Category: 52244-70-9

Achar, Tapas Kumar; Zhang, Xinglong; Mondal, Rahul; Shanavas, M. S.; Maiti, Siddhartha; Maity, Sabyasachi; Pal, Nityananda; Paton, Robert S.; Maiti, Debabrata published the artcile< Palladium-Catalyzed Directed meta-Selective C-H Allylation of Arenes: Unactivated Internal Olefins as Allyl Surrogates>, Computed Properties of 52244-70-9, the main research area is pyrimidine styrenyl preparation diastereoselective regioselective DFT; arene olefin selective allylation palladium catalyst; C−H activation; allylic compounds; olefins; palladium; reaction mechanisms.

Palladium(II)-catalyzed meta-selective C-H allylation of arenes RC6H4(CH2)nXR1 [R = H, 3-Me, 3-Br, 4-F, etc.; R1 = 2-(pyrimidin-5-yl)phenoxy, 2-(pyridin-3-yl)phenoxy, 2-(8-nitroquinolin-3-yl)phenoxy, etc.; X = SO2, C(O), Si(i-Pr)2, CH2; n = 1-4] including 2-(pyrimidin-5-yl)phenyl (2S)-2-(6-methoxynaphthalen-2-yl)propanoate has been developed utilizing synthetically inert unactivated acyclic internal olefins R2CH2CH=CHCH2R3 [R2 = Me, Et, n-Pr, pentyl, etc.; R3 = Me, COOMe, [[(1S,2R,5S)-5-methyl-2-(propan-2-yl)cyclohexyl]oxy]carbonyl, etc.] as allylic surrogates. The strong σ-donating and π-accepting ability of pyrimidine-based directing group facilitates the olefin insertion by overcoming inertness of the typical unactivated internal olefins. Exclusive allyl over styrenyl products, e.g., (E)-I selectivity as well as E stereoselectivity were achieved with broad substrate scope, wide functional-group tolerance, and good to excellent yields. Late-stage functionalizations of pharmaceuticals were demonstrated. Exptl. and computational studies shed light on the mechanism and point to key steric control in the palladacycle, thus determining product selectivities.

Angewandte Chemie, International Edition published new progress about Alkenes Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Computed Properties of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Bowles, Mark R.; Eyles, Darryl W.; Hampson, Edith C. G. M.; Pond, Susan M. published the artcile< Quantitation of paraquat in biological samples by radioimmunoassay using a monoclonal antibody>, HPLC of Formula: 52244-70-9, the main research area is paraquat determination biol sample monoclonal antibody; RIA paraquat urine blood bronchoalveolar lavage.

The authors have developed a sensitive and specific RIA for the quant. determination of paraquat in plasma, urine, and bronchoalveolar lavage fluid using a monoclonal antibody. The synthesis of the iodinated paraquat tracer is novel and less complicated than a previously reported method. Regardless of the type of biol. sample analyzed, the sensitivity of the assay was 0.46 ng/mol in a 200-μL aliquot. The results correlated well with those of another assay performed in a sep. laboratory Paraquat concentrations were determined in plasma and in urine of a dog over several days after the i.v. administration of 7.48 mg paraquat cation/kg and in bronchoalveolar lavage fluid obtained 34 h after the 2-h infusion was discontinued. Concentrations of paraquat measured ranged from 14.1 to 0.03 μg/mL in plasma and 2034 to 0.36 μg/mL in urine. Concentrations of paraquat in plasma obtained at various times after the ingestion of paraquat by three patients ranged from 51.0 to 0.010 μg/mL.

Fundamental and Applied Toxicology published new progress about Alveolus. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, HPLC of Formula: 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Zarate, Cayetana; Nakajima, Masaki; Martin, Ruben published the artcile< A Mild and Ligand-Free Ni-Catalyzed Silylation via C-OMe Cleavage>, Computed Properties of 52244-70-9, the main research area is ligand free nickel catalyzed silylation carbon methoxy cleavage; anisole derivative nickel catalyzed silylation.

Metal-catalyzed transformations that forge carbon-heteroatom bonds are of central importance in organic synthesis. Despite the formidable potential of aryl Me ethers as coupling partners, the scarcity of metal-catalyzed C-heteroatom bond formations via C-OMe cleavage is striking, with isolated precedents requiring specialized, yet expensive, ligands, high temperatures, and π-extended backbones. Authors report an unprecedented catalytic ipso-silylation of aryl Me ethers under mild conditions and without recourse to external ligands. The method is distinguished by its wide scope, which includes the use of benzyl Me ethers, vinyl Me ethers, and unbiased anisole derivatives, thus representing a significant step forward for designing new C-heteroatom bond formations via C-OMe scission. Applications of this transformation in orthogonal silylation techniques as well as in further derivatizations are also described. Preliminary mechanistic experiments suggest the intermediacy of Ni(0)-ate complexes, leaving some doubt that a canonical catalytic cycle consisting of an initial oxidative addition of the C-OMe bond to Ni(0) species comes into play.

Journal of the American Chemical Society published new progress about Bond cleavage (carbon-methoxy). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Computed Properties of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Lu, Xingliang; Silverman, Richard B. published the artcile< Monoamine Oxidase B-Catalyzed Reactions of cis- and trans-5-Aminomethyl-3-(4-Methoxyphenyl)dihydrofuran-2(3H)-ones. Evidence for a Reversible Redox Reaction>, Related Products of 52244-70-9, the main research area is monoamine oxidase B reversible redox reaction.

Monoamine oxidase B (MAO B) was previously shown to catalyze the decarboxylation of cis- and trans-5-(aminomethyl)-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one hydrochloride. By [14C]-labeling of the aryl methoxyl group, it is now shown that the decarboxylated product is 4-(4-methoxyphenyl)butanal, which is in the same oxidation state as the substrate. Two other products are produced, 4-carboxy-4-(4-methoxyphenyl)butanal, and 5-formyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one. Only 5-formyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one is an oxidation product; 4-(4-methoxyphenyl)butanal and 4-carboxy-4-(4-methoxyphenyl)butanal are in the same oxidation state as the substrate. No products are detected under strictly anaerobic conditions. All of these products can be rationalized as arising from the formation of an α-carbon radical, generated either by single-electron amine oxidation and loss of a proton or direct hydrogen atom abstraction. This intermediate then can undergo second electron oxidation and hydrolysis of the iminium ion to give 5-formyl-3-(4-methoxyphenyl)dihydrofuran-2(3H)-one (the normal oxidation product). However, it also can suffer either homolytic C-O bond cleavage, decarboxylation, and electron return from the active site to give 4-(4-methoxyphenyl)butanal or heterolytic cleavage and electron return from the active site to give 4-carboxy-4-(4-methoxyphenyl)butanal. 5-(4-Methoxyphenyl)tetrahydrofuran-2-ol, an oxidation product from the intermediate that leads to 4-(4-methoxyphenyl)butanal, is not detected. These results suggest that MAO B can catalyze reversible redox reactions.

Journal of the American Chemical Society published new progress about Reaction mechanism. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Related Products of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Borjesson, Marino; Moragas, Toni; Martin, Ruben published the artcile< Ni-Catalyzed Carboxylation of Unactivated Alkyl Chlorides with CO2>, Reference of 52244-70-9, the main research area is carboxylic acid preparation; alkyl chloride carboxylation Ni catalyst.

A catalytic carboxylation of unactivated primary, secondary, and tertiary alkyl chlorides with CO2 at atm. pressure is described. This protocol represents the first intermol. cross-electrophile coupling of unactivated alkyl chlorides, thus leading to new knowledge in the cross-coupling arena.

Journal of the American Chemical Society published new progress about Carboxylation. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Reference of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Henley-Smith, Peter; Whiting, Donald A.; Wood, Andrew F. published the artcile< Methods for the construction of linear 1,7-diarylheptanoids; synthesis of di-O-methylcentrolobol and precursors (synthetic and biosynthetic) to the meta,meta-bridged biphenyls myricanol and myricanone>, Application In Synthesis of 52244-70-9, the main research area is heptanoid diaryl; arylheptanoid; centrolobol analog; myricanol open chain analog; myricanone open chain analog; Grignard reaction phenylpropanal arylhaloalkane; propanal phenyl Grignard reaction; oxazine salt Grignard reaction; dithiane lithiation diarylheptanoid.

Grignard couplings of arylhaloalkanes with arylpropanals or oxazonium salts and the reactions of arylhaloalkanes with lithiated dithianes were used to prepare 1,7-diarylheptanoids, including synthetic and biosynthetic precursors of meta,meta-bridged biphenyls and related macrocyclic ethers. Thus, 4-(2-benzyloxy-3,4-dimethoxy)-1-bromobutane was treated with Mg and the product was treated with 4-PhCH2OC6H4(CH2)2CHO to give the desired alc. I (X = H, OH; R = R3 = OCH2Ph, R1 = R2 = OMe). Similarly, 4-MeOC6H4(CH2)4Br was treated with Mg and the Grignard reagent produced was treated with the oxazine salt II to give the desired ketone I (X = O, R = R1 = H, R2 = R3 = OMe). 4-(2,3,4-Trimethoxyphenyl)-1-iodobutane reacted with lithiated 2-[2-(p-methoxyphenyl)ethyl]-1,3-dithiane to give after oxidation the desired ketone I (X = O, R = R1 = R2 = R3 = OMe).

Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) published new progress about Alcohols Role: USES (Uses). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Application In Synthesis of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Dix, Stefan; Jakob, Michael; Hopkinson, Matthew N. published the artcile< Deoxytrifluoromethylthiolation and Selenylation of Alcohols by Using Benzothiazolium Reagents>, Related Products of 52244-70-9, the main research area is trifluoromethylthio methylbenzothiazolium triflate aliphatic alc deoxytrifluoromethylthiolation; trifluoromethylselenyl methylbenzothiazolium triflate aliphatic alc deoxytrifluoromethylselenylation; alcohols; fluorine; reagent development; trifluoromethylselenyl group; trifluoromethylthio group.

Aliphatic compounds substituted with medicinally important trifluoromethylthio (SCF3) and trifluoromethylselenyl (SeCF3) groups were synthesized directly from alcs. by using the new benzothiazolium salts BT-SCF3 and BT-SeCF3. These bench-stable fluorine-containing reagents are facile to use and can be prepared in two steps from non-fluorinated heteroaromatic starting materials. To the best of our knowledge, these are the first reported examples in which the metal-free deoxytrifluoromethylthiolation process and similarly efficient trifluoromethylselenylation reactions proceeded under mild conditions using BT-SCF3 and BT-SeCF3 resp.

Chemistry – A European Journal published new progress about Aliphatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Related Products of 52244-70-9.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Li, Yi-Ning; Liu, Ye; Yang, Han-Han; Zhang, Wen-Fu; Lu, Xiao-Bing published the artcile< Intramolecular Partners in Asymmetric Catalysis Copolymerization: Highly Enantioselective and Controllable at Enhanced Temperatures and Low Loadings>, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol, the main research area is asym catalyst polymerization enantioselective controllable alternating chiral; Asymmetric Ring-Opening Copolymerization; Bifuctional Bimetallic Catalyst; High Molecular Weight Polyester; Intramolecular Synergistic Catalysis; Low Loadings.

Asym. copolymerization of meso-epoxide and anhydride is a powerful strategy for preparing various isotactic polyesters with two contiguous stereogenic centers. However, the previous binary systems suffered from slow rates at low loadings, poor enantioselectivities and transesterification reactions at enhanced temperatures Herein, we report novel dinuclear aluminum complexes with multiple chiralities and ammonium salts anchored on ligand frameworks. These bifunctional catalysts exhibit high activities and enantioselectivities for epoxides/anhydrides copolymerizations at harsh conditions via intramolecularly synergistic catalysis, affording polyesters with unprecedented mol. weights and narrow distributions. Notably, no transesterification reactions were observed, significantly different from the binary catalyst/cocatalyst pairs. This study represents a rare example regarding temperature-independent asym. induction for preparing chiral polymers from achiral monomers.

Angewandte Chemie, International Edition published new progress about Chirality. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Yu, Jianjin; Li, Chao-Jun; Zeng, Huiying published the artcile< Dearomatization-Rearomatization Strategy for ortho-Selective Alkylation of Phenols with Primary Alcohols>, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol, the main research area is palladium catalyzed ortho selective alkylation phenol alc dearomatization rearomatization; aromaticity; cross-coupling; palladium; reaction mechanisms; synthetic methods.

Phenols are common precursors and core structures of a variety of industrial chems. ranging from pharmaceuticals to polymers. However, the synthesis of site-specifically substituted phenols is challenging, and thus the development of new methods for this purpose would be highly desirable. Reported here is a protocol for palladium-catalyzed ortho-selective alkylation reactions of phenols with primary alcs. by a dearomatization-rearomatization strategy, with water as the sole byproduct. Various substituted phenols and primary alcs. were compatible with the standard reaction conditions. The detailed mechanism of this transformation was also investigated.

Angewandte Chemie, International Edition published new progress about Alkylation. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Recommanded Product: 4-(4-Methoxyphenyl)-1-butanol.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Pelter, Andrew; Ward, Robert S.; Rao, Ramohan R. published the artcile< An approach to the biomimetic synthesis of aryltetralin lignans>, Application of C11H16O2, the main research area is cyclization quinone methide ketal; Lewis acid cyclization catalyst; aryltetralin; tetralin aryl.

The BF3 catalyzed cyclization of 3-(arylpropyl)quinone-methide ketals I (R, R1, R2 = H, OMe) affords a mild biomimetic route to aryltetralins II. I were prepared from the corresponding 4-arylbutanoic acids in 5 steps.

Tetrahedron published new progress about Cyclization. 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Application of C11H16O2.

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem