212688-07-8

Upstream product

• 67-56-1 methanol 
• 20503-09-7 2-(2-hydroxy-4-methoxyphenyl)acetic acid 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 209404-16-0 methyl (2-benzyloxy-4-methoxyphenyl)acetate 

Downstream Products

• 35353-87-8 methyl (3,5-dibromo-2-hydroxy-4-methoxyphenyl)acetate 
• 209404-40-0 2-(4-Benzylsulfanyl-7-methoxy-chroman-3-yl)-5-methoxy-phenol 
• 209404-21-7 2-[2-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-hydroxy-3-(4-methoxy-2-methoxymethoxy-phenyl)-propionic acid methyl ester 
• 209404-36-4 4-benzylsulfanyl-2'-tert-butyldimethylsilyloxy-4',7-dimethoxyisoflavan 
• 209404-25-1 3-Benzylsulfanyl-2-[2-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-(2-hydroxy-4-methoxy-phenyl)-propionic acid methyl ester 
• 209404-32-0 3-benzylsulfanyl-2-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-3-(2''-hydroxy-4''-methoxyphenyl)propan-1-ol 
• 209404-26-2 methyl 3-benzylsulfanyl-2-(2'-tert-butyldimethylsilyloxy-4'-methoxyphenyl)-3-(2''-hydroxy-4''-methoxyphenyl)propanoate 
• 212698-13-0 3-[3,5-Dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-N-(4-{3-[3,5-dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-2-[(E)-hydroxyimino]-propionylamino}-butyl)-2-[(E)-hydroxyimino]-propionamide 
• 212688-12-5 3-[3,5-Dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-N-(4-{3-[3,5-dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-2-oxo-propionylamino}-butyl)-2-oxo-propionamide 
• 212688-10-3 4-[3,5-Dibromo-4-methoxy-2-(4-methoxy-benzyloxy)-phenyl]-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-butyronitrile 
• 212688-08-9 methyl [3,5-dibromo-2-(p-methoxybenzyloxy)-4-methoxyphenyl]acetate 
• 212688-09-0 3,5-dibromo-2-(p-methoxybenzyloxy)-4-methoxyphenylacetic acid 
• 28714-26-3 aerothionin 
• 28687-76-5 3-(3,5-Dibromo-2-hydroxy-4-methoxy-phenyl)-N-(4-{3-(3,5-dibromo-2-hydroxy-4-methoxy-phenyl)-2-[(E)-hydroxyimino]-propionylamino}-butyl)-2-[(E)-hydroxyimino]-propionamide 

Relevant academic research and scientific papers

Direct synthesis of pterocarpans via aldol condensation of phenylacetates with benzaldehydes

Aldol condensation between phenylacetates and benzaldehydes affords 2,3- diaryl-3-hydroxypropanoates which are convened into pterocarpans via stepwise deprotection and cyclization in moderate to high yields.

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.

Metal-free oxidation of aromatic carbon-hydrogen bonds through a reverse-rebound mechanism

Methods for carbon-hydrogen (C-H) bond oxidation have a fundamental role in synthetic organic chemistry, providing functionality that is required in the final target molecule or facilitating subsequent chemical transformations. Several approaches to oxidizing aliphatic C-H bonds have been described, drastically simplifying the synthesis of complex molecules. However, the selective oxidation of aromatic C-H bonds under mild conditions, especially in the context of substituted arenes with diverse functional groups, remains a challenge. The direct hydroxylation of arenes was initially achieved through the use of strong Bronsted or Lewis acids to mediate electrophilic aromatic substitution reactions with super-stoichiometric equivalents of oxidants, significantly limiting the scope of the reaction. Because the products of these reactions are more reactive than the starting materials, over-oxidation is frequently a competitive process. Transition-metal-catalysed C-H oxidation of arenes with or without directing groups has been developed, improving on the acid-mediated process; however, precious metals are required. Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C-H bonds are selectively oxidized in preference to activated-H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates. Quantum mechanical calculations indicate that this transformation proceeds through a novel addition-abstraction mechanism, a kind of 'reverse-rebound' mechanism as distinct from the common oxygen-rebound mechanism observed for metal-oxo oxidants. These calculations also identify the origins of the experimentally observed aryl selectivity.

1,2-AZOLE DERIVATIVES WITH HYPOGLYCEMIC AND HYPOLIPIDEMIC ACTIVITY

A compound represented by the formula (1) wherein ring A is a ring optionally having 1 to 3 substituents; ring B is a 1,2-azole ring which may further have 1 to 3 substituents; Xa, Xb and Xc are the same or different and each is a bond, - O -, - S - and the like; Ya is a divalent aliphatic hydrocarbon residue having 1 to 20 carbon atoms; Yb and Yc are the same or different and each is a bond or a divalent aliphatic hydrocarbon residue having 1 to 20 carbon atoms; ring C is a monocyclic aromatic ring which may further have 1 to 3 substituents; and R represents -OR4 (R4 is hydrogen atom or optionally substituted hydrocarbon group) and the like, or a salt thereof or a prodrug thereof is useful as an agent for the prophylaxis or treatment of diabetes and the like.

Synthesis of neoflavenes by ligand coupling reactions with aryllead triacetates

The reaction of 4-methoxycarbonylchroman-3-one with aryllead triacetates gave the 4-aryl derivatives after 3-4h reaction times in moderate to good yields. Unexpectedly, 2,4-diarylated derivatives were also obtained after longer reaction times. The activating methyl ester group proved difficult to remove by standard decarboxylation procedures. 4-Benzyloxycarbonylchroman-3-ones were therefore prepared and reacted with aryllead triacetates to afford the corresponding 4-aryl derivatives. These were subsequently decarboxylated, reduced and dehydrated to afford neoflavenes in modest overall yields.

Synthesis of isoflavonoids. Enantiopure cis- and trans-6a-hydroxypterocarpans and a racemic trans-pterocarpan

Aldol condensation between phenylacetates and benzaldehydes affords 2,3-diaryl-3-hydroxypropanoates which serve as common precursors to both the first racemic trans-pterocarpan and enantiopure cis- and trans-6a-hydroxypterocarpans.

Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin using the cyano ylide coupling methodology

Syntheses of the marine metabolites verongamine, hemibastadin-2, and aerothionin have been accomplished by a methodology involving the conversion of a carboxylic acid to an acyl cyano phosphorane which may be oxidized to an α,β-diketo nitrile. This strong

The first direct synthesis of pterocarpans via aldol condensation of phenylacetates with benzaldehydes

Aldol condensation between phenylacetates and benzaldehydes affords 2,3- diaryl-3-hydroxypropanoates which are converted into pt pans in moderate to high yields.