Day: November 10, 2022

Zhao, Feng published the artcileEnantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Broensted Acid Catalysis, Product Details of C9H10O3, the main research area is aminoarylpropanoate enantioselective preparation; enantioselective aminomethylation pentafluorophenyl arylacetate isothiourea hydrochloride catalyst; mechanism enantioselective aminomethylation pentafluorophenyl arylacetate acylisothiouronium intermediate; aminomethylation; cooperative catalysis; isothiourea; mechanistic studies; α-aryl-β-amino acid.

The synthesis of α-aryl-β2-amino esters such as (S)-Bn2NCH2CHPhCO2Me (Bn = PhCH2) through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Broensted acid catalysis is demonstrated. The scope and limitations of this process are explored (25 examples, up to 94% yield and 96:4 er), and the method was applied to the syntheses of (S)-venlafaxine hydrochloride and (S)-nakinadine B. Mechanistic studies are consistent with a C(1)-ammonium enolate pathway being followed rather than an alternative dynamic kinetic resolution process. Control studies indicate that (i) a linear effect between catalyst and product er is observed; (ii) an acyl ammonium ion can be used as a precatalyst; (iii) reversible isothiourea addition to an in situ generated iminium ion leads to an off-cycle intermediate that can be used as a productive precatalyst.

Angewandte Chemie, International Edition published new progress about Aminomethylation (stereoselective). 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

Kumar, Jogendra published the artcileEnhancing the Extent of Enolization for α-C-H Bonds of Aliphatic Carboxylic Acid Equivalents via Ion Pair Catalysis: Application toward α-Chalcogenation, Related Products of isoquinoline, the main research area is thioether selenoether preparation regioselective; aliphatic carboxamide thiol thiolation potassium phosphate catalyst; diselenide aliphatic carboxamide selenylation potassium phosphate catalyst.

In general, the α-functionalization of carboxylic acid derivatives RCH2C(O)NHR1 [R = Me, n-Bu, Ph, 3-thienyl, etc.; R1 = pyridin-2-yl, 4-Methylpyridin-2-yl, pyrimidin-2-yl, etc.] requires either a transition metal catalyst or a stoichiometric activating agent/strong base/external additive. A transition metal free α-chalcogenation of aliphatic carboxylic acid equivalent was reported via ion pair formation using K3PO4 as a catalyst. Mild conditions, broad scope, scalability of the process, attaining bioactive glucokinase activators, and some synthetic intermediates establish merits of the strategy.

Journal of Organic Chemistry published new progress about C-H bond activation. 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

Peczkowski, Gary R. published the artcile2,7-Diazabicyclo[2.2.1]heptanes: novel asymmetric access and controlled bridge-opening, Safety of 4-Methoxyphenylacetic acid, the main research area is diazabicycloheptane preparation; oxoalkyl triketopiperazine enantioselective preparation rearrangement; triketopiperazine enone Michael addition organocatalyst.

An efficient method was developed for the asym. synthesis of oxoalkyl triketopiperazines I [R = H, Me, Et, Ph; Ar = Ph, 4-BrC6H4, 2-furanyl, etc.] via organocatalyzed Michael addition of triketopiperazines to enones in high yields and enantiomeric ratio. These triketopiperazines I underwent rearrangement to afford 2,7-diazabicyclo[2.2.1]heptanes II and further modification delivered products possessing natural product scaffolds including prolinamide and harmicine.

Chemical Communications (Cambridge, United Kingdom) published new progress about Enantioselective synthesis. 104-01-8 belongs to class isoquinoline, name is 4-Methoxyphenylacetic acid, and the molecular formula is C9H10O3, Safety of 4-Methoxyphenylacetic acid.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Song, Song published the artcileDMSO-catalysed late-stage chlorination of (hetero)arenes, Safety of 1,3-Dimethoxybenzene, the main research area is arene heteroarene chlorination dimethyl sulfoxide catalyst.

A highly efficient aromatic chlorination of arenes such as 1-methyl-indazole, imidazo[1,2-a]pyrazine, phenylthiophene, anthracene, etc. that is catalyzed by DMSO with N-chlorosuccinimide as the chloro source is reported. The mild conditions, easy-availability and stability of the catalyst and reagents, as well as good functional-group tolerance, showed the approach to be a versatile protocol for the late-stage aromatic chlorination of complex natural products, e.g., papaverine, drugs, e.g., diclofenac and peptides, e.g., I. The multi-gram experiment and low-cost of N-chlorosuccinimide and DMSO show great potential for drug discovery and development in industrial applications.

Nature Catalysis published new progress about Chlorination. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Safety of 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Hu, Wenbin published the artcileHeavy-atom-free charge transfer photosensitizers: Tuning the efficiency of BODIPY in singlet oxygen generation via intramolecular electron donor-acceptor interaction, Computed Properties of 86-51-1, the main research area is heavy atom charge transfer photosensitizer Boron dipyrromethenes; intramol electron donor acceptor.

To test the tunability of charge transfer (CT)-based BODIPY photosensitizers in generating singlet oxygen (1Δg), twelve meso-phenyl-BODIPY (donor-acceptor) type compounds have been synthesized and fully characterized, in which the Ph moiety is modified with resp. 0, 1, 2 and 3 methoxy groups to increase its electron-donating ability. The UV-Vis absorption spectra, fluorescence emission spectra, fluorescence quantum yield, fluorescence lifetime, excited triplet state formation, and singlet oxygen formation properties are measured. DFT quantum chem. computation is also carried out to explain the experiments The occurrence of intra-mol. CT is confirmed by UV-Vis absorption, fluorescence properties and quantum chem. computation. The triplet excited state formation is evidenced by laser radiation flash photolysis technique. The quant. photosensitized singlet oxygen formation is demonstrated by DPBF (diphenylisobenzofuran) chem. trapping method. This type of BODIPY CT photosensitizers show good tunability in generating singlet oxygen (1Δg). When the number of methoxy group on the donor is increased (so that CT is enhanced), the efficiency of singlet oxygen generation becomes higher from 0.070 to 0.30. When solvent polarity is increased (CT is also enhanced), the efficiency of singlet oxygen generation is also increased significantly. The increase in singlet oxygen generation is accompanied by the decrease in fluorescence quantum yield and fluorescence lifetime values. These facts show that a higher CT efficiency in a simple phenyl-BODIPY donor-acceptor conjugate can lead to significant higher quantum yield of singlet oxygen generation. These results are useful in designing novel CT-based heavy-atom-free photosensitizers for photodynamic therapy of tumor.

Dyes and Pigments published new progress about Excited triplet state. 86-51-1 belongs to class isoquinoline, name is 2,3-Dimethoxybenzaldehyde, and the molecular formula is C9H10O3, Computed Properties of 86-51-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Cui, Jianguo published the artcileOxidative umpolung selenocyanation of ketones and arenes: An efficient protocol to the synthesis of selenocyanates, Category: isoquinoline, the main research area is ketone potassium selenocyanate oxidative umpolung selenocyanation; keto ester potassium selenocyanate oxidative umpolung selenocyanation; arene potassium selenocyanate regioselective oxidative umpolung selenocyanation.

A practical method for the umpolung selenocyanation of aryl ketones, alkyl ketones, β-ketoesters and electron-rich arenes was developed, afforded various selenocyanates in moderate to excellent yields. This transformation proceeded by an oxidative umpolung selenocyanation through nitrogen oxides-mediated electrophilic selenocyanation process. This method is simpler, more efficient, and less costly than precedent methods. Further transformations of the arylselenocyanate was performed to prove the synthetic utility of this methodol.

Tetrahedron published new progress about Keto esters 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, Category: isoquinoline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

He, Zhen published the artcileSulfoxide-mediated oxidative cross-coupling of phenols, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is phenol nucleophile sulfoxide mediator oxidative cross coupling regioselective; arylphenol preparation; benzofuran preparation; hydroxy teraryl preparation.

A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols was reported. Cross-coupling was mediated by a sulfoxide which inverts the reactivity of the phenol partner. Crucially, the process showed high selectivity for cross-vs. homo-coupling and allowed efficient access to a variety of aromatic scaffolds including biaryls, benzofurans and through an iterative procedure aromatic oligomers.

Chemical Science published new progress about Benzofurans Role: PRP (Properties), SPN (Synthetic Preparation), 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

Yuan, Shuo published the artcileBronsted Acid-Catalyzed Direct C(sp2)-H Heteroarylation Enabling the Synthesis of Structurally diverse Biaryl Derivatives, SDS of cas: 151-10-0, the main research area is chloro heteroarene arene hexafluoroisopropanol catalyst arylation; heterocyclic biaryl preparation.

Bronsted acid-catalyzed direct C(sp2)-H heteroarylation that enabled the synthesis of biaryl fragments in moderate to excellent yields (up to 99% yield), which was also performed at a gram scale and successfully applied to the privileged quinazoline scaffolds of the first-generation epidermal growth factor receptor (EGFR) inhibitors Gefitinib and Erlotinib, offering rapid access to a series of quinazoline-based biaryl compounds Addnl., the late-stage diversifications were performed based on the compound 5-methyl-7-(2,4,6-trimethoxyphenyl)-[1,2,4]triazolo[1,5-a]pyrimidine, generating a library of structurally diverse and complex biaryl compounds

Advanced Synthesis & Catalysis published new progress about Arylation. 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, SDS of cas: 151-10-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Yang, Xiao-Chao published the artcileAccess to Chiral 2,5-Pyrrolidinyl Dispirooxindoles via Dinuclear Zinc-Catalyzed Asymmetric Cascade Reactions, Name: 4-Methoxy-N-methylaniline, the main research area is amino oxindole keto amide diastereoselective enantioselective zinc azacrown ligand; pyrrolidinyl dispirooxindole stereoselective preparation; Michael cyclic keto imine formation Friedel Crafts cascade.

A series of new nonsym. semi-azacrown ether ligands were developed and applied to the asym. Michael/cyclic keto-imine formation/Friedel-Crafts alkylation reactions of 3-amino oxindole hydrochlorides and β,γ-unsaturated α-keto amides. A diversity of 2,5-pyrrolidinyl dispirooxindoles containing two nonadjacent spiro-quaternary stereocenters were obtained in excellent diastereoselectivities and moderate to excellent enantioselectivities (up to 95% ee). A possible catalytic cycle was proposed to explain the origin of the asym. induction.

Journal of Organic Chemistry published new progress about Azacrown ethers Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Name: 4-Methoxy-N-methylaniline.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Rastogi, S. C. published the artcileFragrance chemicals in domestic and occupational products, Synthetic Route of 1205-17-0, the main research area is fragrance occupational product allergy.

Epidemiol. studies have described an increasing prevalence of fragrance allergy and indicated an association with hand eczema. Fifty-nine domestic and occupational products intended for hand exposure were subjected to gas chromatog.-mass spectrometric (GC-MS) analyses to test the hypothesis that fragrance chems. known to have the potential to cause contact allergy but not included in fragrance mix (FM) may be common ingredients in these products. A quant. anal. of 19 selected fragrances was performed by GC-MS. Further anal. of GC-MS data revealed the presence of 43 other fragrance chems./groups of fragrance chems. in the products investigated. Among the 19 target substances the most commonly detected were limonene in 78%, linalool in 61% and citronellol in 47% of the products investigated. The FM ingredients were present in these products with the following frequencies: oak moss (evernic acid Me ester) 2%, cinnamic alc. 2%, cinnamic aldehyde (cinnamal) 3%, isoeugenol 5%, α-amylcinnamic aldehyde (amyl cinnamal) 8%, hydroxycitronellal 12%, eugenol 27%, and geraniol 41%. Thus, the chem. analyses of domestic and occupational products indicates that investigation of potential contact allergy related to these products types should consider fragrance allergens addnl. to those in the FM, since these may occur with high frequency.

Contact Dermatitis published new progress about Aliphatic ketones Role: ADV (Adverse Effect, Including Toxicity), ANT (Analyte), BIOL (Biological Study), ANST (Analytical Study) (C9-11). 1205-17-0 belongs to class isoquinoline, name is 2-Methyl-3-(3,4-methylenedioxyphenyl)propionaldehyde, and the molecular formula is C11H12O3, Synthetic Route of 1205-17-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem