6706-95-2

Usage

InChI:InChI=1/C16H16O4/c1-19-13-7-3-5-11(9-13)15(17)16(18)12-6-4-8-14(10-12)20-2/h3-10,15,17H,1-2H3

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 40101-17-5 3,3'-dimethoxybenzil 
• 586-38-9 3-Methoxybenzoic acid 
• 5368-81-0 methyl 3-methoxybenzoate 

Downstream Products

• 40101-17-5 3,3'-dimethoxybenzil 
• 6266-57-5 1,2-bis(3-methoxyphenyl)ethan-1-one 
• 131376-65-3 3,3'-Dimethoxybenzoin phosphate 
• 143546-91-2 (3-{2-[4,5-Bis-(3-methoxy-phenyl)-oxazol-2-yl]-ethyl}-phenoxy)-acetic acid methyl ester 
• 109770-31-2 3,4-bis(3-methoxyphenyl)-2,5-diphenylcyclopenta-2,4-dienone 
• 56430-20-7 4-Hydroxy-3,4-bis-(3-methoxy-phenyl)-cyclohex-2-enone 
• 56430-31-0 3,4-Dihydroxy-3,4-bis-(3-methoxy-phenyl)-5-phenyl-cyclohexanone 
• 5959-71-7 MetaDES 
• 76473-06-8 trans-3,3'-dimethoxy-α,β-diethylstilbene 
• 5471-44-3 3,3'-dimethoxy-deoxybenzoin oxime 
• 1062158-04-6 2-hydroxy-1,2-bis-(3-methoxy-phenyl)-pent-4-en-1-one 
• 1081978-76-8 (S)-2-hydroxy-1,2-bis(3-methoxyphenyl)ethan-1-one 
• 181655-43-6 (R)-2-hydroxy-1,2-bis(3-methoxyphenyl)ethan-1-one 
• 586-38-9 3-Methoxybenzoic acid 

Relevant academic research and scientific papers

Preparation and Application of Silica Films Supported Imidazolium-Based Ionic Liquid as Efficient and Recyclable Catalysts for Benzoin Condensations

Abstract: Two silica films -immobilized imidazolium-based ionic liquids (TMICl @silica films) were prepared, characterized and utilized as efficient catalysts for the benzoin reaction. Combined characterization results from FT-IR, elemental analysis, N2 adsorption–desorption isotherms and SEM, suggested that the imidazolium-based ionic liquids were successfully immobilized on the silica films. Moreover, the catalytic performance tests demonstrated that silica films immobilized imidazolium-based ionic liquids (ILs) exhibited excellent activity for the benzoin reactions of aromatic aldehydes. The influence of catalyst concentration, temperature and reaction duration on the catalytic activity were investigated by employing 0.7TMICl @silica film(catalyst C) as the catalyst. The results also showed that the benzoin condensations of aromatic aldehydes could give desired products with satisfactory yields under the optimized conditions. Additionally, the catalyst can be effortlessly separated by filtration and reused more than five times without significant loss of activity. Graphic Abstract: [Figure not available: see fulltext.]

Oxazolium Salts as Organocatalysts for the Umpolung of Aldehydes

Oxazolium salts were successfully employed for the first time as organocatalysts for benzoin, Stetter, and redox esterification reactions. An N-mesityl oxazolium salt catalyzed homobenzoin reaction of aromatic, heteroaromatic, and aliphatic aldehydes delivered α-hydroxy ketones in high yields. This new type of catalyst proved remarkably effective for the Stetter reaction of challenging substrates such as β-alkyl-α,β-unsaturated ketones and electron-rich aromatic aldehydes in comparison to common thiazolium and triazolium salts.

Base-Free Asymmetric Transfer Hydrogenation of 1,2-Di- and Monoketones Catalyzed by a (NH)2P2-Macrocyclic Iron(II) Hydride

The hydride isonitrile complex [FeH(CNCEt3)(1 a)]BF4 (2) containing a chiral P2(NH)2 macrocycle (1 a), in the presence of 2-propanol as hydrogen donor, catalyzes the base-free asymmetric transfer hydrogenation (ATH) of prostereogenic ketones to alcohols and the hemihydrogenation of benzils to benzoins, which contain a base-labile stereocenter. Benzoins are formed in up to 83 % isolated yield with enantioselectivity reaching 95 % ee. Ketones give the same enantioselectivity observed with the parent catalytic system [Fe(CNCEt3)2(1 a)] (3 a) that operates with added NaOtBu.

(±)Methanodibenzodiazocine tethered [C-H]δ+ functional site: Study towards benzoin condensation and Baylis-Hillman reactions

Abstract New heterocyclic ring systems consisting of (±) methanodibenzodiazocine and imidazolium/ benzimidazolium salts were synthesized in very good yield. Subsequently, these halide salts were subjected to the anion exchange reaction with KPF6 to yield the corresponding azolium salts in excellent yield. The possible applications of these newly prepared salts were investigated in homogeneous catalysis. Remarkable changes in the catalytic activity were observed by varying the bulkiness of N-substituent at imidazole. Catalytic activity of these newly prepared salts was tested for the benzoin condensation reaction. Exclusive formation of benzoin products were observed in good yield. Similarly, the dimerization of cyclohexen-1-one to Baylis-Hillman type product, 2-(3-oxocyclohexyl)-2-cyclohexen-1-one was studied. [Figure not available: see fulltext.]

Highly enantioselective hydrogenation of o-alkoxy tetrasubstituted enamides catalyzed by a Rh/(R, S)-josiphos catalyst

Rh/(R,S)-JosiPhos complex-catalyzed asymmetric hydrogenation of o-alkoxy tetrasubstituted enamides has been achieved, and it furnished a set of β-amino alcohol analogues in high yields and excellent enantiomeric excesses (>99% conversion, up to 99% ee).This method provides valuable chiral building blocks in chiral pharmaceuticals and useful motifs for catalysts.

HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK

Disclosed herein are new heterocyclic compounds of Formula IIa: and compositions thereof, and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

NHC gold halide complexes derived from 4,5-diarylimidazoles: Synthesis, structural analysis, and pharmacological investigations as potential antitumor agents

A series of novel neutral NHC gold halide complexes derived from 4,5-diarylimidazoles were synthesized, characterized, and analyzed for biological effects. High growth inhibitory effects in MCF-7 and MDA-MB 231 breast cancer as well as HT-29 colon cancer cell lines depended on the presence of the C4,C5-standing aromatic rings. Methoxy groups at these rings did not change the growth inhibitory properties, while F-substituents in the ortho-position (5d) increased the activity in MCF-7 and MDA-MB 231 cells. The substituents at the nitrogen atoms and the oxidation state of the metal play a subordinate role. The most active bromo[1,3-diethyl-4,5-bis(2-fluorophenyl)-1,3- dihydro-2H-imidazol-2-ylidene]gold(I) (5d) was distinctly more active than cisplatin. All complexes caused thioredoxin reductase (TrxR) inhibition (EC 50 = 374-1505 nM) distinctly lower than auranofin (EC50 = 18.6 nM) excluding this enzyme as main target. Because of the low nuclear content, a participation of DNA interaction on the mode of action is very unlikely. The missing ER binding and the missing correlation of growth inhibition and inactivation of COX enzymes exclude these targets, too. (Figure presented)

Stereoselective reduction of 2-hydroxy ketones towards syn- and anti-1,2-diols

Stereoselective reduction of 2-hydroxy ketones should in principle give access to syn- and anti-1,2-diols. anti-1,2-Diols are accessible in a highly selective way using zinc borohydride [Zn(BH4)2] under chelation control (dr>20:1). Diastereoselective reduction of unprotected or even protected 2-hydroxy ketones towards syn-1,2-diols could be achieved only with moderate selectivity of dr≤5:1. Even when using sterically demanding protecting groups and/or polymer-supported borohydride reagents high selectivity could not be achieved. A new ionic liquid-dependent borohydride reduction method, although highly attractive with respect to reaction engineering, resulted in only moderate to good selectivity. An efficient two-step biocatalytic method for the synthesis of syn-1,2-diols is described. The method relies on the whole-cell Pichia glucozyma-catalyzed stereoselective reduction of the unprotected (R)-2-hydroxy ketones (dr>10:1). The latter are accessible through thiamine diphosphate-dependent enzyme-catalyzed synthesis starting from simple aldehydes. Thus, biocatalytic transformations enable a process which is hardly accessible through present non-enzymatic methods. Copyright

NHC triggered cascade metal-free synthesis of 2,3-diarylated indoles under solvent-free conditions

A new cascade strategy to the synthesis of 2,3-diarylated indoles via the metal-free reaction of aryl aldehyde and aryl amine triggered by N-heterocyclic carbene (NHC) under solvent-free conditions, has been disclosed. The protocol has the advantages of easy work-up, high yields, wide application scope, and an environmentally benign procedure compared with the reported methods.

Synthesis of imidazolium and pyridinium-based ionic liquids and application of 1-alkyl-3-methylimidazolium salts as pre-catalysts for the benzoin condensation using solvent-free and microwave activation

An efficient one-pot procedure for the synthesis of ionic liquids based on nitrogen-containing heterocycles, imidazolium or pyridinium under 'green chemistry' conditions has been described. Imidazolium salts and DBU have been found to catalyze efficiently the benzoin condensation giving good yields within very short reaction time using solvent-free microwave activation conditions.