147663-61-4

Upstream product

• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 29584-64-3 ethyl 3,5-dimethoxycinnamate 
• 76104-60-4 methyl 3-(3,5-dimethoxyphenyl)acrylate 
• 20767-04-8 (E)-3,5-dimethoxycinnamic acid 
• 29577-41-1 3-(3,5-dimethoxyphenyl)-2-propyn-1-ol 
• 1499120-79-4 (E)-1-(3-chloroprop-1-en-1-yl)-3,5-dimethoxybenzene 

Downstream Products

• 125187-47-5 3-(3,5-dimethoxyphenyl)-1-propanal 
• 1326634-95-0 trans,trans,trans-1-(3,5-dihydroxyphenyl)-6-(4-hydroxyphenyl)-1,3,5-hexatriene 
• 125187-46-4 3,5-dimethoxycinnamaldehyde 

Relevant academic research and scientific papers

Synthesis of chiral fluorine-containing compounds via Pd-catalyzed asymmetrical allylations of dimethyl 2-fluoromalonate using sulfonamide-pyridine ligands

Chiral o-aniline sulfoxides serving as chiral sulfurous source were synthesized, from which new sulfonamide-pyridine ligands were made in three-steps. These compounds proved to be efficient S,N-ligands for enantiocontrol of palladium-catalyzed allylic sub

Total synthesis of (±)-symbioimine

The synthesis of (±)-symbioimine (1) has been completed in only 12 linear steps in 8% overall yield. The key step is the treatment of 13b with BF3·Et2O to generate N-carboalkoxydihydropyridinium cation 14b, which undergoes a novel stereospecific intramole

Enantioselective α-functionalization of 1,3-dithianes by iridium-catalyzed allylic substitution

An iridium-catalyzed asymmetric allylic substitution reaction with 2-alkoxy carbonyl-1,3-dithianes has been achieved with high regio- and enantioselectivities. The transformation provides a new method for the enantioselective α-functionalization of dithianes. The corresponding dithiane-containing products are easily converted into many other derivatives with high yields and enantioselectivities.

Photocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. We report a photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes. Quantum mechanical calculations (uM06-2X and DLPNO), including TD-DFT calculations, and experimental studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cla￠ radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. We anticipate that the use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity.

Biocatalytic dynamic kinetic reductive resolution with ketoreductase from: Klebsiella pneumoniae: The asymmetric synthesis of functionalized tetrahydropyrans

Ketoreductase from growing cells of Klebsiella pneumoniae (NBRC 3319) acts as an efficient reagent for converting racemic α-benzyl/cinnamyl substituted-β-ketoesters to the corresponding β-hydroxy esters with excellent yields and stereoselectivities (ee and de >99 %). The reactions described herein followed a biocatalytic dynamic kinetic reductive resolution (DKRR) pathway, which is reported for the first time with such substrates. It was found that the enzyme system can accept substituted mono-aryl rings with different electronic natures. In addition, it also accepts a substituted naphthyl ring and heteroaryl ring in the α-position of the parent β-ketoester. The synthesized enantiopure β-hydroxy esters were then synthetically manipulated to valuable tetrahydropyran building blocks.

A chiral sulfoxide-ligated ruthenium complex for asymmetric catalysis: Enantio- and regioselective allylic substitution

The design and synthesis of a novel chiral sulfoxide-ligated cyclopentadienyl ruthenium complex is described. Its utility as an asymmetric variant of [CpRu(MeCN)3]PF6 is demonstrated through its ability to function in the branched-selective asymmetric allylic alkylation of phenols and carboxylic acids. Water has also been shown to act as a competent nucleophile in this reaction to generate branched allyl alcohols with good regio- and enantioselectivities.

Synthesis of 2,3-syn-diarylpent-4-enamides via acyl-Claisen rearrangements of substituted cinnamyl morpholines: Application to the synthesis of magnosalicin

The acyl-Claisen rearrangement of substituted phenylacetyl chlorides and cinnamyl morpholines gives 2,3-syn-diarylpent-4-enamides. Electron-rich cinnamyl morpholines containing alkoxy substituents only reacted with phenylacetyl chlorides; replacement of t

Synthesis of methoxylated goniothalamin, aza-goniothalamin and γ-pyrones and their in vitro evaluation against human cancer cells

The present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the γ-pyrones and the aza-goniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin (1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds.

Synthesis of some phenylpropanoid glycosides (PPGs) and their acetylcholinesterase/xanthine oxidase inhibitory activities

In this research, three categories of phenylpropanoid glycosides (PPGs) were designed and synthesized with PPGs isolated from Rhodiola rosea L. as lead compounds. Their inhibitory abilities toward acetylcholinesterase (AChE) and xanthine oxidase (XOD) were also tested. Some of the synthetic PPGs exhibited excellent enzyme inhibitory abilities.

Finding more active antioxidants and cancer chemoprevention agents by elongating the conjugated links of resveratrol

Resveratrol is the subject of intense research as a natural antioxidant and cancer chemopreventive agent. There has been a great deal of interest and excitement in understanding its action mechanism and developing analogs with antioxidant and cancer chemoprevention activities superior to that of the parent compound in the past decade. This work delineates that elongation of the conjugated links is an important strategy to improve the antioxidant activity of resveratrol analogs, including hydrogen atom- or electron-donating ability in homogeneous solutions and antihemolysis activity in heterogeneous media. More importantly, C3, a triene bearing 4,4′-dihydroxy groups, surfaced as an important lead compound displaying remarkably increased antioxidant, cytotoxic, and apoptosis-inducing activities compared with resveratrol.