70760-15-5

Upstream product

• 4030-17-5 4-methoxyphenylcyclopropane 
• 31706-15-7 3-(4-methoxy-phenyl)-3-oxo-propionaldehyde 
• 1631-83-0 diphenylsilyl chloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 92409-23-9 3-hydroxy-2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)propan-1-one 
• 92409-15-9 2-(2-methoxyphenoxy)-1-(4-methoxyphenyl)-1-hydroxy-3-propanol 
• 79415-36-4 1,3-bis(trifluoroacetoxy)-1-(p-methoxyphenyl)propane 
• 637-69-4 4-Methoxystyrene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 22027-50-5 methyl 3-(4-methoxybenzoyl)acetate 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 24165-60-4 1-(4-methoxyphenyl)but-3-en-1-ol 

Downstream Products

• 473987-30-3 1-(4,4-dimethoxy-cyclohex-1-enyl)-propane-1,3-diol 
• 787552-03-8 3-(tert-butyl-dimethyl-silanyloxy)-1-(4,4-dimethoxy-cyclohex-1-enyl)-propan-1-ol 
• 473987-31-4 C₂₆H₄₁NO₇Si 
• 1160639-60-0 C₁₇H₂₀O₅S 
• 1963-36-6 4-methoxycinnamaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 219745-23-0 3-Chloro-3-(4-methoxy-phenyl)-propan-1-ol 

Relevant academic research and scientific papers

Selective C-O Bond Cleavage of Lignin Systems and Polymers Enabled by Sequential Palladium-Catalyzed Aerobic Oxidation and Visible-Light Photoredox Catalysis

Lignin, which is a highly cross-linked and irregular biopolymer, is nature's most abundant source of aromatic compounds and constitutes an attractive renewable resource for the production of aromatic commodity chemicals. Herein, we demonstrate a practical and operationally simple two-step degradation approach involving Pd-catalyzed aerobic oxidation and visible-light photoredox-catalyzed reductive fragmentation for the chemoselective cleavage of the β-O-4 linkage - the predominant linkage in lignin - for the generation of lower-molecular-weight aromatic building blocks. The developed strategy affords the β-O-4 bond cleaved products with high chemoselectivity and in high yields, is amenable to continuous flow processing, operates at ambient temperature and pressure, and is moisture- and oxygen-tolerant.

Lewis Base-Promoted Ring-Opening 1,3-Dioxygenation of Unactivated Cyclopropanes Using a Hypervalent Iodine Reagent

A facile and effective system has been developed for the regio- and chemoselective ring-opening/electrophilic functionalization of cyclopropanes through C?C bond activation by [bis(trifluoroacetoxy)iodo]benzene with the aid of the Lewis basic promoter p-toluenesulfonamide. The p-toluenesulfonamide-promoted system works well for a wide range of cyclopropanes, resulting in the formation of 1,3-diol products in good yields and regioselectivity.

Investigate cleavage of β-O-4 linkage in lignin model compounds by aerobic oxidation of Cα and Cγ hydroxyl groups

The selective cleavage of common linkages in lignin polymers is a promising approach to generate valuable aromatic hydrocarbons. Herein, we found that on oxidation of Cα and Cγ hydroxyl groups in β-O-4 lignin model compounds with TEMPO catalyst resulted in the formation of 1,3-dicarbonyl TEMPO adduct. These oxidized products readily underwent fragmentation at Cα-Cβ bond in the presence of a catalytic amount of acid to generate corresponding carboxylic acid and phenol monomers.

Studies on the chemoenzymatic synthesis of (R)- and (S)-methyl 3-aryl-3-hydroxypropionates: The influence of toluene-pretreatment of lipase preparations on enantioselective transesterifications

Two series (para- and meta-substituted) of racemic methyl esters of 3-aryl-3-hydroxypropionic acid were prepared after which the enantiomers were separated by an enzyme-catalyzed transesterification. Several lipases were investigated as the catalyst. The influence of the enzyme pretreatment, as well as substrate concentration, reaction temperature, stirring manner, and substrate conversion on the stereochemical outcome of the biotransformation process were investigated in detail. The best results were achieved by using solvent-pretreated lipase from Pseudomonas fluorescens or Burkholderia cepacia suspended in toluene, and vinyl acetate as the acetyl group donor.

Tandem catalysis by lipase in a vinyl acetate-mediated cross-aldol reaction

The lipase Novozym435 (0.6% w/w) was used in tandem with organocatalysts in a first vinyl/isopropenyl acetate-mediated aldol reaction. The reaction was facilitated through the lipase-catalyzed in situ generation of acetaldehyde/acetone. The important features of the present methodology include the mild and facile reaction conditions, regenerability of the lipase, comparatively high yields and minimal side product formation.

Direct conversion of β-hydroxyketones to cyclic disiloxanes

β-Hydroxyketones can be directly converted to cyclic disiloxanes using diphenylchlorosilane in the presence of imidazole and an amine base. The reaction is proposed to proceed via a nucleophilic activation mechanism through a cyclic chairlike transition state affording hydrosilylated products with high diastereoselectivity.

Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation

Reduction of keto esters is a valuable alternative to produce diols. Sodium borohydride/MeOH system at room temperature and short reaction time efficiently reduced α, β, γ, and δ-keto esters having α-keto esters as the most reactive. The ester functionality was reduced effectively due to the presence of oxo group that somehow facilitates the formation of ring intermediate. As expected, the chemoselective experiments showed that ester functionality was not reduced using this system. This study presents a simple, easy, and benign reduction process of various keto esters to its corresponding diols.

Synthetic approach to tetrodotoxin

A novel and stereoselective approach to tetrodotoxin is described. The tricyclic compound having several key functional groups on the cyclohexane ring was synthesized from p-anisaldehyde with control of the four chiral centers. Iodoaminocyclization, 1,3-dipolar cycloaddition, and Baeyer-Villiger oxidation are the key steps of our approach.

Facile reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by an aqueous TiCl3/NH3 system: Selectivity and scope

A simple and rapid procedure for the almost quantitative reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by use of TiCl3/NH3 in aqueous methanol solution is reported. The reducing system distinguishes between different classes of aldehydes and/or ketones, and many functionalities that usually do not survive under reducing conditions are tolerated well. The concept of reversal of chemoselectivity has also been developed. A mechanism based on two sequential one-electron transfers from TiIII to the carbonyl carbon atom is proposed, the second SET becoming operative only in the presence of ammonium ion (either added or formed in situ). Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Electron transfer in P450 mechanisms. Microsomal metabolism of cyclopropylbenzene and p-cyclopropylanisole

The metabolism of cyclopropylbenzene (1a) and 4-cyclopropylanisole (1b) was studied using liver microsomal preparations from control, phenobarbital- and β-naphthoflavone treated rats. With all three types of microsomes 1a was metabolized by benzylic hydroxylation to give 1-phenylcyclopropanol and by aromatic hydroxylation at C-4; the former predominated by a factor of 2-4. BNF-induced microsomes also formed 2-cyclopropylphenol. No cyclopropyl ring-opened metabolites of 1a, including benzoic acid, were detected in any of the incubations. With PB-induced microsomes 1b underwent O-demethylation (90%) and benzylic hydroxylation; no other metabolites were detected. Progress curves for metabolism of 1a are markedly nonlinear after only limited conversion of substrate, suggesting the possibility that 1a, like other cyclopropyl compounds, could be a suicide substrate for one or more isozymes of P450. For both 1a and b, metabolite formation and enzyme inactivation can be explained by conventional P450 reaction mechanisms not involving electron abstraction.