Tag: M.W=100-150

Holmberg-Douglas, Natalie published the artcileArene Cyanation via Cation-Radical Accelerated-Nucleophilic Aromatic Substitution, Recommanded Product: 1,3-Dimethoxybenzene, the main research area is aryl nitrile chemoselective preparation; acridinium catalyst photochem nucleophilic aromatic substitution aryl alkyl ether; chemoselective photochem cyanation aryl alkyl ether acetone cyanohydrin; calculation atomic charge radical cation regioselectivity photochem cyanation.

In the presence of a highly oxidizing acridinium tetrafluoroborate, aryl Me ethers and an aryl benzyl ether underwent chemoselective nucleophilic aromatic substitution reactions with cyanide generated in situ from acetone cyanohydrin and NaHCO3 in 1,2-dichloroethane/2,2,2-trifluoroethanol to yield aryl nitriles. The observed selectivities for nucleophilic aromatic substitution over direct cyanation correlated with the sites with the largest increases in pos. charge between the ethers and their radical cations; the transition state structures and activation barriers for cyanation of veratrole and Me 3,4-dimethoxybenzoate and cyanation kinetics and lack of linear free energy relationships were determined

Organic Letters published new progress about Aromatic nitriles Role: PEP (Physical, Engineering or Chemical Process), RCT (Reactant), SPN (Synthetic Preparation), PROC (Process), 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

Zhao, Chao published the artcileSPME-GCMS Combined AMDIS and KOVATS retention index to analyze the volatile organic compounds in Russula rubra (Krombh.) Bres. Essential Oil, Application of 1,3-Dimethoxybenzene, the main research area is Russula essential oil SPME GCMS AMDIS KOVATS RI.

Volatile components in Russula rubra (Krombh.) Bres. were determined with the use of a solid-phase microextraction (SPME)/gas chromatog.-mass spectrometry (GC-MS) method. The compounds were identified by the automatic mass spectral deconvolution and identification system (AMDIS) and Kovats retention index (RI). Under the optimized conditions of GC-MS, 52 volatile components were identified in Russula rubra, with the relative percentage accounting for 80.2% of the total ion peak. Notably, aristolone (20.4%), benzaldehyde (20.2%), geranyl acetone (11.0%), and 3-octanone (10.7%) were all at higher levels in samples. The main identified compounds were aldehydes, ketones, alcs., ethers, and alkanes.

BioResources published new progress about Aldehydes Role: ANT (Analyte), BSU (Biological Study, Unclassified), PUR (Purification or Recovery), ANST (Analytical Study), BIOL (Biological Study), PREP (Preparation). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Application of 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Huang, Shuang published the artcileN-Methylation of ortho-substituted aromatic amines with methanol catalyzed by 2-arylbenzo[d]oxazole NHC-Ir(III) complexes, Application In Synthesis of 5961-59-1, the main research area is arylamine methanol arylbenzoxazole iridium complex catalyst methylation green chem; methyl arylamine preparation.

Seven new chelated cyclometalated Ir complexes of ABON,P, ABON,O and ABON,C(carbene) based on a rigid and tunable 2-arylbenzo[d]oxazole backbone were prepared for the N-methylation of amines. Among these three coordinated modes, ABON,C(carbene)-chelated iridium-based catalysts exhibited good performance in the monomethylation of aromatic amines with methanol (MeOH) as the green methylation reagent. The steric-modified synthesis of ABON,C(carbene) complexes was described. The most active ABON,C(carbene) complex with marginal steric hindrance as a catalyst was obtained from the benzoxazole ring without a substituent and Me group of the benzimidazole ring on the N-heterocyclic carbene (NHC) ligand. A variety of amines including para- and meta-substituted aromatic amines, as well as heterocyclic amines, were formulated as suitable substrates. Importantly, this catalyst considerably promoted the yield of the N-methylation of ortho-substituted aromatic amines. Controlled kinetic experiments and deuterium-labeling reactions of these ortho-substituted amines were conducted under optimized conditions. On the basis of the exptl. results, a plausible mechanism was proposed.

Dalton Transactions published new progress about Green chemistry. 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Application In Synthesis of 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Wang, Baolu published the artcileA Borane Lewis Acid in the Secondary Coordination Sphere of a Ni(II) Imido Imparts Distinct C-H Activation Selectivity, Name: 1,3-Dimethoxybenzene, the main research area is aromatic compound carbon hydrogen bond activation kinetics nickel imide; crystal structure boryldiphosphine nickel imido metallacyclic complex.

Two borane-functionalized bidentate phosphine ligands that vary in tether length were prepared to examine cooperative metal-substrate interactions. Ni(0) complexes react with aryl azides at low temperatures to form structurally unusual κ2-(N,N)-N3Ar adducts. Warming these adducts affords products of N2 extrusion and in one case, a Ni-imido compound that is capped by the appended borane. Reactions with 1-azidoadamantane (AdN3) provide a distinct outcome, where a proposed Ni imido intermediate activates the sp2 C-H bonds of arenes, even in the presence of benzylic C-H sites. Combined exptl. and computational mechanistic studies demonstrate that the unique reactivity is a consequence of Lewis-acid-induced polarization of the Ni-NR bond, potentially providing a synthetic strategy for chemoselective reaction engineering.

Journal of the American Chemical Society published new progress about Aryl azides Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent). 151-10-0 belongs to class isoquinoline, name is 1,3-Dimethoxybenzene, and the molecular formula is C8H10O2, Name: 1,3-Dimethoxybenzene.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Vodnala, Nagaraju published the artcileLewis Acid-Promoted Typical Friedel-Crafts Reactions Using DMSO as a Carbon Source, Safety of 1,3-Dimethoxybenzene, the main research area is diarylmethane preparation; arene dimethyl sulfoxide Friedel Craft reaction Lewis acid catalyst.

A mild and efficient synthetic protocol for the synthesis of sym. and unsym. diarylmethanes (DAMs) R1CH2R2 (R1 = 4-methoxyphenyl, 2,4,6-trimethylphenyl, 1H-indol-3-yl, 4-hydroxy-2-oxo-2H-chromen-3-yl, etc.; R2 = 4-hydroxy-3,5-dimethylphenyl, 5-methylfuran-2-yl, 4-amino-3,5-bis(propan-2-yl)phenyl, etc.) was reported. Using DMSO as the C1 source and TMSOTf as the Lewis acid promoter, a series of functionalized sym. and unsym. DAMs was synthesized in high yields. Gratifyingly, DMSO plays a dual role as a solvent and a C1 source and can also be replaced with its deuterated counterpart, DMSO-d6, enabling the incorporation of the -CD2 moiety into the diarylmethane skeleton. The developed approach has been applied to a wide range of substrates having various functional groups, and this protocol has also been extended to the synthesis of an anti-breast cancer agent and an anticoagulant agent using common feedstock compounds In addition, the postulated mechanism has been explicitly demonstrated via control experiments

Journal of Organic Chemistry published new progress about Anticoagulants. 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

Daneshmand, Pargol published the artcileCyclic Ureate Tantalum Catalyst for Preferential Hydroaminoalkylation with Aliphatic Amines: Mechanistic Insights into Substrate Controlled Reactivity, Synthetic Route of 5961-59-1, the main research area is cyclic ureate tantalum catalyst preferential hydroaminoalkylation aliphatic amine.

The efficient and catalytic amination of unactivated alkenes with simple secondary alkyl amines is preferentially achieved. A sterically accessible, N,O-chelated cyclic ureate tantalum catalyst was prepared and characterized by X-ray crystallog. This optimized catalyst can be used for the hydroaminoalkylation of 1-octene with a variety of aryl and alkyl amines, but notably enhanced catalytic activity can be realized with challenging N-alkyl secondary amine substrates. This catalyst offers turnover frequencies of up to 60 h-1, affording full conversion at 5 mol% catalyst loading in approx. 20 min with these nucleophilic amines. Mechanistic investigations, including kinetic isotope effect (KIE) studies, reveal that catalytic turnover is limited by protonolysis of the intermediate 5-membered azametallacycle. A Hammett kinetic anal. shows that catalytic turnover is promoted by electron rich amine substrates that enable catalytic turnover. This more active catalyst is shown to be effective for late stage drug modification.

Journal of the American Chemical Society published new progress about Alkenes Role: PEP (Physical, Engineering or Chemical Process), PRP (Properties), RCT (Reactant), PROC (Process), RACT (Reactant or Reagent) (unactivated). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Synthetic Route of 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Karmel, Caleb published the artcileMechanism of the Iridium-Catalyzed Silylation of Aromatic C-H Bonds, Category: isoquinoline, the main research area is arene silylation mechanism iridium catalysis.

Phenanthroline ligands and [Ir(cod)(OMe)]2 form complexes that catalyze the silylation of aromatic and aliphatic C-H bonds. However, no exptl. data on the identity of complexes related to the mechanism of this process or the mechanisms by which they react to functionalize C-H bonds have been reported. Herein, we describe our studies on the mechanism of the iridium-catalyzed silylation of aryl C-H bonds. The resting state of the catalyst is an iridium disilyl hydride complex (phenanthroline)Ir(SiMe(OTMS)2)2(H)(L), in which L varies with the arene and additives. An iridium disilyl hydride complex was isolated, characterized, and allowed to react with arenes to form aryl silanes. The kinetics of the reactions of electron-rich and electron-poor arenes showed that the rate-limiting step varies with the electronic properties of the arene. Computational studies on related iridium silyl complexes revealed that the high activity of iridium complexes with sterically encumbered phenanthroline ligands is due to a change in the number of silyl groups bound to iridium between the resting state of the catalyst containing the hindered phenanthroline and that containing less hindered phenanthroline.

Journal of the American Chemical Society published new progress about C-H bond activation. 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

Marinova, Maya published the artcileSynthesis, Resolution, Configurational Stability, and Properties of Cationic Functionalized [5]Helicenes, Safety of 1,3-Dimethoxybenzene, the main research area is helicene dye preparation resolution configurational stability.

A straightforward approach to the synthesis of two different series of cationic [5]helicenes has been achieved including, in dioxa series, the possibility to introduce aromatic functional groups at the periphery of the helical structure. While photophys. study highlights that the introduction of aryl substituents at position 23 of the helical moieties has a negligible impact on the optical properties, styryl substituents allow a welcoming extension of the conjugation pathways. Finally, a red shift of the optical properties was evidenced upon introduction of nitrogen atoms in the helicene scaffold, leading to particularly good fluorescence efficiencies in the red domain for a helicenic dye. Detailed information on racemization kinetics was collected for the most stable species upon direct high-performance liquid chromatog. (HPLC) resolution or, when configurational lability was too high, through VT-HPLC anal. on the chiral stationary phase (ΔG‡ values ranging from 85.0 to 137.1 kJ·mol-1 and above).

Journal of Organic Chemistry published new progress about Activation enthalpy (for racemization). 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

Yu, Zhifeng published the artcileDiscovery and characterization of bromodomain 2-specific inhibitors of BRDT, Quality Control of 5961-59-1, the main research area is carboximido indazole preparation bromodomain inhibitor SAR mol docking; BET bromodomains; DNA-encoded chemistry; male contraceptive; small-molecule inhibitors.

To assess the contribution of each BRDT bromodomain, collection of DNA-encoded chem. libraries I [R = Me, MeO; R1 = 2,4-dimethylphenyl, 4-amino-2-methyl-Ph, 1-methylindol-2-yl, etc.] II [R2 = Me, Et, i-Pr; R3 = acetamido, [4-(methylcarbamoyl)benzoyl]amino; R4 = 6-amino-3-pyridyl, 2-aminopyrimidin-5-yl, 6-amino-4-methyl-3-pyridyl, 6-amino-2-methyl-3-pyridyl] and III [R5 = R6 = R7 = H, Me; R8 = H, acetamido, methylcarbamoyl, benzamido; R9 = H, Me, MeO] for BRDT-BD1 and BRDT-BD2 binders was screened. High-enrichment hits was identified and resynthesized off-DNA and examined for their ability to compete with JQ1 in BRDT and BRD4 bromodomain AlphaScreen assays. These studies identified I [R = Me, R1 = 4-amino-2-methyl-phenyl] as a selective BRDT-BD2 inhibitor with low nanomolar potency and >1,000-fold selectivity over BRDT-BD1. Structure-activity relationship studies of I [R = Me, R1 = 4-amino-2-methyl-phenyl] produced a series of addnl. BRDT-BD2/BRD4-BD2 selective inhibitors, including III [R5 = Me, R6 = R7 = H, R8 = acetamido, R9 = Me], a truncated analog of I [R = Me, R1 = 4-amino-2-methyl-phenyl] with similar activity, and II [R2 = Me, R3 = [4-(methylcarbamoyl)benzoyl]amino, R4 = 6-amino-4-methyl-3-pyridyl] an analog with sixfold selectivity for BRDT-BD2 vs. BRD4-BD2. BROMOscan bromodomain profiling confirmed the great affinity and selectivity of I [R = Me, R1 = 4-amino-2-methyl-phenyl] and III [R5 = Me, R6 = R7 = H, R8 = acetamido, R9 = Me] on all BET BD2 vs. BD1 with the highest affinity for BRDT-BD2. Cocrystals of BRDT-BD2 with CDD-1102 and CDD-1302 were determined at 2.27 and 1.90 Å resolution, resp., and revealed BRDT-BD2 specific contacts that explain the high affinity and selectivity of these compounds These BD2-specific compounds and their binding to BRDT-BD2 are unique compared with recent reports and enabled further evaluation of their nonhormonal contraceptive potential in-vitro and in-vivo.

Proceedings of the National Academy of Sciences of the United States of America published new progress about Arylboronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 5961-59-1 belongs to class isoquinoline, name is 4-Methoxy-N-methylaniline, and the molecular formula is C8H11NO, Quality Control of 5961-59-1.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem

Fier, Patrick S.; Maloney, Kevin M. published the artcile< Reagent Design and Ligand Evolution for the Development of a Mild Copper-Catalyzed Hydroxylation Reaction>, Application In Synthesis of 3336-49-0, the main research area is aryl halide oxime copper dicarboxamide hydroxylation catalyst; phenol preparation; dicarboxamide preparation hydroxylation ligand.

Parallel synthesis and mass-directed purification of a modular ligand library, high-throughput experimentation, and rational ligand evolution have led to a novel copper catalyst for the synthesis of phenols with a traceless hydroxide surrogate. The mild reaction conditions reported here enable the late-stage synthesis of numerous complex, druglike phenols.

Organic Letters published new progress about Amides Role: CAT (Catalyst Use), SPN (Synthetic Preparation), USES (Uses), PREP (Preparation) (di-). 3336-49-0 belongs to class isoquinoline, and the molecular formula is C9H7NO, Application In Synthesis of 3336-49-0.

Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem