1198340-26-9

Upstream product

• 79-01-6 Trichloroethylene 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 1198340-29-2 (Z)-1-(4-methoxy)phenoxy-1-(4-methoxyphenyl)-2-chloroethylene 
• 19803-11-3 6-methoxy-2-(4-methoxyphenyl)benzofuran 
• 1421257-58-0 methyl (2R,3R,E)-2-(((2R,4S,5R)-2-(4-chlorophenyl)-4-vinyl-1,3-dioxan-5-yl)oxy)-3-(4-methoxyphenoxy)hex-5-enoate 
• 1421257-52-4 (S,Z)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxyphenoxy)allyl 2-(((2R,4S,5R)-2-(4-chlorophenyl)-4-vinyl-1,3-dioxan-5-yl)oxy)acetate 
• 1421257-50-2 (R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxyphenoxy)propan-1-ol 
• 1421257-49-9 (S,Z)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxyphenoxy)prop-2-en-1-ol 
• 1421257-48-8 (R,Z)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-3-(4-methoxyphenoxy)prop-2-en-1-ol 
• 75290-86-7 methoxy-4-(prop-2-ynyloxy)benzene 
• 7182-32-3 2-phenyl-5-methoxybenzo[b]furan 
• 1020002-96-3 (S)-5-methoxy-2-(4-methoxyphenyl)-2,3-dihydrobenzofuran 
• 1381964-95-9 (S)-2-(4-fluorophenyl)-5-methoxy-2,3-dihydrobenzofuran 
• 1025330-18-0 (S)-5-methoxy-2-phenyl-2,3-dihydrobenzofuran 
• 1257325-93-1 2-(3-acetylphenyl)-5-methoxybenzo[b]furan 
• 1257325-92-0 2-(3,4-dimethoxyphenyl)-5-methoxybenzo[b]furan 

Relevant academic research and scientific papers

Enantioselective Heck Arylation of Acyclic Alkenol Aryl Ethers: Synthetic Applications and DFT Investigation of the Stereoselectivity

Herein we report the enantioselective Heck-Matsuda arylation of acyclic E and Z-alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck-Matsuda arylation has shown a broad scope (25 examples), and some key Heck-Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)-Fluoxetine, (R)-Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory. (Figure presented.).

Cs2CO3-promoted vinylation of phenols with trichloroethylene: Facile synthesis of (E)-1,2-dichloro-1-phenoxyethenes

An efficient method for the synthesis of (E)-1,2-dichloro-1-phenoxyethenes 2 has been developed. The reaction of phenol derivatives 1 with trichloroethylene at ambient temperature by means of Cs2CO3-DMSO system furnished the correspo

Synthesis of the ABCDEF-ring of ciguatoxin 3C

The synthesis of the ABCDEF-ring of ciguatoxin 3C was achieved via a route that included anion coupling of a dimethyldithioacetal mono-S-oxide derivative corresponding to the AB-ring and an aldehyde corresponding to the EF-ring, followed by cyclization us

A Fluorescence Polarization Assay for Binding to Macrophage Migration Inhibitory Factor and Crystal Structures for Complexes of Two Potent Inhibitors

Human macrophage migration inhibitory factor (MIF) is both a keto-enol tautomerase and a cytokine associated with numerous inflammatory diseases and cancer. Consistent with observed correlations between inhibition of the enzymatic and biological activities, discovery of MIF inhibitors has focused on monitoring the tautomerase activity using l-dopachrome methyl ester or 4-hydroxyphenyl pyruvic acid as substrates. The accuracy of these assays is compromised by several issues including substrate instability, spectral interference, and short linear periods for product formation. In this work, we report the syntheses of fluorescently labeled MIF inhibitors and their use in the first fluorescence polarization-based assay to measure the direct binding of inhibitors to the active site. The assay allows the accurate and efficient identification of competitive, noncompetitive, and covalent inhibitors of MIF in a manner that can be scaled for high-throughput screening. The results for 22 compounds show that the most potent MIF inhibitors bind with Kd values of ca. 50 nM; two are from our laboratory, and the other is a compound from the patent literature. X-ray crystal structures for two of the most potent compounds bound to MIF are also reported here. Striking combinations of protein-ligand hydrogen bonding, aryl-aryl, and cation-π interactions are responsible for the high affinities. A new chemical series was then designed using this knowledge to yield two more strong MIF inhibitors/binders.

Metal-free oxidative cyclization of alkynyl aryl ethers to benzofuranones

Readily available phenols can be converted into substituted aryl alkynyl ethers, which react with an N-oxide as an oxidant and catalytic amounts of a Bronsted acid to provide benzofuranones. If non-terminal alkynyl ethers are applied, a 1,2-hydride shift takes place and phenyl acrylates are obtained. Thus activated alkynes can serve as α-oxy carbene precursors even in the absence of a metal catalyst. Copyright

Fluorinated 5- and 7-membered carbacycle motifs by reaction of difluorocarbene with acetylene ethers

The reaction of acetylene ethers with difluorocarbene (CF2), generated from the Ruppert-Prakash reagent, unexpectedly gave rise to co-produced fluorinated bicyclic [2.1.1]-hex-2-ene and cyclohepta-1,4-diene ring products.

Highly asymmetric synthesis of (+)-corsifuran A. Elucidation of the electronic requirements in the Ruthenium-NHC catalyzed hydrogenation of benzofurans

A short and efficient synthesis of ent-corsifuran A by a highly asymmetric hydrogenation of a benzofuran precursor is reported. In addition, the electronic influence of the substituents on the asymmetric hydrogenation of benzofurans is provided. Whereas the hydrogenation of electron-deficient benzofurans was achieved under very mild conditions, the presence of electron-donating groups in the benzofuran required harsher reaction conditions for achieving full conversion to the 2,3-dihydrobenzofuran.

2-substituted benzo[b]furans from (E)-1,2-dichlorovinyl ethers and organoboron reagents: Scope and mechanistic investigations into the one-pot Suzuki coupling/direct arylation

2-Substituted benzo[b]furans can easily be assembled from simple phenols, boronic acids or other organoboron reagents, and trichloroethylene. The overall process requires only two synthetic steps, with the key step being a one-pot sequential Suzuki cross-coupling/direct arylation reaction. The method tolerates many useful functional groups and does not require the installation of any other activating functionality. The modular nature of the process permits the rapid synthesis of many analogues using essentially the same chemistry, of particular value in drug development. Results of kinetic isotope effect studies and investigations into the regioselectivity of the process indicate that the direct arylation step most likely does not involve an electrophilic palladation. The most likely mechanism lies somewhere on the continuum between a C-H bond metathesis and an assisted palladation or concerted metallation-deprotonation pathway. A very efficient modular approach to the construction of benzo[b]furans using trichloroethylene as a scaffold is described. This method gives easy access to highlysubstituted heterocycles in only two synthetic operations, and is especially suitable for rapid construction of compound libraries.

Modular construction of 2-substituted benzo[b]furans from 1,2-Dichlorovinyl ethers

"Chemical Equation Presented" (E)-1,2-Dichlorovinyl ethers and amides are easily accessible from trichloroethylene via nucleophilic addition across in situ synthesized dlchloroacetylene. A one-pot, sequential Suzukl-Miyaura coupling/intramolecular direct