261925-13-7Relevant academic research and scientific papers
Method for functionalizing o-dihalogenated aromatic hydrocarbon compound
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Paragraph 0034-0035, (2020/12/15)
The invention provides a method for functionalizing an o-dihalogenated aromatic hydrocarbon compound, which comprises the following steps: dissolving the o-dihalogenated aromatic hydrocarbon compoundin an organic solvent, controlling the temperature of th
Unusual Fusion of α-Fluorinated Benzophenones under McMurry Reaction Conditions
Akhmetov, Vladimir,Feofanov, Mikhail,Ioutsi, Vitaliy,Hampel, Frank,Amsharov, Konstantin
supporting information, p. 1910 - 1913 (2019/01/14)
By exposure of α-fluorinated benzophenones to McMurry reaction conditions, we have observed the remarkable formation of 9,10-diphenylanthracene derivatives. This unexpected transformation necessitates the cleavage of the exceptionally stable aromatic C?F bond under mild McMurry conditions. In this work, the condensation of several related fluorinated benzo- and acetophenones has been investigated, which allow us to propose a domino-like fusion mechanism for this unusual transformation. The scope and limitations of the fluorine-promoted benzophenone fusion are subsequently discussed.
Tailoring Diindenochrysene through Intramolecular Multi-Assemblies by C?F Bond Activation on Aluminum Oxide
Akhmetov, Vladimir,Feofanov, Mikhail,Troyanov, Sergey,Amsharov, Konstantin
supporting information, p. 7607 - 7612 (2019/05/15)
The unique nature of the alumina-mediated cyclodehydrofluorination gives the opportunity to execute the preprogrammed algorithm of the C?C couplings rationally built into a precursor. Such multi-assemblies facilitate the construction of the carbon-skeleton, superseding the conventional step-by-step by the one-pot intramolecular assembly. In this work, the feasibility of the alumina-mediated C?F bond activation approach for multi-assembly is demonstrated on the example of a fundamental bowl-shaped polycyclic aromatic hydrocarbon (diindenochrysene) through the formation of all “missing” C?C bonds at the last step. Beside valuable insights into the reaction mechanism and the design of the precursors, a facile pathway enabling the two-step synthesis of diindenochrysene was elaborated, in which five C?C bonds form in a single synthetic step. It is shown that the relative positions of fluorine atoms play a crucial role in the outcome of the assembly and that governing the substituent positions enables the design of effective precursor molecules “programmed” for the consecutive C?C bond formations. In general, these findings push the state of the field towards the facile synthesis of sophisticated bowl-shaped carbon-based nanostructures through multi-assembly of fluoroarenes.
Pd-catalyzed enantioselective C-H iodination: Asymmetric synthesis of chiral diarylmethylamines
Chu, Ling,Wang, Xiao-Chen,Moore, Curtis E.,Rheingold, Arnold L.,Yu, Jin-Quan
supporting information, p. 16344 - 16347 (2013/12/04)
An enantioselective C-H iodination reaction using a mono-N-benzoyl- protected amino acid has been developed for the synthesis of chiral diarylmethylamines. The reaction uses iodine as the sole oxidant and proceeds at ambient temperature and under air.
MODULATORS OF C3A RECEPTOR AND METHODS OF USE THEREOF
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Page/Page column 103, (2008/12/07)
Provided are compounds that are modulators of C3a receptor activity, compositions containing the compounds and methods of use of the compounds and compositions. In certain embodiments, the compounds are pyridones. In certain embodiments, provided are methods for treatment or amelioration of diseases associated with modulation of C3a receptor activity.
Novel inhibitors of the gardos channel for the treatment of sickle cell disease
McNaughton-Smith, Grant A.,Burns, J. Ford,Stocker, Jonathan W.,Rigdon, Gregory C.,Creech, Christopher,Arlington, Susan,Shelton, Tara,De Franceschi, Lucia
, p. 976 - 982 (2008/12/20)
Sickle cell disease (SCD) is a hereditary condition characterized by deformation of red blood cells (RBCs). This phenomenon is due to the presence of abnormal hemoglobin that polymerizes upon deoxygenation. This effect is exacerbated when dehydrated RBCs experience a loss of both water and potassium salts. One critical pathway for the regulation of potassium efflux from RBCs is the Gardos channel, a calcium-activated potassium channel. This paper describes the synthesis and biological evaluation of a series of potent inhibitors of the Gardos channel. The goal was to identify compounds that were potent and selective inhibitors of the channel but had improved pharmacokinetic properties compared to 1, Clotrimazole. Several triarylamides such as 10 and 21 were potent inhibitors of the Gardos channel (IC50 of 10 nM) and active in a mouse model of SCD. Compound 21 (ICA-17043) was advanced into phase 3 clinical trials for SCD.
NOVEL TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL WITH THE COMPLEX
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Page/Page column 63, (2008/06/13)
A novel transition metal complex, preferably a ruthenium-phosphine complex or rhodium-phosphine complex, which is effectively usable in various asymmetric syntheses and, in particular, is more effectively usable in the asymmetric hydrogenation of various ketones; and a novel process for producing an optically active alcohol with the complex. The novel transition metal complex includes a ligand obtained by introducing a diarylphosphino group into each of the 2- and 2'-positions of diphenyl ether, benzophenone, benzhydrol, or the like. It preferably further includes an optically active 1,2-diphenylethylenediamine coordinated thereto. The complex preferably is a novel diphosphine-ruthenium-optically active diamine complex or diphosphine-rhodium-optically active diamine complex. The process comprises using the complex as an asymmetric hydrogenation catalyst to conduct the asymmetric hydrogenation of a ketone compound to thereby obtain an optically active alcohol in a high optical purity and a high yield.
Design of Bronsted acid-assisted chiral Bronsted acid catalyst bearing a bis(triflyl)methyl group for a Mannich-type reaction
Hasegawa, Aiko,Naganawa, Yuki,Fushimi, Makoto,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 3175 - 3178 (2007/10/03)
A new Bronsted acid-assisted chiral Bronsted (chiral BBA) acid catalyst (1) was developed by substituting a hydroxy group of optically active 1,1′-bi(2-naphthol) with a stronger Bronsted acidic group such as a bis(trifluoromethanesulfonyl)methyl group. The enantioselective Mannich-type reaction of ketene silyl acetals with aldimines catalyzed by (R)-1 in the presence of stoichiometric achiral proton sources gave (S)-β-amino esters in high yield with moderate to good enantiomeric excesses.
BENZENE DERIVATIVES,PROCESS FOR PREPARING THE SAME AND USE THEREOF
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Page 41, (2010/02/07)
Novel benzene derivatives represented by the formula (I) : wherein R1, R4 and R6 each independently represents a hydrogen atom, a halogen atom or a hydrocarbon group, R2 represents a hydrocarbon group or a heterocyclic group, R3 represents a hydrocarbon group, NR7'R7 or OR8 (wherein R7' represents a hydrogen atom or a hydrocarbon group, R7 represents a non-aromatic group, or R7' and R7 may form a ring with the adjacent nitrogen atom, and R8 represents a hydrocarbon group or a heterocyclic group), R5 represents a hydrocarbon group or a heterocyclic group (except for a quinolyl group), R5' represents a hydrogen atom, or a hydrocarbon group, or R5 and R5' may form a ring with the adjacent nitrogen atom, and R5" represents a hydrogen atom or a hydrocarbon group, which have vanilloid receptor agonist activity and are useful as a drug such as an analgesic and an agent for preventing and/or treating urinary frequency and/or urinary incontinence.
