Category: 52244-70-9

Zhang, Jing; Li, Yang; Zhang, Fuyuan; Hu, Chenchen; Chen, Yiyun published the artcile< Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp3)-H Functionalization under Mild Reaction Conditions>, Electric Literature of 52244-70-9, the main research area is visible light redox reaction carbon hydrogen bond functionalization; C−H functionalization; alkoxyl radicals; allylic compounds; photochemistry; reaction mechanisms.

Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-(alkoxy)phthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp3)-H allylation and alkenylation reactions under mild reaction conditions at room temperature Broad substrate variations, including a structurally complex steroid, undergo the C(sp3)-H functionalization reaction effectively with high regioselectivity and chemoselectivity. The synthesis of the target compounds was achieved using 2-[(phenylsulfonyl)methyl]-2-propenoic acid Et ester as a starting material in a reaction with 2-[2-[(4-methylphenyl)methoxy]ethoxy]-1H-isoindole-1,3(2H)-dione [i.e., cyclic N-(alkoxy)imide, phthalimide] derivatives Under optimized conditions tris[2-(2-pyridinyl-κN)phenyl-κC]iridium(1+) um(1+) hexafluorophosphate(1-) [i.e., fac-Ir(ppy)3] was used as a catalyst. The title compounds thus formed included 2-[[(2E)-3-phenyl-2-propen-1-yl]oxy]ethanol derivatives, γ-(2-hydroxyethoxy)-α-(methlyene)benzenebutanoic acid esters,.

Angewandte Chemie, International Edition published new progress about Aliphatic alcohols, radicals Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Electric Literature of 52244-70-9.

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

Schenkels, Peter; Duine, Johannis A. published the artcile< Nicotinoprotein (NADH-containing) alcohol dehydrogenase from Rhodococcus erythropolis DSM 1069: an efficient catalyst for coenzyme-independent oxidation of a broad spectrum of alcohols and the interconversion of alcohols and aldehydes>, Product Details of C11H16O2, the main research area is Rhodococcus alc dehydrogenase NADH oxidation alc aldehyde.

Extracts from benzyl-alc.-grown Rhodococcus erythropolis DSM 1069 showed NAD(P)-independent, N,N-dimethyl-4-nitrosoaniline (NDMA)-dependent alc. dehydrogenase activity. The enzyme exhibiting this activity was purified to homogeneity and characterized. It appears to be a typical nicotinoprotein as it contains tightly bound NADH acting as cofactor instead of coenzyme. Other characteristics indicate that it is highly similar to the known nicotinoprotein alc. dehydrogenase (np-ADH) from Amycolatopsis methanolica: it is a homotetramer of 150 kDa; N-terminal amino acid sequencing (22 residues) showed that 77% of these amino acids are identical in the two enzymes; it has optimal activity at pH 7.0; it lacks NAD(P)H-dependent aldehyde reductase activity; it catalyzes the oxidation of a broad range of (preferably) primary and secondary alcs., either aliphatic or aromatic, and formaldehyde, with the concomitant reduction of the artificial electron acceptor NDMA. NDMA could be replaced by an aldehyde, but not formaldehyde, the substrate specificity of the enzyme for the aldehydes reflecting that for the corresponding alcs. The latter also applied to the low aldehyde dismutase activity displayed by the enzyme. From this, together with the results of the induction studies, it is concluded that np-ADH functions as the main alc.-oxidizing enzyme in the dissimilation of many, but not all, alcs. by R. erythropolis and may also catalyze coenzyme-independent interconversion of alcs. and aldehydes under certain circumstances. It is anticipated that the enzyme may be of even wider significance since structural data indicate that np-ADH is also present in other (nocardioform) actinomycetes.

Microbiology (Reading, United Kingdom) published new progress about Alcohols Role: BSU (Biological Study, Unclassified), PRP (Properties), BIOL (Biological Study). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Product Details of C11H16O2.

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

Albiniak, Philip A.; Amisial, Shawn M.; Dudley, Gregory B.; Hernandez, Joseph P.; House, Sarah E.; Matthews, Margaret E.; Nwoye, Ernest O.; Reilly, Maureen K.; Tlais, Sami F. published the artcile< Stable oxypyridinium triflate (OPT) salts for the synthesis of halobenzyl ethers>, HPLC of Formula: 52244-70-9, the main research area is pyridinium triflate halobenzyloxy preparation benzylation alc; ether halobenzyl preparation.

A collection of new 2-arylmethoxy-1-methylpyridinium triflate reagents (aryl = 4-BrC6H4, 4-ClC6H4, 4-IC6H4, 2-BrC6H4) for the synthesis of halobenzyl ethers ROCH2Ar [R = Ph(CH2)3, 4-MeOC6H4(CH2)4, 1-adamantyl, (R)-MeO2CCHMeCH2, 5α-cholester-3β-yl] from alcs. ROH under mix-and-heat conditions is described. The reagents are stable organic salts that can be stored indefinitely and handled without special precautions, making them attractive for general use in organic synthesis. Halobenzylation of representative alcs. occurs in good to excellent yields.

Synthetic Communications published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Koch, Vanessa; Brase, Stefan published the artcile< An Intramolecular Iodine-Catalyzed C(sp3)-H Oxidation as a Versatile Tool for the Synthesis of Tetrahydrofurans>, Product Details of C11H16O2, the main research area is THF preparation regioselective; alc carbon hydrogen activation oxidation cyclization iodine catalyst.

The formation of ubiquitous occurring THF patterns has been extensively investigated in the 1960s as it was one of the first examples of a non-directed remote C-H activation. These approaches suffer from the use of toxic transition metals in overstoichiometric amounts An attractive metal-free solution for transforming carbon-hydrogen bonds into carbon-oxygen bonds lies in applying economically and ecol. favorable iodine reagents. The presented method involves an intertwined catalytic cycle of a radical chain reaction and an iodine(I/III) redox couple by selectively activating a remote C(sp3)-H bond under visible-light irradiation The reaction proceeds under mild reaction conditions, is operationally simple and tolerates many functional groups giving fast and easy access to different substituted tetrahydrofurans.

European Journal of Organic Chemistry published new progress about Alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Product Details of C11H16O2.

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

Yang, Xiaojuan; Liang, Jinying published the artcile< Alum: an efficient catalyst for trimethylsilylation of alcohols and phenols with hexamethyldisilazane>, Synthetic Route of 52244-70-9, the main research area is trimethylsilylation alc alum catalyst green chem hexamethyldisilazane.

A highly convenient method for the trimethylsilylation of alcs. and phenols via treatment by hexamethyldisilazane in the presence of alum as a catalyst has been developed. A wide variety of hydroxyl groups were selectively protected in CH3CN under mild conditions.

Asian Journal of Chemistry published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Synthetic Route of 52244-70-9.

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

Aikawa, Haruo; Tago, Sakie; Umetsu, Kazuteru; Haginiwa, Naomichi; Asao, Naoki published the artcile< Gold-catalyzed substitution reaction with ortho-alkynylbenzoic acid alkyl ester as an efficient alkylating agent>, Name: 4-(4-Methoxyphenyl)-1-butanol, the main research area is alkynylbenzoic acid alkyl ester alc gold etherification; ether preparation; gold etherification catalyst; alkylating agent alkynylbenzoic acid alkyl ester.

Ortho-Alkynylbenzoic acid alkyl esters behave as alkylating agents in combination with gold catalysts. The reaction with alcs. occurs smoothly in the presence of catalytic amounts of Ph3PAuCl and AgOTf under mild conditions to produce the corresponding ether products in high yields. The protocol is also useful for Friedel-Crafts alkylation and N-alkylation of sulfonamides. The reaction likely proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack of nucleophiles, such as alcs., aromatic compounds, and sulfonamides.

Tetrahedron 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, Name: 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>, HPLC of Formula: 52244-70-9, the main research area is methoxyphenylpropylquinonemethide ketal cyclization; quinonemethide ketal methoxyphenylpropyl cyclization; anisyltetralin; tetralin anisyl.

The aryltetralins I (R = H, R1 = R2 = H, OMe; R = R1 = OMe, R2 = H) were prepared from the corresponding 2,3,5,4-RR1R2(MeO)C6H(CH2)3CO2H in 6 steps, the key step being the biomimetic cyclization of the quinonemethide ketals II to I on treatment with BF3.Et2O.

Tetrahedron Letters published new progress about 52244-70-9. 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

Baird, Richard; Winstein, S. published the artcile< Neighboring carbon and hydrogen. XLVI. Spiro[4.5]-deca-1,4-dien-3-one from Ar1--5 participation>, COA of Formula: C11H16O2, the main research area is .

The formation of I from 4-HOC6H4(CH2)4O3SC6H4Br-4 (II) by Ar1-5 participation in the phenoxide anion of II was designated Ar1–5. This reaction was studied by kinetic investigation of the behavior of II in basic solution The reaction was favored in tert-BuOH but not in MeOH. Solvolysis rates for II, the Me ether (III), and p-BrC6H4S(O3)( CH2)4OH (IV) were determined in various solvents at different temperatures and concentrations With II, Ar1-5 participation was slightly more important in formolysis than with III. With II, III, and IV in neutral MeOH, Ar1-5 assisted ionization was negligible. The rate of methanolysis of II was increased by the addition of NaOMe. II appeared to be initially at least 90% in the phenoxide ion form. From the basic solvolysis reactions of II in MeOH and tert-BuOH were obtained (by extraction with pentane) 20 and 50-60% yields, resp., of I, m. 34-5° (pentane at -70°), b1.3 83.5-5°, v 1594, 1617, 1655, 1707 cm.-1 (CHCl3), λ242 mμ, ε 16,000; semicarba zone m. 224-5.5°; 2,4-dinitrophenylhydrazone m. 140.5-3.5°, λ 390, 253, 223 mμ, log ε 4.53, 4.21, 2.92. Catalytic reduction of I (reduced PrO2) gave a tetrahydro ketone; 2,4-dinitrophenylhydrazone (V), C16H20N4O4, m. 161.9-2.8°, λ 363, 229 mμ, ε 22,500 and 17,000. I underwent dienonephenol rearrangement (Wilds and Djerassi, CA 40, 72239), to give an almost quant. yield of 5,6,7,8-tetrahydro-2-naphthol (VI). Treating I in buffered formic acid gave 95% VI. p-MeOC6H4(CH2)3CO2H (VII), b.9.9 194-5.5°, m. 56-6.5°, was prepared from succinic anhydride, anisole, and AlCl3 via p-MeC6H4CO(CH2)2CO2H by the procedures of Fieser (CA 32, 84345) and Martin (CA 30, 67262) in 78.5% yield. VII, was reduced with LiAlH4 to give 93% p-MeOC6H4(CH2)4OH b8 160-60.9°, m. 3.0-4.0°, n25D 1.5248. This was converted to the p-bromobenzenesulfonate. VII and HBr gave pHOC6H4(CH2)3CO2H (VIII), which was reduced with LiAlH4 (4 mol/mol acid and refluxing 1 wk) to p-HOC6H4(CH2)4OH (IX) (92% yield), b0.5 144-6°, m. 55.5-8°, 56.5-7.8° (purified by sublimation). IX (25 g.) in 300 mL. pyridine at -30° treated with 50 g. p-BrC6H4SO2Cl, the solution warmed to 0° 1 h., poured into ice water, the oil extracted with ether, the ether washed, concentrated, the residue (a solution in CH2Cl2 partly crystallized after 1-2 wk) dissolved in 350-400 mL. MeOH, diluted with ice water until a 2nd phase appeared, seeded, and cooled 24 h. at 0° gave 50% II, m. 59.5-61.5° (CH2Cl2-hexane). II was also prepared by treating VIII with excess dihydropyran and a trace of H2SO4 and reducing the solution with LiAlH4 to give 4-[p-(2-tetrahydropyranoxy)phenyl]-1-butanol, which was converted to the p-bromobenzenesulfonate (X), m. 57-60° (ether-pentane), in 77% yield. This was hydrolyzed by gentle acid hydrolysis (304 g. X, 2.5 1. MeOH, 200 mL. H2SO4, 400 mL. water, left overnight in ice box) to give II (68% yield from VIII).

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

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

Zimmermann, Birte M.; Ngoc, Trung Tran; Tzaras, Dimitrios-Ioannis; Kaicharla, Trinadh; Teichert, Johannes F. published the artcile< A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides>, Synthetic Route of 52244-70-9, the main research area is bifunctional azaheterocyclic carbene copper catalyst guanidine ester reduction alc.

Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcs. with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered “”soft”” copper(I) hydrides to previously unreactive “”hard”” ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.

Journal of the American Chemical Society published new progress about Alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 52244-70-9 belongs to class ethers-buliding-blocks, and the molecular formula is C11H16O2, Synthetic Route of 52244-70-9.

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

Xia, Aiyou; Lv, Peizhuo; Xie, Xin; Liu, Yuanhong published the artcile< Nickel-Catalyzed Cyanation of Unactivated Alkyl Sulfonates with Zn(CN)2>, HPLC of Formula: 52244-70-9, the main research area is nickel catalyst cyanation unactivated alkyl sulfonate zinc cyanide; alkyl nitrile preparation.

Cyanation of unactivated primary and secondary alkyl mesylates with Zn(CN)2 catalyzed by nickel has been developed. The reaction provides an efficient route for the synthesis of alkyl nitriles with wide substrate scope, good functional group tolerance, and compatibility with heterocyclic compounds Mechanistic studies indicate that alkyl iodide generated in situ serves as the reactive intermediate and the gradual release of alkyl iodide is crucial for the success of the reaction.

Organic Letters published new progress about Alkanesulfonates Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 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