20657-34-5

Upstream product

• 1711-05-3 m-anisoyl chloride 
• 591-31-1 3-methoxy-benzaldehyde 
• 59647-77-7 bis(3-methoxyphenyl)acetylene 
• 768-70-7 1-ethynyl-3-methoxybenzene 
• 766-85-8 3-methoxy-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 603-35-0 triphenylphosphine 
• 824-98-6 m-methoxybenzyl chloride 
• 18880-05-2 3-methoxybenzyl-triphenylphosphonium chloride 
• 2398-37-0 3-methoxyphenyl bromide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 7388-28-5 sodium 2-hydroxyethoxide 
• 40252-74-2 3-methoxybenzaldehyde azine 
• 74-85-1 ethene 

Downstream Products

• 6325-63-9 (E)-3,3'-dimethoxystilbene 
• 1407523-46-9 benzyl 2-[(tert-butoxycarbonyl)amino]-3-(5,11-dimethoxy-8-oxodibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-1(8H)-yl)propanoate 
• 1407523-42-5 1-benzyl-5,11-dimethoxydibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-8(1H)-one 
• 1407523-44-7 5,11-dimethoxy-1-(4-methoxyphenyl)dibenzo[3,4:7,8]cyclopropa[5,6]cycloocta[1,2-d][1,2,3]triazol-8(1H)-one 
• 70709-65-8 (E)-1-(3-hydroxyphenyl)-2-(3-hydroxyphenyl)ethene 
• 156091-01-9 (1RS,2RS)-1,2-Bis(3-methoxyphenyl)ethane-1,2-diol 
• 10127-54-5 4,5-dimethoxy-phenanthrene 
• 74307-30-5 2,7-dimethoxyphenanthrene 
• 108840-81-9 2,5-dimethoxy-phenanthrene 
• 335152-88-0 (R,R)-(+)-1,2-bis(3-methoxyphenyl)ethane-1,2-diol 
• 36707-27-4 1,2-bis(3-methoxyphenyl)ethane 
• 1454309-28-4 3,3'-(3,3-dibromocyclopropane-1,2-diyl)bis(methoxybenzene) 

Relevant academic research and scientific papers

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

Efficient preparation method of symmetric diarylethene compound

The invention belongs to the technical field of fine chemicals and related chemistry, and provides an efficient preparation method of a symmetric diarylethene compound. The method comprises the following steps: with halomethyl-containing aromatic hydrocarbon and derivatives thereof as raw materials, conducting reacting at 100 DEG C for 12 hours in the presence of a catalyst, alkali, additives andan anhydrous organic solvent so as to obtain the corresponding diarylethene compound with symmetry. The method has the beneficial effects that no transition metal reaction exists, reaction conditionsare mild, operation is simple and convenient, the possibility of industrialization is realized, and the diarylethene compound is obtained at high yield; and the diarylethene compound synthesized by using the method can be further functionalized to obtain various compounds, and is applied to development and research of natural products, functional materials and fine chemicals.

Selenenate Anions (PhSeO?) as Organocatalyst: Synthesis of trans-Stilbenes and a PPV Derivative

The selenenate anion (RSeO?) is introduced as an active organocatalyst for the dehydrohalogen coupling of benzyl halides to form trans-stilbenes. It is shown that RSeO? is a more reactive catalyst than the previously reported sulfur analogues (sulfenate anion, RSO?) and selenolate anions (RSe?) in the aforementioned reaction. This catalytic system was also applied to the benzylic-chloromethyl-coupling polymerization (BCCP) of a bis-chloromethyl arene to form ppv (poly(p-phenylene vinylene))-type polymers with high yields, Mn (average molecular weight) up to 13,000 and ? (dispersity) of 1.15. (Figure presented.).

Photo-induced and Rapid Labeling of Tetrazine-Bearing Proteins via Cyclopropenone-Caged Bicyclononynes

Inverse electron-demand Diels–Alder cycloadditions (iEDDAC) between tetrazines and strained alkenes/alkynes have emerged as essential tools for studying and manipulating biomolecules. A light-triggered version of iEDDAC (photo-iEDDAC) is presented that confers spatio-temporal control to bioorthogonal labeling in vitro and in cellulo. A cyclopropenone-caged dibenzoannulated bicyclo[6.1.0]nonyne probe (photo-DMBO) was designed that is unreactive towards tetrazines before light-activation, but engages in iEDDAC after irradiation at 365 nm. Aminoacyl tRNA synthetase/tRNA pairs were discovered for efficient site-specific incorporation of tetrazine-containing amino acids into proteins in living cells. In situ light activation of photo-DMBO conjugates allows labeling of tetrazine-modified proteins in living E. coli. This allows proteins in living cells to be modified in a spatio-temporally controlled manner and may be extended to photo-induced and site-specific protein labeling in animals.

Photoinitiated carbonyl-metathesis: Deoxygenative reductive olefination of aromatic aldehydes: Via photoredox catalysis

Carbonyl-carbonyl olefination, known as McMurry reaction, represents a powerful strategy for the construction of olefins. However, catalytic variants that directly couple two carbonyl groups in a single reaction are less explored. Here, we report a photoredox-catalysis that uses B2pin2 as terminal reductant and oxygen trap allowing for deoxygenative olefination of aromatic aldehydes under mild conditions. This strategy provides access to a diverse range of symmetrical and unsymmetrical alkenes with moderate to high yield (up to 83%) and functional-group tolerance. To follow the reaction pathway, a series of experiments were conducted including radical inhibition, deuterium labelling, fluorescence quenching and cyclic voltammetry. Furthermore, NMR studies and DFT calculations were combined to detect and analyze three active intermediates: a cyclic three-membered anionic species, an α-oxyboryl carbanion and a 1,1-benzyldiboronate ester. Based on these results, we propose a mechanism for the CC bond generation involving a sequential radical borylation, "bora-Brook" rearrangement, B2pin2-mediated deoxygenation and a boron-Wittig process.

Alkenylation of arenes using disubstituted ethynes by palladium/carboxylic acid catalysis

Palladium/carboxylic acid-catalyzed alkenylation of heteroarenes and electron-deficient arenes using alkynes underwent C(sp2)H bond activation in arene substrates to give the corresponding alkenylarenes straightforwardly. The versatility of this transformation is demonstrated by the double alkenylation of functionalized thiophenes and 5,6-difluorobenzothiadiazole with alkynes and provides a one-step access to vinylenearylene- vinylene units.

Direct Conversion of Alcohols into Alkenes by Dehydrogenative Coupling with Hydrazine/Hydrazone Catalyzed by Manganese

We have developed unprecedented methods for the direct transformation of primary alcohols to alkenes in the presence of hydrazine, and for the synthesis of mixed alkenes by the reaction of alcohols with hydrazones. The reactions are catalyzed by a manganese pincer complex and proceed in absence of added base or hydrogen acceptors, liberating dihydrogen, dinitrogen, and water as the only byproducts. The proposed mechanism, based on preparation of proposed intermediates and control experiments, suggests that the transformation occurs through metal–ligand cooperative N?H activation of a hydrazone intermediate.

Highly Selective Semihydrogenation of Alkynes to Alkenes by Using an Unsupported Nanoporous Palladium Catalyst: No Leaching of Palladium into the Reaction Mixture

We report the highly chemoselective and stereoselective semihydrogenation of alkynes to Z-internal and terminal alkenes by using unsupported nanoporous palladium (PdNPore) as a heterogeneous catalyst under mild reaction conditions (room temperature and 1 atm of H2). The semihydrogenation of various terminal/internal and aromatic/aliphatic alkynes afforded the corresponding alkenes in good chemical yields with high selectivities. PdNPore further showed high chemoselectivity toward terminal alkynes in the presence of internal alkynes, which has not yet been achieved using supported palladium nanoparticle catalysts. H-H heterolysis of H2 on the surface of PdNPore was strongly suggested by deuterium labeling experiments. No Pd leached from PdNPore during the reaction, and the catalyst was easily recovered and reused without a loss of activity.

Method for preparing trans-diphenylethylene compound

The invention relates to a preparation method of organic compounds and provides a method for preparing a trans-diphenylethylene compound. The method comprises adding a gem-dibromomethyl aromatic hydrocarbon compound, copper and polyamine into a reactor in the presence of a solvent, carrying out deoxidizing treatment, adding an oxygen-free water-free solvent into the reactor, carrying out a coupling reaction process to obtain C-C- double bonds, and carrying out separation and purification to obtain the trans-diphenylethylene compound. The method has mild synthesis conditions and has good reaction compatibility to different functional groups. The gem-dibromomethyl aromatic hydrocarbon compound as a raw material is easy to synthesize, may have different substituent groups and has a variable structure. The product obtained by coupling a raw material can be simply treated and has high purity. The asymmetric trans-diphenylethylene compound can be prepared from two different raw materials.

E-Stilbene derivatives synthesized by stereoselective reductive coupling of benzylic gem-dibromide promoted by Cu/polyamine

Stereoselective reductive coupling reaction of benzylic gem-dibromide promoted by Cu/polyamine produces E-stilbene derivatives with high yield under mild conditions. It provides a short pathway to synthesize symmetrical and asymmetrical E-stilbene derivatives using cheap reagents and alkenyl-free starting material together with easy workup.