54648-50-9

Upstream product

• 100-52-7 benzaldehyde 
• 104-47-2 p-methoxybenzylnitrile 
• 95549-10-3 (4-Dimethylamino-phenylsulfanyl)-(4-methoxy-phenyl)-acetonitrile 
• 6114-57-4 (Z)-2,3-diphenylacrylonitrile 
• 130728-46-0 3c-(4-cyano-phenyl)-2-(4-methoxy-phenyl)-acrylonitrile 
• 4086-15-1 3-phenyl-1-(1H-pyrrol-2-yl)-2-propen-1-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 140-29-4 phenylacetonitrile 
• 5432-07-5 (Z)-3-(4-methoxyphenyl)-2-phenylacrylonitrile 
• 100-39-0 benzyl bromide 

Downstream Products

• 1346463-51-1 4-(4-methoxyphenyl)-5-phenylpenta-(2E,4Z)-dienoyl azide 
• 1346463-38-4 4-(4-methoxyphenyl)-5-phenylpenta-(2E,4Z)-dienoic acid 
• 1346463-28-2 (E)-2-(4-methoxyphenyl)-3-phenylacrylaldehyde 
• 181421-22-7 (Z)-2-(4-methoxyphenyl)-3-phenylacrylaldehyde 
• 5218-97-3 2-<4-Methoxy-phenyl>-3-oxo-3-phenyl-propionsaeure-amid 
• 72433-40-0 (Z)-2-(4-Methoxy-phenyl)-3-nitro-3-phenyl-acrylonitrile 
• 5840-58-4 2-(4-methoxyphenyl)-3-phenylpropanenitrile 

Relevant academic research and scientific papers

Accelerated Discovery of α-Cyanodiarylethene Photoswitches

Cyanodiarylethene chromophores are able to undergo constitutional exchange via dynamic covalent chemistry (DCC). During this process, the central ethylene bridge of the molecular scaffold can be broken and thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible CC double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially improved properties. When subject to irradiation with light of adequate wavelength, α-cyanodiarylethenes undergo Z/E isomerization followed by ring-closure. By screening the thus accessible dynamic chromophore libraries using a desired detection wavelength, we could identify specific dithienyl analogues that exhibit three-state photochromism. The combination of dynamic constitutional libraries of functional chromophores in combination with the light-guided screening and selection should lead to more rapid exploration of structural diversity dye chemistry.

Pd(II)-Catalyzed CC Bond Cleavage by a Formal Group-Exchange Reaction

A chelation-assisted palladium-catalyzed CC bond cleavage of α, β-unsaturated ketone to form alkenyl nitrile in the presence of nitrile is disclosed on the basis of a formal group-exchange reaction formulated as C1C2 + C3 → C1C3 + C2, differing from normal alkene oxidative cleavage and metathesis type. The isolated key active Pd(II) complex as well as deuterium-labeled experiment revealed the necessity of the chelation group, and a plausible catalytic pathway was proposed.

Facile Preparation of α-Cyano-α,ω-Diaryloligovinylenes: A New Class of Color-Tunable Solid Emitters

An efficient Knoevenagel condensation reaction was used to construct a series of α-cyano-α,ω-diaryloligovinylenes, which show prominent fluorescence emission in the solid state. On investigating the effect of conjugation length on fluorescent properties,

Substituent effects on the iodine-catalyzed thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates: Mechanistic studies

The thermal cyclization of 3,4-diphenylbuta-1,3-dienyl isocyanates 1, generated in situ from the corresponding azides, was investigated using iodine as a catalyst. Diphenylpyridinones 2, phenylnaphthalenes 3, and indenes 4 were produced via intramolecular ring closure. The nature of the substituents on the phenyl rings was found to be crucial to the distribution of cyclized products 2 - 4. The mechanism of the reaction is also discussed.

Synthesis, characterisation and photophysical properties of a,a-diaryl-acrylonitrile derivatives

a,b-Diarylacrylonitrile derivatives can be prepared by two different routes: (1) the intermolecular condensation of the same arylacetonitriles (2) the condensation of arylaldehydes and arylacetonitriles with a catalytic amount of NaOCH3 at room temperature. Several a,b-diarylacrylonitrile derivatives have been synthesised in this paper and characterised. The UV-vis absorption and photoluminescent (PL) spectra of the products were investigated.

Generation and reaction of ammonium ylides in basic two-phase systems

Reaction of the quaternary ammonium salts 2a-i with electrophilic alkenes 3, active alkylating agents 7 or aromatic aldehydes 11, carried out in basic two-phase systems A-D, afforded cyclopropanes 4, cyanoalkenes 8 or cyanooxiranes 12 respectively, via the corresponding ammonium ylides 2+-. The method is very simple, and gives cyclopropanes 4 and cyanoalkenes 8 in high yield. Under similar conditions, 1-cyanodienes 8aa,ba were cyclopropanated at the γ,δ-double bond with formation of vinylcyclopropanes 9a,b. The stereochemistry of the prepared cyclopropanes was elucidated from literature, 1H NMR spectroscopic data, NOE experiments or X-ray single crystal analysis. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Solvent-free condensation of phenylacetonitrile and nonanenitrile with 4-methoxybenzaldehyde: Optimization and mechanistic studies

The condensation of phenylacctonitrile with 4-methoxybenzaldehyde can he carried out by two solvent-free methods: i) using neat powdered KOH at room temperature with equivalent amounts of aldehyde, nitrile and base for 3 min, and ii) using K2CO3 in the presence of a phase transfer agent for 3 min under microwave activation or conventional heating. By extending the reaction time up to 10 min, four different products were obtained from phenyl or nitrile group migration. With nonanenitrile, only the second method could be applied to give two kinds of condensed compounds with or without phenyl (or nitrile) group migration. The intervention of non-thermal MW-specific effects was proved in some cases and interpreted. The Royal Society of Chemistry 2005.

Estrogen receptor-β potency-selective ligands: Structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues

Through an effort to develop novel ligands that have subtype selectivity for the estrogen receptors alpha (ERα) and beta (ERβ), we have found that 2,3-bis(hydroxyphenyl)propionitrile (DPN) acts as an agonist on both ER subtypes, but has a 70-fold higher relative binding affinity and 170-fold higher relative potency in transcription assays with ERβ than with ERα. To investigate the ERβ affinity- and potency-selective character of this DPN further, we prepared a series of DPN analogues in which both the ligand core and the aromatic rings were modified by the repositioning of phenolic hydroxy groups and by the addition of alkyl substituents and nitrile groups. We also prepared other series of DPN analogues in which the nitrile functionality was replaced with acetylene groups or polar functions, to mimic the linear geometry or polarity of the nitrile, respectively. To varying degrees, all of the analogues show preferential binding affinity for ERβ (i.e., they are ERβ affinity-selective), and many, but not all of them, are also more potent in activating transcription through ERβ than through ERα (i.e., they are ERβ potency-selective). meso-2,3-Bis(4-hydroxyphenyl)succinonitrile and dl-2,3-bis(4-hydroxyphenyl)succinonitrile are among the highest ERβ affinity-selective ligands, and they have an ERβ potency selectivity that is equivalent to that of DPN. The acetylene analogues have higher binding affinities but somewhat lower selectivities than their nitrile counterparts. The polar analogues have lower affinities, and only the fluorinated polar analogues have substantial affinity selectivities. This study suggests that, in this series of ligands, the nitrile functionality is critical to ERβ selectivity because it provides the optimal combination of linear geometry and polarity. Furthermore, the addition of a second nitrile group β to the nitrile in DPN or the addition of a methyl substitutent at an ortho position on the β-aromatic ring increases the affinity and selectivity of these compounds for ERβ. These ERβ-selective compounds may prove to be valuable tools in understanding the differences in structure and biological function of ERα and ERβ.

Kinetic Study of the Base-catalysed Reactions of Benzaldahehyde and Thiophene-2-carbaldehyde with Acetonitriles

The reaction rates of the sodium methoxide-catalysed condensation of benzaldehyde and thiophene-2-carbaldehyde with heteroaromatic acetonitriles ArCH2CN; Ar = C6H5, C6H4CH3(p), C6H4-OCH3(p), C6H4F(p), C6H4Cl(p), C6H4Br(p), 2-thienyl, 3-thienyl, 3-pyridyl

Reaction of Aryl Aldehydes with Thiocyanates in the Presence of Tributylphosphine

Aryl aldehydes react with methyl thiocyanate in the presence of tributylphosphine to afford S-methyl thiobenzoates and arylacetonitriles in good yields.This is a novel disproportionation reaction involving carbon-carbon bond formation.These compounds thus obtained are easily converted into deoxybenzoins using sodium hydride.On the other hand, p-dialkylaminobenzaldehydes react with methyl thiocyanate under the same conditions to furnish both the corresponding trans-dicyanostilbenes and succinonitriles in moderate yields.Finally, the reaction was carried out with aryl thiocyanates resulting in the formation of addition products.