927-56-0Relevant academic research and scientific papers
Direct preparation of nitriles from carboxylic acids in continuous flow
Cantillo, David,Kappe, C. Oliver
, p. 10567 - 10571 (2013/11/06)
A continuous-flow protocol for the preparation of organic nitriles from carboxylic acids has been developed. The method is based on the acid-nitrile exchange reaction with acetonitrile, used as the solvent, and takes place without any catalyst or additives under the high-temperature/high-pressure conditions employed. At 350 C and 65 bar, where acetonitrile is in its supercritical state, the transformation of benzoic acid to benzonitrile requires 25 min. The protocol has been tested for a variety of nitriles, including aromatic and aliphatic substrates.
METHOD FOR MANUFACTURING KETONE
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Page/Page column 7-8; 9, (2012/08/08)
A method for manufacturing a ketone, includes oxidizing an internal olefin or a cyclic olefin having a functional group containing a hetero atom and one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, without oxidizing the functional group, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond. The amide-based solvent is represented by formula (1): wherein R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.
Wacker-type oxidation of internal olefins using a PdCl2/N,N- dimethylacetamide catalyst system under copper-free reaction conditions
Mitsudome, Takato,Mizumoto, Keiichi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information; experimental part, p. 1238 - 1240 (2010/05/17)
(Figure Presented) A simple catalyst system consisting of PdCl2 and N,N-dimethylacetamide (DMA) as the solvent can successfully promote Wacker-type oxidation of internal olefins. This catalyst system does not require copper compounds and is tolerant of a wide range of substrates having internal olefins.
Probing the active site of rat porphobilinogen synthase using newly developed inhibitors
Li, Nan,Chu, Xiusheng,Liu, Xiaojun,Li, Ding
scheme or table, p. 33 - 40 (2009/05/30)
The structurally related tetrapyrrolic pigments are a group of natural products that participate in many of the fundamental biosynthetic and catabolic processes of living organisms. Porphobilinogen synthase catalyzes a rate-limiting step for the biosyntheses of tetrapyrrolic natural products. In the present study, a variety of new substrate analogs and reaction intermediate analogs were synthesized, which were used as probes for studying the active site of rat porphobilinogen synthase. The compounds 1, 3, 6, 9, 14, 16, and 28 were found to be competitive inhibitors of rat porphobilinogen synthase with inhibition constants ranging from 0.96 to 73.04 mM. Compounds 7, 10, 12, 13, 15, 17, 18, and 26 were found to be irreversible enzyme inhibitors. For irreversible inhibitors, loose-binding inhibitors were found to give stronger inactivation. The amino group and carboxyl group of the analogs were found to be important for their binding to the enzyme. This study increased our understanding of the active site of porphobilinogen synthase.
Multiple Carbon Bond Formation via the Radical Cyclization of Cycloalkenol Acetals. Application to trans Hydrindan Steroid Precursors
Stork, Gilbert,Franklin, Paul J.
, p. 275 - 284 (2007/10/02)
The cyclization of the α-iodo mixed acetals derived from properly substituted cyclohexanols, a process which has already been shown to permit the stereoselective and regioselective introduction of a different carbon chain at each of the termini of the all
C-C Bond Formation via Carbon-Centered Radicals Generated from Dicarbonyl(η5-cyclopentadienyl)organoiron Complexes
Giese, Bernd,Gebhard, Thoma
, p. 1143 - 1155 (2007/10/02)
Irradiation of benzyldicarbonyl(η5-cyclopentadienyl)iron complex (2) leads to homolytic cleavage of the Fe-C bond.In the presence of activated alkenes, radical addition occurs, and both saturated and unsaturated addition products 7-9 are formed.Photolysis of alkyliron complexes 2, 3, and 20 in the presence of acrylonitrile leads to the same products as the irradiation of the respective acyliron complexes 28-30.This indicates that, under photolytical conditions, alkyl and acyl complexes are in equilibrium with each other.
Decomposition du percarbonate de O,O-t-butyle et O-isopropenyle en solution: acetonylation des esters, acides et nitriles
Lalande, Robert,Filliatre, Claude,Villenave, Jean-Jacques,Jaouhari, Rabih
, p. 149 - 159 (2007/10/02)
The free-radical decomposition of O,O-t-butyl and O-isopropenyl peroxycarbonate in substrates possessing mobile H-atoms (S-H) consists mainly in an induced chain process leading to acetonylated derivatives of the solvent.Fairly good yields are obtained but the acetonylation of functional substrates often gives mixtures of isomers.In the case of methyl acetate, the acetonylation occurs on the C-atoms adjacent to the carbonyl (acyloxy moiety) and to the O-atom (alkoxy moiety).However, the relative amounts of the isomeric products depend on the concentration of the peroxycarbonate solutions; at lowest concentration, methyl 4-oxopentanoate (acyloxy moiety) is obtained selectively.It is assumed that the free radicals issued from the solvent are able to abstract H-atoms of other molecules of solvent before adding to the double bond of the peroxycarbonate; the more the peroxycarbonate solution is diluted the more the transfers from the C-atom adjacent to the carbonyl to the radicals adjacent to the O-atom are favoured.In the case of methyl alkanoates, H-transfers from the α-C-atoms to β-radicals of the acyloxy moiety may account for the orientation of the process.Owing to similar H-transfer processes, the acetonylation of functional esters, of acids and nitriles is selective in most cases.
Aminoacid derivatives of cephalosporin compounds
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, (2008/06/13)
Novel organic amide compounds which are N-[6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl]cephalosporin compounds having broad spectrum antibacterial utility are provided by (a) reacting the free amino acid of the appropriate cephalosporin or the acid salt or silylated derivative or complex thereof with a reactive derivative of the corresponding N-6-[(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinic acid or (b) reacting the free amino acid 7-aminocephalosporanic acid or a related compound or the acid salt or silylated derivative thereof with a reactive derivative of the corresponding D-N-[6-(acylaminoacylamino or aminoacylamino)phenyl]-1,2-dihydro-2-oxonicotinyl]-2-substituted glycine. Pharmaceutical compositions containing said compounds and methods for treating infections using said compositions are also disclosed.
