63221-88-5

Usage

Uses

Used in Organic Synthesis:
1-(4-ETHYLPHENYL)-2-(4-METHOXYPHENYL)ACETYLENE is used as a building block in organic synthesis for the production of various other compounds. Its unique structure and functional groups make it a valuable component in the synthesis of complex organic molecules.
Used in Research:
In the field of research, 1-(4-ETHYLPHENYL)-2-(4-METHOXYPHENYL)ACETYLENE is employed as a subject of study to explore its potential applications and properties. Its unique structure and reactivity provide opportunities for understanding and developing new synthetic pathways and methodologies.
Used in Pharmaceutical and Biological Activities:
1-(4-ETHYLPHENYL)-2-(4-METHOXYPHENYL)ACETYLENE is used as a compound of interest in the field of medicinal chemistry due to its potential pharmaceutical and biological activities. Researchers are investigating its interactions with biological systems and its potential as a therapeutic agent for various diseases and conditions.
Used in Medicinal Chemistry:
In the application industry of medicinal chemistry, 1-(4-ETHYLPHENYL)-2-(4-METHOXYPHENYL)ACETYLENE is used as a compound with potential for drug development. Its unique structure and properties make it a promising candidate for the design and synthesis of new pharmaceutical agents, targeting specific biological pathways and mechanisms.

InChI:InChI=1/C17H16O/c1-3-14-4-6-15(7-5-14)8-9-16-10-12-17(18-2)13-11-16/h4-7,10-13H,3H2,1-2H3

Upstream product

• 768-60-5 4-methoxyphenylacetylen 
• 4748-78-1 4-ethylbenzylaldehyde 
• 1181615-23-5 3-(4-ethylphenyl)propiolic acid 
• 1950-68-1 4-methoxybenzenesulfonyl hydrazide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 40307-11-7 1-ethyl-4-ethynylbenzene 
• 696-62-8 para-iodoanisole 
• 25309-64-2 4-ethyl-1-iodobenzene 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 1352608-46-8 [(η4-C4(C6H4-4-C2H5)2(C6H4-4-OMe)2)Co(η5-C5H5)] 
• 1352608-64-0 [(η4-C4(C6H4-4-C2H5)2(C6H4-4-OMe)2)Co(η5-C5H5)] 
• 1380401-20-6 1-(4-ethylphenyl)-2-(4-methoxyphenyl)ethane-1,2-dione 

Relevant academic research and scientific papers

Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

Photoinduced copper-catalyzed site-selective C(sp2)-C(sp) cross-coupling via aryl sulfonium salts

The classical Sonogashira reaction of aryl electrophiles in the presence of Pd catalysts has been well established as a potent method for arylalkyne synthesis. However, the site-selective C(sp2)-C(sp) cross-coupling strategy using a non-noble-metal catalyst is rare. An efficient alternative approach for the synthesis of arylalkynes via a Cu-catalyzed Sonogashira-type reaction promoted by visible light is described. This method enables site-selective alkynylation from aryl sulfonium salts derived from diverse arenes to a set of arylalkynes with high selectivity and high functional-group compatibility. Moreover, rapid alkynylation of drug molecules is demonstrated.

Shuttling Catalyst: Facilitating C?C Bond Formation via Cross-Couplings with a Thermoresponsive Polymeric Ligand

A poly(ethylene glycol) (PEG) linked ortho-MeO-phenyldicyclohexylphosphine (MeO-WePhos) ligand has been synthesized to promote Pd-catalyzed carbon-carbon bond formation by cross-couplings including Sonogashira, Heck, Hiyama and Stille reactions, providing corresponding (hetero)aryl substituted alkynes, alkenes and bi(hetero)aryls in good to excellent isolated yields with low Pd loadings. Facilitated by the lower critical solution temperature behaviour of the polymeric monophosphine ligand, the metal-complex could rapidly shuttle between organic and water phases as regulated by temperature, enabling highly efficient catalyst recycling via a simple phase separation. The chemical structure of ligand was determined by matrix-assisted laser desorption/ionization-time of flight mass spectrometry, nuclear magnetic resonance spectrometry and size-exclusion chromatography measurements. Notably, as demonstrated by the inductively coupled plasma-atomic emission spectrometry measurement, 98% Pd was kept in the water phase after 6 cycles of catalyst recycling experiments. Given the profound impact of transition-metal-catalyzed covalent bond formation and the increasing demand of sustainable chemistry, this work provides an alternative method to conduct cross-couplings with a polymeric shuttling catalyst.

Method for preparing aryl internal alkyne compound through light-mediated copper catalysis

The invention relates to a method for preparing an aryl internal alkyne compound through light-mediated copper catalysis, and belongs to the field of organic chemistry. An aryl sulfide salt and a terminal alkyne are used as raw materials, a + 1 valent copper salt is used as a catalyst, potassium carbonate is used as alkali, reaction is performed in solvents such as DMSO to obtain the aryl internalalkyne compound, and the yield is 50%-86%. According to the synthetic method, the raw materials are easy to obtain, the reaction conditions are mild, a simple, convenient, green and efficient synthetic route of the internal alkyne compound is provided, and an effective method for introducing alkynyl into aromatic ring-containing drug molecules is provided.

Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides via a desulfinative process

In the presence of a Pd(ii)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the protection of inert gas or oxygen and are tolerant to many functional groups.

A palladium catalyzed aryl alkyne preparation method

The invention discloses a palladium catalyzed aryl alkyne of the preparation method, comprises the following steps: in the catalyst, under the action of the ligand and alkali, substituted with aryl sulfonyl chloride alkynoic occurs in the organic solvent escapes suosuo the coupling reaction, after the reaction is finished after treatment to obtain the aryl alkyne. Used in the preparation method of the cheap raw material, the reaction and simple post treatment operation, at the same time, the reaction less side reaction, high yield of the product.

Visible-Light-Assisted Cobalt-2-(hydroxyimino)-1-phenylpropan-1-one Complex Catalyzed Pd/Cu-Free Sonogashira–Hagihara Cross-Coupling Reaction

An effective and inexpensive strategy for the Co(C9H9NO2)3 catalyzed Sonogashira–Hagihara cross-coupling reaction of aryl bromides containing electron-rich and electron-poor substituents with terminal alkynes wa

Method for synergistically catalyzing Sonogashira cross-coupling reaction with carbonyl iron cluster compounds and trace palladium

The invention discloses a method for synergistically catalyzing a Sonogashira cross-coupling reaction with carbonyl iron cluster compounds and trace palladium. According to the method, palladium chloride and triiron dodecarbonyl are taken as catalysts, acetylenic ketone is taken as a ligand, methanol is taken as a solvent, aryl halide, terminal alkyne and K2CO3 are subjected to a reaction , and arylethynylene compounds are obtained. With the adoption of the method, the use amount of palladium metal is reduced obviously, reaction operation is simple, the condition is mild (the temperature is commonly about 60 DEG C), compatibility of functional groups is good, the yield is high, the use quantity of the catalysts is low, and the productivity is high.

Functionalized α,β-ynones: Efficient ligand for Cu catalyzed Sonogashira-type cross-coupling reaction

Under the classic reaction conditions, a large excess of copper catalyst and N, O donor ligands were mandatory for the catalytic cross-coupling of Csp2-Csp bonds. Herein, we wish to report α,β-ynones as σ-, π-electron donating ligands for copper catalyzed Sonogashira-type reaction. As low as 0.25-2.5 mol% of L11 (3-(4-bromophenyl)-1-(4-methoxyphenyl)prop-2-yn-1-one) significantly accelerated the 0.1-1.0 mol% of CuI catalyzed cross-coupling of aryl iodides with terminal alkynes and alkynylcarboxylic acids, respectively. This low-mol% catalyst system showed satisfactory activity and tolerance with 36 examples of substituted alkynes.

Acetyenic-ketone-promoted CuI-catalyzed method for conducting Sonogashira coupled reaction

The invention discloses an acetyenic-ketone-promoted CuI-catalyzed method for conducting a Sonogashira coupled reaction. The method includes the steps that acetyenic ketone rich in pi-sigma electrons serves as a ligand, CuI serves as a catalyst, a Sonogashira cross coupling reaction between aryl halide and terminal alkyne is catalyzed, and arylethynylene compounds are synthesized. The method is simple in operation and mild in condition, a substrate is good in applicability, a toxic phosphine ligand is avoided, CuI consumption is obviously reduced, and the method can be widely applied to synthesis of the arylethynylene compounds.