39207-65-3Relevant articles and documents
Method for preparing alkane carboxylic acid by increasing alkane carbon chains
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Paragraph 0031; 0045; 0048, (2021/06/09)
The invention discloses a method for preparing alkane carboxylic acid by increasing alkane carbon chains. The method comprises the following steps: (1) carrying out Stork enamine alkylation on cyclopentanone or cyclohexanone and a secondary amine compound to generate a corresponding 1-position secondary amine substituted cyclopentene or cyclohexene crude product, namely Stork enamine; (2) carrying out electrophilic reagent reaction on the Stork enamine and acyl halide to form a 2-acyl cyclic ketone compound; and (3) carrying out ring opening on the 2-acyl cyclic ketone compound under the action of alkali to generate a carbonyl carboxylic acid compound, and carrying out a Wolff-Huang Minglong reduction reaction on the carbonyl carboxylic acid compound to obtain the corresponding alkane carboxylic acid. According to the method disclosed by the invention, cyclopentanone or cyclohexanone can be flexibly selected to meet the requirement of increasing different carbon numbers according to the required carbon number and different sources of target carburant alkane carboxylic acid or corresponding acyl halide. The method has the advantages of simple reaction process and no complex operation difficulty, and is suitable for industrial mass production.
Synthesis of 1,3-Diketones and β-Keto Thioesters via Soft Enolization
Aderibigbe, Sabrina O.,Coltart, Don M.
, p. 9770 - 9777 (2019/08/27)
Ketones and thioesters undergo soft enolization and acylation using crude acid chlorides on treatment with MgBr2·OEt2 and i-Pr2NEt to give 1,3-diketones and β-keto thioesters, respectively. The use of crude acid chlorides adds efficiency and cost reduction by avoiding the need to purify and/or purchase them. The process is conducted in a direct fashion that does not require prior enolate formation, further enhancing its efficiency and making it very easy to carry out. The method is suitable for large scale applications. ?
Targeting Staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors
Murray, Ewan J.,Crowley, Rebecca C.,Truman, Alex,Clarke, Simon R.,Cottam, James A.,Jadhav, Gopal P.,Steele, Victoria R.,O'Shea, Paul,Lindholm, Catharina,Cockayne, Alan,Chhabra, Siri Ram,Chan, Weng C.,Williams, Paul
supporting information, p. 2813 - 2819 (2014/04/17)
A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.
COMPOUNDS, THEIR PHARMACEUTICAL COMPOSITIONS AND THEIR USES AS IDH1 MUTANTS INHIBITORS FOR TREATING CANCERS
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Page/Page column 110, (2013/02/28)
Provided are compounds of formula (I), wherein X, Y, Z, W, V, R2, R3 and m are defined as in the description. Their pharmaceutical compositions and their uses as IDH1 mutants inhibitors for treating cancers are also provided
Amidine dications as superelectrophiles
Corr, Michael J.,Roydhouse, Mark D.,Gibson, Kirsty F.,Zhou, Sheng-Ze,Kennedy, Alan R.,Murphy, John A.
supporting information; experimental part, p. 17980 - 17985 (2010/04/01)
2-Dimethylalkylammonium pyridinium and 2-dimethylalkylammonium pyrimidinium ditriflate salts are very powerful methylating agents toward phosphorus (triphenylphosphine) and nitrogen (triethylamine) nucleophiles. In competition experiments with triethylamine as nucleophile, these N-methyl disalts are more reactive methylating agents than dimethyl sulfate. Reaction of the pyridinium dications with water as an oxygen nucleophile leads to attack at the 2-position of the heteroaromatic ring and displacement of an ammonium group; 2-hydroxypyridinium compounds are formed in the first instance, which are easily converted to 2-pyridones. Extending the scope of the reactions, a tricationic 2,6-bis(dimethylalkylammonium) pyridinium salt has also been prepared and characterized and its reactivity as a methylating agent assessed in comparison with that of the dications.
N- versus O-arylation of aminoalcohols: Orthogonal selectivity in copper-based catalysts
Shafir, Alexandr,Lichtor, Phillip A.,Buchwald, Stephen L.
, p. 3490 - 3491 (2008/01/01)
Two complementary protocols for copper-catalyzed arylation of aminoalcohols were developed. Selective N-arylation was accomplished at room temperature using 2-isobutyrylcyclohexanone (a β-diketone) as supporting ligand, while selective O-arylation require
Highly selective room-temperature copper-catalyzed C-N coupling reactions
Shafir, Alexandr,Buchwald, Stephen L.
, p. 8742 - 8743 (2007/10/03)
Through the use of cyclic β-diketones as supporting ligands, the copper-catalyzed coupling of aryl iodides with aliphatic amines occurs at room temperature in as little as 1 h. These high reaction rates allow for the coupling of a wide range of aryl and heteroaryl iodides at room temperature. This method is highly tolerant of a number of reactive functional groups, including -Br and aromatic -NH2 as well as phenolic and aliphatic -OH. The high selectivity of the CuI-β-diketone catalyst for aliphatic amines represents a useful complement to the palladium-based methods. Copyright
A Short Route to Dihydrocapsaicinoids
Kaga, Harumi,Miura, Masakatsu,Orito, Kazuhiko
, p. 864 - 866 (2007/10/02)
Huang-Minlon reduction of 8-methyl-7-oxononanoic acid (4ba), obtained by the acylation of cyclohexanone enamine 2a with 2-methylpropanoyl chloride (1b) followed by ring cleavage of the resultant β-diketone 3ba affords 8-methylnonanoic acid (5ba), the chloride of which reacts readily with 4-hydroxy-3-methoxybenzylamine to give dihydrocapsaicin (7ba).This reaction sequence works also efficiently for other dihydrocapsaicinoids such as 7aa and 7bb.
IMINOALKYLATION DES ENAMINES AVEC DES NITRILES VIA LE SEL DE NITRILIUM : UNE NUOVELLE METHODE DE SYNTHESE D'ENAMINOCETONES ET DE β-DICETONES
Baudoux, Dominique,Fuks, Robert
, p. 1009 - 1018 (2007/10/02)
The reaction of nitrilium salts with enamines leads to a mixture of enamines 4 and enaminoketones 5 by an iminoalkylation reaction.Partial hydrolysis of 4 with diluted acetic acid leads to the isolation of these new enaminoketones 5 in high yields.Refluxi