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Query: CAS:3349-70-0 (cyclobutanone)
 148 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

We investigated the usefulness of hydrocarbons and 2-alkylcyclobutanones as markers for irradiated, dried shrimps. A method was developed to detect the irradiation of dried shrimps (Penaeus aztecus) by identifying radiation-induced hydrocarbons and 2-alkylcyclobutanones extracted from dried shrimps, which were separated by Florisil column chromatography and identified by a method using gas chromatography/mass spectrometry. Radiation-induced hydrocarbons and 2-alkylcyclobutanones are formed from the fatty acids of the irradiated fats. The quantity of the hydrocarbons and 2-alkylcyclobutanones formed from some fatty acids is related to the composition of fatty acids in a sample. The concentrations of hydrocarbons and 2-alkylcyclobutanones increased with radiation dose. The major hydrocarbons in the irradiated, dried shrimps were 1-tetradecene and pentadecane from palmitic acid; small amounts of heptadecane and 1-hexadecene from stearic acid; and 8-heptadecene and 1,7-hexadecadiene from oleic acid. 2-(5'-Tetradecenyl)cyclobutanone, one of the 2-alkylcyclobutanones, was present at the highest concentration. The radiation-induced hydrocarbons and 2-alkylcyclobutanones were detected at radiation doses of 0.5 kGy and greater. These compounds were not detected in nonirradiated, dried shrimps.
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PMID:Analysis of radiation-induced hydrocarbons and 2-alkylcyclobutanones from dried shrimps (Penaeus aztecus). 1471 64

Palladium-catalyzed transformation of cyclobutanone O-benzoyloximes to a variety of nitriles is described. The reaction may proceed via two important steps, that is, (i) oxidative addition of the N-O bond of oximes to Pd(0) to give a cyclobutylideneaminopalladium(II) species and (ii) beta-carbon elimination of this species to afford a reactive alkylpalladium species. The kind of products is very dependent on the nature of substituents on the cyclobutane ring. The direction of the C-C bond cleavage is controlled by the kind of ligand employed. The sequential reaction composed of the C-C bond cleavage and the subsequent intra- and intermolecular C-C bond formations via the corresponding alkylpalladium species is also demonstrated. For example, an oxime having an alkynyl moiety at a suitable position reacts with a variety of alkenes to afford nitriles bearing dienylcyclopentane moiety in moderate to good yields.
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PMID:Palladium-catalyzed transformation of cyclobutanone O-benzoyloximes to nitriles via C-C bond cleavage. 1528 80

Oxidation of cyclobutanol by aqueous Fe(IV) generates cyclobutanone in approximately 70% yield. In addition to this two-electron process, a smaller fraction of the reaction takes place by a one-electron process, believed to yield ring-opened products. A series of aliphatic alcohols, aldehydes, and ethers also react in parallel hydrogen atom and hydride transfer reactions, but acetone and acetonitrile react by hydrogen atom transfer only. Precise rate constants for each pathway for a number of substrates were obtained from a combination of detailed kinetics and product studies and kinetic simulations. Solvent kinetic isotope effect for the self-decay of Fe(IV), kH2O/kD2O = 2.8, is consistent with hydrogen atom abstraction from water.
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PMID:Reactivity of aqueous Fe(IV) in hydride and hydrogen atom transfer reactions. 1549 35

A novel boronated aminocyclobutanecarboxylic acid (1) was synthesized for potential use in boron neutron capture therapy. Starting from the readily available 3-(bromomethyl)cyclobutanone ketal (4), several synthetic routes to 1 were evaluated. After several unsuccessful attempts with traditional synthetic methods, a novel synthetic strategy to generate the new boronated cyclic amino acid was developed. The tolerance of the hydantoin group to the selenoxide elimination reaction conditions in the preparation of alkenyl compound 7 proved to be the key step in the new strategy.
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PMID:Synthesis of 1-amino-3-[(dihydroxyboryl)methyl]- cyclobutanecarboxylic acid as a potential therapy agent. 1554 98

Alkylcyclobutanones (2-ACBs) are radiolytic products formed when fatty acids are irradiated. These cyclobutanones are unique irradiation byproducts and therefore may serve as indicators of irradiation exposure. As only limited information exists about 2-ACB formation in retail meat products, reliable methods that can quantify 2-ACBs and thus estimate irradiation dose in commercial meat products are desired. The cyclobutanone studied in this experiment was 2-dodecylcyclobutanone (2-DCB), which is formed from palmitic acid. The formation of 2-DCB was evaluated in fresh irradiated ground beef patties at two fat levels. Patties containing 15% and 25% fat were irradiated by electron beam at 1.0, 2.0, 3.0, and 4.5 kGy. Commercially available 1-lb irradiated ground beef chubs with different fat levels were analyzed in order to estimate dose absorbed by these samples. The 2-DCB was extracted using supercritical fluid extraction (SFE) and analyzed by gas chromatography-mass spectroscopy (GC-MS) and was detected in all the irradiated samples. The concentration of 2-DCB increased linearly with dose with R2 = 0.9646 for 25% fat samples and R2 = 0.9444 for 15% fat samples. Further, there was no significant difference in 2-DCB concentrations between the two fat levels. The estimated doses applied to the commercial samples ranged between 1.38 and 1.55 kGy, values consistent with doses normally used in the industry (1.0-2.0 kGy). Our results show that 2-DCB can be used to monitor fresh irradiated beef and approximate the absorbed dose.
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PMID:Evaluation of 2-dodecylcyclobutanone as an irradiation dose indicator in fresh irradiated ground beef. 1576 9

Cyclobutanones reacted with alkynes in the presence of nickel(0) catalysts to produce cyclohexenones. Oxidative cyclization of the carbonyl group of the cyclobutanone and the alkyne with the nickel(0) was followed by beta-carbon elimination from the resulting oxanickelacyclopentene and subsequent reductive elimination. This reaction achieves a formal alkyne insertion between the carbonyl carbon and the alpha-carbon, providing a six-membered carbocyclic skeleton.
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PMID:Nickel-catalyzed intermolecular alkyne insertion into cyclobutanones. 1588 19

[reaction: see text] Iridium-catalyzed ring cleavage reaction of cyclobutanone O-benzoyloximes in the presence of 9,10-dihydroanthracene and potassium carbonate proceeds to give saturated nitriles via C-C bond fission at the sterically more hindered site.
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PMID:Iridium-catalyzed ring cleavage reaction of cyclobutanone O-benzoyloximes providing nitriles. 1593 14

Pd-catalyzed intramolecular selenocarbamoylation of alkynes leading to alpha-alkylidene-beta-lactams was developed. This reaction can be applied to thiocarbamoylation and to the synthesis of delta- and epsilon-lactams and a cyclobutanone.
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PMID:Palladium-catalyzed intramolecular selenocarbamoylation of alkynes with carbamoselenoates: formation of alpha-alkylidene-beta-lactam framework. 1599 73

The molecular beam Fourier transform microwave spectrum of cyclobutanone-trifluoromethane has been assigned and measured. The carbon atom of trifluoromethane lies in the plane of the heavy atoms of cyclobutanone. The complex is stabilized by one C-H...O=C and two C-H...F-C weak hydrogen bonds. The C-H...O=C interaction, involving one carbonylic oxygen, is studied for the first time in detail with rotationally resolved spectroscopy. The two C-H...F-C weak hydrogen bonds involve two fluorine atoms of trifluoromethane and two hydrogens of the same methylenic group in the alpha position.
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PMID:Molecular beam rotational spectrum of cyclobutanone-trifluoromethane: nature of weak CH...O=C and CH...F hydrogen bonds. 1622 5

The hydrogen-bonded complex cyclobutanone-water has been studied by Fourier-transform molecular-beam microwave spectroscopy in the frequency range of 6-18.5 GHz. The rotational spectra of ten isotopomers have been assigned and measured. Five of them have been obtained from different isotopic species (or configurations) of water (H2O, D2O, DOH, HOD, and H2 18O). The remaining five correspond to the four singly substituted 13C and to the 18O species of cyclobutanone, observed in natural abundance. For all species the inertial defect is in the range from -10.44 to -10.50 uA2, showing that the cyclobutanone frame is effectively planar and that the water molecule is coplanar to this frame. The hydrogen bond, almost linear, is formed between a water proton and one of the lone pairs of the cyclobutanone oxygen.
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PMID:Water-ketones hydrogen bonding: the rotational spectrum of cyclobutanone-water. 1626 94


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