16700-55-3

Usage

Chemical Properties

White solid

InChI:InChI=1/C9H12O3/c1-11-8-4-3-5-9(12-2)7(8)6-10/h3-5,10H,6H2,1-2H3

Upstream product

• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 64957-86-4 2-(2,6-dimethoxy-phenyl)-4,4-dimethyl-4,5-dihydro-oxazole 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 151-10-0 1,3-Dimethoxybenzene 
• 2065-27-2 methyl 2,6-dimethoxybenzoate 

Downstream Products

• 5673-07-4 2,6-dimethoxytoluene 
• 16929-73-0 2,6-dimethoxybenzyl methyl ether 
• 109682-57-7 2,6-dimethoxybenzyl ethyl ether 
• 3166-95-8 2-(2,6-dimethoxyphenyl)acetonitrile 
• 3392-97-0 2,6-dimethoxybenzaldehyde 
• 67698-76-4 Acetic acid 2,6-dimethoxy-benzyl ester 
• 109682-58-8 2,6-dimethoxybenzyl isopropyl ether 
• 127042-09-5 2-(2,6-dimethoxybenzyloxy)-2-methyl-4H-1,3-benzodioxin-4-one 
• 109682-59-9 2,6-dimethoxybenzyl t-butyl ether 
• 57802-46-7 [2-(2,6-Dimethoxy-benzyloxy)-ethyl]-diethyl-amine 
• 318955-90-7 5-(2,6-dimethoxy-benzyloxy)-isophthalic acid dimethyl ester 
• 562839-22-9 3-[bis(4-fluorophenyl)methyl]-1-(2,6-dimethoxybenzyl)piperidin-4-one 
• 71819-90-4 2-(chloromethyl)-1,3-dimethoxybenzene 
• 169610-52-0 2-(bromomethyl)-1,3-dimethoxybenzene 

Relevant academic research and scientific papers

Phosphorylation Organocatalysts Highly Active by Design

The activity of nucleophilic organocatalysts for alcohol/phenol phosphorylation was enhanced through attaching oligoether appendages to a benzyl substituent on imidazole- or aminopyridine-based active units, presumably because of stabilizing n-cation interactions of the ethereal oxygens with the positively charged aza-heterocycle in the catalytic intermediates, and was substantially higher than that of known benchmark catalysts for a range of substrates. Density functional theory calculations and the study of analogues having a lower potential for such stabilizing interactions support our hypothesis.

Dual utility of a single diphosphine-ruthenium complex: A precursor for new complexes and, a pre-catalyst for transfer-hydrogenation and Oppenauer oxidation

The diphosphine-ruthenium complex, [Ru(dppbz)(CO)2Cl2] (dppbz = 1,2-bis(diphenylphosphino)benzene), where the two carbonyls are mutually cis and the two chlorides are trans, has been found to serve as an efficient precursor for the synthesis of new complexes. In [Ru(dppbz)(CO)2Cl2] one of the two carbonyls undergoes facile displacement by neutral monodentate ligands (L) to afford complexes of the type [Ru(dppbz)(CO)(L)Cl2] (L = acetonitrile, 4-picoline and dimethyl sulfoxide). Both the carbonyls in [Ru(dppbz)(CO)2Cl2] are displaced on reaction with another equivalent of dppbz to afford [Ru(dppbz)2Cl2]. The two carbonyls and the two chlorides in [Ru(dppbz)(CO)2Cl2] could be displaced together by chelating mono-anionic bidentate ligands, viz. anions derived from 8-hydroxyquinoline (Hq) and 2-picolinic acid (Hpic) via loss of a proton, to afford the mixed-tris complexes [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], respectively. The molecular structures of four selected complexes, viz. [Ru(dppbz)(CO)(dmso)Cl2], [Ru(dppbz)2Cl2], [Ru(dppbz)(q)2] and [Ru(dppbz)(pic)2], have been determined by X-ray crystallography. In dichloromethane solution, all the complexes show intense absorptions in the visible and ultraviolet regions. Cyclic voltammetry on the complexes shows redox responses within 0.71 to -1.24 V vs. SCE. [Ru(dppbz)(CO)2Cl2] has been found to serve as an excellent pre-catalyst for catalytic transfer-hydrogenation and Oppenauer oxidation.

Heteroleptic 1,4-Diazabutadiene Complexes of Ruthenium: Synthesis, Characterization and Utilization in Catalytic Transfer Hydrogenation

Reaction of [Ru(trpy)Cl3] with 1,4-diazabutadienes (p-RC6H4N=C(H)-(H)C=NC6H4R-p; R = OCH3, CH3, H and Cl; abbreviated as L-R) in refluxing ethanol in the presence of triethylamine has afforded a family of complexes, isolated as perchlorate salts, of type [Ru(trpy)(L-R)Cl]ClO4 [depicted as complexes 1 (R = OCH3), 2 (R = CH3), 3 (R = H) and 4 (R = Cl)]. Crystal structures of complexes 1, 2 and 4 have been determined, and structure of complex 3 has been optimized by DFT method. The 1,4-diazabutadiene ligand in each complex is bound to ruthenium as a N,N-donor forming five-membered chelate. Complexes 1–4 catalyze transfer hydrogenation of aryl aldehydes to the corresponding alcohols with high (ca. 106) TON. They are also found to catalyze transfer hydrogenation of aryl ketones to corresponding secondary alcohols, but with much less efficiency. Catalytic transfer hydrogenation of nitroarenes to the corresponding amines has also been achieved.

Methanol as hydrogen source: Transfer hydrogenation of aromatic aldehydes with a rhodacycle

A cyclometalated rhodium complex has been shown to perform highly selective and efficient reduction of aldehydes, deriving the hydrogen from methanol. With methanol as both the solvent and hydrogen donor under mild conditions and an open atmosphere, a wide range of aromatic aldehydes were reduced to the corresponding alcohols, without affecting other functional groups.

Novel leucine ureido derivatives as aminopeptidase N inhibitors using click chemistry

The over-expression of aminopeptidase N on diverse malignant cells is associated with the tumor angiogenesis and metastasis. In this report, one new series of leucine ureido derivatives containing the triazole moiety was designed, synthesized and evaluated as APN inhibitors. Among them, compound 13v showed the best APN inhibition with an IC50 value of 0.089 ± 0.007 μM, which was two orders of magnitude lower than that of bestatin (IC50 = 9.4 ± 0.5 μM). Compound 13v also showed dose-dependent anti-angiogenesis activities. Even at the lower concentration (10 μM), compound 13v presented similar anti-angiogenesis activity compared with bestatin at 100 μM in both the human umbilical vein endothelial cells (HUVECs) capillary tube formation assay and the rat thoracic aorta rings test. Moreover, compared with bestatin, 13v exhibited comparable, if not better in vivo anti-metastasis activity in a mouse H22 pulmonary metastasis model.

Aluminum Monohydride Catalyzed Selective Hydroboration of Carbonyl Compounds

The well-defined aluminum monohydride compound [{(2,4,6-Me3-C6H2)NC(Me)}2(Me)(H)]AlH·(NMe2Et) (1) catalyzes hydroboration of a wide range of aldehydes and ketones under mild reaction conditions. Moreover, compound 1 displayed chemoselective hydroboration of aldehydes over ketones at rt.

Compounds for the treatment of metabolic disorders

Compounds useful for the treatment of various metabolic disorders, such as insulin resistance syndrome, diabetes, hyperlipidemia, fatty liver disease, cachexia, obesity, atherosclerosis and arteriosclerosis, are disclosed.

FeCl3-catalyzed self-cleaving deprotection of methoxyphenylmethyl-protected alcohols

4-Methoxyphenylmethyl ethers are widely utilized as alcohol protecting groups. FeCl3 effectively catalyzes the deprotection of methoxyphenylmethyl-type ethers in a self-cleaving manner to produce oligomeric derivatives and alcohols. Remarkably, the highly pure mother alcohols can be obtained without silica gel column chromatography by using the 2,4-dimethoxyphenylmethyl group as a protective group.

Ruthenium Catalyzed Selective Hydroboration of Carbonyl Compounds

Using the [Ru(p-cymene)Cl2]2 (1) complex, catalytic hydroboration of aldehydes and ketones with pinacolborane under neat and mild conditions is reported. At rt, chemoselective hydroboration of aldehydes over the ketones is also attained. Mechanistic studies confirmed the immediate formation of monohydride bridged dinuclear complex [{(μ6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1b) from the reaction of 1 with pinacolborane, which catalyzed the highly efficient hydroboration reactions. The catalytic cycle containing mononuclear Ru-H species and intramolecular 1,3-hydride transfer is postulated.

Synthesis and in vitro antibacterial activity of gemifloxacin derivatives containing a substituted benzyloxime moiety

A series of novel gemifloxacin (GMFX) derivatives containing a substituted benzyloxime moiety with remarkable improvement in lipophilicity were synthesized. The target compounds evaluated for their in vitro antibacterial activity against representative strains. Our results reveal that most of the target compounds have considerable potency against all of the tested Gram-positive strains including MRSA and MRSE (MIC: 90: 1 μg/mL) is 8-fold more active than GMFX, and 2-fold more active than GMFX and moxifloxacin against MRSE clinical isolates (MIC90: 4 μg/mL). Crown Copyright