Month: December 2022

Breno, Kerry L. published the artcileAqueous Phase Organometallic Catalysis Using (MeCp)₂Mo(OH)(H₂O)⁺. Intramolecular Attack of Hydroxide on Organic Substrates, Quality Control of 16332-06-2, the publication is Organometallics (2004), 23(8), 1738-1746, database is CAplus.

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 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Quality Control of 16332-06-2.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Breno, Kerry L. published the artcileOrganometallic Chemistry in Aqueous Solution. Hydration of Nitriles to Amides Catalyzed by a Water-Soluble Molybdocene, (MeCp)₂Mo(OH)(H₂O)⁺, Recommanded Product: 2-Methoxyacetamide, the publication is Organometallics (2003), 22(6), 1203-1211, database is CAplus.

[Cp’₂Mo(μ-OH)₂MoCp’₂]²⁺ (1) (Cp’ = η⁵-CH₃C₅H₄) is a precatalyst for the hydration of nitriles in aqueous solution under mild conditions (∼80°). Among the nitriles hydrated were acetonitrile, isobutyronitrile, benzonitrile, 3-hydroxypropionitrile, 3-bromopropioamide, 4-cyanopyridine, succinonitrile, Me cyanoacetate, 2-methoxyacetonitrile, and acrylonitrile. Except in the case of 2-methoxyacetonitrile, hydrolysis of the resulting amide products did not occur. Hydration of the C:C double bond did not occur in acrylonitrile, but hydrolysis of ester and ether linkages did occur in nitriles containing those functional groups. The apparent rate constants and turnover frequencies of the catalytic reactions were determined using an iterative kinetics-fitting program. The rates and turnover frequencies are comparable to those reported for many homogeneous nitrile hydration catalysts described in the literature. In aqueous solution, 1 is in equilibrium with [Cp’₂Mo(OH)(H₂O)]⁺ (2), and this monomer is proposed to be the active hydration catalyst. The hydration is proposed to occur by an intramol. attack of a hydroxide ligand on a coordinated nitrile. The hydration reaction is irreversibly inhibited by product and reversibly inhibited by substrate (nitrile).

Organometallics published new progress about 16332-06-2. 16332-06-2 belongs to ethers-buliding-blocks, auxiliary class Amine,Aliphatic hydrocarbon chain,Amide,Ether, name is 2-Methoxyacetamide, and the molecular formula is C3H7NO2, Recommanded Product: 2-Methoxyacetamide.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Weickmann, Daniel published the artcileThe Ru-Catalyzed Alkylative Dearyloxylation of L-type 2-Aryloxyethanols, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, the publication is ChemCatChem (2013), 5(8), 2170-2173, database is CAplus.

The authors report the ruthenium-catalyzed cleavage of the β-C-O linkage in different lignin model compounds; this also allow for direct sequential alkylation of the resulting acetophenone derivatives using alcs. as alkylation agents. Thus, reacting PhCH(OH)CH₂OPh with (Ph₃P)₃RuCl₂ gave PhCOMe and PhOH in excellent yields. Adding PhCH₂OH led to PhCOCH₂CH₂Ph in 71% yield.

ChemCatChem published new progress about 183303-74-4. 183303-74-4 belongs to ethers-buliding-blocks, auxiliary class Benzene,Alcohol,Ether, name is 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol, and the molecular formula is C8H15NO, Safety of 1-(3,4-Dimethoxyphenyl)-2-phenoxyethanol.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Trost, Barry M. published the artcileA short and concise asymmetric synthesis of hamigeran B, Synthetic Route of 725251-81-0, the publication is Chemistry – A European Journal (2005), 11(3), 951-959, database is CAplus and MEDLINE.

The interesting biol. properties of the hamigerans wherein hamigeran B (I) is a potent antiviral agent with low cytotoxicity to host cells make these deceptively simple looking structures challenging synthetic targets. A strategy to hamigeran B evolved wherein the three contiguous stereocenters are established ultimately from a Pd catalyzed asym. allylic alkylation (AAA). The latter involves an asym. allylation of a non-stabilized ketone enolate in 77% yield and 93% ee. By using this process, (S)-5-allyl-2-isopropyl-5-methyl-1-trifluoromethanesulfonyloxycyclopentene becomes available in four steps from 2-methylcyclopentanone. Introduction of the aryl unit by cross-coupling proceeded intermolecularly but failed intramolecularly. On the other hand, reductive removal of the triflate permitted a Heck reaction to effect intramol. introduction of the aryl ring. The unusual conformational properties of this mol. architecture are revealed by the regioselectivity of the β-hydrogen elimination in the Heck reaction and the diastereoselectivity of the reduction establishing the stereochem. of the carbon bearing the iso-Pr group. The successful route consists of 15 steps from 2-methylcyclopentanone and dimethylorcinol illustrating the efficiency of the route based upon the Pd AAA.

Chemistry – A European Journal published new progress about 725251-81-0. 725251-81-0 belongs to ethers-buliding-blocks, auxiliary class Boronic acid and ester,Benzene,Ether,Boronic Acids,Boronic acid and ester, name is (3-Methoxy-5-methylphenyl)boronic acid, and the molecular formula is C9H12O, Synthetic Route of 725251-81-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Roush, W. R. published the artcile[(E)-γ-(Dimethylphenylsilyl)allyl]diisopinocampheylborane: a highly enantioselective reagent for the synthesis of anti-β-hydroxyallylsilanes, COA of Formula: C21H37BO, the publication is Tetrahedron Letters (2000), 41(49), 9413-9417, database is CAplus.

Anti-β-Hydroxyallylsilanes, MeCH(OH)CH(CH:CH₂)SiMe₂Ph for example, were prepared with 88-95% e.e. via asym. allylboration reactions of aldehydes, MeCHO for example, with [(E)-γ-(dimethylphenylsilyl)allyl]diisopinocampheylborane.

Tetrahedron Letters published new progress about 99438-28-5. 99438-28-5 belongs to ethers-buliding-blocks, auxiliary class Chiral,Aliphatic cyclic hydrocarbon, name is (+)-B-Methoxydiisopinocampheylborane, and the molecular formula is C21H37BO, COA of Formula: C21H37BO.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Patriciu, Oana-Irina published the artcileSynthesis of nitro N,N’-dipyridinylamines via oxidative nucleophilic substitution of hydrogen, Quality Control of 52818-63-0, the publication is Synthesis (2007), 3868-3876, database is CAplus.

The amination of 3-nitropyridines with aromatic amides generated from various aminopyridine derivatives proceeded unexpectedly in the position para to the nitro group, giving the oxidative nucleophilic substitution of hydrogen (ONSH) derived compounds After optimization, this reaction allowed easy access to interesting 3-nitro-substituted N,N’-dipyridinylamines.

Synthesis published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Quality Control of 52818-63-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Luong, Tuan Minh published the artcileTotal Asymmetric Synthesis and Stereochemical Confirmation of (+)- and (-)-Lyoniresinol and Its Deuterated Analogues, Quality Control of 134-96-3, the publication is Journal of Organic Chemistry (2022), 87(6), 4254-4262, database is CAplus and MEDLINE.

Lyoniresinol and its derivatives are lignans which have been isolated from a plethora of plant species. In addition to exhibiting a range of interesting biol. activities including anticancer, anti-inflammatory, antimicrobial, and others, these compounds have also been discovered in wines and spirits and shown to have gustatory effects in these alc. matrixes. (+)-Lyoniresinol 1 is reported to impart a strong bitter taste while its enantiomer (-)-lyoniresinol 2 is tasteless. The first total asym. synthesis of both natural enantiomers (+)-1 and (-)-2 and their deuterated analogs (D₄)-(+)-3 and (D₄)-(-)-4 has been achieved, confirming the structure and stereochem. of the natural products. The synthesized compounds can be utilized as internal standards in stable isotope dilution anal. for improving and optimizing the existing lyoniresinol quantitation methods in the future.

Journal of Organic Chemistry published new progress about 134-96-3. 134-96-3 belongs to ethers-buliding-blocks, auxiliary class Immunology/Inflammation,COX,Natural product, name is 4-Hydroxy-3,5-dimethoxybenzaldehyde, and the molecular formula is C9H10O4, Quality Control of 134-96-3.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kerdouci, Jamila published the artcilePrediction of rate constants for gas-phase reactions of nitrate radical with organic compounds: A new structure-activity relationship, Name: 2-Methoxypropan-1-ol, the publication is ChemPhysChem (2010), 11(18), 3909-3920, database is CAplus and MEDLINE.

A new structure-activity relationship (SAR), based on parametrization of the mol. structure according to the group-additivity method, is presented. On the basis of existing exptl. data for the degradability of approx. 150 organic compounds by the NO₃ radical, this new SAR is developed to estimate the rate constants for reactions with NO₃ radical. At night, nitrate radicals are the most important oxidant of volatile organic compounds The rate constants for their reactions are therefore essential to the understanding of VOC degradation and atm. modeling. The database used for the SAR development includes most classes of compounds such as alkanes, alkenes (acyclic and cyclic), dienes, terpenes and saturated and unsaturated oxygenated compounds (including alcs., ketones, ethers and esters). The proposed SAR shows good efficiency, as 91% of the rate constants are reproduced within a factor of two. The overall agreement between measured and predicted rate constants is very good for most of the unsaturated and saturated compounds, although for saturated alcs. it is less reliable.

ChemPhysChem published new progress about 1589-47-5. 1589-47-5 belongs to ethers-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-Methoxypropan-1-ol, and the molecular formula is C4H10O2, Name: 2-Methoxypropan-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Kerdouci, Jamila published the artcileStructure-activity relationship for the gas-phase reactions of NO₃ radical with organic compounds: Update and extension to aldehydes, Computed Properties of 1589-47-5, the publication is Atmospheric Environment (2014), 363-372, database is CAplus.

In this work is presented an extension and an update of a recently published structure-activity relationship (SAR) for the prediction of rate constants for gas-phase reactions of VOCs with NO₃ radicals (See previous version in Kerdouci et al., 2011). Such predictive tools are very useful to describe the reactivity of organic compounds in atm. models. This SAR is constructed on the group-additivity method and is based on a wide kinetic database for 185 organic compounds In addition to alkanes, alkenes and saturated and unsaturated oxygenated species already included in the first version of this SAR, this extended version comprises now aldehydes and unsaturated aldehydes. Indeed, since then, new kinetic studies have been performed for alkenals which allow the parameterization of this class of compounds In addition, since new rate constants have been measured for unsaturated ethers, the parameterization of this family of compounds has been completed. Finally, this new version of the SAR shows very good predictive capabilities with more than 90% of the exptl. rate coefficients being reproduced within a factor of two.

Atmospheric Environment published new progress about 1589-47-5. 1589-47-5 belongs to ethers-buliding-blocks, auxiliary class Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-Methoxypropan-1-ol, and the molecular formula is C4H10O2, Computed Properties of 1589-47-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Maurer, Hans published the artcileToxicological detection of ethylenediamine and piperazine antihistamines and their metabolites in urine by computerized gas chromatography-mass spectrometry, Formula: C13H14N2O, the publication is Fresenius’ Zeitschrift fuer Analytische Chemie (1988), 331(7), 744-56, database is CAplus.

A gas chromatog.-mass spectrometric procedure for the detection of the ethylenediamine and piperazine antihistamines and their metabolites in urine after acid hydrolysis, extraction and acetylation is described for adeptolon, antazoline, bamipine, buclizine, chlorcyclizine, chloropyramine, cinnarizine, clemizole, cyclizine, etodroxizine, histapyrrodine, hydroxyzine, meclozine, mepyramine, oxatomide, and tripelenamine. The acetylated extract was analyzed by computerized gas chromatog.-mass spectrometry. Using ion chromatog. with the selective ions m/z 58, 72, 85, 125, 165, 183, 198, and 201, the possible presence of ethylenediamine or piperazine antihistamines or their metabolites was indicated. The identity of pos. signals in the reconstructed ion chromatograms was then confirmed by a visual or computerized comparison of the stored full mass spectra with the reference spectra. The chromatograms, reference mass spectra, and gas chromatog. retention indexes (OV-101) are documented. The procedure presented was integrated in a general screening procedure (general unknown anal.) for several groups of drugs.

Fresenius’ Zeitschrift fuer Analytische Chemie published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Formula: C13H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem