87305-70-2Relevant academic research and scientific papers
Intramolecular Cyclization of Brominated Oxime Ether Promoted with Ytterbium(0) to the Synthesis of Cyclic Imines
Wang, Yiqiong,Huang, Fei,Zhang, Songlin
supporting information, p. 5178 - 5181 (2020/08/13)
The first utility of ytterbium(0) as a mediating-metal in the intramolecular cyclization of brominated oxime ether was reported in this paper. In contrast to the prior methods, the N–O bond was used as a receptor of nucleophilic reagent, rather than as a source of N-centered radicals. Cyclic imines were obtained in this one-pot reaction with a broad scope of substrates and feasible reaction conditions.
Iminyl Radicals by Reductive Cleavage of N-O Bond in Oxime Ether Promoted by SmI2: A Straightforward Synthesis of Five-Membered Cyclic Imines
Huang, Fei,Zhang, Songlin
supporting information, p. 7430 - 7434 (2019/10/11)
A new generation method of N-centered radicals from the reductive cleavage of the N-O bond in oxime ether promoted by SmI2 is reported for the first time. The in-situ-generated N-centered radicals underwent intramolecular cyclization to afford five-membered cyclic imines in two manners: N-centered radical addition and N-centered anion nucleophilic substitution. From a synthetic point of view, an efficient synthetic method of five-membered cyclic imines was developed. A mechanism of the transformation was proposed.
The influence of phenyl and phenoxy modification in the hydrophobic tails of di-n-alkyl phosphate amphiphiles on aggregate morphology
Visscher, Inge,Stuart, Marc C. A.,Engberts, Jan B. F. N.
, p. 707 - 712 (2007/10/03)
A series of di-n-alkyl phosphate amphiphiles containing phenyl and phenoxy groups in the hydrophobic tails were synthesised, and their aggregation behaviour was investigated using fluorescence spectroscopy, differential scanning calorimetry, and cryo-electron microscopy. The aggregates displayed a wide variety of aggregate morphologies. The incorporation of a phenyl group into the end or in the middle of the alkyl chain lowered the main phase transition temperature, resulting in closed vesicles only above the phase transition temperature. Introducing a phenoxy group at the end of the alkyl chain resulted in open bilayer structures and bicelles. The Royal Society of Chemistry.
Synthesis and Evaluation of Radioiodinated Terminal p-Iodophenyl-Substituted α- and β-Methyl-Branched Fatty Acids
Goodman, M. M.,Kirsch, G.,Knapp, F. F.
, p. 390 - 397 (2007/10/02)
Methods have been developed for the preparation of terminal p-iodophenyl-substituted α- and β-methyl-branched long-chain fatty acids.The syntheses and physical properties of 14-(p-iodophenyl)-2(RS)-methyltetradecanoic acid and 15-(p-iodophenyl)-3(RS)-methylpentadecanoic acid are described.The radioiodinated agents are of interest as a result of the expected pronounced uptake and prolonged myocardial retention that may result from the inhibition of fatty acid metabolism.Tissue distribution studies in rats with 14-(p-iodophenyl)-2(RS)-methyltetradecanoic acidand 15-(p-iodophenyl)-3(RS)-methylpentadecanoic acid show significant heart uptake and prolonged retention accompanied by low in vivo deiodination and high blood levels.A comparison of the heart uptake of the radioiodinated methyl-branched fatty acids and their unbranched analogues has demonstrated a greater myocardial retention of the methyl-branched fatty acids than the unbranched analogues.These results suggest that the mechanism of myocardial retention results from steric or chemical inhibition of the metabolism of these fatty acids by the presence of the methyl group.
Synthetic Utility of the Palladium-Catalyzed Coupling Reaction of Acid Chlorides with Organotins
Labadie, Jeff W.,Tueting, David,Stille, J. K.
, p. 4634 - 4642 (2007/10/02)
The palladium coupling of acid chlorides with unsymmetrical organotin reagents R''3SnR' can be carried out in chloroform under mild conditions in high yields to give the ketone RCOR'in which only one of the four organic groups on tin appears in the ketone product.Alkyl partners (R''= methyl or butyl) on tin serve as anchoring groups and do not transfer.When R' is acetylenic, vinyl, aryl, methoxymethylene, allyl, or benzyl, transmetalation takes place preferentially, resulting in coupling with the acyl group from the acid chloride.The reaction is tolerant of functional groups both on the acid chloride and the tin reagent.A palladium-catalyzed coupling reaction of an organotin reagent bearing acrylate functionality with an acid chloride serves as a method to introduce both a ketone and an acrylate functionality into a carbon framework.The coupling reaction of 4-(tert-butyldiphenylsiloxy)pentanoyl chloride with benzyl 3-(tributylstannyl)acrylate gave a 71percent yield of benzyl 7-(tert-butyldiphenylsiloxy)-4-oxo-2-octenoate, a precursor to the macrolide antibiotic pyrenophorin.
