Day: November 11, 2022

Huang, Mouxin published the artcileDeracemization through photochemical E/Z isomerization of enamines, Application of 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is aldehyde enamine deracemization; photosensitizer aminocatalyst isomerization.

Catalytic deracemization of α-branched aldehydes is a direct strategy to construct enantiopure α-tertiary carbonyls, which are essential to pharmaceutical applications. Here, authors report a photochem. E/Z isomerization strategy for the deracemization of α-branched aldehydes by using simple aminocatalysts and readily available photosensitizers. A variety of racemic α-branched aldehydes could be directly transformed into either enantiomer with high selectivity. Rapid photodynamic E/Z isomerization and highly stereospecific iminium/enamine tautomerization are two key factors that underlie the enantioenrichment. This study presents a distinctive photochem. E/Z isomerization strategy for externally tuning enamine catalysis.

Science (Washington, DC, United States) published new progress about Diastereoselective synthesis. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Application of 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Dong, Jianyang published the artcileFormyl-selective deuteration of aldehydes with D2O via synergistic organic and photoredox catalysis, Application In Synthesis of 1205-17-0, the main research area is aldehyde deuterium oxide tetrabutylammonium decatungstate thiol photocatalyst selective deuteration; deuterated aldehyde preparation.

A mild general method for formyl-selective deuterium labeling of aldehydes with D2O, an inexpensive deuterium source, via a synergistic combination of light-driven, polyoxometalate-facilitated hydrogen atom transfer and thiol catalysis was reported. This highly efficient, scalable reaction showed excellent deuterium incorporation, a broad substrate scope and excellent functional group tolerance and selectivity and was therefore a practical method for late-stage modification of synthetic intermediates in medicinal chem. and for generating libraries of deuterated compounds

Chemical Science published new progress about Deuteration (photochem.). 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Application In Synthesis of 1205-17-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Lipp, Alexander published the artcileCatalyst-Free Decarbonylative Trifluoromethylthiolation Enabled by Electron Donor-Acceptor Complex Photoactivation, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is aldehyde acyl dihydropyridine trifluoromethylthiolation electron donor acceptor light DFT; trifluoromethylthio ether preparation; aldehydes; density functional calculations; electron donor-acceptor complexes; photocatalysis; radical reactions; trifluoromethylthiolation.

A catalyst- and additive-free decarbonylative trifluoromethylthiolation of aldehyde feedstocks has been developed. This operationally simple, scalable, and open-to-air transformation is driven by the selective photoexcitation of electron donor-acceptor (EDA) complexes, stemming from the association of 1,4-dihydropyridines (donor) with N-(trifluoromethylthio)phthalimide (acceptor), to trigger intermol. single-electron transfer events under ambient- and visible light-promoted conditions. Extension to other electron acceptors enables the synthesis of thiocyanates and thioesters, as well as the difunctionalization of [1.1.1]propellane. The mechanistic intricacies of this photochem. paradigm are elucidated through a combination of exptl. efforts and high-level quantum mech. calculations [dispersion-corrected (U)DFT, DLPNO-CCSD(T), and TD-DFT]. This comprehensive study highlights the necessity for EDA complexation for efficient alkyl radical generation. Computation of subsequent ground state pathways reveals that SH2 addition of the alkyl radical to the intermediate radical EDA complex is extremely exergonic and results in a charge transfer event from the dihydropyridine donor to the N-(trifluoromethylthio)phthalimide acceptor of the EDA complex. Exptl. and computational results further suggest that product formation also occurs via SH2 reaction of alkyl radicals with 1,2-bis(trifluoromethyl)disulfane, generated in-situ through combination of thiyl radicals.

Advanced Synthesis & Catalysis published new progress about Density functional theory. 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

Pan, Gao-Fei published the artcileAn efficient Pd@Pro-GO heterogeneous catalyst for the α, β-dehydrogenation of saturated aldehyde and ketones, Recommanded Product: 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, the main research area is aldehyde ketone dehydrogenation palladium proline graphene oxide catalyst; enal enone preparation Saegusa oxidation.

An Efficient Pd@Pro-GO heterogeneous catalyst was developed that can promote the α, β-dehydrogenation of saturated aldehyde and ketones in the yield of 73% – 92% at mild conditions without extra oxidants and additives. Pd@Pro-GO heterogeneous catalyst was synthesized via two steps: firstly, the Pro-GO was obtained by the esterification reaction between graphene oxide (GO) and N-(tert-Butoxycarbonyl)-L-proline (Boc-Pro-OH), followed by removing the protection group tert-Butoxycarbonyl (Boc), which endowed the proline-functionalized GO with both the lewis acid site (COOH) and the bronsted base site (NH), besides, the pyrrolidine of proline also can form imine with aldehydes to activate these substrates; Second, palladium was dispersed on the proline-functionalized GO (Pro-GO) to obtained heterogeneous catalyst Pd@Pro-GO. Mechanistic studies have shown that the Pd@Pro-GO-catalyzed α,β-dehydrogenation of saturated aldehyde and ketones was realized by an improved heterogeneously catalyzed Saegusa oxidation reaction. Based on the above characteristics, the Pd@Pro-GO will be widely used in the transition metal catalytic field.

Tetrahedron Letters published new progress about Dehydrogenation. 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

Pan, Zhangjin published the artcilePalladium/TY-Phos-Catalyzed Asymmetric Intermolecular α-Arylation of Aldehydes with Aryl Bromides, Computed Properties of 104-01-8, the main research area is arylated aldehyde preparation enantioselective; aldehyde aryl bromide arylation palladium catalyst; Z/E-enolates; acyclic aldehydes; all-carbon quaternary centers; asymmetric catalysis; α-arylation.

Herein, an efficient Pd-catalyzed asym. intermol. α-arylation reaction of α-alkyl-α-aryl disubstituted aldehydes with aryl bromides, which provided a rapid access to chiral aldehydes bearing an α-all-carbon quaternary stereocenter in moderate to good yields with good er in most cases was reported. In addition, a pair of enantiomers could be easily prepared with the use of the same ligand by exchanging the aryl groups of aldehyde and aryl bromide.

Angewandte Chemie, International Edition published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Zhang, Xing-Long published the artcileDehydrogenative β-Arylation of Saturated Aldehydes Using Transient Directing Groups, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is dehydrogenative beta arylation saturated aldehyde transient directing group; diastereoselective cinnamaldehyde preparation cross dehydrogenative coupling aldehyde arene.

An unprecedented cross-dehydrogenative-coupling (CDC) reaction of saturated aldehyde β-C-H with arenes to form cinnamaldehydes via the cleavages of four C-H bonds has been developed. The reaction possesses complete E-stereoselectivity for the C=C double bond. The protocol is featured by atom and step economy, mild reaction conditions, and convenient operation.

Organic Letters published new progress about Aromatic hydrocarbons Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Recommanded Product: 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Zheng, Jie published the artcileCascade intramolecular Prins/Friedel-Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols, COA of Formula: C8H10O2, the main research area is aryl tetralinol diastereoselective preparation; acetaldehyde nucleophile Prins Friedel Craft boron trifluoride etherate catalyst; tetrahydrobenzoannulinol aryl diastereoselective preparation; propanal nucleophile Prins Friedel Craft boron trifluoride etherate catalyst; 4-aryltetralin-2-ol; 5-aryl-benzo[7]annulen-7-ol; Prins/Friedel–Crafts; cascade reaction.

The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanal with BF3·Et2O catalyzed intramol. Prins reaction afforded intermediary benzyl carbenium ions, which were then trapped by a variety of electron-rich aromatics via Friedel-Crafts alkylation. This cascade Prins/Friedel-Crafts cyclization protocol paved an expedient path to medicinally useful 4-aryltetralin-2-ol I [R1 = H, OMe, Cl, NO2; R2 = H, Me; R3 = H, Me, Ph; R4 = 2-furyl, 2-thienyl, 3,4-(MeO)2C6H3, etc.] and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol derivatives II [R5 = 2-furyl, 3,4-(MeO)2C6H3].

Beilstein Journal of Organic Chemistry published new progress about Aromatic alcohols Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, COA of Formula: C8H10O2.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Farooq, Saleem published the artcileDihydropyrimidinones: efficient one-pot green synthesis using Montmorillonite-KSF and evaluation of their cytotoxic activity, Application In Synthesis of 86-51-1, the main research area is Montmorillonite KSF support heteropoly acid catalyst preparation surface area; aldehyde acetoacetate urea heterogeneous catalyst Biginelli reaction green chem; dihydropyrimidinone preparation antitumor cytotoxicity SAR docking.

A simple, efficient, cost-effective, recyclable and green approach was developed for the synthesis of new dihydropyrimidinone analogs I [X = O, S; R = Ph, (E)-2-(4-methoxyphenyl)vinyl, 1-chloro-3,4-dihydronaphthalenyl, etc.] via Biginelli reaction. The methodol. involved a multicomponent reaction catalyzed by “”HPA-Montmorillonite-KSF”” as a reusable and heterogeneous catalyst. This method gave an efficient and much improved modification of the original Biginelli reaction, in terms of yield and short reaction times under solvent free conditions. All the derivatives were subjected to cytotoxicity screening against a panel of four different human cancer cell lines viz. colon (Colo-205), prostate (PC-3), leukemia (THP-1) and lung (A549) to check their effect on percentage growth. MTT [3-(4,5-dimethylthiazol-yl)-diphenyl tetrazoliumbromide] cytotoxicity assay was employed to check IC50 values. Of the synthesized analogs, I [X = O, R = (E)-2-(4-methoxyphenyl)vinyl] showed the best activity with IC50 of 7.1 ± 0.8, 13.1 ± 1.4, 13.8 ± 0.9 and 14.7 ± 1.1μM against lung (A549), leukemia (THP-1), prostate (PC-3) and colon (Colo-205) cancer lines, resp. Synthesized compound I [X = O, R = (E)-2-(4-methoxyphenyl)vinyl] were further checked for its effect on cancer cell properties through clonogenic (colony formation) and scratch motility (wound healing) assays and thereby were found that it reduced both the colony formation and migratory properties of the lung cancer cell line (A549). Mol. docking studies were performed with I [X = O, R = (E)-2-(4-methoxyphenyl)vinyl], which showed its binding mode.

RSC Advances published new progress about Antitumor agents. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Application In Synthesis of 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Su, Yong-Liang published the artcileAsymmetric α-Allylation of Aldehydes with Alkynes by Integrating Chiral Hydridopalladium and Enamine Catalysis, Application In Synthesis of 1205-17-0, the main research area is alkenal derivative enantioselective preparation; alkyne aldehyde enantioselective allylation palladium catalyst.

A palladium-catalyzed asym. α-allylation of aldehydes with alkynes has been established by integrating the catalysis of enamine and chiral hydridopalladium complex that is reversibly formed from the oxidative addition of Pd(0) to chiral phosphoric acid. The ternary catalyst system, consisting of an achiral palladium complex, a primary amine, and a chiral phosphoric acid allows the reaction to tolerate a wide scope of α,α-disubstituted aldehydes and alkynes, affording the corresponding allylation products in high yields and with excellent levels of enantioselectivity.

Organic Letters published new progress about Allylation. 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Application In Synthesis of 1205-17-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Shishlikova, Maria A. published the artcileDirected Synthesis of Regioisomeric Monoaryl-Substituted Pyridines Containing a Tricyanobutadiene Fragment and Study on Their Optical Properties, Category: isoquinoline, the main research area is tricyanobutadieyl pyridine preparation regioselective optical study; chlorocinnamaldehyde malononitrile dimer heterocyclization; arylmalondialdehyde malononitrile dimer heterocyclization; enaminoketone malononitrile dimer heterocyclization.

A series of regioisomeric monoaryl-substituted pyridines I (Ar = H, Ph, 4-methoxyphenyl, 3,4-dimethoxyphenyl; Ar1 = H, Ph, 4-methoxyphenyl, 3,4-dimethoxyphenyl; Ar2 = H, Ph, 4-methoxyphenyl, 3,4-dimethoxyphenyl) containing a tricyanobutadiene fragment was prepared using modified known and novel developed synthetic approaches. Advantages and limitations of the used methods were discussed. Dependence of the optical absorption and emission characteristics on the position of aromatic substituent was studied. An unusual intramol. charge transfer from malononitrile fragment to the pyridine ring was found, which was consistent with observed exptl. and theor. data.

ChemistrySelect published new progress about Alkyl aryl ketones Role: RCT (Reactant), RACT (Reactant or Reagent). 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem