Tag: M.W=150-200

Nagasawa, Shota; Sasano, Yusuke; Iwabuchi, Yoshiharu published the artcile< Catalytic Oxygenative Allylic Transposition of Alkenes into Enones with an Azaadamantane-Type Oxoammonium Salt Catalyst>, Category: ethers-buliding-blocks, the main research area is allylic transposition oxygenative alkene azaadamantane type oxoammonium salt catalyst; enone preparation catalytic oxygenative allylic transposition alkene; alkenes; enones; organocatalysis; oxygenation; synthetic methods.

The first catalytic oxygenative allylic transposition of unactivated alkenes, e.g., Me2C:CH2(CH2)3OCOPh, into enones, e.g., H2C:C(Me)CO(CH2)3OCOPh, has been developed using an oxoammonium salt, azaadamantane I, as the catalyst. This reaction converts various tri- and trans-disubstituted alkenes into their corresponding enones with transposition of their double bonds at ambient temperature in good yields. The use of a less-hindered azaadamantane-type oxoammonium salt as the catalyst and a combination of two distinct stoichiometric oxidants, namely, iodobenzene diacetate and magnesium monoperoxyphthalate hexahydrate (MMPP·6H2O) are essential to facilitate the enone formation efficiently.

Chemistry – A European Journal published new progress about Alkenes 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, Category: ethers-buliding-blocks.

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

Liu, Yu; Cornella, Josep; Martin, Ruben published the artcile< Ni-Catalyzed Carboxylation of Unactivated Primary Alkyl Bromides and Sulfonates with CO2>, Application of C11H16O2, the main research area is nickel catalyzed carboxylation primary alkyl bromide sulfonate carbon dioxide; carboxylic acid synthesis.

A Ni-catalyzed carboxylation of unactivated primary alkyl bromides and sulfonates with CO2 at atm. pressure is described. The method is characterized by its mild conditions and remarkably wide scope without the need for air- or moisture-sensitive reagents, which make it a user-friendly and operationally simple protocol en route to carboxylic acids. Thus, e.g., reductive carboxylation 1-bromo-6-(4-methoxyphenyl)hexane using NiCl2.glyme, 2,9-diethyl-1,10-phenanthroline ligand, Mn as reducing agent and CO2 afforded 7-(4-methoxyphenyl)heptanoic acid in 76% isolated yield.

Journal of the American Chemical Society published new progress about Bromoalkanes Role: RCT (Reactant), RACT (Reactant or Reagent) (primary). 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

Leed, Andrew R.; Boettger, Susan D.; Ganem, Bruce published the artcile< Studies on the synthesis of substituted phenanthrenoids>, Reference of 56724-03-9, the main research area is juncusol; phenanthrene substituted; halogenation regioselective benzene.

Highly regioselective reactions for the construction of polysubstituted benzenes I (R = H, Me, SiMe2CMe3; R1, R2 = H, Br) and II (R3 = CO2H, CH2OH, CH2Br, CH2PPh3Br) are described, including some remarkable site-selective halogenations. These were used to prepare halo-, nitro-, amino-, and urethane-substituted stilbenes e.g., (E)-III (R4 = NO2, NH2, NHCO2Et; R5, R6 = H, iodo). Thermal as well as photochem. cyclizations were attempted. Stilbene III (R4 = NO2, R5 = H, R6 = iodo) gave the IV (R7 = H, Br; R8 = NO2, NH2); likewise III (R4 = NHCO2Et, R5 = H, R6 = iodo) furnished two new tricyclics, IV (R7 = Br; R8 = NH2, NHCO2Et), whereas irradiation of III (R4 = NHCO2Et, R5 = R6 = H) in HOCMe3 captured solvent to produce phenanthrenes IV (R7 = NHCO2Et; R8 = OH, OCMe3). Strategies for the total synthesis of juncusol (V), a cytotoxic phytoalexin, are considered.

Journal of Organic Chemistry published new progress about Halogenation, regioselective. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Reference of 56724-03-9.

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

Flippin, Lee A.; Muchowski, Joseph M.; Carter, David S. published the artcile< Directed metalation of aromatic aldimines with lithium 2,2,6,6-tetramethylpiperidide>, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde, the main research area is lithiation aromatic aldimine lithium tetramethylpiperidide; piperidide lithiotetramethyl lithiation aldimine; benzaldehyde methyl.

N-Cyclohexyl aromatic aldimines are ortho-lithiated or o-methyl-lithiated with 2 equiv of lithium 2,2,6,6-tetramethylpiperidide (LTMP) in THF solution at -15°. The lithiated intermediates generally reacted with alkyl halides or CO2 to provide ortho-functionalized aldimine products which could be readily converted to the corresponding aldehydes by hydrolysis with aqueous 4 M HCl. Aromatic aldimines derived from (±)-trans-2-methylcyclohexylamine or 3-amino-2,4-dimethylpentane are resistant toward C=N addition with 1 equiv of n-BuLi at 0° in THF solution; however, they are also surprisingly resistant toward directed metalation reactions with either LTMP or n-BuLi. Exceptions to the ortho-directing and o-methyl-directing effects of the aldimine group were observed in a reaction of 3-methylthiophene-2-carboxaldehyde cyclohexylimine with LTMP, followed by CH3I, which gave a 9:1 mixture of 3,5-dimethylthiophene-2-carboxaldehyde cyclohexylimine and 5-ethyl-3-methylthiophene-2-carboxaldehyde cyclohexylimine, and a reaction of p-tolualdehyde 2,4-dimethylpent-3-ylimine with either n-BuLi or LTMP, followed by CH3I, which gave p-ethylbenzaldehyde 2,4-dimethylpent-3-ylimine.

Journal of Organic Chemistry published new progress about Aldimines Role: RCT (Reactant), RACT (Reactant or Reagent). 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Recommanded Product: 3-Methoxy-2-methylbenzaldehyde.

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

Hirsh, Andrew J.; Molino, Bruce F.; Zhang, Jianzhong; Astakhova, Nadezhda; Geiss, William B.; Sargent, Bruce J.; Swenson, Brian D.; Usyatinsky, Alexander; Wyle, Michael J.; Boucher, Richard C.; Smith, Rick T.; Zamurs, Andra; Johnson, M. Ross published the artcile< Design, Synthesis, and Structure-Activity Relationships of Novel 2-Substituted Pyrazinoylguanidine Epithelial Sodium Channel Blockers: Drugs for Cystic Fibrosis and Chronic Bronchitis>, Application In Synthesis of 52244-70-9, the main research area is pyrazinoylguanidine epithelial sodium channel blocker preparation.

Amiloride, the prototypical epithelial sodium channel (ENaC) blocker, has been administered with limited success as aerosol therapy for improving pulmonary function in patients with the genetic disorder cystic fibrosis. This study was conducted to synthesize and identify more potent, less reversible ENaC blockers, targeted for aerosol therapy and possessing minimal systemic renal activity. A series of novel 2-substituted acylguanidine analogs of amiloride were synthesized and evaluated for potency and reversibility on bronchial ENaC. All compounds tested were more potent and less reversible at blocking sodium-dependent short-circuit current than amiloride. Compounds I [R = NH(CH2)4C6H4O(CH2)2OH-4, NH(CH2)4C6H4O(CH2)3OH-4, NH(CH2)4C6H4OCH2CH(OH)CH2OH-4 (both R and S isomers)] showed the greatest potency on ENaC with IC50 values below 10 nM. A regioselective difference in potency was found, whereas no stereospecific difference in potency on ENaC was displayed. Lead compound I [R = NH(CH2)4C6H4OCH2CH(OH)CH2OH-4 (racemic)] was 102-fold more potent and 5-fold less reversible than amiloride and displayed the lowest IC50 value ever reported for an ENaC blocker.

Journal of Medicinal Chemistry published new progress about Chronic bronchitis. 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

Sparey, Tim; Beher, Dirk; Best, Jonathan; Biba, Mirlinda; Castro, Jose L.; Clarke, Earl; Hannam, Joanne; Harrison, Timothy; Lewis, Huw; Madin, Andrew; Shearman, Mark; Sohal, Bindi; Tsou, Nancy; Welch, Christopher; Wrigley, Jonathan published the artcile< Cyclic sulfamide γ-secretase inhibitors>, Product Details of C3H8ClNO2S, the main research area is cyclic sulfamide derivative preparation gamma secretase inhibitor.

A novel series of N-alkyl-substituted cyclic sulfamides were developed from a screening hit. Chemistries were developed which allowed surveys of N-alkyl groups and amines resulting in the identification of N-trifluoroethyl-substituted cyclic sulfamides with good in vitro and in vivo γ-secretase activity. One compound with subnanomolar activity elicited a reduction in brain Aβ40 after oral dosing in APP-YAC mice.

Bioorganic & Medicinal Chemistry Letters published new progress about Alzheimer disease. 10305-42-7 belongs to class ethers-buliding-blocks, and the molecular formula is C3H8ClNO2S, Product Details of C3H8ClNO2S.

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

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

Resch, Verena; Lechner, Horst; Schrittwieser, Joerg H.; Wallner, Silvia; Gruber, Karl; Macheroux, Peter; Kroutil, Wolfgang published the artcile< Inverting the Regioselectivity of the Berberine Bridge Enzyme by Employing Customized Fluorine-Containing Substrates>, Name: 3-Methoxy-2-methylbenzaldehyde, the main research area is fluorine substrate preparation regiochem berberine bridge enzyme.

Fluorine is commonly applied in pharmaceuticals to block the degradation of bioactive compounds at a specific site of the mol. Blocking of the reaction center of the enzyme-catalyzed ring closure of 1,2,3,4-tetrahydrobenzylisoquinolines by a fluoro moiety allowed redirecting the berberine bridge enzyme (BBE)-catalyzed transformation of these compounds to give the formation of an alternative regioisomeric product, namely 11-hydroxy-functionalized tetrahydroprotoberberines instead of the commonly formed 9-hydroxy-functionalized products. Alternative strategies to change the regioselectivity of the enzyme, such as protein engineering, were not applicable in this special case due to missing substrate-enzyme interactions. Medium engineering, as another possible strategy, had clear influence on the regioselectivity of the reaction pathway, but did not lead to perfect selectivity. Thus, only substrate tuning by introducing a fluoro moiety at one potential reactive carbon center switched the reaction to the formation of exclusively one regioisomer with perfect enantioselectivity.

Chemistry – A European Journal published new progress about Enzyme functional sites, active. 56724-03-9 belongs to class ethers-buliding-blocks, and the molecular formula is C9H10O2, Name: 3-Methoxy-2-methylbenzaldehyde.

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