-δ-Decalactone
Manning, Jack,Tavanti, Michele,Porter, Joanne L.,Kress, Nico,De Visser, Sam P.,Turner, Nicholas J.,Flitsch, Sabine L.
supporting information, p. 5668 - 5671 (2019/03/29)
The conversion of saturated fatty acids to high value chiral hydroxy-acids and lactones poses a number of synthetic challenges: the activation of unreactive C?H bonds and the need for regio- and stereoselectivity. Here the first example of a wild-type cytochrome P450 monooxygenase (CYP116B46 from Tepidiphilus thermophilus) capable of enantio- and regioselective C5 hydroxylation of decanoic acid 1 to (S)-5-hydroxydecanoic acid 2 is reported. Subsequent lactonization yields (S)-δ-decalactone 3, a high value fragrance compound, with greater than 90 % ee. Docking studies provide a rationale for the high regio- and enantioselectivity of the reaction.
ATP3 and MTP3: Easily Prepared Stable Perruthenate Salts for Oxidation Applications in Synthesis
Moore, Peter W.,Read, Christopher D. G.,Bernhardt, Paul V.,Williams, Craig M.
supporting information, p. 4556 - 4561 (2018/03/13)
The Ley–Griffith tetra-n-propylammonium perruthenate (TPAP) catalyst has been widely deployed by the synthesis community, mainly for the oxidation of alcohols to aldehydes and ketones, but also for a variety of other synthetic transformations (e.g. diol cleavage, isomerizations, imine formation and heterocyclic synthesis). Such popularity has been forged on broad reaction scope, functional group tolerance, mild conditions, and commercial catalyst supply. However, the mild instability of TPAP creates preparation, storage, and reaction reproducibility issues, due to unpreventable slow decomposition. In search of attributes conducive to catalyst longevity an extensive range of novel perruthenate salts were prepared. Subsequent evaluation unearthed a set of readily synthesized, bench stable, phosphonium perruthenates (ATP3 and MTP3) that mirror the reactivity of TPAP, but avoid storage decomposition issues.
Synthetic method of high-purity delta-decalactone
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Paragraph 0031; 0034-0035, (2019/01/13)
The invention provides a synthetic method of high-purity delta-decalactone. The method comprises following steps: 1-octen-3-one and dimethyl malonate are taken as raw materials, an alkaline substanceA is taken as a catalyst, the raw materials and the catalyst are subjected to micheal addition, distilled water is dropwise added to an obtained addition product, decarboxylic reaction is performed, and an intermediate product methyl-ketone-5-decenoate is obtained with content higher than 92%; methyl-5-decenoate is put in a four-port glass reactor, a sodium hydroxide solution is dropwise added, then a potassium borohydride aqueous solution is dropwise added for reduction reaction, PH value is regulated to 4-5 by hydrochloric acid after the reduction reaction is finished, stirring is stopped, and an oil layer and a water layer are obtained after stand layering; the water layer is layered again after being repeatedly extracted by MTBE, an oil phase product mixed with the MTBE is obtained andcombined with the oil layer obtained in the step three, the solvent MTBE is recovered, reduced-pressure distillation is performed, and the product delta-decalactone is obtained. According to the method, not only is content increased by 1%, but also product taste is greatly improved, and content of delta-decalactone is higher than 99%.
Biotransformation of linoleic acid into hydroxy fatty acids and carboxylic acids using a linoleate double bond hydratase as key enzyme
Oh, Hye-Jin,Kim, Sae-Um,Song, Ji-Won,Lee, Jung-Hoo,Kang, Woo-Ri,Jo, Ye-Seul,Kim, Kyoung-Rok,Bornscheuer, Uwe T.,Oh, Deok-Kun,Park, Jin-Byung
, p. 408 - 416 (2015/03/05)
Hydroxy fatty acids are used as starting materials for the production of secondary metabolites and signalling molecules as well as in the manufacture of industrial fine chemicals. However, these compounds are usually difficult to produce from renewable biomass by chemical means. In this study, linoleate double bond hydratases of Lactobacillus acidophilus NBRC 13951 were cloned for the first time. These enzymes were highly specific for the hydration of the C-9 or the C-12 double bond of unsaturated fatty acids (e.g., linoleic acid). Thereby, the enzymes allowed the selective production of hydroxy fatty acids such as 13-hydroxy- cis -9-octadecenoic acid and 10-hydroxy- cis -12-octadecenoic acid from linoleic acid. In addition, the hydroxy fatty acids were further converted into industrially relevant carboxylic acids (e.g., 12-hydroxy-cis-9-dodecenoic acid, a, w-tridec-9-enedioic acid) and lactones (i.e., d-decalactone, g-dodecelactone) via whole-cell biocatalysis using an enzyme cascade. This study thus contributes to the preparation of hydroxy fatty acids, unsaturated carboxylic acids, and lactones from renewable unsaturated fatty acids.
Synthesis of d-decalactone
Bu, Jia,Li, Guangxue,Zhao, Mingzhu,Li, Jiaming,Jiang, Feng,Zhan, Hualu,Chu, Yang
, p. 4520 - 4522 (2013/07/19)
The application and shortcomings of typical synthetic method of title d-decalactone was introduced in brief. A synthesis of 2-pentylidene cyclopentanone starting from cyclopentanone and n-valeraldehyde through aldol condensation, followed by dehydration, was studied and the yield reached 86.3 %. Then 2-pentenyl cyclopentanone was prepared in a yield of 91.5 % from 2-pentylidene cyclopentanone with a hydrogenation methodology under atmospheric pressure and use Pt/C as catalytic. Through Baeyer-Villiger oxidation, d-decalactone was synthesized in a yield of 61.2 %. Experiments by orthogonal experiment method to optimize the reaction conditions to determine the response of a reasonable process parameters and the analysis of the factors affecting the reactions. The structures and compositions of these compounds were accomplished by IR and GC-MS.
Screening of a selection of commercially available homogeneous Ru-catalysts in valuable olefin metathesis transformations
Caijo, Frederic,Tripoteau, Fabien,Bellec, Aurelien,Crevisy, Christophe,Basle, Olivier,Mauduit, Marc,Briel, Oliver
, p. 429 - 435 (2013/03/14)
A library of thirteen different commercially available Ru-based catalysts was evaluated in valuable metathesis reactions for the production of fragrance and bioactive molecule precursors. Rigorous library screening clearly illustrated the different catalytic behaviour of the catalyst selection and highlighted its significant advantage to provide efficiency in specific metathesis applications. Interestingly, this strategy offered substantial improvement over the state of the art, with the efficient synthesis of the macrocyclic Exaltolide 2 at low catalyst loading and dilution conditions. The Royal Society of Chemistry 2013.
Oxidation of the cyclopentanone and cyclohexanone alkyl derivatives in a pseudohomogeneous system without a phase transfer agent
Alimardanov,Garibov,Abbasov,Sadygov,Abdullaeva,Dzhafarova
experimental part, p. 1664 - 1670 (2011/12/02)
The reaction of catalytic oxidation of C5-C12 alkyl- and cycloalkylcyclopentanones and -cyclohexanones to lactones in a pseudohomogeneous system without the participation of phase transfer agents was investigated. It was established that the catalytic systems prepared on the basis of molybdenum and tungsten blue (MeOnBrm, where Me = Mo, W, n = 1, 2, m = 2, 3) and H3PO4 deposited on powdered activated carbon AG-3 at 40-60°C, at 5-6 h duration exhibit a high selectivity in the reaction of nucleophilic addition of oxygen to the ketones with the formation of the valero- and caprolactones. Pleiades Publishing, Ltd., 2011.
