Tag: M.W=150-200

Filatov, Vadim E. published the artcilecis-Diastereoselective Synthesis of Spirooxindolo-β-Lactams by Staudinger Cycloaddition with TsCl as Activating Co-reagent, Computed Properties of 104-01-8, the main research area is spirooxindolo beta lactam preparation cis diastereoselective Staudinger cycloaddition TsCl.

A convenient and versatile one-pot method for synthesis of 1,3-bis-aryl spirooxindolo-β-lactams from isatin Schiff bases and substituted phenylacetic acids using ketene-imine cycloaddition reaction with TsCl for a ketene generation has been developed. The reaction procedure does not require absolute solvents and unstable starting reagents. The studied reactions lead to cis-diastereoselective β-lactam formation for all tested phenylacetic acids except 4-MeOC6H4CH2COOH. An increase of trans-diastereomers yields with increasing temperature and solvent polarity was demonstrated.

ACS Omega published new progress about Diastereoselective synthesis. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Computed Properties of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Shimbo, Daisuke published the artcileN-Alkenylation of hydroxamic acid derivatives with ethynyl benziodoxolone to synthesize cis-enamides through vinyl benziodoxolones, Application In Synthesis of 104-01-8, the main research area is methoxyamide vinyl benziodoxolone preparation diastereoselective; alkyl hydroxamic acid ethynyl benziodoxolone acetonitrile complex alkenylation.

The stereoselective synthesis of cis-β-N-alkoxyamidevinyl benziodoxolones (cis-β-N-RO-amide-VBXs) I (R = 4-iodophenyl, cyclopropyl, pyridin-3-yl, etc.) from O-alkyl hydroxamic acids RC(O)NHOCH3 in the presence of an ethynyl benziodoxolone-acetonitrile complex (EBX-MeCN) is reported herein. The reaction was performed under mild conditions including an aqueous solvent, a mild base, and room temperature The reaction tolerated various O-alkyl hydroxamic acids derived from carboxylic acids, such as amino acids, pharmaceuticals, and natural products. Vinyl dideuterated cis-β-N-MeO-amide-VBXs, e.g., II, were also synthesized using deuterium oxide as the deuterium source. Valine-derived cis-β-N-MeO-amide-VBX was stereospecifically derivatized to hydroxamic acid-derived cis-enamides, e.g., III, without the loss of stereoselectivity or reduction in the deuterium/hydrogen ratio.

Organic & Biomolecular Chemistry published new progress about Alkenylation, stereoselective. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Application In Synthesis of 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Grotjahn, Sascha published the artcilePhotosubstitution in Dicyanobenzene-based Photocatalysts, SDS of cas: 104-01-8, the main research area is photosubstitution cyano group dicyanobenzene photocatalysts; dicyanobenzene photocatalysts photosubstitution.

We report the photosubstitution of one cyano group in dicyanobenzene-based photocatalysts and thermally activated delayed fluorescence (TADF) emitters. The reaction is a general degradation pathway for some widely used organic photocatalysts such as 4CzIPN and suggests that the active photocatalyst in many reactions is likely different from 4CzIPN. On the contrary, photosubstitution is a facile route to diverse highly reducing photocatalysts and blue TADF emitters.

Organic Letters published new progress about Benzylation (decarboxylative). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, SDS of cas: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wu, Xiaofan published the artcileAsymmetric Synthesis of a Key Dextromethorphan Intermediate and Its Analogues Enabled by a New Cyclohexylamine Oxidase: Enzyme Discovery, Reaction Development, and Mechanistic Insight, HPLC of Formula: 104-01-8, the main research area is cyclohexylamine oxidase dextromethorphan intermediate asym synthesis.

(S)-1-(4-Methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline [(S)-1-(4-methoxybenzyl)-OHIQ, (S)-1a] is a key synthetic intermediate in the industrial production of dextromethorphan, one of the most widely used over-the-counter antitussives. We report here that a new cyclohexylamine oxidase discovered by genome mining, named CHAOCCH12-C2, was able to completely deracemize 100 mM 1a under Turner’s deracemization conditions to afford (S)-1a in 80% isolated yield and 99% ee at a semipreparative scale (0.4 mmol). When this biocatalytic reaction was scaled up to a gram scale (5.8 mmol), without reaction optimization (S)-1a was still isolated in 67% yield and 96% ee. The relatively higher kcat determined for CHAOCCH12-C2 was rationalized as one major factor rendering this enzyme capable of oxidizing 1a effectively at elevated substrate concentrations Protein sequence alignment, anal. of our co-crystal structure of CHAOCCH12-C2 complexed with the product 1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinoline [1-(4-methoxybenzyl)-HHIQ, 2a], and the structure-guided mutagenesis study together indicated L295 is one of the critical residues for this efficient enzymic oxidation process and supported the presence of two cavities as well as a catalytically important “”aromatic cage”” formed by F342, Y433, and FAD. The synthetic applicability of CHAOCCH12-C2 was further underscored by the stereoselective synthesis of various enantioenriched 1-benzyl-OHIQ derivatives of potential pharmaceutical importance at a semipreparative scale.

Journal of Organic Chemistry published new progress about Biochemical reaction kinetics. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, HPLC of Formula: 104-01-8.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Matzel, Philipp published the artcileSynthesis of β-Chiral Amines by Dynamic Kinetic Resolution of α-Branched Aldehydes Applying Imine Reductases, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is imine reductase dynamic kinetic resolution.

Imine reductases (IREDs) allow the one-step preparation of optically active secondary and tertiary amines by reductive amination of ketones. Until now, mainly α-chiral amines have been prepared by this route. In this study, we explored the possibility of synthesizing β-chiral amines, a class of compounds which is also frequently found as structural motif in pharmaceuticals but much more challenging to prepare due to the following reasons: (i) The aldehyde substrate already contains the chiral center and needs to be racemized to enable full conversion. (ii) Because the intermediate imine bears the stereo center two carbon atoms remote to the imine nitrogen, it is more challenging to achieve high enantioselectivity compared to α-chiral amine synthesis. For investigating the proof of concept, we first confirmed that different IREDs are able to convert a variety of α-branched aldehydes when combined with five different amine substrates. The IRED from Streptomyces ipomoeae was a suitable enzyme facilitating the dynamic kinetic resolution of 2-phenylpropanal and a substituted 2-methyl-3-phenylpropanal: the corresponding N-methylated β-chiral amines were obtained with >95 % conversion and 78 and 95 %ee. Other amines were formed with low to moderate enantiomeric excess. This exemplifies the potential of IREDs for the one-step synthesis of secondary β-chiral amines, but also the challenge to identify highly selective enzymes for a desired amine product.

ChemCatChem published new progress about Biochemical reaction kinetics. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Kang, Yang published the artcileTwo-Step Synthesis of π-Expanded Maleimides from 3,4-Diphenylfuran-2(5H)-ones, Recommanded Product: 4-Methoxyphenylacetic acid, the main research area is primary amine diphenylfuranone photoinduced dehydrogenative annulation light fluorescent; pi expanded maleimide preparation.

An efficient two-step synthesis of π-expanded maleimide derivatives was reported, which proceeded via a photoinduced dehydrogenative annulation of 3,4-diphenylfuran-2(5H)-ones in EtOH at room temperature for 5 h under an argon atm., followed by interaction with primary amine in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene and O2. The synthesis of highly conjugated maleimides demonstrated that 3,4-diphenylfuran-2(5H)-ones were useful precursors for synthesis of π-expanded lactones and π-expanded maleimides with no need of a transition-metal catalyst. Addnl., the fluorescent properties of the highly conjugated maleimides were characterized and were found to possess high fluorescence quantum yields in dichloromethane solution

Journal of Organic Chemistry published new progress about Cyclization (dehydrogenative). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Recommanded Product: 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Jeon, Dong Bok published the artcileDetermination of volatile organic compounds, catechins, caffeine and theanine in Jukro tea at three growth stages by chromatographic and spectrometric methods, Computed Properties of 21834-92-4, the main research area is catechin caffeine theanine Junko tea growth; High performance liquid chromatography (HPLC); Jukro tea; Simultaneous distillation solvent-extraction gas chromatography-mass spectrometry (SDE-GC/MS); Theanine; Volatile organic compounds.

Tea contains characteristic volatile organic compounds, polyphenols, caffeine and catechins, and is therefore among the most widely consumed beverages all over the world. In this study, fresh Jukro tea leaves collected from Damyang-gun (Jeollanam-do) at 40, 60 and 90 day growth stages, were semi-fermented. The volatile organic compounds (VOCs) were extracted by simultaneous distillation-solvent extraction (SDE) and analyzed by gas chromatog./mass spectrometry (GC/MS). Catechins, caffeine and theanine were analyzed by high performance liquid chromatog. (HPLC). A total of 159 VOCs were identified in the analyzed Jukro tea leaves. Comparatively, the increase in the concentrations of VOCs was high in 60 day leaves. The content of catechins increased along the three growth stages, whereas caffeine, compared to 90 day leaves, was higher for 40 and 60 day leaves. Based on the results, the 60 day leaves were found to be the most suitable and useful for making semi-fermented Jukro tea.

Food Chemistry published new progress about Growth and development, plant. 21834-92-4 belongs to class isoquinoline, name is 5-Methyl-2-phenylhex-2-enal, and the molecular formula is C13H16O, Computed Properties of 21834-92-4.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Maeta, Naoya published the artcileProbing Intramolecular Electron Transfer in Redox Tag Processes, Related Products of isoquinoline, the main research area is intramol electron transfer photocatalytic cycloaddition double bond metathesis.

Herein, we show that redox tag-guided intermol. formal [2 + 2] cycloaddition can be used as a probe to investigate intramol. single-electron transfer (SET) mechanisms. The efficacy of intramol. SET can be evaluated in association with concomitant carbon-carbon bond formation and/or cleavage, leading to cycloaddition or cross-metathesis. Exptl. and theor. results suggest that the intramol. SET is under both thermodn. and kinetic control and can also occur through bonds, not only through space.

Organic Letters published new progress about [2+2] Cycloaddition reaction. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Related Products of isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Ivanov, Konstantin L. published the artcileOne-Pot Synthesis of γ-Azidobutyronitriles and Their Intramolecular Cycloadditions, Name: 2,3-Dimethoxybenzaldehyde, the main research area is aldehyde cyanoacetate one pot cycloaddition reaction; azidocyanoester preparation; tetrazole preparation.

Efficient gram-scale, one-pot approached to azidocyanobutyrates and their amidated or decarboxylated derivatives was developed, starting from com. available aldehydes and cyanoacetates. These techniques combine (1) Knoevenagel condensation, (2) Corey-Chaykovsky cyclopropanation and (3) nucleophilic ring opening of donor-acceptor cyclopropanes with the azide ion, as well as (4) Krapcho decarboxylation or (4′) amidation. The synthetic utility of the resulting γ-azidonitriles was demonstrated by their transformation into tetrazoles via intramol. (3+2)-cycloaddition A condition-dependent activation effect of the α-substituent was revealed in that case. Thermally activated azide-nitrile interaction did not differentiate the presence of an α-electron-withdrawing substituent in γ-azidonitriles, whereas the Lewis acid mediated (SnCl4or TiCl4) reaction proceeded much easier for azidocyanobutyrates. This allowed us to develop an efficient procedure for converting azidocyanobutyrates into the corresponding tetrazoles.

Synthesis published new progress about [3+2] Cycloaddition reaction. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Name: 2,3-Dimethoxybenzaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hong, Seung Youn published the artcileStereodefined Access to Lactams via Olefin Difunctionalization: Iridium Nitrenoids as a Motif of LUMO-Controlled Dipoles, Product Details of C9H10O3, the main research area is lactam stereodefined synthesis olefin difunctionalization iridium nitrenoid dipole.

Reported herein is a general platform of a stereodefined access to γ-lactams via Cp*Ir-catalyzed olefin difunctionalization, where in situ generated Ir-nitrenoid is utilized as a key motif of 1,3-dipoles to enable amido transfer in a syn-selective manner. Computational studies suggested that the stereodefined process can be attributed to the proposed working mode of concerted [3+2] cyclization. Frontier MO (FMO) anal. implied that a low-lying LUMO (LUMO) of the Ir-imido fragment engages in the olefin interaction. Mechanistic understanding on the nitrene transfer process led us to develop mild catalytic protocols of stereoselective difunctionalization of alkenyl dioxazolones to furnish α-(haloalkyl)- or (oxyalkyl)lactam products which are of high synthetic and medicinal utility. Product stereochem. (threo and erythro) was found to be designated by the olefin geometry (E/Z) of substrates.

Journal of the American Chemical Society published new progress about [3+2] Cycloaddition reaction. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Product Details of C9H10O3.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem