123871-50-1

Basic information

• Product Name: Naphthalene, 2-[(1E)-2-(4-methoxyphenyl)ethenyl]-
• Synonyms: methyl 4-[2-(2-naphthyl)vinyl]phenyl ether
• CAS NO: 123871-50-1
• Molecular Formula: C₁₉H₁₆O
• Molecular Weight: 260.32974
• Mol File: 123871-50-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Naphthalene, 2-[(1E)-2-(4-methoxyphenyl)ethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene, 2-[(1E)-2-(4-methoxyphenyl)ethenyl]-(123871-50-1)
• EPA Substance Registry System: Naphthalene, 2-[(1E)-2-(4-methoxyphenyl)ethenyl]-(123871-50-1)

Safety Data

• Hazardous Substances Data: 123871-50-1(Hazardous Substances Data)

Upstream product

• 696-62-8 para-iodoanisole 
• 827-54-3 2-naphthylethylene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 836-41-9 p-methoxybenzylidene-phenylamine 
• 91-57-6 2-Methylnaphthalene 
• 6303-59-9 (E)-4-(2-bromo-vinyl)-anisole 
• 21473-01-8 2-naphthalenylmagnesium bromide 
• 637-69-4 4-Methoxystyrene 
• 450-58-8 2-naphthyldiazonium tetrafluoroborate 
• 91-59-8 naphthalen-2-ylamine 
• 1145-93-3 diethyl 4-methoxybenzylphosphonate 
• 66-99-9 β-naphthaldehyde 
• 105-13-5 4-Methoxybenzyl alcohol 
• 7228-47-9 2-(2-naphthyl)ethanol 

Downstream Products

• 4176-45-8 2-methoxy-benzo[c]phenanthrene 
• 22717-94-8 2-hydroxybenzo[c]phenanthrene 
• 39070-97-8 (4-methoxyphenyl)(2-naphthyl)methanone 

Relevant articles and documents

Synthesis of Helical Quinone Derivatives by Oxidative Coupling of Substituted 2-Hydroxybenzo[c]phenanthrenes

A concise synthesis of novel substituted quinone derivatives from commercially available starting materials was developed. For this synthesis, classical photo-induced 6π-electrocyclization was utilized, followed by oxidative aromatization reaction, and su

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.

Stereospecific Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Cross-Coupling of Aryllithium with Vinyl Halides

We present herein an efficient synthetic protocol involving iron-catalyzed cross-coupling of organolithium compounds with vinyl halides as key coupling partners. More than 30 examples were obtained with moderate to good yields and high stereoselectivities. The practicality of this method is evidenced by a gram-scale synthesis. In addition, a preliminary mechanistic investigation was also performed.

Novel Carbazole-Based N-Heterocyclic Carbene Ligands to Access Synthetically Relevant Stilbenes in Pd-Catalyzed Coupling Processes

A series of new carbazole-based N-heterocyclic carbene (NHC) ligands have been synthesized in a simple and facile synthetic route and subsequently used in a Pd/carbazole-based NHC catalytic system, which was found to be effective in catalyzing Heck reactions to provide substituted stilbene derivatives in good yields. Several bioactive stilbenes, including pterostilbene, pinosylvin, trimethoxy resveratrol, and resveratrol, were synthesized in good yields, and a 10 mmol scale-up was also performed for trimethoxy resveratrol. The synthetic application was also extended by performing a double-tandem chemoselective Heck reaction followed by Miyaura borylation in a one-pot procedure to give single-step access to synthetically useful stilbenyl boronate esters. Similarly, a unique triple-tandem protocol of a chemoselective Heck reaction/Miyaura borylation/Suzuki–Miyaura coupling reaction sequence was performed for the one-pot modification of biologically relevant molecules.

Model Guided Development of a Simple Catalytic Method for the Synthesis of Unsymmetrical Stilbenes by Sequential Heck Reactions of Aryl Bromides with Ethylene

Stilbenes are important and useful structural moieties, but methods for their preparation typically possess numerous inefficiencies. Presented here is a methodology for the two-step, one pot preparation of unsymmetrical stilbenes via sequential Heck reactions. The first Heck reaction with ethylene gas was analysed as a function of temperature and pressure for electronically differentiated naphthyl bromides and model-aided reaction optimization was utilized to define the system. In addition, reactNMR was utilized to determine ethylene solubility in common organic solvents useful for Heck reactions. Finally, an optimized sequential Heck reaction process was developed and applied to a range of substrates allowing for efficient preparation of unsymmetrical stilbenes, including the natural antioxidant, pterostilbene. (Figure presented.).

Nickel-catalyzed synthesis of (E)-olefins from benzylic alcohol derivatives and arylacetonitriles via C-O activation

An efficient Ni-catalyzed synthesis of (E)-olefins using the readily available benzylic alcohol derivatives and arylacetonitriles is described. This transformation should proceed via a tandem process involving nickel-catalyzed cross coupling via C-O activation and subsequent stereoselective E2 elimination.

THERAPEUTIC AGENTS FOR SKIN DISEASES AND CONDITIONS

The present invention relates to method(s) of treating a subject afflicted with a skin disease or condition, the method comprising administering to the subject or patient in need a composition comprising a therapeutically effective amount of a substituted cis or trans- stilbene or a stilbene hybrid. A method of treating or reducing the likelihood of a skin disease or condition in a patient is an additional embodiment of the present invention. Preferred pharmaceutical compositions of the invention include nanoemulsions comprising a therapeutically effective amount of a substituted cis or trans-stilbene or stilbene hybrid and at least one antibiotic.

N,N′-Mono substituted acyclic thioureas: Efficient ligands for the palladium catalyzed Heck reaction of deactivated aryl bromides

A series of N,N′-mono substituted acyclic thiourea ligands are found to be highly active phosphine-free catalysts for palladium catalyzed Heck reaction of aryl iodides and bromides with olefins. We have achieved high turnover numbers for aryl iodides with olefins (TONs up to 970,000 for the reaction of iodobenzene with styrene).

Asymmetric catalysis on the nanoscale: The organocatalytic approach to helicenes

The first asymmetric organocatalytic synthesis of helicenes is reported. A novel SPINOL-derived phosphoric acid, bearing extended π-substituents, catalyzes the asymmetric synthesis of helicenes through an enantioselective Fischer indole reaction. A variety of azahelicenes and diazahelicenes could be obtained with good to excellent yields and enantioselectivities. Twisting indoles: A novel chiral Bronsted acid, specifically designed for long-range control on a nanoscale, catalyzes the asymmetric synthesis of azahelicenes through a Fischer indolization. The method has the advantage of starting from simple achiral starting materials, which can be modified by changing the protecting group (R2) or the terminal substituents (R1, R3). The products can be further oxidized to polyaromatic systems.

Palladium nanoparticles in glycerol: A versatile catalytic system for C-X bond formation and hydrogenation processes

Palladium nanoparticles stabilised by tris(3-sulfophenyl)phosphine trisodium salt in neat glycerol have been synthesised and fully characterised, starting from both Pd(II) and Pd(0) species. The versatility of this innovative catalytic colloidal solution has been proved by its efficient application in C-X bond formation processes (X=C, N, P, S) and C-C multiple bond hydrogenation reactions. The catalytic glycerol phase could be recycled more than ten times, preserving its activity and selectivity. The scope of each of these processes has demonstrated the power of the as-prepared catalyst, isolating the corresponding expected products in yields higher than 90%. The dual catalytic behaviour of this glycerol phase, associated to the metallic nanocatalysts used in wet medium (molecular- and surface-like behaviour), has allowed attractive applications in one-pot multi-step transformations catalysed by palladium, such as C-C coupling followed by hydrogenation, without isolation of intermediates using only one catalytic precursor. Copyright