Category: 6136-93-2

Kotani, Shunsuke; Sakamoto, Midori; Osakama, Kazuki; Nakajima, Makoto published the artcile< A Sterically Congested α-Cyanoamine as a Cyanating Reagent: Cyanation of Acetals and Orthoesters>, Formula: C6H11NO2, the main research area is alkoxy alkanenitrile nitrile cyanation.

The cyanation of acetals and ortho-esters by using a sterically congested α-cyanoamine as a cyanation reagent was investigated. The α-cyanoamine effectively facilitated cyanation in the presence of trichlorosilyl triflate to produce a variety of cyanated adducts in excellent yields. Anal. of the reaction mixture by 1H NMR spectroscopy revealed that trichlorosilyl triflate produced an oxocarbenium cation species as an intermediate. Under optimized conditions the synthesis of the target compounds was achieved using 1,1,1-trifluoromethanesulfonic acid trichlorosilyl ester as a reagent and 2-(dicyclohexylamino)acetonitrile (cyanation agent amine-cyanide) and (dimethoxymethyl)benzene (benzaldehyde acetal), (3,3-dimethoxy-1-propen-1-yl)benzene, (dimethoxymethyl)cyclohexane, 1,1′-[(phenylmethylene)bis(oxymethylene)]bis[benzene], 2-phenyl-1,3-dioxolane (cyclic acetal) as starting materials. The title compounds thus formed included α-(methoxy)benzeneacetonitrile derivatives, α-(methoxy)-1-naphthaleneacetonitrile, 2-methoxy-4-phenyl-2-butenenitrile, α-(2-hydroxyethoxy)benzeneacetonitrile. Ortho-ester reactants included (trimethoxymethyl)benzene, 1,1′,1”-[methylidynetris(oxy)]tris[ethane] and 1,1,1-triethoxypentane. Products therefrom included α,α-dimethoxybenzeneacetonitrile.

European Journal of Organic Chemistry published new progress about Acetals Role: RCT (Reactant), RACT (Reactant or Reagent). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Sanchez-Viesca, F.; Gomez, M. R. published the artcile< Anomalous Hoesch reaction>, Category: nitriles-buliding-blocks, the main research area is Hoesch reaction ethoxyacetonitrile; methane methoxyphenyl; acetonitrile ethoxy Hoesch reaction; methoxybenzene Hoesch reaction ethoxyacetonitrile; acetophenone dichlorotrimethoxy reaction.

Treating 1,2,4-trimethoxybenzene (I) with (EtO)2CHCN gave II instead of the Hoesch product III (R = R1 = EtO)(IV). Similar treatment of I with EtOCH2CN gave III (R = H, R1 = Cl). IV could not be prepared from III (R = R1 = Cl).

Revista Latinoamericana de Quimica published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Category: nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Patterson, Andrew W.; Peltier, Hillary M.; Ellman, Jonathan A. published the artcile< Expedient Synthesis of N-Methyl Tubulysin Analogues with High Cytotoxicity>, Related Products of 6136-93-2, the main research area is asym synthesis methyl tubulysin analog alkylation acylation heterocyclization esterification.

An optimized and highly efficient synthesis of potent, bioactive N-Me tubulysin analogs I and II has been achieved with > 40% overall yields. This synthesis represents a significant improvement over previously reported syntheses of these and related tubulysin analogs. The stereoselective synthesis of the unnatural amino acid tubuvaline is accomplished using tert-butanesulfinamide chem. N-Alkylation to form N-Me tubuvaline is performed without protection of the tubuvaline alc. by implementing a unique N-methylation strategy via formation and reduction of a 1,3-tetrahydrooxazine heterocycle. Acylation of the hindered N-Me tubuvaline amine utilizes a novel sequence of O-acylation followed by an O- to N-acyl transfer to form the hindered amide bond between N-Me tubuvaline and isoleucine. This high-yielding synthesis should enable the production of large quantities of material for biol. studies.

Journal of Organic Chemistry published new progress about Alkylation. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Related Products of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Clark, Robin D.; Jahangir, Alam published the artcile< Lateral lithiation reactions promoted by heteroatomic substituents>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is review Reactions; review Promoted; review Heteroatomic; review Substituents; review Lithiation; review Lateral.

A review of the article Lateral lithiation reactions promoted by heteroat. substituents.

Organic Reactions (Hoboken, NJ, United States) published new progress about Organic synthesis. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

McElvain, S. M.; Clarke, Robert L. published the artcile< Ketene acetals. XVIII. Pentaethoxyethane and tetraethoxyethylene (diethoxyketene diethyl acetal)>, Recommanded Product: 2,2-Diethoxyacetonitrile, the main research area is .

Because Scheibler (C.A. 20, 2824) has reported that tetraethoxyethylene (diethoxyketene di-Et acetal) (I) dissociate spontaneously into C(OEt)2, an unequivocal synthesis of I was desirable. (EtO)2CHCO2Et (II) yields 84% (EtO)2CHCONH2 (III) and this with Et3N gives 76-9% (EtO)2CHCN (IV). By the method of M. and Nelson (C.A. 36, 5772.3) IV yields 66-71% (EtO)2CHC(OEt):NH2Cl (V); addition of 23.3 g. V to 30.6 g. K2CO3 in 40 ml. H2O (covered with 60 ml. ether) at -5° and shaking 1 min. give 80% Et diethoxyacetimidate (VI), b20 91-2°, nD25 1.4147, d425 0.957. VI (47.5 g.) and 104 g. absolute EtOH, kept 4 days at room temperature, give 42% NH4Cl; the remainder of the N was recovered as III; when the alc. solution was distilled, the only products isolated were a small quantity of ether and 26% II; however, if the alc. filtrate was made alk. (to phenolphthalein) with EtONa before heat was applied, there were formed 8% II, 44% III, 8% V, and 12% Et diethoxyorthoacetate (pentaethoxyethane) (VII), b8 85-6°, b. 205-7°, nD25 1.4072, d425 0.935. VII (4.7 g.), added (10 min.) to 0.08 mole EtNa in petr. ether in a N atm., gives 39% I, b5 70-1°, b740 195-6°, nD25 1.4213, d425 0.949; it shows no tendency to dissociate With EtOH I gives VII; with Br it yields (CO2Et)2 and, presumably, EtBr. (CONH2)2 m. 350° (decomposition, Cu block) or decompose 340° in a sealed tube; Michael (Ber. 28, 1632 (1895)) reported a m.p. of 417-19° (decomposition).

Journal of the American Chemical Society published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Recommanded Product: 2,2-Diethoxyacetonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Lei; Rogers, Bruce N.; Duplantier, Allen J.; McHardy, Stanley F.; Efremov, Ivan; Berke, Helen; Qian, Weimin; Zhang, Andy Q.; Maklad, Noha; Candler, John; Doran, Angela C.; Lazzaro, John T.; Ganong, Alan H. published the artcile< 3-(Imidazolylmethyl)-3-aza-bicyclo[3.1.0]hexan-6-yl)methyl ethers: A novel series of mGluR2 positive allosteric modulators>, Application In Synthesis of 6136-93-2, the main research area is imidazolylmethylazabicyclohexanol ether preparation metabotropic glutamate receptor modulator.

The synthesis and structure-activity relationship of a novel series of 3-(imidazolylmethyl)-3-azabicyclo[3.1.0]hexan-6-ylmethyl ethers, derived from a high throughput screening, are described. Subsequent optimization led to identification of potent, metabolically stable and orally available mGluR2 pos. allosteric modulators.

Bioorganic & Medicinal Chemistry Letters published new progress about Metabotropic glutamate receptor 2 Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Application In Synthesis of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Scheibler, Helmuth; Beiser, Willy; Cobler, Heinz; Schmidt, Anton published the artcile< Compounds of bivalent carbon. VIII. Some derivatives of diethoxyacetic acid and their adaptation to carbon monoxide acetal cleavage>, COA of Formula: C6H11NO2, the main research area is .

In the reaction between (EtO)2CHCO2Et and NaOEt or Et2NMgBr the C(OEt)2 formed by the cleavage of the C chain readily reacts with the EtOH which is split off simultaneously, forming pentaethoxyethane and heptaethoxypropane. Since the sec. NHEt2, is indifferent toward C(OEt)2, attempts were made to prepare dialkylamides of (EtO)2CHCO2H for use instead of (EtO)2CHCO2Et for the C(OEt)2 cleavage. These dialkylamides cannot be prepared under the usual conditions but (EtO)2CHCONMe2 (I) was finally obtained by heating the components in a sealed tube at 100° in the presence of CaCl2 to bind the EtOH set free, and (EtO)2CHCON(CH2Ph)2 (II) was obtained from (EtO)2CHCO2Et and (PhCH2)2NMgBr in boiling C6H6. When I and II were treated with Me2NMgBr and (PhCH2)2NMgBr, resp., and, after removal of the ether (both that used as solvent and the ether of constitution), the products were subjected to dry distillation in vacuo, the product obtained from Me2NMgBr yielded a compound m. 134° containing no trace of EtO (Zeisel) and giving NH3 instead of NHMe2 on hydrolysis. Analysis indicated that it was OHCCONH2.3H2O, and from the low-boiling products of the reaction (condensed in liquid air) was isolated Et2O after removal of the NHMe2 with C6H4(CO)2O in the presence of quinoline. In the experiment with II there was obtained no low-boiling distillate; the product was N(CH2Ph)3. formed according to the scheme (EtO)2CHC(OMgBr)[N(CH2Ph)2]2 → N(CH2Ph)3 + (EtO)2CHC(OMgBr):NCH2Ph. These dialkylamides are therefore not adapted to the C(OEt)2 cleavage. As (EtO)2CHCO2Et can be used for this purpose but the EtOH formed simultaneously gives rise to secondary reactions, attempts were made to prepare the Ph instead of the Et ester. (EtO)2CHCOCl cannot be made because 1 of the 2 EtO groups in (EtO)2CHCO2H immediately reacts with PCl5 or SOCl2. The Ph ester can be obtained by treating the acid in the presence of excess of pyridine first with SOCl2 and then with PhOH, but the. ester so prepared is difficultly purified. Favorable results were obtained only when ClSO2Ph was used with the acid in ether in the presence of pyridine, the resulting (EtO)2CHCOOSO2Ph decomposing on heating in ether into SO2 and (EtO)2CHCO2Ph. As the ester is very sensitive to acids it was freed from admixed pyridine with MeI. With Et2NMgBr the ester gave (EtO)2CHCONEt2 but the chief product was a non-distillable mass which decomposed at higher temperatures and was perhaps formed by combination of PhOH with a polymerization product of C(OEt)2. Furthermore, in the part of the product consisting chiefly of NHEt2, monomeric C(OEt)2 was detected and determined by means of HgCl2 after it had been hydrolyzed to HCO2H with dilute alkali. Diethoxyacetdimethylamide (I), b12 105°; yield, 50.5%. Dibenzylamide (II), light yellow, b1 168-70° (yield, 26%). Ph diethoxyacetate, b13 150-2°; yield, 61.1%. Diethoxyacetonitrile, obtained in 30% yield from the amide in quinoline slowly treated at 90° with P2O6, b12 55-6°.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen published new progress about 6136-93-2. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, COA of Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Tang, Wei; Li, Huiying; Doud, Emma H.; Chen, Yunqiu; Choing, Stephanie; Plaza, Carla; Kelleher, Neil L.; Poulos, Thomas L.; Silverman, Richard B. published the artcile< Mechanism of inactivation of neuronal nitric oxide synthase by (S)-2-amino-5-(2-(methylthio)acetimidamido)pentanoic acid>, Formula: C6H11NO2, the main research area is neuron nitric oxide synthase rat crystal structure inactivation mechanism.

Nitric oxide synthase (NOS) catalyzes the conversion of L-arginine to L-citrulline and the second messenger nitric oxide. Three mechanistic pathways are proposed for the inactivation of neuronal NOS (nNOS) by (S)-2-amino-5-(2-(methylthio)acetimidamido)pentanoic acid (1): sulfide oxidation, oxidative dethiolation, and oxidative demethylation. Four possible intermediates were synthesized. All compounds were assayed with nNOS, their IC50, KI, and kinact values were obtained, and their crystal structures were determined The identification and characterization of the products formed during inactivation provide evidence for the details of the inactivation mechanism. On the basis of these studies, the most probable mechanism for the inactivation of nNOS involves oxidative demethylation with the resulting thiol coordinating to the cofactor heme iron. Although nNOS is a heme-containing enzyme, this is the first example of a NOS that catalyzes an S-demethylation reaction; the novel mechanism of inactivation described here could be applied to the design of inactivators of other heme-dependent enzymes.

Journal of the American Chemical Society published new progress about Crystal structure. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mettry, Magi; Moehlig, Melissa P.; Hooley, Richard J. published the artcile< Synthesis, Guest Binding, and Metal Coordination of Functionalized Self-Folding Deep Cavitands>, Quality Control of 6136-93-2, the main research area is cavitand self folding preparation guest binding metal coordination.

A simple method to introduce donor functions to the upper rim of self-folding benzimidazole-based deep cavitands is described. The upper rim donors allow controlled noncovalent binding of suitably sized guest species via both self-complementary hydrogen bonding and space-filling interactions; and metal-mediated self-folding is possible if bidentate coordinators are incorporated.

Organic Letters published new progress about Cavitands Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Quality Control of 6136-93-2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chiang, Ming-Chien; Tai, Tsui-Chen published the artcile< A quantitative relation between molecular structure and chemical reactivity. III. Addition reaction of aliphatic nitriles and methanol>, Formula: C6H11NO2, the main research area is .

The addition of MeOH to aliphatic nitriles with NaOMe as catalyst was studied. The % conversion of the nitriles plotted vs. the inductive index I for the alkyl groups in their mols. constitute a “”sigmoid”” curve, while the logs of the rate and equilibrium constants for the addition gave straight lines when plotted, resp., against the corresponding I. From the position of the point corresponding to 50% conversion on the sigmoid curve, it can be shown that the % conversion for all the aliphatic nitriles in this reaction would be very low and the reaction would proceed very slowly. α-Substituted (halogen, CO2H, CN) nitriles would undergo reaction very rapidly with very high % conversion. When the substituents are beyond the γ-position, however, the % conversion and the reaction rate would be very close to those of the simple aliphatic nitriles. The direction of turning of the sigmoid curve vs. % conversion and the direction of inclination of the straight lines vs. the rate and equilibrium constants demonstrate that this reaction is a nucleophilic addition of MeOH to aliphatic nitriles.

Huaxue Xuebao published new progress about Addition reaction. 6136-93-2 belongs to class nitriles-buliding-blocks, and the molecular formula is C6H11NO2, Formula: C6H11NO2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts