1516-95-6Relevant academic research and scientific papers
Non-innocent Radical Ion Intermediates in Photoredox Catalysis: Parallel Reduction Modes Enable Coupling of Diverse Aryl Chlorides
Chernowsky, Colleen P.,Chmiel, Alyah F.,Wickens, Zachary K.,Williams, Oliver P.,Yeung, Charles S.
supporting information, p. 10882 - 10889 (2021/07/31)
We describe a photocatalytic system that elicits potent photoreductant activity from conventional photocatalysts by leveraging radical anion intermediates generated in situ. The combination of an isophthalonitrile photocatalyst and sodium formate promotes diverse aryl radical coupling reactions from abundant but difficult to reduce aryl chloride substrates. Mechanistic studies reveal two parallel pathways for substrate reduction both enabled by a key terminal reductant byproduct, carbon dioxide radical anion.
Amphipathic sulfonamidobenzamides mimicking small antimicrobial marine natural products; investigation of antibacterial and anti-biofilm activity against antibiotic resistant clinical isolates
Igumnova, Elizaveta M.,Mishchenko, Ekaterina,Haug, Tor,Blencke, Hans-Matti,Sollid, Johanna U. Ericson,Fredheim, Elizabeth G. Aarag,Lauksund, Silje,Stensv?g, Klara,Str?m, Morten B.
, p. 4930 - 4941 (2018/09/11)
There is an urgent need for novel antimicrobial agents to address the threat of bacterial resistance to modern society. We have used a structural motif found in antimicrobial marine hit compounds as a basis for synthesizing a library of antimicrobial sulf
Investigation of oxygen-free Sonogashira step growth synthesis of mono-terminated di-tert-butyl-substituted oligo(phenylene ethynylene)s (OPEs)
Bai, Xinyan,Chen, Xueyi,Barnes, Charles,Dias, Jerry R.,Sandreczki
, p. 1105 - 1111 (2013/02/23)
A series of oligomers, the hetero-coupled mono-terminated di-tert-butyl-substituted phenylene ethynylene dimer, trimer, tetramer, and pentamer have been successfully synthesized in a stepwise process and characterized. Their electronic properties have bee
Microwave mediated protection of hindered phenols and alcohols
Pothi, Tejas,Dawange, Mahesh,Chavan, Kamlesh,Sharma, Rajiv,Deka, Nabajyoti
, p. 706 - 711 (2013/03/28)
Hindered phenols and alcohols were protected as their corresponding ethers using different alkylating agents in presence of KOH/DMSO under microwave irradiation.
Easier preparation of 2,6-Di-tert-butylphenyl derivatives 1
Knorr, Rudolf,Rossmann, Eva Christine,Knittl, Monika
experimental part, p. 2124 - 2128 (2010/09/04)
Despite steric shielding by the 2,6-di-tert-butylphenyl group (super-2,6-xylyl=xyl*), inexpensive sodium phenolate (xyl*-ONa) reacts with dimethyl sulfate to produce only xyl*-OCH3 (94%) with complete suppression of the alternative 4-methylation. Reductive cleavage of xyl*-OCH3 by elemental lithium with the help of an electron carrier generates xyl*-Li, which in turn yields xyl*-CO2H (63%). The corresponding 4-methyl-derivatives of these compounds were obtained analogously. The acid chloride xyl*-COCl (77% yield) acylates HalMgCH 2R to give only xyl*-COCH3 (86%) or xyl*-COEt (97%). These two ketones react with n-butyllithium (no carbonyl addition) and Cl-PO(OEt)2 to furnish only the enol phosphates xyl*-C(=CH 2)OPO(OEt)2 (84%) or xyl*-C(=CHCH 3)OPO(OEt)2 (up to 70%), respectively. Only 1,2-elimination occurs when the latter two products are treated with tert-butyllithium, affording xyl*-CCH (68%) or xyl*-CCMe (88%), respectively. Georg Thieme Verlag Stuttgart - New York.
Pyridine, Pyrimidine and Pyrazine Derivatives as Cxcr3 Receptor Modulators
-
Page/Page column 15, (2009/02/11)
The invention encompasses compounds of Formula I or pharmaceutically acceptable salts thereof, which are modulators of the CXCR3 chemokine receptor function useful for the treatment or prevention of pathogenic inflammatory processes, autoimmune diseases o
Syntheses of sterically hindered zwitterionic pyridinium phenolates as model compounds in nonlinear optics
Diemer, Vincent,Chaumeil, Helene,Defoin, Albert,Fort, Alain,Boeglin, Alex,Carre, Christiane
experimental part, p. 1767 - 1776 (2009/04/11)
Pyridinium phenolates possess a dissymmetric delocalised π-electron system providing a huge quadratic nonlinearity. They are a promising class of molecules for applications in photoelectronics and photonics. Semiempirical calculations indicate that the interplanar angle between the two aromatic rings leads to enhancement in the NLO properties of these compounds. The confirmation of this feature may be provided by the study of a new series of sterically hindered pyridinium phenolates 2a-e bearing two tert-butyl substituents at the ortho position(s) of the phenolate functionality. Such bulky groups would enhance the solubility of zwitterions in organic solvents and would limit the formation of aggregates. Their efficient preparations by using Suzuki cross-coupling reactions involving 3,5-dialkylated 4-bromopyridine N-oxides are described herein. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Highly Diastereoselective Intermolecular β-Addition of Alkyl Radicals to Chiral 2-(Arylsulfinyl)-2-cycloalkenones
Mase, Nobuyuki,Watanabe, Yoshihiko,Ueno, Yoshio,Toru, Takeshi
, p. 7794 - 7800 (2007/10/03)
The diastereoselectivity of intermolecular β-addition of alkyl radicals to 2-(arylsulfinyl)-2-cycloalkenones depends largely upon the structure of the arylsulfinyl group. The reaction of 2-cyclopentenones or 2-cyclohexenones having a sterically bulky arylsulfinyl group such as (3,5-di-tert-butyl-4-methoxyphenyl)sulfinyl, (2,4,6-triisopropylphenyl)sulfinyl or (2,4,6-trimethylphenyl)sulfinyl group gives 3-alkyl-2-(arylsulfinyl)-1-cyclopentanones or 3-alkyl-2-(arylsulfinyl)-1-cyclohexanones in excellent yields and with high diastereoselectivity. Both the X-ray crystallographic analysis and the NOE experiment in the 1H NMR spectrum of (S)-2-[(2,4,6-triisopropylphenyl)sulfinyl]- and (S)-2-[(2,4,6-trimethylphenyl)sulfinyl]-2-cyclopentenone reveal an effective shielding of one of the olefin faces at the β-position by o-isopropyl and o-methyl groups. The addition of bidentate Lewis acids reverses the stereoselection through chelating the intermediates to give the addition products with high diastereoselectivity.
Factors Influencing the Acid Lability of Substituted Arylsulphonyl Arginine Protecting Groups
Ali, Syed Safdar,Echner, Hartmut,Khan, Khalid Mohammed,Schroeder, Christoph,Hasan, Mashooda,et al.
, p. 1425 - 1433 (2007/10/02)
The kinetics of hydrolysis of new, NG-protected 2,4,6-triisopropylbenzene-sulphonyl (6), 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (12) and phenanthrene-3-sulphonyl (17) Fmoc derivatives of L-arginine (1) in comparison with commercially available Fmoc-Arg(Mtr)-OH (Mtr = 4-methoxy-2,3,6-trimethyl-benzenesulphonyl (2)) are studied.The acid lability of the arylsulphonyl group is decreasing as follows Mtr > Tip > Mtbs > Phen.The effect of electron-donating alkyl groups as substituents in increasing the acid lability of the arylsulphonyl residue seems to be in the order of methyl > isopropyl > tert-butyl, while the effect of extended delocalization does not appreciably increase the acid lability. - Keywords: 2,4,6-Triisopropylbenzenesulphonyl (Tip), 4-methoxy-3,5-di-tert-butylbenzenesulphonyl (Mtbs), Phenanthrene-3-sulphonyl (Phen) Residues
Enhancement of the Resonance Interaction of Out-of-Plane Methoxy Groups By Ortho Substituents in Crowded Anisoles
Schuster, Ingeborg I.,Parvez, Masood,Freyer, Alan J.
, p. 5819 - 5825 (2007/10/02)
The 17O and 13C NMR chemical shifts of substituted anisoles provide evidence that the resonance interaction of methoxy groups which are perpendicular to the aromatic ring in crowded anisoles is influenced, to varying degrees, by ortho substituents.Enhance
