53446-63-2Relevant academic research and scientific papers
B(C6F5)3-Catalyzed Highly Stereoselective Hydrogenation of Unfunctionalized Tetrasubstituted Olefins
Dai, Yun,Feng, Xiangqing,Du, Haifeng
supporting information, p. 6884 - 6887 (2019/10/02)
A metal-free hydrogenation of unfunctionalized tetrasubstituted olefins were successfully realized using a combination of B(C6F5)3 and Ph2NMe catalyst. The corresponding products were afforded in 58-98% yields with up to >99:1 cis/trans selectivity.
Design, synthesis and evaluation of indene derivatives as retinoic acid receptor α agonists
Guan, Xianghong,Luo, Peihua,He, Qiaojun,Hu, Yongzhou,Ying, Huazhou
, (2017/01/24)
A series of novel indene-derived retinoic acid receptor α (RARα) agonists have been designed and synthesized. The use of receptor binding, cell proliferation and cell differentiation assays demonstrated that most of these compounds exhibited moderate RARα binding activity and potent antiproliferative activity. In particular, 4-((3-isopropoxy-2,3-dihydro-1H-inden-5-yl)-carbamoyl) benzoic acid (36d), which showed a moderate binding affinity, exhibited a great potential to induce the differentiation of NB4 cells (68.88% at 5 μM). Importantly, our work established indene as a promising skeleton for the development of novel RARα agonists.
Nickel-catalyzed enantioselective C-C bond formation through C sp 2 -O cleavage in aryl esters
Cornella, Josep,Jackson, Evan P.,Martin, Ruben
supporting information, p. 4075 - 4078 (2015/03/30)
We report the first enantioselective C-C bond formation through C-O bond cleavage using aryl ester counterparts. This method is characterized by its wide substrate scope and results in the formation of quaternary stereogenic centers with high yields and asymmetric induction.
Synthesis of Chiral 3-Alkyl-3,4-dihydroisocoumarins by dynamic kinetic resolutions catalyzed by a Baeyer-Villiger Monooxygenase
Rioz-Martinez, Ana,De Gonzalo,Torres Pazmino, Daniel E.,Fraaije, Marco-W.,Gotor, Vicente
supporting information; experimental part, p. 2073 - 2076 (2010/06/17)
"Chemical Equation Presented" Baeyer-Villiger monooxygenases have been tested, in the oxidation of racemic benzofused ketones. When employing a single mutant of phenylacetone monooxygenase (M.446G PAMO) under the proper reaction conditions, it was possible to achieve 3-substituted 3,4-dihydroisocoumarins with, high yields and optical purities through regioselective dynamic kinetic resolution processes.
Indanones and indenols from 2-alkylcinnamaldehydes via the intramolecular friedel-crafts reaction of geminal diacetates
Womack, Gary B.,Angeles, John G.,Fanelli, Vincent E.,Indradas, Brinda,Snowden, Roger L.,Sonnay, Philippe
experimental part, p. 5738 - 5741 (2009/12/06)
(Figure Presented) When treated with Ac2O at rt in the presence of 4-6mol% FeCl3, 2-alkylcinnamaldehydes are converted to 2-alkyl-1H-inden-1-yl acetates through the intermediacy of gem-diacetates. Methanolysis of the indenyl acetates
Photochemical preparation of highly functionalized 1-indanones
Wessig, Pablo,Glombitza, Clemens,Mueller, Gunnar,Teubner, Janek
, p. 7582 - 7591 (2007/10/03)
A series of o-alkylphenyl alkyl ketones 1 were synthesized by different methods. The presence of a leaving group X adjacent to the carbonyl group is the special peculiarity of these ketones. Upon irradiation the keto carbonyl group of these compounds undergoes an n-π* excitation followed by a 1,5-hydrogen migration from the o-alkyl substituent to the carbonyl oxygen atom. The thus formed 1,4-diradicals are subject to a very rapid elimination of acid HX, giving 1,5-diradicals. We called this process spin center shift. After intersystem crossing these diradicals cyclize to 1-indanones 20 in good yields. Depending on the solvent and on substituents, o-alkoxyalkyl ketones 22 or benzo-[c]furanes 21 are obtained as byproducts. The mechanism of the cyclization was elucidated by quantum chemical calculations and kinetic measurements.
Catalytic cross-coupling of alkylzinc halides with α-chloroketones
Malosh, Chrysa F.,Ready, Joseph M.
, p. 10240 - 10241 (2007/10/03)
The cross-coupling of alkylzinc halides with α-chloroketones catalyzed by Cu(acac)2 is described. Using this method, primary and secondary alkyl groups are introduced adjacent to a ketone carbonyl under mild reaction conditions and in good yield. Cyclic, acyclic, aromatic, and aliphatic α-chloroketones are suitable substrates. Optically active α-chloroketones are converted to optically active products. The reaction was found to proceed stereospecifically with inversion of stereochemistry. The reaction is proposed to occur by direct substitution of the chloride with the alkyl group of an organocopper, -magnesium, or -zinc species. Copyright
REDUCTION PAR LE BOROHYDRURE DE SODIUM D'INDANONES CHROME TRICARBONYLE ENDO SUBSTITUEES EN α ET β. POSITION DE L'ETAT DE TRANSITION ET FACTEURS DE REACTIVITE
Caro, B.,Jaouen, G.
, p. 93 - 102 (2007/10/02)
In the indanone Cr(CO)3 series the substitution of the β endo hydrogen atom by alkyl groups has shown an increased reactivity towards NaBH4 reduction attributed to a deconjugation of carbonyl group.While in the endo α-substituted series, a decreased reactivity controlled by an enhancement of the activation enthalpy has been observed.The steric origin of this effect and its influence on the position of the transition state are discussed.
