83303-64-4Relevant academic research and scientific papers
Cooperative Palladium/Lewis Acid-Catalyzed Transfer Hydrocyanation of Alkenes and Alkynes Using 1-Methylcyclohexa-2,5-diene-1-carbonitrile
Bhunia, Anup,Bergander, Klaus,Studer, Armido
supporting information, p. 16353 - 16359 (2018/11/25)
Catalytic transfer hydrocyanation represents a clean and safe alternative to hydrocyanation processes using toxic HCN gas. Such reactions provide access to pharmaceutically important nitrile derivatives starting with alkenes and alkynes. Herein, an efficient and practical cooperative palladium/Lewis acid-catalyzed transfer hydrocyanation of alkenes and alkynes is presented using 1-methylcyclohexa-2,5-diene-1-carbonitrile as a benign and readily available HCN source. A large set of nitrile derivatives (>50 examples) are prepared from both aliphatic and aromatic alkenes with good to excellent anti-Markovnikov selectivity. A range of aliphatic alkenes engage in selective hydrocyanation to provide the corresponding nitriles. The introduced method is useful for chain walking hydrocyanation of internal alkenes to afford terminal nitriles in good regioselectivities. This protocol is also applicable to late-stage modification of bioactive molecules.
Synthesis and activity of putative small-molecule inhibitors of the F-box protein SKP2
Shouksmith, Andrew E.,Evans, Laura E.,Tweddle, Deborah A.,Miller, Duncan C.,Willmore, Elaine,Newell, David R.,Golding, Bernard T.,Griffin, Roger J.
, p. 660 - 679 (2015/04/27)
The tetrahydropyran 4-(((3-(2,2-dimethyltetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline was reported to disrupt the SCFSKP2 E3 ligase complex. Efficient syntheses of this tetrahydropyran derivative and analogues, including the des-dimethyl derivative 4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline, are described. The enantiomers of the des-dimethyl compound were obtained using Evans' chiral auxiliaries. Structure-activity relationships for these tetrahydropyrans and analogues have been determined by measurement of growth-inhibitory activities in HeLa cells, which indicated a non-specific mechanism of action that correlates with inhibitor lipophilicity. However, preliminary data with (R)-and (S)-4-(((3-(tetrahydro-2H-pyran-4-yl)-4-phenylbutyl)amino)methyl)-N,N-dimethylaniline showed enantioselective inhibition of the degradation of p27 in a cell-based assay that acts as a reporter of SKP2 activity.
Design, synthesis, structure, and dehydrogenation reactivity of a water soluble o-iodoxybenzoic acid derivative bearing a trimethylammonium group
Cui, Li-Qian,Dong, Zhi-Lei,Liu, Kai,Zhang, Chi
supporting information; experimental part, p. 6488 - 6491 (2012/02/02)
5-Trimethylammonio-1, 3-dioxo-1, 3-dihydro-1λ5-benzo[d][1, 2]iodoxol-1-ol anion (AIBX 1a), an o-iodoxybenzoic acid (IBX) derivative having the trimethylammonium moiety on its phenyl ring, possesses very good solubility in water and distinct oxidative properties from IBX, which is demonstrated in the oxidation of various β-keto esters to the corresponding dehydrogenated products using water as cosolvent. The regeneration of AIBX 1a can be easily realized from the reaction mixture due to its good water solubility.2011 American Chemical Society.
Dimeric Metal Complexes as Mediator for Radical C-C Bond-Forming Reactions
Giese, Bernd,Thoma, Gebhard
, p. 1135 - 1142 (2007/10/02)
Irradiation of dicarbonyl(η5-cyclopentadienyl)iron dimer 1 or decacarbonyldimanganese (2) in the presence of alkyl halides leads to C-centered radicals which can be trapped by alkenes and yields saturated and/or unsaturated addition products.Carbon radicals are generated via halogen abstraction by the initially formed metal-centered radicals resulting from homolysis of the metal-metal bond of dimeric mediators 1 and 2.No reaction occurs using octacarbonyl dicobalt (3).
C-C Bond Formation via Carbon-Centered Radicals Generated from Dicarbonyl(η5-cyclopentadienyl)organoiron Complexes
Giese, Bernd,Gebhard, Thoma
, p. 1143 - 1155 (2007/10/02)
Irradiation of benzyldicarbonyl(η5-cyclopentadienyl)iron complex (2) leads to homolytic cleavage of the Fe-C bond.In the presence of activated alkenes, radical addition occurs, and both saturated and unsaturated addition products 7-9 are formed.Photolysis of alkyliron complexes 2, 3, and 20 in the presence of acrylonitrile leads to the same products as the irradiation of the respective acyliron complexes 28-30.This indicates that, under photolytical conditions, alkyl and acyl complexes are in equilibrium with each other.
Directed ortho metalation reactions. Convergent synthesis of "angular" anthracyclinones ochromycinone and X-14881 C
Katsuura, K.,Snieckus, V.
, p. 124 - 130 (2007/10/02)
Convergent syntheses of the benzanthraquinone natural products X-14881 C (2c) and ochromycinone (2d) have been achieved using aromatic directed metalation strategies.Key steps involve (a) the condensations of dilithiated cis-tetralol (13a) with the ald
Synthese de methoxycarbonylindenes, dihydro-1,2 naphtalenes et benzocycloheptene. Obtention des indanones-1, des tetralones-1 et de la benzosuberone correspondantes
Verbel, Joel,Carrie, Robert
, p. 116 - 124 (2007/10/02)
The synthesis of methoxycarbonylindenes, 1,2-dihydro-naphtalenes, and benzocycloheptene starting from the corresponding 1-indanones, 1-tetralones, and benzosuberone is reported.The starting ketones were synthesized by methods described in the literature which were optimized; in some cases new processes are described.
