47241-75-8

Upstream product

• 659-22-3 trans-4,4'-dihydroxystilbene 
• 75-36-5 acetyl chloride 
• 878-00-2 4-formylphenyl acetate 
• 637-69-4 4-Methoxystyrene 
• 2628-16-2 p-acetoxystyrene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 6380-23-0 3,4-dimethoxystyrene 
• 617-86-7 triethylsilane 
• 101737-00-2 4,4'-bis(acetoxy)diphenylacetylene 
• 540-38-5 p-Iodophenol 
• 35135-54-7 (E)-1,2-bis(4-ethoxyphenyl)ethene 
• 736-31-2 trans-4,4'-dinitrostilbene 
• 619-93-2 (Z)-4,4'-dinitrostilbene 
• 1073-67-2 4-vinylbenzyl chloride 

Downstream Products

• 659-22-3 trans-4,4'-dihydroxystilbene 

Relevant academic research and scientific papers

Ruthenium macrocycles bearing pyridine bis(carboxamide): Synthesis, structure, and catalytic activity for hydrosilylation

Ruthenium complexes Ru(MC33)(CO)n(L)2-n (L = H2O, PPh3, P(OEt)3; n = 1, 2) with a pincer-type macrocyclic ligand MC33 with a cavity were synthesized and characterized. Ru(MC33)(CO)2(H2O) was obtained in yields of up to 97% using a pincer-type ligand containing the bis(carboxamide) moiety and ruthenium(0) carbonyl precursor. Ru(AC)(CO)2(H2O) having a pincer-type acyclic ligand AC was also synthesized in a similar manner to Ru(MC33)(CO)2(H2O). Mono(phosphine) and bis(phosphite) complexes were formed via the selective thermal ligand exchange of CO with phosphorus ligands. The structure of the complexes was studied by nuclear magnetic resonance spectroscopy, infrared spectroscopy, electrospray ionization-high-resolution mass spectroscopy, and X-ray analyses. In addition, their catalytic activity for hydrosilylation was demonstrated.

Supramolecular gels derived from nucleoside based bolaamphiphiles as a light-sensitive soft material

Light-sensitive Low Molecular Weight Gelators (LMWGs) derived from glyconucleoside bolaamphiphiles containing a stilbene unit displayed gelation abilities in hydroalcoholic mixtures. These materials showed a gel-sol transition under UV irradiation thanks to E-Z isomerization of stilbene and could find potential applications as drug delivery systems.

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.

Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450 from Thermobifida fusca YX

Since the past decades, the plant stilbenoid resveratrol has gained significant attention of the general public as well as the research community due to its versatile medicinal properties. Apart from resveratrol, there is also an increasing interest in other plant stilbenoids because of their different potential biological activities. In order to meet the increasing demand for stilbenoids, alternative and sustainable approaches for their production are needed. We identified the cytochrome P450 monooxygenase 154E1 from Thermobifida fusca YX (CYP154E1) which enables the synthesis of (E)-4,4′-dihydroxystilbene via direct double hydroxylation of (E)-stilbene. The construction of a triple mutant led to a more than six-fold increased catalytic efficiency compared to the wild type enzyme. CYP154E1 and variants thereof accepted not only (E)-stilbene but also possessed remarkable activity towards ortho- and meta-substituted hydroxystilbenes leading to resveratrol, (E)-2,4′-dihydroxystilbene, (E)-2,4′,5-trihydroxystilbene and (E)-3,4′-dihydroxystilbene. The combination of protein engineering and the use of methyl-β-cyclodextrin as substrate solubilizing agent resulted in product titers of up to 4.2 g L?1 and enzyme total turnover numbers (TTN) of up to 20,000. (Figure presented.).

APPARATUS AND METHOD FOR CARRYING OUT MULTIPLE REACTIONS

The invention provides methods and an apparatus useful for site-isolating reagents or catalysts during chemical reactions. The methods and apparatus are useful for carrying out cascade or domino reactions.

A materials approach to site-isolation of grubbs catalysts from incompatible solvents and m-chloroperoxybenzoic acid

The development of a method for site-isolation of Grubbs second-generation catalyst from MCPBA is described. In these reactions, Grubbs catalyst was dissolved in a solvent consisting of a mixture (1:1 v/v) of 1-butyl-3- methylimidazolium hexafluorophosphate and methylene chloride and completely encapsulated within a thimble fabricated from polydimethylsiloxane (PDMS). A series of molecules that react by cross metathesis or ring-closing metathesis were added to the interior of the thimble and allowed to react. In the last step, m-chloroperoxybenzoic acid (MCPBA) dissolved in MeOH/H2O (1:1 v/v) was added to the exterior of the PDMS thimble. Small organic molecules diffused through the PDMS to react with MCPBA to form epoxides, but the Grubbs catalyst remained encapsulated. This result is important because Grubbs catalyst catalytically decomposes MCPBA at ratios of MCPBA to Grubbs of 3000 to 1. The yields for this two-step cascade sequence ranged from 67 to 83%. The concept behind this sequence is that small organic molecules have high flux through PDMS but large molecules - such as Grubbs catalyst - and ionic reagents-such as MCPBA-have much lower flux through PDMS. Small molecules can thus react both outside and inside PDMS thimbles, whereas incompatible catalysts and reagents remain site-isolated from each other. This method does not require alteration of structures of the catalysts or reagents, so it may be applied to a wide range of homogeneous catalysts and reagents. To demonstrate further that the catalyst was encapsulated, the Grubbs catalyst was successfully recycled within the cascade sequence.

Homobimetallic ruthenium-N-heterocyclic carbene complexes: Synthesis, characterization, and catalytic applications

Two new homobimetallic ruthenium-arene complexes [(p-cymene)Ru(μ-Cl) 3RuCl(η2-C2H4)(L)], where L = 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (3a) or 1,3-bis(2,4,6- trimethylphenyl)-4,5-dichloroimidazolin-2-ylidene (3b), were isolated in high yields upon heating a toluene solution of [RuCl2 (p-cymene)] 2 with 1 equivalent of carbene ligand under an ethylene atmosphere. They were characterized by NMR and TGA. Their catalytic activity was investigated in the atom transfer radical polymerization of vinyl monomers. In the polymerization of methyl methacrylate, complex 3a displayed faster reaction rates than 3b and the related phosphine-based complex 2a (L = tricyclohexylphosphine), although control was more effective with the latter catalyst. When n-butyl acrylate or styrene served as monomer, a major shift of reactivity was observed between complex 2a that promoted controlled radical polymerization, and complexes 3a or 3b that favored metathetical coupling. Further homocoupling experiments with various styrene derivatives confirmed the outstanding aptitude of complex 3a (and to a lesser extent of 3b) to catalyze olefin metathesis reactions. Contrary to monometallic ruthenium-arene complexes of the [RuCl2(p-cymene)(L)] type, the new homobimetallic species did not require the addition of a diazo compound or visible light illumination to initiate the ring-opening metathesis of norbornene or cyclooctene. When α,ω-dienes were exposed to 3a or 3b, a mixture of cycloisomerization and ring-closing metathesis products was obtained in a non-selective way. Addition of a terminal alkyne co-catalyst enhanced the metathetical activity while completely repressing the cycloisomerization process. Thus, quantitative conversions of diethyl 2,2-diallylmalonate and N,N-diallyltosylamide were achieved within 2 h at room temperature using 2 mol% of catalyst precursor 3 a and 6 mol % of phenylacetylene.

A simple access to biologically important trans-stilbenes via Ru-catalyzed cross metathesis

The cross metathesis of methoxy- or acetoxy-substituted styrenes using the Grubbs II catalyst affords unsymmetrical (mixed) E-stilbenes with astonishingly high selectivity (up to 79% yield). This approach offers a short and flexible synthesis of variously substituted stilbenes, which are derivatives or precursors of biologically important compounds such as resveratrol, piceatannol, and pinostilbene. Georg Thieme Verlag Stuttgart.

A short and efficient synthetic approach to hydroxy (E)-stilbenoids via solid-phase cross metathesis

Solid-phase cross metathesis of supported styrenyl ether with styrene derivatives afforded stilbenoids in high yields with complete (E)-selectivity, and this approach could be readily applied for a facile synthesis of a biologically important natural product, resveratrol.

ENANTIOSELECTIVITY IN ENEDIOL-HYDROXYKETONE TAUTOMERIZATION

The conversion of racemic α-hydroxyketone into optically active α-hydroxyketone with e.e. as high as 80percent and in good yield is reported.This is accomplished by a low temperature enantioselective protonation of the enediol using (2R,3R) O,O-dipivaloyltartaric acid.