25006-88-6Relevant academic research and scientific papers
A Tethered Tolane: Twisting the Excited State
Kozhemyakin, Yury,Kr?mer, Maximilian,Rominger, Frank,Dreuw, Andreas,Bunz, Uwe H. F.
, p. 15219 - 15222 (2018)
The synthesis of a doubly bridged tolane is reported. The target is obtained in a five-step synthesis, starting from commercially available 2-amino-meta-xylene by a combination of a Sandmeyer reaction, radical bromination, and Stille-type coupling, followed by double ring closing. The doubly tethered tolane is crystalline; the two phenyl rings are highly twisted with respect to each other both in solution and in the solid state. Optical spectroscopy and quantum chemical calculations show that the doubly bridged tolane is twisted not only in the ground state, but also in the excited state, leading to emission from the twisted state in solution and in the solid state. Strong phosphorescence is observed at cryogenic temperatures.
2-Bromo-1,3-bis(bromomethyl)-benzene, with Z′ = 1.5: Whole-molecule disorder of one of the two independent molecules
Kirsop, Peter,Storey, John M. D.,Harrison, William T. A.
, p. o376-o378 (2006)
The title compound, C8H7r3, possesses normal geometrical parameters. There are two independent molecules; one shows whole-molecule disorder with respect to an inversion-symmetry-generated partner, while the other is undiso
A Convenient New Synthesis of Benzo[a]pyrene
Harvey, Ronald G.,Lim, Keunpoong,Dai, Qing
, p. 1372 - 1373 (2004)
A convenient new synthesis of the ubiquitous environmental carcinogen benzo[a]pyrene (BaP) is described. In the key step, the method entails Suzuki coupling of naphthalene 2-boronic acid with 2-bromobenzene-1,3-dialdehyde and requires only three steps. It is considerably shorter and simpler than the older methods and provides BaP in higher overall yield.
Synthesis and biological evaluation of thielocin B1 analogues as protein-protein interaction inhibitors of PAC3 homodimer
Ohsawa, Kosuke,Yoshida, Masahito,Izumikawa, Miho,Takagi, Motoki,Shin-ya, Kazuo,Goshima, Naoki,Hirokawa, Takatsugu,Natsume, Tohru,Doi, Takayuki
, p. 6023 - 6034 (2018/11/23)
The synthesis and biological evaluation of thielocin B1 analogues have been demonstrated. Fourteen analogues modified in the central core and terminal carboxylic acid moiety were concisely synthesized by simple esterification or etherification reaction. The evaluation of synthetic analogues as inhibitors of proteasome assembling chaperone (PAC) complexes (the PAC3 homodimer and PAC1/PAC2) revealed that the natural product-like bending structure and terminal carboxylic acid groups were crucial for its biological activity. Moreover, SAR and in silico docking studies indicated that all methyl groups on the diphenyl ether moiety of thielocin B1 contribute to the potent and selective inhibition of the PAC3 homodimer via hydrophobic interactions.
PYRROLO SULFONAMIDE COMPOUNDS FOR MODULATION OF ORPHAN NUCLEAR RECEPTOR RAR-RELATED ORPHAN RECEPTOR-GAMMA (RORGAMMA, NR1F3) ACTIVITY AND FOR THE TREATMENT OF CHRONIC INFLAMMATORY AND AUTOIMMUNE DISEASES
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Page/Page column 36, (2012/11/06)
The invention provides modulators for the orphan nuclear receptor RORy and methods for treating RORy mediated diseases by administrating these novel RORy modulators to a human or a mammal in need thereof. Specifically, the present invention provides pyrrolo sulfonamide compounds of Formula (1) and the enantiomers, diastereomers, tautomers, solvates and pharmaceutically acceptable salts thereof.
Synthetic scope, computational chemistry and mechanism of a base induced 5-endo cyclization of benzyl alkynyl sulfides
Motto, John M.,Castillo, álvaro,Greer, Alexander,Montemayer, Laura K.,Sheepwash, Erin E.,Schwan, Adrian L.
supporting information; experimental part, p. 1002 - 1010 (2011/03/19)
We present an experimental and computational study of the reaction of aryl substituted benzyl 1-alkynyl sulfides with potassium alkoxide in acetonitrile, which produces 2-aryl 2,3-dihydrothiophenes in poor to good yields. The cyclization is most efficient with electron withdrawing groups on the aromatic ring. Evidence indicates there is rapid exchange of protons and tautomerism of the alkynyl unit prior to cyclization. Theoretical calculations were also conducted to help rationalize the base induced 5-endo cyclization of benzyl 1-propynyl sulfide (1a). The potential energy surface was calculated for the formation of 2,3-dihydrothiophene in a reaction of benzyl 1-propynyl sulfide (1a) with potassium methoxide. Geometries were optimized with CAM-B3LYP/6-311+G(d,p) in acetonitrile with the CPCM solvent model. It is significant that the benzyl propa-1,2-dien-1-yl sulfane (6) possessed a lower benzylic proton affinity than the benzyl prop-2-yn-1-yl sulfane (8) thus favoring the base induced reaction of the former. From benzyl(propa-1,2-dien-1- yl sulfane (6), 2,3-dihydrothiophene can be formed via a conjugate base that undergoes 5-endo-trig cyclization followed by a protonation step.
Bronsted base-assisted boronic acid catalysis for the dehydrative intramolecular condensation of dicarboxylic acids
Sakakura, Akira,Ohkubo, Takuro,Yamashita, Risa,Akakura, Matsujiro,Ishihara, Kazuaki
supporting information; experimental part, p. 892 - 895 (2011/05/02)
Bronsted base-assisted boronic acid catalysis for the dehydrative self-condensation of carboxylic acids is described. Arylboronic acid bearing bulky (N,N-dialkylamino)methyl groups at the 2,6-positions can catalyze the intramolecular dehydrative condensation of di-and tetracarboxylic acids. This is the first successful method for the catalytic dehydrative self-condensation of carboxylic acids.(Figure Presented)
METHOD FOR PRODUCING CARBOXYLIC ANHYDRIDE AND ARYLBORONIC ACID COMPOUND
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Page/Page column 8, (2012/01/13)
When phthalic acid is heated in heptane under azeotropic reflux conditions in the presence of a catalytic amount of an arylboronic acid compound (such as 2,6-(diisopropylaminomethyl)phenylboronic acid or 2,6-bis(diisopropylaminomethyl)phenylboronic acid), phthalic anhydride is obtained in high yield.
Nucleophilic aryl fluorination and aryl halide exchange mediated by a CuI/CuIII catalytic cycle
Casitas, Alicia,Canta, Merce,Sola, Miquel,Costas, Miquel,Ribas, Xavi
supporting information; experimental part, p. 19386 - 19392 (2012/01/15)
Copper-catalyzed halide exchange reactions under very mild reaction conditions are described for the first time using a family of model aryl halide substrates. All combinations of halide exchange (I, Br, Cl, F) are observed using catalytic amounts of Cus
Highly twisted triarylamines for photoinduced intramolecular charge transfer
Chudomel, J. Matthew,Yang, Boqian,Barnes, Michael D.,Achermann, Marc,Mague, Joel T.,Lahti, Paul M.
scheme or table, p. 8361 - 8368 (2011/10/17)
9-(N,N-Dianisylamino)anthracene (9DAAA), 9-(N,N-dianisylamino)dinaphth([1, 2-a:2′-1′-j]-anthracene (9DAAH), and 9,10-bis(N,N-dianisylamino) anthracene (910BAA) were synthesized as highly twisted triarylamines with potential for photoexcited internal charg
