437611-95-5

Usage

Aldehyde derivative

Benzaldehyde group
A derivative of benzaldehyde, with additional substituents attached to the benzene ring.

Substituents

4-Trifluoromethyl and phenylethynyl
Two functional groups attached to the benzene ring, providing unique properties and reactivity.

Usage in organic synthesis

Building block for pharmaceuticals and agrochemicals
A key intermediate compound used to synthesize various pharmaceutical and agrochemical products.

Potential biological and pharmacological activities

Studied for possible applications
The compound has been researched for its potential effects on biological systems and pharmacological properties.

Unique physical and chemical properties

Trifluoromethyl group
The presence of a trifluoromethyl group imparts special characteristics, making the compound valuable in research and applications.

Upstream product

• 705-31-7 4-trifluoromethylphenylacetylene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 38846-64-9 2-ethynylbenzaldehyde 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 77123-58-1 2-[2-(trimethylsilyl)ethynyl]benzaldehyde 
• 5159-41-1 2-iodobenzyl alcohol 
• 455-13-0 4-Iodobenzotrifluoride 
• 753454-92-1 [2-(4-trifluoromethyl-phenylethynyl)-phenyl]-methanol 

Downstream Products

• 612-94-2 2-phenylnaphthalene 
• 1361016-91-2 C₂₄H₁₅F₃O 
• 1226977-90-7 6-[4-(trifluoromethyl)phenyl]-11bH-isoquinolino[2,1-a]pyrrolo-[2,1-c]quinoxaline 
• 1403583-64-1 6-[4-(trifluoromethyl)phenyl]benzo[4,5]imidazo[2,1-a]isoquinoline 
• 1389315-59-6 2-benzyl-4-bromo-3-(4-trifluoromethylphenyl)isoquinolin-1(2H)-one 
• 1360811-35-3 furan-2-yl(2-((4-(trifluoromethyl)phenyl)ethynyl)phenyl)methanone 

Relevant academic research and scientific papers

Tunable Synthesis of Indeno[1,2- c]furans and 3-Benzoylindenones via FeCl3-Catalyzed Carbene/Alkyne Metathesis Reaction of o-Alkynylbenzoyl Diazoacetates

An efficient synthesis of indeno[1,2-c]furan and 3-benzoylindenone derivatives through a FeCl3-catalyzed carbene/alkyne metathesis reaction of o-alkynylbenzoyl diazoacetates is presented. Mechanistically, the key intermediate, vinyl iron carbene, is formed by 5-exo-dig carbocyclization and terminated with a formal [3 + 2] cycloaddition or carbonylation. To the best of our knowledge, this is the first example in which FeCl3 is used as a catalyst for a carbene/alkyne metathesis reaction. Finally, derivatization reactions were carried out to showcase the value of the products.

One-pot Synthesis of Isoquinoline-Fused Isoquinolines via Intramolecular Hydroamination/Aza-Claisen Type Rearrangement Cascade

A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from α-amino acid esters and 2-alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet-Spengler reaction between α-amino acid esters and 2-alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold-catalyzed intramolecular hydroamination furnishes isoquinoline-fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines via subjecting the N-allylated isoquinoline intermediates to gold-catalyzed intramolecular hydroamination followed by aza-Claisen type rearrangement. (Figure presented.).

Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding β-aminophosphonates or PARP1-inhibitor analogues.

Transition-Metal-Free Reverse Reactivity of (2-Alkynyl)-Arylaldimines: Assembly of Functionalized Amino-Indinones

Transition-metal-free regioselective synthesis of functionalized amino-indenones by the reaction of ortho-alkynylaldehydes with a broad range of primary amines by intramolecular cyclization has been described. The designed reaction proceeds through KOH-mediated Prins-type cyclization and DMSO-promoted oxidation of the cyclopent-2-en-1-one system. The proposed mechanism and role of solvent were well supported by control experiments. For the first time, we have disclosed the reverse reactivity of (2-alkynyl)-arylaldimines in a super basic system.

A Mild and Regioselective Synthesis of α-Fluoroketones via Gold and Selectfluor Partnership

An efficient, mild and rapid synthesis of α-fluoroketones has been developed, via a fruitful association between gold and Selectfluor starting from aldehyde-yne and alkynylaryl ketone derivatives. Several functionalized and synthetically highly valuable α-fluoroketones (21 compounds, up to 92%) were isolated in good to excellent yields via a remarkable regioselective oxyfluorination reaction in EtOH/H2O at room temperature. We have shed some light on parts of the mechanism by reacting diphenylacetylene and aldehyde-yne with or without Selectfluor. The reaction most presumably occurs via a sequential gold-catalyzed regioselective hydration followed by the α-fluorination reaction, but the presence of aldehyde moiety is crucial for the reactivity of alkyne function. The fluoroketones were efficiently transformed to 4-fluoroisoquinolines (9 compounds, 82–95%) of high pharmaceutical interest. (Figure presented.).

Hydrophilic Pd-phosphines catalyzed one-pot synthesis of substituted isoquinolines, furopyridines and thienopyridines in aqueous medium

A first example of simple and efficient hydrophilic Pd-phosphine complexes catalyzed one-pot three-component reaction of ortho-bromo aldehydes, terminal alkynes and ammonium acetate proceeds through the tandem coupling-imination-annulation path for the synthesis of substituted isoquinolines, furopyridines and thienopyridines in good to excellent yields in green aqueous medium at mild temperature was described.

NOVEL COMPOUNDS EXHIBITING PHOTOPHYSICAL PROPERTIES UPON FORMATION OF LEWIS ACID-BASE ADDUCTS USING NON-CHELATING BORANES, METHOD FOR PRODUCING THE SAME AND DEVICES INCLUDING THE SAME

The present invention relates to novel compounds exhibiting photophysical properties upon formation of Lewis acid-base adducts using non-chelating boranes and methods for producing the same as well as devices that include such Lewis acid-base adducts of the following general formula (I).

Synthesis of selectively 4-substituted 9,9′-spirobifluorenes and modulation of their photophysical properties

Synthesis of selectively 4-substituted 9,9′-spirobifluorenes was accomplished by using catalytic [2 + 2 + 2]-cyclotrimerization of specifically substituted diynols with alkynes to the corresponding fluorenols. Further synthetic transformations provided the target molecules. The measurement of the photophysical properties of the prepared 4-substituted 9,9′-spirobifluorenes revealed that their emission maxima depended on the electronic properties of the substituents present in the para position: the presence of an electron accepting group strongly favored the maxima red shift toward the blue VIS region (CF3λmax = 361 nm vs. MeO λmax = 330 nm). Adding further substituents (aryl or arylethynyl moieties) on the phenyl ring in position 4 did not lead to a dramatic improvement in the emission maxima (CF3C6H4, λmax = 369 nm, CF3C6H4CC, λmax = 370 nm), but increased their quantum yields considerably. In addition, a series of 9,9′-spirobifluorenes possessing various extended π-systems (pyrene, anthracene, etc.) were synthesized. In general, the emission maxima pattern reflected that of the parent π-systems, but they were red shifted by 10-30 nm. Finally, also a 1-[4-(9,9′-spirobifluorene-4-yl)phenyl]-2-aryl-ortho-carborane was prepared. These data thus may provide guidelines for further design of 9,9′-spirobifluorenes with tailored properties.

A gold(i)-catalyzed intramolecular tandem cyclization reaction of alkylidenecyclopropane-containing alkynes

A novel gold(i)-catalyzed intramolecular tandem cyclization reaction of ortho-(arylethynyl)arenemethylenecyclopropanes provided an efficient approach to prepare functionalized 11H-benzo[a]fluorene derivatives in moderate to good yields. Further transformations as well as applications of the products have been presented and a plausible reaction mechanism has also been proposed on the basis of deuterium labeling and control experiments.

Gold-Catalyzed Ring Expansion of Enyne-Lactone: Generation and Transformation of 2-Oxoninonium

An efficient gold-catalyzed ring-expansion reaction of enyne-lactones to form 2-oxoninonium intermediates is reported. The 2-oxoninonium generated in this work could undergo further 6π electrocyclization and aromatization reaction to produce different aromatic compounds.