74809-43-1

Basic information

• Product Name: Benzene, 1,2,3-trimethoxy-5-(2-phenylethenyl)-, (E)-
• CAS NO: 74809-43-1
• Molecular Formula: C17H18O3
• Molecular Weight: 270.328
• Mol File: 74809-43-1.mol

Chemical Properties

• CAS DataBase Reference: Benzene, 1,2,3-trimethoxy-5-(2-phenylethenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,2,3-trimethoxy-5-(2-phenylethenyl)-, (E)-(74809-43-1)
• EPA Substance Registry System: Benzene, 1,2,3-trimethoxy-5-(2-phenylethenyl)-, (E)-(74809-43-1)

Safety Data

• Hazardous Substances Data: 74809-43-1(Hazardous Substances Data)

Upstream product

• 2959-74-2 benzyldiphenylphosphine oxide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 7751-69-1 α-chlorobenzyl(diphenyl)phosphine oxide 
• 7016-55-9 benzyl-triethylphosphonium bromide 
• 588-73-8 (Z)-β-bromostyrene 
• 182163-96-8 3,4,5-trimethoxyphenylboronic Acid 
• 312600-72-9 2-(E-2-bromo-1-ethenyl)-3,4,5-trimethoxybenzene 
• 98-80-6 phenylboronic acid 
• 100-52-7 benzaldehyde 
• 134029-74-6 [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 
• 579-43-1 (1S,2R)-1,2-diphenylethane-1,2-diol 
• 100-42-5 styrene 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 

Downstream Products

• 74809-44-2 1,2,3-trimethoxy-5-[(1Z)-2-phenylethenyl]benzene 
• 133462-61-0 2-phenyl-1-(3,4,5-trimethoxyphenyl)ethanol 
• 21956-56-9 (E)-3,5-dimethoxystilbene 
• 78916-50-4 1,3-dimethoxy-5-(2-phenylethyl)benzene 
• 133462-62-1 1,2,3-trimethoxy-5-phenethylbenzene 
• 1236211-45-2 5-phenethylbenzene-1,2,3-triol 

Relevant articles and documents

Pd-Catalyzed Coupling of N-Tosylhydrazones with Benzylic Phosphates: Toward the Synthesis of Di- or Tri-Substituted Alkenes

This study shows that various di- and tri-substituted alkenes with high chemoselectivity were obtained in good to high yields by coupling N-tosylhydrazones (NTHs) with benzylic phosphates as electrophilic partners. The obtained new catalytic system consis

METHODS OF ARENE ALKENYLATION

The present disclosure provides for a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. For example, the present disclosure provides for method of making arenes or substituted arenes, in particular stilbene and stilbene derivatives, from a reaction of an optionally substituted arene and/or optionally substituted styrene. The reaction includes a Rh catalyst or Rh pre-catalyst material and an oxidant, where the Rh catalyst or Rh catalyst formed Rh pre-catalyst material selectively functionalizes CH bond on the arene compound (e.g., benzene or substituted benzene).

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and mechanistic investigations

Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at ?5 ?C within 2 h. These bis-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)3 with various functionalized alkenyl iodides and bromides in 1 h at 25 ?C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process.

Inhibitors of protein activity for the treatment of angiogenesis and SOX18/or lymphangiogenesis-related diseases

Disclosed are compounds of a formula provided herein that show efficacy in the inhibition of SOX18 protein activity, and in particular with respect to the ability of SOX18 to bind DNA and/or particular protein partners. Further, methods of treating angiog

Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2

A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.

Synthesis and Characterization of C, C -Type Palladacycles and Their Catalytic Application in Mizoroki-Heck Coupling Reaction

Two series of ligand precursors, based on imidazo[1,2-a]pyridine and C2-phenyl substituted imidazole moieties, were developed and synthesized in high yields, featuring an N-CH2(C=O)Ar substituent on the imidazole ring. Upon reacting with palladium acetate, both series of ligands underwent double C-H bond activations at the methylene and o-aryl carbon sites on the N-CH2(C=O)Ar substituent, yielding C,C-type palladacycles bearing five-membered chelate rings. A dimeric palladium complex with bridging bromides was obtained from the ligand precursor with the bromide anion, whereas an ionic palladium complex with two "throw away" pyridine ligands was formed with the precursor of the tetrafluoroborate anion. All complexes are air-stable and were characterized by 1H and 13C NMR spectroscopy and elemental analysis. The structures of three of the new complexes were further established by single-crystal X-ray diffraction studies. These complexes have been screened for catalyzing Mizoroki-Heck coupling reaction using ionic salt as solvent. The complex based on imidazo[1,2-a]pyridine, which has an electron-donating 4-methoxyphenyl ring on the ligand scaffold, was the most efficient catalyst, capable of using activated aryl chloride and sterically hindered aryl bromide as substrates. It was also successfully applied in the green process of one-pot Mizoroki-Heck coupling/trans-esterification reaction in molten ionic salt.