- Synthesis method of high-content dihydrojasmonic spice (by machine translation)
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The synthetic method comprises the following steps: 2 - octanol serving as a solvent and di-tert-butyl peroxide as an initiator, and refluxing to separate t-butyl alcohol and water, vacuum distillation to obtain 2 - octyl 2 - (3H) furanone, and then dehydrating and dehydrating 5 - methyl -5 - hexyl -2 -2 -5 - (3H) furanone molecules under the action of a solid acid catalyst to recover the dihydrojasmonic spice product after the reflux reaction is carried out 5 . The synthesis method provided by the invention has the advantages of relatively simple steps, no acid waste water generation and high total yield, and moreover, the content of the product and the dihydrojasmonone synthesized through the synthetic method provided by the invention is higher than 98% and above. (by machine translation)
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Paragraph 0018; 0030-0037
(2020/07/13)
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- Radical-polar crossover reactions of vinylboron ate complexes
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Vinyl boronic esters are valuable substrates for Suzuki-Miyaura cross-coupling reactions. However, boron-substituted alkenes have drawn little attention as radical acceptors, and the radical chemistry of vinylboron ate complexes is underexplored. We show here that carbon radicals add efficiently to vinylboron ate complexes and that their adduct radical anions undergo radical-polar crossover: A 1,2-alkyl/aryl shift from boron to the α-carbon sp2 center provides secondary or tertiary alkyl boronic esters. In contrast to the Suzuki-Miyaura coupling, a transition metal is not required, and two carbon-carbon bonds are formed. The valuable boronic ester moiety remains in the product and can be used in follow-up chemistry, enlarging the chemical space of the method. The cascade uses commercial starting materials and provides access to perfluoroalkylated alcohols, γ-lactones, γ-hydroxy alkylnitriles, and compounds bearing quaternary carbon centers.
- Kischkewitz, Marvin,Okamoto, Kazuhiro,Mück-Lichtenfeld, Christian,Studer, Armido
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p. 936 - 938
(2017/03/15)
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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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- A new coupling reaction between β-lactones and electrophiles mediated by a SmI2/(NiI2 catalytic) system
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β-lactones react with ketones aldehydes and imines in the presence of a SmI2/(NiI2 catalytic) system to afford substituted tetrahydrofuranones and pyrrolidinones.
- Machrouhi, Fouzia,Namy, Jean-Louis
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p. 11111 - 11122
(2007/10/03)
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- Palladium(II)-catalyzed formation of γ-butyrolactones from 4-trimethylsilyl-3-alkyn-1-ols: Synthetic and mechanistic aspects
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γ-butyrolactones are obtained in good yields from 4-trimethylsilyl-3-alkyn-1-ols via Wacker-type oxidation reaction. A mechanism is proposed for this transformation: it involves two successive trans-hydroxypalladations followed by a [PdXSiMe3] syn-elimination and explains why the presence of the silyl group is essential in such a process.
- Compain, Philippe,Gore, Jacques,Vatele, Jean-Michel
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p. 10405 - 10416
(2007/10/03)
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- Oxygenation of Tetrahydrofurans with Combined Use of Molecular Oxygen and α-Diketone Catalyzed by Cobalt(III) Complex
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In the presence of catalytic amount of cobalt(III) complex such as tris(acetylacetonato)cobalt(III), tetrahydrofurans are oxygenated into the corresponding γ-butyrolactones under mild conditions on treatment with an atmospheric pressure of molecular oxygen and α-diketones having hydrogen atom next to the carbonyl carbon.
- Hata, Eiichiro,Takai, Toshihiro,Mukaiyama, Teruaki
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p. 1513 - 1516
(2007/10/02)
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- SmCl3-catalysed Electrosynthesis of γ-Butyrolactones from 3-Chloroesters and Carbonyl Compounds
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Electrosynthesis of γ-butyrolactones has been achieved by the direct reductive coupling of ethyl 3-chloropropionate and a series of carbonyl compounds in the presence of a catalytic amount of SmCl3.
- Hebri, Hassan,Dunach, Elisabet,Perichon, Jacques
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p. 499 - 500
(2007/10/02)
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- N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide as Thiohomoenolatesynthon. Application to a Synthesis of Some Heterocycles
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N-Benzyl-3-(tri-n-butylstannyl)thiopropionamide undergoes metalexchange with n-butyllithium.The resulting thiohomoenolate dianion reacts with elestrophiles (aldehydes and ketones) to give the γ-hydroxythioamides, which are transformed into lactones, iminothiolactones, and thiolactams with simple elaboration.
- Takahata, Hiroki,Ohkura, Etsuko,Ikuro, Kazumi,Yamazaki, Takao
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p. 285 - 292
(2007/10/02)
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- A General Approach to the Synthesis of Butanolides: Synthesis of the Sex Pheromone of the Japanese Beetle
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A variety of substituted γ-hydroxy olefins 1 have been converted to butanolides 4 in very high yield in a three-step sequence involving bromoetherification, elimination, and oxidative cleavage.The key step in the overall transformation is the highly selective oxidative cleavage of enol ethers 3 with PCC under very mild reaction conditions.Application of this methodology has been exemplified in the synthesis of the Japanese beetle pheromone.
- Baskaran, Sundarababu,Islam, Imadul,Chandrasekaran, Srinivasan
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p. 891 - 895
(2007/10/02)
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- Direct Preparation of Lanthanoid Ester Homoenolates from 3-Halo Esters and Lanthanoid Metals: Their Homo-Reformatsky-Type Reaction with Carbonyl Compounds
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The direct reaction of ethyl 3-bromopropionate (2a) or 3-iodopropionate (2b) with lanthanoid metals (La, Ce, Nd, Sm) in tetrahydrofuran produces lanthanoid ester homoenolates (3), which react with ketones to give γ-lactones in good yields under mild conditions.The isolation of 3-phenylseleno (8a), 3-phenyltelluro (8b), and 3-tri-n-butylstannyl esters (10) from the reaction with diphenyl diselenide (7a), ditelluride (7b), and tri-n-butyltin iodide (9), respectively, suggests the formation of the lanthanoid ester homoenolate.
- Fukuzawa, Shin-ichi,Sumimoto, Norifumi,Fujinami, Tatsuo,Sakai, Shizuyoshi
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p. 1628 - 1631
(2007/10/02)
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- Samarium(II) Di-iodide Induced Reductive Coupling of α,β-Unsaturated Esters with Carbonyl Compounds Leading to a Facile Synthesis of γ-Lactone
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Samarium(II) di-iodide, which is a strong one-electron transfer reducing agent, is effective for the reductive coupling of α,β-unsaturated esters with carbonyl compounds, whereby substituted γ-lactones can easily be prepared in good to excellent yields under very mild conditions.Two mole equiv. of samarium(II) di-iodide to each mole equiv. of starting substrate always give reasonable yields.The presence of an alcohol is essential in the reaction, complex unidentified products being formed in the absence of an alcohol; t-butyl alcohol gave more satisfactory results than methanol and ethanol.The alcohol acts as a proton donor, the use of MeOD leading to a deuteriated γ-lactone.The reaction is applicable to both aliphatic and aromatic ketones or aldehydes, whereas the electrochemical method is limited to aliphatic substrates.The diastereoselectivity is examined in the reaction of 4-t-butylcyclo-hexanone with ethyl acrylate; an anti-isomer is produced predominantly (syn:anti = 1:9) as the result of selective axial attack.The reaction may proceed by a radical mechanism, and reaction may not involve a samarium ester homoenolate.The reaction is extended to the intramolecular reaction of an α,β-unsaturated keto ester (8-oxonon-2-enoate) leading to the ready synthesis of a bicyclic γ-lactone.
- Fukuzawa, Shin-ichi,Nakanishi, Akira,Fujinami, Tatsuo,Sakai, Shizuyoshi
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p. 1669 - 1676
(2007/10/02)
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- A Facile and Direct Synthesis of γ-Lactones from Methyl β-Bromopropionate and Ketones mediated by Lanthanoid Metals
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ψ-Lactones were easily prepared from the direct reaction of methyl β-bromopropionate with ketones mediated by lanthanoid metals; a lanthanoid metal ester homoenolate (β-lanthanoid metal substituted ester) is postulated as a reaction intermediate.
- Fukuzawa, Shin-ichi,Fujinami, Tatsuo,Sakai, Shizuyoshi
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p. 475 - 476
(2007/10/02)
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- A HIGHLY EFFICIENT SYNTHESIS OF γ- AND δ-LACTONES BY OXIDATIVE CYCLIZATION
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Treatment of tertiary γ- and δ-hydroxyolefins with pentavalent chromium reagent, (BipyH2)CrOCl5, give good yields of γ- and δ-lactones by oxidative cyclization, with loss of one carbon.Pyridinium chlorochromate (PCC) also effect this transformation to γ-lactones in reasonable yields.
- Chakraborty, T. K.,Chandrasekaran, S.
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p. 551 - 554
(2007/10/02)
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- Process for producing lactones from unsaturated carbonyl compounds
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A method for producing an alkyl substituted lactone including the steps of alkylating an unsaturated ketone with a C1 -C12 alkyl organometallic reagent such as a Grignard reagent or an alkali metal alkyl, to form an unsaturated alcohol, and oxidatively cleaving the unsaturated alcohol to form the lactone, and recovering the lactone.
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- Cyclodepsipeptides from Beauveria bassiana. Part 3. The Isolation of Beauverolides Ba, Ca, Ja, and Ka
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Beauverolides Ja and Ka are shown to be the cyclotetradepsipeptides cyclo- and the 3-hydroxy-4-methyldecanoyl homologue, respectively.Pairs of beauverolides differing only in the hydroxy-acid residue are readily separated by high-pressure liquid chromatography and beauverolides Ba and Ca have been isolated using this technique.
- Grove, John Frederick
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p. 2878 - 2880
(2007/10/02)
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