Category: 16332-06-2

Manley, Peter J. published the artcileA new synthesis of naphthyridinones and quinolinones: palladium-catalyzed amidation of o-carbonyl-substituted aryl halides, Computed Properties of 16332-06-2, the main research area is haloaryl aldehyde amide amidation aldol condensation palladium catalyst; naphthyridinone preparation; quinolinone preparation; palladium amidation aldol condensation catalyst.

An alternative to the Friedlaender condensation for the synthesis of naphthyridinones, e.g., I, and quinolinones has been discovered. Palladium-catalyzed amidation of halo aromatics substituted in the ortho position by a carbonyl functional group or its equivalent with primary or secondary amides leads to the formation of substituted naphthyridinones and quinolinones.

Organic Letters published new progress about Aldol condensation. 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Computed Properties of 16332-06-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Breno, Kerry L. published the artcileAqueous Phase Organometallic Catalysis Using (MeCp)2Mo(OH)(H2O)+. Intramolecular Attack of Hydroxide on Organic Substrates, Formula: C3H7NO2, the main research area is aqueous phase methylcyclopentadienyl molybdenum hydroxide hydrate catalysis; intramol attack hydroxide organic substrate methylcyclopentadienylmolybdenum hydroxide hydrate catalyzed; ester hydrolysis nitrile hydration oxidation catalyst methylcyclopentadienylmolybdenum hydroxide hydrate; kinetics oxidation ester hydrolysis nitrile hydration methylcyclopentadienylmolybdenum hydroxide catalyzed.

The hydrolysis of esters and difunctional ethers catalyzed by Cp’2Mo(OH)(H2O)+ (1) (Cp’ = η5-C5H4CH3) and the stoichiometric oxidation of CO to CO2 in the presence of 1 are described. These reactions, combined with the previously reported nitrile hydrations and phosphate esters hydrolyzes catalyzed by 1, demonstrate that 1 is an effective homogeneous catalyst for hydration, hydrolysis, and oxidation reactions in aqueous solution under mild conditions (pH ∼ 7, ∼ 80°). Each reaction is proposed to proceed by intramol. attack of the hydroxide ligand on a bound substrate. The intramol. nature of the reaction is supported by the ester hydrolysis activation parameters (ΔH⧧ = 5.9 ± 0.7 kcal/mol and ΔS⧧ = -48 ± 9 eu), the lack of H/D exchange, and the significant increase (106-108) in the rate of hydrolysis over uncatalyzed hydrolysis.

Organometallics published new progress about Activation enthalpy. 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Formula: C3H7NO2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Liu, Jin published the artcileA Comparison of Acetyl- and Methoxycarbonylnitrenes by Computational Methods and a Laser Flash Photolysis Study of Benzoylnitrene, Application of 2-Methoxyacetamide, the main research area is acetylnitrene methoxycarbonylnitrene comparison laser flash photolysis benzoylnitrene.

D. functional theory (DFT), CCSD(T), and CBS-QB3 calculations were performed to understand the chem. and reactivity differences between acetylnitrene (CH3C(:O)N) and methoxycarbonylnitrene (CH3OC(:O)N) and related compounds CBS-QB3 theory alone correctly predicts that acetylnitrene has a singlet ground state. We agree with previous studies that there is a substantial N-O interaction in singlet acetylnitrene and find a corresponding but weaker interaction in methoxycarbonylnitrene. Methoxycarbonylnitrene has a triplet ground state because the oxygen atom stabilizes the triplet state of the carbonyl nitrene more than the corresponding singlet state. The oxygen atom also stabilizes the transition state of the Curtius rearrangement and accelerates the isomerization of methoxycarbonylnitrene relative to acetylnitrene. Acetyl azide is calculated to decompose by concerted migration of the Me group along with nitrogen extrusion; the free energy of activation for this concerted process is only 27 kcal/mol, and a free nitrene is not produced upon pyrolysis of acetyl azide. Methoxycarbonyl azide, on the other hand, does have a preference for stepwise Curtius rearrangement via the free nitrene. The bimol. reactions of acetylnitrene and methoxycarbonylnitrene with propane, ethylene, and methanol were calculated and found to have enthalpic barriers that are near zero and free energy barriers that are controlled by entropy. These predictions were tested by laser flash photolysis studies of benzoyl azide. The absolute bimol. reaction rate constants of benzoylnitrene were measured with the following substrates: acetonitrile (k = 3.4 × 105 M-1 s-1), methanol (6.5 × 106 M-1 s-1), water (4.0 × 106 M-1 s-1), cyclohexane (1.8 × 105 M-1 s-1), and several representative alkenes. The activation energy for the reaction of benzoylnitrene with 1-hexene is -0.06 ± 0.001 kcal/mol. The activation energy for the decay of benzoylnitrene in pentane is -3.20 ± 0.02 kcal/mol. The latter results indicate that the rates of reactions of benzoylnitrene are controlled by entropic factors in a manner reminiscent of singlet carbene processes.

Journal of Organic Chemistry published new progress about Electron spin density. 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Application of 2-Methoxyacetamide.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Beller, Matthias published the artcilePalladium-catalyzed reactions for fine chemical synthesis, Part 6. Efficient chemoenzymic synthesis of enantiomerically pure α-amino acids, Recommanded Product: 2-Methoxyacetamide, the main research area is amino acid asym chemoenzymic synthesis; amidocarbonylation aldehyde amino acid preparation; enzymic hydrolysis acylamino acid.

A general two-step chemoenzymic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymic enantioselective hydrolysis yields the free optically pure α-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.

Chemistry – A European Journal published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Schmidtchen, Franz P. published the artcilePolyprenylpyridinols. Synthesis of piericidin analogs, SDS of cas: 16332-06-2, the main research area is piericidin A analog synthesis; pyridinol polypropenyl; prenylpyridinol preparation coenzyme Q inhibitor; coenzyme Q inhibitor; polyprenylpyridinol preparation coenzyme inhibitor.

The piericidin A analogs I (n = 1, 2, 3, 9) and II were prepared for structure-activity studies on coenzyme Q inhibitors. To prepare the nucleus, 3-methoxyacetylamino-2-methylacrylonitrile was cyclized to a 4-amino-2-pyridone which Me3O+ BF4- converted to the 4-amino-2,3-dimethoxypyridine. Bromination of the acylated amine formed the 6-bromo derivative in which the 4-amino group was then replaced by hydroxy and the latter blocked by conversion to its benzyl ether with a benzylisourea. Transmetalation now gave the 6-lithio compound which was coupled with various prenyl bromides, leading to introduction of all trans polyprenyl side chains. The final 4-pyridinols were formed on selective debenzylation with butyl mercaptide. All the polyprenylpyridinols inhibited coenzyme Q electron transport to some extent, with the farnesyl analog having the same activity as piericidin A.

Journal of the American Chemical Society published new progress about Ubiquinones Role: RCT (Reactant), RACT (Reactant or Reagent). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, SDS of cas: 16332-06-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Goto, Akihiro published the artcileRhI-catalyzed hydration of organonitriles under ambient conditions, Recommanded Product: 2-Methoxyacetamide, the main research area is hydration nitrile rhodium catalyst; amide preparation.

The hydration of organonitriles catalyzed by a RhI(OMe) species under nearly pH-neutral and ambient conditions (25°C, 1 atm) is chemoselective and high-yielding (93 to 99%) and has a broad substrate scope, and may thus be complementary to enzymic hydration methods for the introduction of a terminal amido group (CONH2) onto a carbon chain.

Angewandte Chemie, International Edition published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Tomas-Mendivil, Eder published the artcileExploring Rhodium(I) Complexes [RhCl(COD)(PR3)] (COD = 1,5-Cyclooctadiene) as Catalysts for Nitrile Hydration Reactions in Water: The Aminophosphines Make the Difference, Synthetic Route of 16332-06-2, the main research area is amide preparation; rhodium phosphine catalyst preparation hydration nitrile; rufinamide preparation.

Several rhodium(I) complexes, [RhCl(COD)(PR3)], containing potentially cooperative phosphine ligands, have been synthesized and evaluated as catalysts for the selective hydration of organonitriles into amides in water. Among the different phosphines screened, those of general composition P(NR2)3 led to the best results. In particular, complex [RhCl(COD){P(NMe2)3}] was able to promote the selective hydration of a large range of nitriles in water without the assistance of any additive, showing a particularly high activity with heteroaromatic and heteroaliph. substrates. Employing this catalyst, the antiepileptic drug rufinamide was synthesized in high yield by hydration of 4-cyano-1-(2,6-difluorobenzyl)-1H-1,2,3-triazole. For this particular transformation, complex [RhCl(COD){P(NMe2)3}] was more effective than related ruthenium catalysts.

ACS Catalysis published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Synthetic Route of 16332-06-2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Matsuoka, Aki published the artcileHydration of nitriles to amides by a chitin-supported ruthenium catalyst, Related Products of ethers-buliding-blocks, the main research area is amide preparation; nitrile chitin ruthenium catalyst hydration.

Chitin-supported ruthenium (Ru/chitin) promoted the hydration of nitriles to carboxamides under aqueous conditions. The nitrile hydration was performed on a gram-scale and was compatible with the presence of various functional groups including olefins, aldehydes, carboxylic esters and nitro and benzyloxycarbonyl groups. The Ru/chitin catalyst was easily prepared from com. available chitin, ruthenium(III) chloride and sodium borohydride. Anal. of Ru/chitin by high-resolution transmission electron microscopy indicated the presence of ruthenium nanoparticles on the chitin support.

RSC Advances published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Related Products of ethers-buliding-blocks.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Knapp, Spring Melody M. published the artcileCatalytic Nitrile Hydration with [Ru(η6-p-cymene)Cl2(PR2R’)] Complexes: Secondary Coordination Sphere Effects with Phosphine Oxide and Phosphinite Ligands, Recommanded Product: 2-Methoxyacetamide, the main research area is cymene ruthenium phosphine oxide phosphinite preparation catalyst nitrile hydration; crystal mol structure cymeneruthenium phosphine oxide phosphinite complex; mol structure calculation cymeneruthenium phosphine oxide phosphinite nitrile hydration.

The rates of nitrile hydration reactions were investigated using [Ru(η6-p-cymene)Cl2(PR2R’)] complexes as homogeneous catalysts, where PR2R’ = PMe2(CH2P(O)Me2), PMe2(CH2CH2P(O)Me2), PPh2(CH2P(O)Ph2), PPh2(CH2CH2P(O)Ph2), PMe2OH, P(OEt)2OH. These catalysts were studied because the rate of the nitrile-to-amide hydration reaction was hypothesized to be affected by the position of the hydrogen bond accepting group in the secondary coordination sphere of the catalyst. Experiments showed that the rate of nitrile hydration was fastest when using [Ru(η6-p-cymene)Cl2PMe2OH]: i.e., the catalyst with the hydrogen bond accepting group capable of forming the most stable ring in the transition state of the rate-limiting step. This catalyst is also active at pH 3.5 and at low temperatures-conditions where α-hydroxynitriles (cyanohydrins) produce less cyanide, a known poison for organometallic nitrile hydration catalysts. The [Ru(η6-p-cymene)Cl2PMe2OH] catalyst completely converts the cyanohydrins glycolonitrile and lactonitrile to their corresponding α-hydroxyamides faster than previously investigated catalysts. [Ru(η6-p-cymene)Cl2PMe2OH] is not, however, a good catalyst for acetone cyanohydrin hydration, because it is susceptible to cyanide poisoning. Protecting the -OH group of acetone cyanohydrin was an effective way to prevent cyanide poisoning, resulting in quant. hydration of acetone cyanohydrin acetate.

Organometallics published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Babon, Juan C. published the artcileHydration of Aliphatic Nitriles Catalyzed by an Osmium Polyhydride: Evidence for an Alternative Mechanism, Formula: C3H7NO2, the main research area is aliphatic nitrile hydration mechanism osmium polyhydride catalyst crystal structure.

The hexahydride OsH6(PiPr3)2 competently catalyzes the hydration of aliphatic nitriles to amides. The main metal species under the catalytic conditions are the trihydride osmium(IV) amidate derivatives OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2, which have been isolated and fully characterized for R = iPr and tBu. The rate of hydration is proportional to the concentrations of the catalyst precursor, nitrile, and water. When these exptl. findings and d. functional theory calculations are combined, the mechanism of catalysis has been established. Complexes OsH3{κ2-N,O-[HNC(O)R]}(PiPr3)2 dissociate the carbonyl group of the chelate to afford κ1-N-amidate derivatives, which coordinate the nitrile. The subsequent attack of an external water mol. to both the C(sp) atom of the nitrile and the N atom of the amidate affords the amide and regenerates the κ1-N-amidate catalysts. The attack is concerted and takes place through a cyclic six-membered transition state, which involves Cnitrile···O-H···Namidate interactions. Before the attack, the free carbonyl group of the κ1-N-amidate ligand fixes the water mol. in the vicinity of the C(sp) atom of the nitrile.

Inorganic Chemistry published new progress about Amides Role: SPN (Synthetic Preparation), PREP (Preparation). 16332-06-2 belongs to class ethers-buliding-blocks, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Formula: C3H7NO2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem