52988-36-0Relevant academic research and scientific papers
Reactions of benzyltriphenylphosphonium salts under photoredox catalysis
Boldt, Andrew M.,Dickinson, Sidney I.,Ramirez, Jonathan R.,Benz-Weeden, Anna M.,Wilson, David S.,Stevenson, Susan M.
supporting information, p. 7810 - 7815 (2021/09/28)
The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.
Styrylphenylphthalimides as Novel Transrepression-Selective Liver X Receptor (LXR) Modulators
Nomura, Sayaka,Endo-Umeda, Kaori,Aoyama, Atsushi,Makishima, Makoto,Hashimoto, Yuichi,Ishikawa, Minoru
supporting information, p. 902 - 907 (2015/08/24)
Anti-inflammatory effects of liver X receptor (LXR) ligands are thought to be largely due to LXR-mediated transrepression, whereas side effects are caused by activation of LXR-responsive gene expression (transactivation). Therefore, selective LXR modulators that preferentially exhibit transrepression activity should exhibit anti-inflammatory properties with fewer side effects. Here, we synthesized a series of styrylphenylphthalimide analogues and evaluated their structure-activity relationships focusing on LXRs-transactivating-agonistic/antagonistic activities and transrepressional activity. Among the compounds examined, 17l showed potent LXR-transrepressional activity with high selectivity over transactivating activity and did not show characteristic side effects of LXR-transactivating agonists in cells. This representative compound, 17l, was confirmed to have LXR-dependent transrepressional activity and to bind directly to LXRβ. Compound 17l should be useful not only as a chemical tool for studying the biological functions of LXRs transrepression but also as a candidate for a safer agent to treat inflammatory diseases.
Synthesis of 2-phenylnaphthalenes from styryl-2-methoxybenzenes
Mudududdla, Ramesh,Sharma, Rohit,Abbat, Sheenu,Bharatam, Prasad V.,Vishwakarma, Ram A.,Bharate, Sandip B.
supporting information, p. 12076 - 12079 (2015/02/19)
A new simple and efficient method for the synthesis of 2-phenylnaphthalenes from electron-rich 1-styryl-2-methoxybenzenes has been described. The reaction proceeds via TFA catalyzed C-C bond cleavage followed by intermolecular [4+2]-Diels-Alder cycloaddition of an in situ formed styrenyl trifluoroacetate intermediate. The quantum chemical calculations identified the transition state for the cycloaddition reaction and helped in tracing the reaction mechanism. The method has been efficiently utilized for synthesis of the phenanthrene skeleton and a naphthalene-based potent and selective ER-β agonist. This journal is
Selective oxidation of an electronically unsymmetrical distyrylbenzene at either of two sites
Davis, Anthony P.,Fry, Albert J.
, p. G3091-G3096 (2013/07/05)
A p-distyrylbenzene bearing electron-withdrawing groups on one terminal ring and electron-supplying groups on the other was synthesized and one ring was found to be significantly more electron rich than the other. Electrochemical oxidative cleavage was sh
Chiral bis(N-sulfonylamino)phosphine- and TADDOL-phosphite-oxazoline ligands: Synthesis and application in asymmetric catalysis
Hilgraf, Robert,Pfaltz, Andreas
, p. 61 - 77 (2007/10/03)
A series of N,P-ligands has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts for enantioselective allylic alkylation and olefin hydrogenation, respectively.
Synthesis and x-ray analysis of new [5]helicenes - HMO calculations on the photocyclization of the stilbene precursors
Stammel, Christian,Froehlich, Roland,Wolff, Christian,Wenck, Hans,De Meijere, Armin,Mattay, Jochen
, p. 1709 - 1718 (2007/10/03)
The syntheses of the new pentahelicenes 5, 11, 17, 21, and 28 with various substituents are described. In the case of 2,13-dicyano-[5]helicene (11) optical resolution was achieved by HPLC using a column packed with γ- cyclodextrin. However, the enantiomers racemized within a few hours. On the other hand, the enantiomers of 28 turned out to be stable after separation on triacetylcellulose using MPLC. The crystal structures of 11, 17, and 21 were solved and indicated the typical distortions which are expected for helicenes. The model of the sum of free valence numbers was applied in order to rationalize the reactivity pattern of the photochemical phenanthrene cyclization.
Spatial Structure of 4n? Helicene Dianions
Frim, R.,Goldblum, A.,Rabinovitz, M.
, p. 267 - 274 (2007/10/02)
Helicene dianions, e.g. phenanthrene derivatives, once believed to be non-helical, maintain their chirality as 4n? dianions.Phenanthrene 5, as well as substituted phenanthrene derivatives, undergo a two-electron reduction to form the respective 4n? dianion e.g. 52-/2Li+.Phenanthrene derivatives substituted at the 4- and 5-positions (bay substituents) e.g. 6-11, which are helical, afford stable dianions.These dianions are also prepared by a two-electron reduction of the (4n+2)? electron hydrocarbons and show, in their 1H NMR spectra, a quench of the paratropicity compared to 52- as well as a line shape dependence on their twist angle.The quench of paratropicity was also observed in the closely related charged helicenes derived from the benzochrysene system, i.e. anions 122- and 132-.The twist angles were calculated by MMX and MNDO calculations for the neutral systems, i.e., 5-11, and by MNDO for the dianions.MNDO calculations also included the preferred location of the counter cation.A dynamic NMR spectroscopic study proves experimentally the helicity of anion 112- thus shedding light on the behaviour of this novel class of dianions.
