5854-19-3

Upstream product

• 326886-35-5 C₁₇H₁₇NO₃ 
• 108-59-8 malonic acid dimethyl ester 
• 120-14-9 3,4-dimethoxy-benzaldehyde 

Downstream Products

• 2132-80-1 4,4'-Dimethoxybiphenyl 
• 75327-40-1 2-[(3,4-Dimethoxy-phenyl)-(4-methoxy-phenyl)-methyl]-malonic acid dimethyl ester 
• 138334-92-6 2-[1-(3,4-Dimethoxy-phenyl)-2-(2-nitro-6-trifluoromethyl-phenyl)-ethyl]-malonic acid dimethyl ester 
• 5854-22-8 dimethyl 2-(3,4-dimethoxybenzyl)malonate 
• 138335-14-5 (3R,4R)-4-(3,4-Dimethoxy-phenyl)-3-methyl-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 
• 138335-29-2 (3S,4S)-4-(3,4-Dimethoxy-phenyl)-1-(2-dimethylamino-ethyl)-3-methyl-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 
• 74402-00-9 dimethyl benzyl-3,4-dimethoxybenzylmalonate 
• 74402-01-0 2-(3,4-dimethoxybenzyl)-3-phenylpropionic acid 
• 74402-05-4 2-(3,4-dimethoxybenzyl)-3-phenylpropionyl chloride 

Relevant academic research and scientific papers

Reductive Knoevenagel Condensation with the Zn-AcOH System

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Protic Ionic Liquid as Reagent, Catalyst, and Solvent: 1-Methylimidazolium Thiocyanate

We propose a new concept of the triple role of protic ionic liquids with nucleophilic anions: a) a regenerable solvent, b) a Br?nsted acid inducing diverse transformations via general acid catalysis, and c) a source of a nucleophile. The efficiency of this strategy was demonstrated using thiocyanate-based protic ionic liquids for the ring-opening of donor-acceptor cyclopropanes. A wide variety of activated cyclopropanes were found to react with 1-methylimidazolium thiocyanate under mild metal-free conditions via unusual nitrogen attack of the ambident thiocyanate ion on the electrophilic center of the three-membered ring affording pyrrolidine-2-thiones bearing donor and acceptor substituents at the C(5) and C(3) atoms, respectively, in a single time-efficient step. The ability of 1-methylimidazolium thiocyanate to serve as a triplex reagent was exemplarily illustrated by (4+2)-annulation with 1-acyl-2-(2-hydroxyphenyl)cyclopropane, epoxide ring-opening and other organic transformations.

Total synthesis of (+)-virgatusin via AlCl3-catalyzed [3+2] cycloaddition

The AlCl3-catalyzed cycloaddition of a donor-acceptor (don-acc) cyclopropane and piperonal succinctly provides the core of virgatusin in a selective, high-yielding manner. The Royal Society of Chemistry 2009.

Condensation of dimethyl malonate with benzal-4-acetyIanilines: A chemoselective reaction

Dimethyl malonate has reacted chemoselectively with carbon- nitrogen double bond of benzal-4-acetylanilines (1-8) leaving the carbon-oxygen double bond, considered to be more reactive, intact under reaction conditions, leading to the formation of mono addition-elimination products rather than bis attack at both the double bonds, even when the reaction has been carried out with two moles of dimethyl malonate.

Synthesis of Amaryllidaceae Alkaloids, (+/-)-Cherylline and (+/-)-Latifine

Synthesis of the alkaloids, (+/-)-cherylline (1) and (+/-)-latifine (2), was accomplished by application of an isocyanate cyclization reaction according to Tsuda's two step procedure for constructing 1,2,3,4-tetrahydroisoquinol-1-one and a regioselective

Dependence of Aryl Ether Acylation upon Lewis Acid Stoichiometry

Acylation of alkyl aryl ethers has been observed to be uniquely dependent on the stoichiometry of the Friedel-Crafts catalyst.With 100 molpercent catalyst, acylation proceeds rapidly and in high yield; with large molar excesses of catalyst, the reaction is essentially completely arrested.This inhibition can be reversed by using sterically bulky alkyl groups which effectively prevent complexing between catalyst and aryl ether.Based on these observations, we have developed processes for regioselective intramolecular acylation of either a phenyl or an alkoxylated phenyl ring when both are present.