- Photo-induced radical borylation of hemiacetals via C–C bond cleavage
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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.
- Liu, Qianyi,Zhang, Jianning,Zhang, Lei,Mo, Fanyang
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supporting information
(2021/01/05)
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- 3D-Network porous polymer bonded metalloporphyrin: An efficient and reusable catalyst for the Baeyer-Villiger oxidation
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A new, green catalyst was prepared through immobilization of metalloporphyrin on the surface of 3D-network polymer based on calix[4]resorcinarene (PC4RA), which efficiently catalyze B-V oxidation reaction using O2/benzaldehyde. The catalyst demonstrated excellent activity, which is highly potential for cyclic aliphatic ketones oxidation under mild conditions. IR spectroscopy, UV-Vis spectroscopy, thermal gravimetric analysis, energy dispersive spectroscopy and scanning electron microscopy are some of the spectroscopic methods used to characterize the new synthesized solid support.
- Hamid, Sheida,Mouradzadegun, Arash
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- Synthesis, antibacterial activities, and sustained perfume release properties of optically active5-hydroxy- And 5-acetoxyalkanethioamide analogues
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5-Acetoxy- and 5-hydroxyalkanethioamide analogues showed high antibacterial activity against Staphylococcus aureus. Antibacterial thioamides were prepared from 5-alkyl-δ-lactones by amidation, thionation, and subsequent deacetylation. Optically active thioamides with 99% diastereomeric excesses were prepared by diastereomeric resolution using Cbz-L-proline as the resolving agent. Antibacterial thioamides were slowly lactonized by a lipase catalyst. Therefore, these thioamides are potential sustained-release perfume compounds having antibacterial properties.
- Shimotori, Yasutaka,Hoshi, Masayuki,Ogawa, Narihito,Miyakoshi, Tetsuo,Kanamoto, Taisei
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- Synthesis method of deltalactone
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The invention discloses a synthesis method of deltalactone. The synthesis method is characterized by comprising the following steps: taking 5-oxo fatty acid as a starting raw material, and reacting under hydrogen pressure of 5atm to 30atm and at 120 DEG C to 180 DEG C in the presence of catalysts including Ru/C and the like; firstly, carrying out a hydrogenation reaction of carbonyl to obtain an intermediate product 5-hydroxyl fatty acid M1; meanwhile, carrying out intramolecular dehydration and esterification on M1 and carrying out a one-pot reaction to generate the deltalactone. A specific reaction formula is shown in the description, wherein R=CH3(CH2)n- and n is equal to 1 to 8.
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Paragraph 0022-0023; 0027-0028; 0029-0039
(2017/08/29)
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- Catalytic oxidation method to synthesize lactone compound with cyclic ketones
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The invention discloses a method for synthesizing a lactone compound through catalytic oxidation of cyclic ketone. The method is characterized by using a transition metal oxide as a catalyst, a hydrogen peroxide solution as an oxidizing reagent and acetonitrile as a solvent to catalytically oxidize cyclic ketone to synthesize the lactone compound, wherein the transition metal oxide is selected from any one of TiO2, Fe2O3, Co3O4, ZrO2 and WO3. The method has the obvious advantages that the conversion rate of cyclic ketone and atom utilization of reaction are increased by adopting the transition metal oxide as the catalyst; the used transition metal oxide catalyst can be reused; waste acid treatment and strong acid corrosivity are avoided, energy is saved, emission is reduced, and the safety is high; the cleanliness and safety of industrial preparation reaction are improved and the environmental pollution is reduced by applying the hydrogen peroxide solution as the oxidizing reagent.
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Paragraph 0032; 0033
(2017/04/03)
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- Baeyer-villiger oxidation of cyclic ketones using aqueous hydrogen peroxide catalyzed by potassium salts of tungstophosphoric acid
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The salts of 12-tungstophosphoric acid catalysts are prepared with varying potassium content. The resulting catalysts are active for the Baeyer-Villiger oxidation of cyclic ketones with 30 wt% H2O2 and achieve good conversions and yields. KHPW is the preferred catalyst in the reaction because of its reusability and environmental benefits.
- Ma, Qingguo,Xing, Wanzhen,Xu, Junhui,Peng, Xinhua
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p. 941 - 943
(2014/06/23)
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- PROCESS FOR THE OXIDATION OF ORGANIC CARBONYL COMPOUNDS
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A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.
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Page/Page column 36
(2014/05/24)
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- Process for the Oxidation of Organic Carbonyl Compounds
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A process for the oxidation of an organic carbonyl compound comprising reacting the organic carbonyl compound, optionally in the presence of a solvent, with hydrogen peroxide in the presence of a catalyst comprising a tin-containing zeolitic material having an MWW-type framework structure.
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Paragraph 0212-0213
(2014/05/20)
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- METHOD FOR MANUFACTURING ESTER
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The present invention relates to a method for manufacturing an ester from a ketone or an aldehyde, which is a reactive substrate, by a Baeyer-Villiger oxidation reaction using hydrogen peroxide, and in this method, as a catalyst, M(BAr4)n, which is a metal borate, is used (M represents an alkali metal or an alkaline earth metal; Ar represents an aryl; and n is the same number as the valence of M). For example, when cyclohexanone was used as the reactive substrate, and Sr[B(3,5-CF3C6H3)4]2 was used as the catalyst, ε-caprolactone was obtained at an isolated yield of 82%.
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Paragraph 0070; 0074; 0086; 0087
(2013/08/28)
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- Cascade biotransformations via enantioselective reduction, oxidation, and hydrolysis: Preparation of (R)-δ-lactones from 2-alkylidenecyclopentanones
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The first cascade biotransformation involving enantioselective reduction of a C=C double bond, Baeyer-Villiger oxidation, and lactone hydrolysis was developed as a green and sustainable tool for synthesizing enantiopure δ-lactones. One-pot cascade biotransformations were achieved with Acinetobacter sp. RS1 containing a novel enantioselective reductase and an enantioselective lactone hydrolase and Escherichia coli coexpressing cyclohexanone monooxygenase and glucose dehydrogenase, converting easily available 2-alkylidenecyclopentanones 1-2 into the corresponding valuable flavors and fragrances (R)-δ-lactones 5-6 in high ee. The one-pot synthesis is better than the reported two-step preparation. This concept is useful in developing other redox cascades with the substrates containing C=C double bond.
- Liu, Ji,Li, Zhi
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p. 908 - 911
(2013/07/25)
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- Oxidation of the cyclopentanone and cyclohexanone alkyl derivatives in a pseudohomogeneous system without a phase transfer agent
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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.
- Alimardanov,Garibov,Abbasov,Sadygov,Abdullaeva,Dzhafarova
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experimental part
p. 1664 - 1670
(2011/12/02)
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- PROCESS FOR THE PREPARATION OF LACTONES OR EPOXIDES
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The present invention relates to a process for the oxidation, in an inert solvent, of a non-aromatic or non-enonic ethylenic bond or of a non-conjugated cyclic ketones into the corresponding epoxides, respectively lactone, using H?2#191O?2#191 as oxidant, a content in water of the reaction medium below 15% w/w and, as sole catalyst, an alkaline or alkaline earth salt or complex.
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- A Ru catalyzed divergence: Oxidative cyclization vs cycloisomerization of bis-homopropargylic alcohols
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During the course of investigating the development of catalytic reactions involving ruthenium vinylidene intermediates, a novel divergence of reactivity was discovered. The oxidative cyclization of bis-homopropargylic alcohols with Ru(+2) complexes as catalysts and N-hydroxysuccinimide as oxidant, which requires formation of a ruthenium vinylidene intermediate, is complicated by the simple electrophilically initiated direct attack of the hydroxyl group on π-complex of the alkyne and ruthenium. A catalytic system composed of CpRu[(p-CH3O6H4)3P]2Cl and excess (p-CH3O-C6H4)3P directs the reaction toward the oxidative cyclization to form δ-lactones in good yields. Significantly, a simple switch of catalyst to CpRu[(p-FC6H4)3P]2Cl redirects the reaction to a cycloisomerization to form dihydropyrans in good yields. The synthetic utility of the oxidative cyclization is illustrated by the synthesis of oviposition attractant pheromone of the mosquito Culex pipens. The utility of the cycloisomerization to dihydropyrans is demonstrated by an iterative process leading to the antiviral agent narbosine B. A rationale for this dramatic switch by simple ligand modification is proposed.
- Trost, Barry M.,Rhee, Young Ho
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p. 2528 - 2533
(2007/10/03)
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Compounds having protected hydroxy groups
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The present invention relates to compounds with protected hydroxy groups of formula (I) These compounds are precursors for organoleptic agents, such as fragrances, and masking agents and for antimicrobial agents. When activated, the compounds of formula (I) are cleaved and form one or more organoleptic and/or antimicrobial compounds.
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- Precursor compounds
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The compounds of the formula I are precursors for organoleptic and antimicrobial compounds. The latter are generated in the presence of skin bacteria, enzymes or acidic or alkaline conditions. One precursor molecule can provide one or more different compounds.
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- Beta-ketoester compounds
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The beta-ketoesters of formula I are useful as precursors for organoleptic compounds, especially for flavors, fragrances and masking agents and antimicrobial compounds.
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- Catalytic oxidation of alkyl- and cycloalkylcyclanones into lactones
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Pilot-plant syntheses of alkyl and cycloalkylcyclanones and their subsequent liquid-phase oxidation into lactones are described. Characteristics of resulting intermediates and target products are reported.
- Abbasov,Alimardanov,Suleimanova
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p. 621 - 626
(2007/10/03)
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- CLEAVAGE OF SPIROOXAZIRIDINES BY THE ACTION OF FERROUS SULFATE
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The reaction of 2-butyl-3,3-(1'-heptyl)tetramethyleneoxaziridine with ferrous sulfate gave the N-butylamides of E- and Z-4-dodecenecarboxylic and E- and Z-5-dodecenecarboxylic acids in ca. 1:1 ratio.Analogously, 2-butyl-3,3-(1'-alkyl)pentamethyleneoxaziridines gave the N-butylamides of the corresponding E- and Z-unsaturated carboxylic acids.
- Schmitz, E.,Kapustina, N. I.,Sonnestein, H.,Nikishin, G. I.
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p. 849 - 853
(2007/10/02)
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- A NEW SYNTHESIS OF δ-LACTONES FROM OXETANES
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Oxetanes were reacted with lithium enolates generated from esters or amides in the presence of boron trifluoride etherate to give δ-hydroxyesters or amides in high yield, which were hydrolyzed and converted to δ-lactones.
- Yamaguchi, Masahiko,Shibato, Keisuke,Hirao, Ichiro
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p. 1159 - 1162
(2007/10/02)
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