38460-95-6Relevant articles and documents
Undec-10-enoic Acid in the Synthesis of Macroheterocycles Containing Hydrazide and Ester Fragments
Mingaleeva,Yakovleva,Salakhutdinov,Tolstikov,Ishmuratov, G. Yu.
, p. 514 - 517 (2019)
Four potentially biologically active 31-, 32-, and 33-membered macroheterocycles with ester and hydrazide fragments have been synthesized by [1 + 1]-condensation of ethane-1,2-diyl bis(10-oxoundecanoate) with malonic, glutaric, L-(+)-tartaric, and pyridine-2,6-dicarboxylic acid dihydrazides. The product structure has been confirmed by IR, NMR, and mass spectra.
Photo- and Metallo-responsive N-Alkyl α-Bisimines as Orthogonally Addressable Main-Chain Functional Groups in Metathesis Polymers
Greb, Lutz,Mutlu, Hatice,Barner-Kowollik, Christopher,Lehn, Jean-Marie
, p. 1142 - 1145 (2016)
N-alkyl α-bisimines were employed as main-chain functional groups in acyclic diene metathesis (ADMET)-polymers, conferring dual responsiveness for the controlled switching of the polymeric particle shape with light and metal ions. Photochemical Z/E-isomerization leads to a significant and reversible change in hydrodynamic volume, thus introducing simple imines as novel photoswitches for light-responsive materials. Mild imine-directed CH activation by Pd(OAc)2 is demonstrated as a new single-chain nanoparticle (SCNP) folding process, enabling a controlled atom- and step-economic SCNP synthesis. The combination of light- and metallo-responsiveness in the same polymer provides the ability for orthogonal switching, a valuable tool for advanced functional material design.
Immobilization of catalytic virus-like particles in a flow reactor
Liu,Yang,Traulsen,Cornelissen
, p. 7632 - 7634 (2017)
A functional microfluidic reactor is constructed by the immobilization of gold containing virus-based protein cages that catalyze the reduction of nitro-arenes with high efficiency.
Synthesis and crystal structure of a meso-decene-BODIPY dye as a functional bright fluorophore for silicone matrices
Pakhomov, Alexey A.,Mironiuk, Veronika B.,Kononevich, Yuriy N.,Korlyukov, Alexander A.,Volodin, Alexander D.,Pryakhina, Tatyana A.,Martynov, Vladimir I.,Muzafarov, Aziz M.
, p. 363 - 365 (2017)
A meso-decene-BODIPY dye was synthesized and conjugated to a polydimethylsiloxane. Fluorescence properties of the obtained polymer drastically changed in different solvents. The polymer showed an unusual for other siloxane polymers trend to structuration.
Infrared reflection-absorption study of ordering and hydrogen bonding within chiral and nonchiral self-assembled monolayers on gold
Nissink,Van Der Maas
, p. 33 - 39 (1999)
Ordering processes in chiral and racemic monolayers of three phenylalanyl-substituted ω-thiol alkanoic acids on gold have been investigated with the use of infrared reflection absorption spectroscopy. For chiral molecules, packing is influenced by both hydrogen-bonding interactions between the end groups at the air/monolayer interface and the length of the spacer chain within the monolayer. Results for a mixed monolayer of octadecylmercaptane and phenylalanyl-substituted ω-thiol docosanoic acid indicate that formation of large islands of either one of the compounds can be excluded. For a racemic monolayer of phenylalanyl-substituted ω-thiol undecanoic acid, a dense, yet unregular, packing is observed.
Methyl Radical Initiated Kharasch and Related Reactions
Tappin, Nicholas D. C.,Renaud, Philippe
supporting information, p. 275 - 282 (2020/12/07)
An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).
Synthesis of N-trifluoromethyl amides from carboxylic acids
Flavell, Robert R.,Liu, Jianbo,Parker, Matthew F. L.,Toste, F. Dean,Wang, Sinan,Wilson, David M.
supporting information, p. 2245 - 2255 (2021/08/12)
Found in biomolecules, pharmaceuticals, and agrochemicals, amide-containing molecules are ubiquitous in nature, and their derivatization represents a significant methodological goal in fluorine chemistry. Trifluoromethyl amides have emerged as important functional groups frequently found in pharmaceutical compounds. To date, there is no strategy for synthesizing N-trifluoromethyl amides from abundant organic carboxylic acid derivatives, which are ideal starting materials in amide synthesis. Here, we report the synthesis of N-trifluoromethyl amides from carboxylic acid halides and esters under mild conditions via isothiocyanates in the presence of silver fluoride at room temperature. Through this strategy, isothiocyanates are desulfurized with AgF, and then the formed derivative is acylated to afford N-trifluoromethyl amides, including previously inaccessible structures. This method shows broad scope, provides a platform for rapidly generating N-trifluoromethyl amides by virtue of the diversity and availability of both reaction partners, and should find application in the modification of advanced intermediates.
Modular Tuning of Electrophilic Reactivity of Iridium Nitrenoids for the Intermolecular Selective α-Amidation of β-Keto Esters
Lee, Minhan,Jung, Hoimin,Kim, Dongwook,Park, Jung-Woo,Chang, Sukbok
supporting information, p. 11999 - 12004 (2020/08/06)
We report herein an Ir-catalyzed intermolecular amino group transfer to β-keto esters (amides) to access α-aminocarbonyl products with excellent chemoselectivity. The key strategy was to engineer electrophilicity of the putative Ir-nitrenoids by tuning electronic property of the κ2-N,O chelating ligands, thus facilitating nucleophilic addition of enol π-bonds of 1,3-dicarbonyl substrates.
