171290-53-2

Usage

Uses

3-Ethynylbenzonitrile is a useful research chemical.

InChI:InChI=1/C9H5N/c1-2-8-4-3-5-9(6-8)7-10/h1,3-6H

Upstream product

• 190771-22-3 3-((trimethylsilyl)ethynyl)benzonitrile 
• 69113-59-3 3-iodobenzonitrile 
• 1066-54-2 trimethylsilylacetylene 
• 24964-64-5 3-Cyanobenzaldehyde 
• 90965-06-3 dimethyl 1-(1-diazo-2-oxopropyl)phosphonate 
• 994-89-8 tributylethynyltin 
• 2074-87-5 carbon nitride 
• 536-74-3 phenylacetylene 
• 766539-54-2 3-(3-hydroxy-3-methylbut-1-ynyl)benzonitrile 
• 253684-22-9 3-(2,2-dibromovinyl)benzonitrile 
• 1785-61-1 1,3-diethynylbenzene 
• 74-86-2 acetylene 
• 558-13-4 carbon tetrabromide 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 

Downstream Products

• 956297-44-2 (R)-2-[5-(3-Cyano-phenyl)-isoxazol-3-yl]-piperidine-1-carboxylic acid tert-butyl ester 
• 866686-09-1 3-(5-methylsulfanylpyridin-3-ylethynyl)-benzonitrile 
• 866684-62-0 3-(5-chloropyridin-3-ylethynyl)-benzonitrile 
• 866684-69-7 3-(5-fluoropyridin-3-ylethynyl)-benzonitrile 
• 914942-92-0 tert-butyl 6-amino-7-(2-(3-cyanophenyl)ethynyl)-1-methyl-1H-imidazo[4,5-c]pyridin-4-yl(methyl)carbamate 
• 1025053-94-4 C₂₀H₁₅N₃O₂ 
• 1025053-21-7 C₁₈H₁₀F₃N₃ 
• 1015419-95-0 (S,E)-3-(5-(2-methoxyphenylimino)-1,2,3,5,8,8a-hexahydroindolizin-7-yl)benzonitrile 
• 1017259-38-9 2-(3-cyanophenyl)benzofuran-5-carbonitrile 
• 1017261-15-2 2-(3-cyanophenyl)benzofuran-6-carbonitrile 
• 1201666-82-1 3,3'-(1H-1,2,3-triazole-1,4-diyl)dibenzonitrile 
• 1204834-32-1 (Z)-1-(3-cyanophenyl)-3,3-dimethyl-1-phenyl-1-butene 
• 1261302-48-0 3,3'-(E)-but-1-en-3-yne-1,4-diylbis(benzonitrile) 
• 1201666-83-2 1-(4-cyanophenyl)-4-(3-cyanophenyl)-1H-1,2,3-triazole 

Relevant academic research and scientific papers

A chemical dynamics, kinetics, and theoretical study on the reaction of the cyano radical (CN; X2Σ+) with phenylacetylene (C6H5CCH; X1A1)

The chemical reaction dynamics to form o-, m-, and p-cyanophenylacetylene via the neutral-neutral reaction of ground state cyano radicals with phenylacetylene and D1-phenylacetylene were investigated in crossed beam experiments; these studies were combined with kinetics measurements of the rate coefficients at temperatures of 123, 200, and 298 K and supplemented by electronic structure calculations. The data suggest that the reaction is initiated by a barrier-less addition of the electrophilic cyano radical to the o-, m-, or p-position of the aromatic ring. The eventually fragmented via atomic hydrogen elimination to form o-, m-, and p-cyanophenylacetylene via tight exit transition states with the hydrogen atom being ejected almost perpendicularly to the molecular plane of the rotating complex. The overall reaction to form o-, m-, and p-cyanophenylacetylene was found to be exoergic by 89 ± 18 kJ mol-1 in nice agreement with the calculations. The o-cyanophenylacetylene isomer is of particular relevance as a potential building block to the formation of nitrogen-substituted didehydronaphthalene molecules in analogy to didehydronaphthalene in Titan's aerosol layers - a pathway hitherto neglected by the planetary science modeling community.

Application of FSO2N3 in preparation of diazo reagent

The invention discloses application of FSO2N3 in preparation of a diazo reagent. The application comprises the following step: in the presence of alkali, FSO2N3 and acetone dimethyl phosphate as shown in a formula 2 are subjected to a reaction as shown in the specification, and a Bestmann-Ohira and/or Seyferth-Gilbert reagent is obtained. According to the application, the Seyferth-Gilbert reagent and/or the Bestmann-Ohira reagent can be obtained at a high yield in half an hour, the two mixed reagents generated in the reaction do not need to be separated, and the one-pot method is directly applied to the synthesis of the terminal alkyne compound. And/or like.

DBU-Mediated Synthesis of Aryl Acetylenes or 1-Bromoethynylarenes from Aldehydes

Two well known synthetic organic reactions Ramirez olefination and Corey-fuchs reactions are integrated in one-pot sequential manner for the synthesis of arylacetylenes and 1,3-enynes starting directly from commercially available aldehydes. The bicyclic amidine 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) along with additive NaOH not only exclusively afforded the terminal alkynes directly from the aldehydes, but also enhanced the reaction rate. The dynamic nature of DBU also facilitated the isolation of 1-bromoalkynes intermediate products. Selection of additive from NaOH and H2O served as a switch for the synthesis of terminal alkyne and 1-bromoalkynes, respectively. (Figure presented.).

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes

Gold(i)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium salts.

Reaction discovery using acetylene gas as the chemical feedstock accelerated by the stop-flow micro-tubing reactor system

Acetylene gas has been applied as a feedstock under transition-metal catalysis and photo-redox conditions to produce important chemicals including terminal alkynes, fulvenes, and fluorinated styrene compounds. The reaction discovery process was accelerated through the use of stop-flow micro-tubing reactors. This reactor prototype was developed by joining elements from both continuous micro-flow and conventional batch reactors, which was convenient and effective for gas/liquid reaction screening. Notably, the developed transformations were either inefficient or unsuccessful in conventional batch reactors. Its success relies on the unique advantages provided by this stop-flow micro-tubing reactor system.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

COMPOUND HAVING AGONISTIC ACTIVITY TO SOMATOSTATIN RECEPTOR AND MEDICINAL USE THEREOF

Provided is a somatostatin receptor subtype-2 agonist. A compound represented by general formula (I) [wherein each symbol has the same meaning as defined in the description], a salt thereof, an N-oxide thereof or a solvate thereof, or prodrugs of the same, which are low-molecular compounds having potent agonistic activity to somatostatin receptor subtype-2 and, therefore, can be administered in a simpler manner and have high safety and low toxicity, are useful in preventing and/or treating somatostatin-related diseases such as acromegaly and gastrointestinal obstruction.

COMPOUND HAVING SOMATOSTATIN RECEPTOR AGONIST ACTIVITY AND MEDICAL USE THEREOF

This invention provides a somatostatin receptor subtype 2 agonist. The compound of the present invention represented by general formula (I): [wherein the definitions of all signals therein are the same as the specification defined] or salt, N-oxide or solvate thereof, or prodrug thereof, is a low molecular compound having strong somatostatin receptor subtype 2 agonist activity, and therefore can be administered via simple methods. Further, the compound of the present invention is useful for prophylaxis and/ or treatment of somatostatin associated diseases such as acromegaly, alimentary tract obstruction, and the likes due to its high stability and low toxity.

The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity

The dual role of the bicyclic amidine base 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was demonstrated in a synthesis of terminal aryl- and styryl-acetylenes. Mechanistically, a tandem process involving elimination/Umpolung/protonation occurs in a single step to generate terminal aryl- and styryl-acetylenes from geminal dibromoalkenes. The key to the success of this transformation lies in the organobase-mediated generation of the acetylide from the 1-bromoalkynes at room temperature. The unique characteristics of DBU as an inherently safer reagent make it an attractive alternative to previous systems wherein required pyrophoric reagents and nonambient temperatures remain unsolved issues. The procedure does not work for the synthesis of alkyl-acetylenes.

Design, Synthesis, and Evaluation of Triazole Derivatives That Induce Nrf2 Dependent Gene Products and Inhibit the Keap1-Nrf2 Protein-Protein Interaction

The transcription factor Nrf2 regulates the expression of a large network of cytoprotective and metabolic enzymes and proteins. Compounds that directly and reversibly inhibit the interaction between Nrf2 and its main negative regulator Keap1 are potential pharmacological agents for a range of disease types including neurodegenerative conditions and cancer. We describe the development of a series of 1,4-diphenyl-1,2,3-triazole compounds that inhibit the Nrf2-Keap1 protein-protein interaction (PPI) in vitro and in live cells and up-regulate the expression of Nrf2-dependent gene products.