7018-92-0Relevant articles and documents
The enantiomeric discrimination of 5-hexyl-2-methyl3,4-dihydro-2h-pyrrole by sulfobutyl ether-β-cyclodextrin: A case study
Costa, Bruna Z.,Kawano, Daniel F.,Loureiro, Hugo C.,Marsaioli, Anita J.,Romero-Orejón, Katherine L.,de Jesus, Dosil P.
, (2021)
1-Pyrrolines are important intermediates of active natural products, such as the 2,5dialkyl-1-pyrroline derivatives found in fire ant venoms. Here, 5-hexyl-2-methyl-3,4-dihydro-2Hpyrrole was synthesized by the enzymatic transamination/cyclization of 2,5-undecadione, and enantiodifferenciation was successfully achieved by capillary electrophoresis with sulfobutyl ether-βcyclodextrin as the chiral selector. The rationale of the enantiomeric discrimination was based on the results of a docking simulation that revealed the higher affinity of (S)-5-hexyl-2-methyl-3,4-dihydro2H-pyrrole for the sulfobutyl ether-β-cyclodextrin.
Polymer-supported Thiazolium Salt Catalysts: A Model System for the Thiamine Dependent Enzymes
Sell, Charles S.,Dorman, Linda A.
, p. 629 - 630 (1982)
A polymer-supported thiazolium salt has been prepared which catalyses the addition of aldehydes to activated olefins in the absence of added base.
Synthesis method of dihydrojasmonone
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Paragraph 0024-0027, (2021/07/31)
The invention discloses a synthesis method of dihydrojasmonone, belongs to the technical field of perfume synthesis, aims to solve the problems that raw materials are difficult to prepare and high in price, and the fragrance of a product is impure, and relates to a method for synthesizing dihydrojasmonone by reacting halogenated n-hexane and magnesium chips under a solvent condition to generate an n-hexyl Grignard reagent under anhydrous and nitrogen protection, carrying out catalytic coupling on the n-hexyl Grignard reagent and acetyl propionyl chloride through vanadium trichloride to generate undecane-2,5-dione, and carrying out condensation ring closing on undecane-2,5-dione under an alkaline condition. In the synthesis route, the used raw materials are cheap and easy to obtain, and other auxiliary reagents are all industrial basic raw materials, so that the price is low; reaction steps are short, and reaction conditions are simple; and in addition, the reaction yield is relatively high and is kept at 64-72%, and the purity is relatively high and is kept at about 98%, so that the method is suitable for realizing industrial production and has relatively high application value.
Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Du, Le,Luo, Xiya,Markó, István E.,Dewez, Damien F.,Lam, Kevin
, p. 12044 - 12055 (2019/03/01)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
Synthesis of 2,5-Disubstituted Pyrrolidine Alkaloids via A One-Pot Cascade Using Transaminase and Reductive Aminase Biocatalysts
Costa, Bruna Z.,Galman, James L.,Slabu, Iustina,France, Scott P.,Marsaioli, Anita J.,Turner, Nicholas J.
, p. 4733 - 4738 (2018/09/25)
A multi-enzymatic cascade process involving transaminases (TAs) and reductive aminases (RedAms) to produce enantiomerically pure 2,5-disubstituted pyrrolidine alkaloids from their respective 1,4-diketones is reported. Several TAs were screened and the best results for diketone monoamination were obtained with an R-selective TA from Mycobacterium chlorophenicum and with an S-selective TA from Bacillus megaterium. Pyrroline reduction was best performed by a reductive aminase from Ajellomyces dermatitidis (AdRedAm). Finally, a biocatalytic one-pot cascade was implemented using the aforementioned enzymes and a variety of 2-methyl-5-alkylpyrrolidines were produced with high (>99 %) conversion, diastereomeric and enantiomeric excess values.
Synthesis of Diketones, Ketoesters, and Tetraketones by Electrochemical Oxidative Decarboxylation of Malonic Acid Derivatives: Application to the Synthesis of cis-Jasmone
Ma, Xiaofeng,Dewez, Damien F.,Du, Le,Luo, Xiya,Markó, István E.,Lam, Kevin
, (2018/10/15)
Disubstituted malonic acid derivatives are smoothly converted into diketones and ketoesters in good to excellent yield (68% to 91%) under electrochemical conditions. The scope can be extended to transform trisubstituted bis-malonic acids into tetraketones in 77% to 86% yield. The new method was applied to the total synthesis of cis-jasmone.
NOVEL PROCESS FOR PREPARING SYNTHESIS INTERMEDIATES USING PRODUCTS OF NATURAL ORIGIN AND USE OF THE INTERMEDIATES OBTAINED
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Paragraph 0229-0230, (2017/12/15)
Disclosed is a process for preparing a product of formula I: wherein the reaction is catalyzed both by thiamine or a thiamine salt and by ascorbic acid in a form which is free or salified or an organic acid salt of an alkaline metal, preferably sodium acetate, potassium tartrate, sodium succinate, or a reductone, preferably 2-hydroxypropanedial or 2,3-dihydroxycyclopent-2-ene-1-one in an organic solvent.
Flow synthesis using gaseous ammonia in a Teflon AF-2400 tube-in-tube reactor: Paal-Knorr pyrrole formation and gas concentration measurement by inline flow titration
Cranwell, Philippa B.,O'Brien, Matthew,Browne, Duncan L.,Koos, Peter,Polyzos, Anastasios,Pe?a-López, Miguel,Ley, Steven V.
scheme or table, p. 5774 - 5779 (2012/08/28)
Using a simple and accessible Teflon AF-2400 based tube-in-tube reactor, a series of pyrroles were synthesised in flow using the Paal-Knorr reaction of 1,4-diketones with gaseous ammonia. An inline flow titration technique allowed measurement of the ammonia concentration and its relationship to residence time and temperature.
Regioselective cobalt-catalysed hydrovinylation for the synthesis of non-conjugated enones and 1,4-diketones
Kersten, Laura,Hilt, Gerhard
supporting information; experimental part, p. 863 - 869 (2012/05/04)
The highly regioselective cobalt-catalysed 1,4-hydrovinylation of terminal alkenes with 2-trimethylsilyloxy-1,3-butadiene generates in a stereospecific fashion unsaturated E-configured silyl enol ether intermediates that are suitable for diastereoselective Mukaiyama-aldol reactions with bulky aliphatic aldehydes. The acidic hydrolysis of the enol ethers to γ,δ- unsaturated ketones followed by ozonolysis can be used for the synthesis of various 1,4-diketones and polycarbonyl derivatives. The 1,4-diketones and polycarbonyl derivatives were successfully tested for the synthesis of some mono- and bis-pyrrole derivatives. The γ,δ-unsaturated ketones are useful building blocks (e.g., in natural product synthesis) and can be generated in a one-pot procedure. Copyright
Acylation of electrophilic olefins through decatungstate-photocatalyzed activation of aldehydes
Esposti, Silvia,Dondi, Daniele,Fagnoni, Maurizio,Albini, Angelo
, p. 2531 - 2534 (2008/03/11)
(Chemical Equation Presented) With tungsten and lamp: Ketones were prepared by the photocatalytic generation of acyl radicals from aldehydes and trapping them with equimolar amounts of electrophilic alkenes. Photocatalysis with tetrabutylammonium decatungstate is effective also at low temperatures (-20 to -50°C), thus minimizing radical decarbonylation and allowing acylation by highly substituted aldehydes. EWG = electron-withdrawing group.
