917-64-6Relevant articles and documents
Affinity of Rimantadine Enantiomers against Influenza A/M2 Protein Revisited
Drakopoulos, Antonios,Tzitzoglaki, Christina,Ma, Chulong,Freudenberger, Kathrin,Hoffmann, Anja,Hu, Yanmei,Gauglitz, Günter,Schmidtke, Michaela,Wang, Jun,Kolocouris, Antonios
, p. 145 - 150 (2017)
Recent findings from solid state NMR (ssNMR) studies suggested that the (R)-enantiomer of rimantadine binds to the full M2 protein with higher affinity than the (S)-enantiomer. Intrigued by these findings, we applied functional assays, such as antiviral assay and electrophysiology (EP), to evaluate the binding affinity of rimantadine enantiomers to the M2 protein channel. Unexpectedly, no significant difference was found between the two enantiomers. Our experimental data based on the full M2 protein function were further supported by alchemical free energy calculations and isothermal titration calorimetry (ITC) allowing an evaluation of the binding affinity of rimantadine enantiomers to the M2TM pore. Both enantiomers have similar channel blockage, affinity, and antiviral potency.
Pentadienyl chemistry of the heavy alkaline-earth metals revisited
Reiners, Matthias,Fecker, Ann Christin,Freytag, Matthias,Jones, Peter G.,Walter, Marc D.
, p. 6614 - 6617 (2014)
Open-metallocenes of the heavy alkaline-earth metals [(η5- Pdl′)2M(thf)n] (M = Ca (1), Sr (2), n = 1; M = Ba (3), n = 2; Pdl′ = 2,4-tBu2C5H5) are readily prepared by salt-metathesis between MI2 and KPdl′ and characterized by NMR spectroscopy and X-ray diffraction studies. This journal is the Partner Organisations 2014.
Method for preparing 1, 1 and 1 -trifluoro -2 -methyl -2 - propanol
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Paragraph 0038, (2021/12/07)
The invention discloses a method for preparing 1, 1 and 1 -trifluoro -2 -methyl -2 - propanol. To the method, methyl magnesium halide Grignard reagent is prepared from halogenated methane as a raw material in ether solvents, 1, 1 and 1 - trifluoroacetone are reacted in the presence of a catalyst to obtain 1, 1, 1 -trifluoro -2 -methyl -2 -propanol. The method has the advantages of easily available raw materials, convenience in post-treatment and purification, simplicity in operation, relatively low cost, high yield and the like.
Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides
Adamo, Andrea,Berton, Mateo,McQuade, D. Tyler,Sheehan, Kevin
supporting information, p. 1343 - 1356 (2020/07/10)
Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to fresh organomagnesium reagents on a discovery scale and will do so independent from the operator’s experience in flow and/or organometallic chemistry.
Identification of the Active Catalyst for Nickel-Catalyzed Stereospecific Kumada Coupling Reactions of Ethers
Borovik, Andy S.,Dawson, David D.,Jarvo, Elizabeth R.,Oswald, Victoria F.
supporting information, (2020/03/04)
A series of nickel complexes in varying oxidation states were evaluated as precatalysts for the stereospecific cross-coupling of benzylic ethers. These results demonstrate rapid redox reactions of precatalysts, such that the oxidative state of the precatalyst does not dictate the oxidation state of the active catalyst in solution. These data provide the first experimental evidence for a Ni0–NiII catalytic cycle for a stereospecific alkyl–alkyl cross-coupling reaction, including spectroscopic analysis of the catalyst resting state.
Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes
Chen, Pan-Pan,Hong, Xin,Jarvo, Elizabeth R.,McGinnis, Tristan M.,Sanford, Amberly B.,Thane, Taylor A.
supporting information, (2020/03/23)
Cross-electrophile coupling reactions of two Csp3-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.
Compounds of the menthane series. Synthesis of unsaturated primary alcohols with the o- and p-menthane skeletons
Fedorov,Fedorova,Sheverdov,Pavlov,Eremkin
, p. 806 - 812 (2016/07/30)
Precursors to terpene alcohols of the o- and p-menthane series (o-cimen-7-ol and o- and p-cimen-9-ols) were synthesized, and their reduction with lithium in ethylenediamine was studied. The reduction of o- and p-cimen-9-ols in the presence of isopropyl alcohol selectively afforded the corresponding 1,4-dihydro derivatives. Under analogous conditions, o-cimen-7-ol was converted into a mixture of unsaturated hydrocarbons. The reduction with lithium in ethylenediamine in the absence of isopropyl alcohol in all cases gave mixtures of menthene alcohols.
Nickel-Catalyzed Cross-Electrophile Coupling of Alkyl Fluorides: Stereospecific Synthesis of Vinylcyclopropanes
Erickson, Lucas W.,Lucas, Erika L.,Tollefson, Emily J.,Jarvo, Elizabeth R.
supporting information, p. 14006 - 14011 (2016/11/06)
The stereospecific reductive cross-electrophile coupling reaction of 2-vinyl-4-halotetrahydropyrans for vinylcyclopropane synthesis is reported. The nickel-catalyzed reaction occurs with both alkyl fluorides and alkyl chlorides. To the best of our knowledge, this is the first reported cross-electrophile coupling reaction of an alkyl fluoride. Ring contraction proceeds with high stereospecificity, providing selective synthesis of either diastereomer of di- and trisubstituted cyclopropanes. The utility of this methodology is demonstrated by several synthetic applications including the synthesis of the natural product dictyopterene A. 2-Vinyl-4-fluorotetrahydrofurans also undergo stereospecific ring contractions, providing access to synthetically useful hydroxymethyl cyclopropanes.
Efficient C(sp3)-H bond functionalization of isochroman by azadol catalysis
Muramatsu, Wataru,Nakano, Kimihiro
supporting information, p. 1549 - 1552 (2015/03/30)
A novel organocatalytic C(sp3)-H bond functionalization of isochroman under practical conditions has been developed. In the presence of 5.0 mol % of AZADOL, the catalysis proceeded successfully with a broad range of substrates and nucleophiles in excellent yields.
Locking out ants - Synthesis and biological evaluation of some fluorinated repellents
Csuk, Rene,Tamba, Maria Gabriela,Kluge, Ralph
experimental part, p. 1069 - 1075 (2011/12/13)
We synthesized a series of fluorinated compounds and tested them in an easy assay for their repellent activity against the ant Myrmica rubra. Depending on their chain length and pattern of fluorination these molecules are efficient repellents for this ant. Fluorinated compounds are stronger repellents than their unfluorinated analogs. 1,1,1-Trifluorotridecan-2-one (4) is an even better repellent against M. rubra than "gold standard" N,N-diethyl-m- toluamide (DEET).
