78725-57-2

Upstream product

• 67-36-7 4-phenoxy benzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 913976-99-5 C₁₈H₁₆O₂ 
• 276884-31-2 rac-(Z)-1,3-dihydro-4-[3-hydroxy-3-(4-phenoxyphenyl)-1-propynyl]-3-[(3-methoxy-1H-pyrrol-2-yl)methylene]-2H-indol-2-one 
• 935749-27-2 2,3-dimethylpropionic acid 1-(4-phenoxyphenyl)-buta-2,3-dienyl ester 
• 913977-10-3 acetic acid 1-(4-phenoxyphenyl)-hex-5-en-2-ynyl ester 

Relevant academic research and scientific papers

Coupling-isomerization synthesis of chalcones

The Sonogashira coupling of electron-deficient (hetero)aryl halides 1 and (hetero)aryl or alkenyl 1-propargyl alcohols 2 does not terminate at the stage of the expected internal propargyl alcohols, but rather gives rise to the formation of α,β-unsaturated ketones 3 with a variety of acceptor substituents. This new domino reaction, a coupling-isomerization reaction (CIR), can be rationalized as a sequence of rapid Pd/Cu-catalyzed alkynylation followed by a slow amine-base-catalyzed propargyl alcohol-enone isomerization. Performing the CIR in deuterated protic solvents or with a selectively deuterated propargyl alcohol revealed that the base-catalyzed isomerization step proceeds through a formal 1,3-H shift with minimal H/D exchange with the surrounding solvent. Additionally, 19F NMR kinetic measurements on the isomerization step with the fluorinated propargyl alcohol 4r support the mechanistic rationale.

Regioselectivity Switch in Palladium-Catalyzed Allenylic Cycloadditions of Allenic Esters: [4+1] or [4+3] Cycloaddition/Cross-Coupling

The first Pd-catalyzed asymmetric allenylic [4+1] cycloaddition was successfully developed. Alternatively, tuning the Pd catalyst switched the reactivity toward an unprecedented [4+3] cycloaddition/cross-coupling. Ligands play a vital role in controlling the reaction pathway, allowing highly selective access to different products from identical substrates. Biological evaluation of the obtained compounds led to the discovery of new antitumor targets. A possible mechanism is proposed, suggesting two interesting catalytic cycles for the cycloaddition with palladium-butadienyls. This study also demonstrated the potential and utility of allenic esters as 1,4-biselectrophiles and C4 synthons for participating in cycloaddition reactions.

Parallel synthesis of "Click" chalcones as antitubulin agents

It has been shown that some chalcones are able to inhibit tubulin polymerization, giving cytotoxicity and destruction of tumoral vasculature. A library of 180 novel chalcone analogs has been synthesized via click chemistry and screened for their cytotoxic

Gold(I) catalyzed isomerization of 5-en-2-yn-1-yl acetates: An efficient access to acetoxy bicyclo[3.1.0]hexenes and 2-cycloalken-1-ones

The gold(I) catalyzed rearrangement of 5-en-2-yn-1-yl acetates into functionalized acetoxy bicyclo[3.1.0]hexenes is described. The mild reaction conditions employed allow the efficient and rapid synthesis of a variety of such bicyclic compounds via a sequence of two gold(I)-catalyzed isomerization steps. Acetoxy bicyclo[3.1.0]hexenes products can be further transformed to 2-cycloalkenones by simple methanolysis. Copyright

4- AND 5-ALKYNYLOXINDOLES AND 4- AND 5-ALKENYLOXINDOLES

4- and 5-alkynyloxindoles as well as 4- and 5-alkenyloxindoles having formula (I) and (II), wherein R, R, R, R, R, X and z have the meaning indicated in the specification, inhibit or modulate protein kinases, in particular JNK protein kinases and are useful as anti-inflammatory agents, particularly in the treatment of rheumatoid arthritis.

Alkyne compounds and method of use

Alkyne compounds of the formula STR1 wherein R1 is H, alkyl of up to 4 carbon atoms or phenyl; R2 is H, aliphatic acyl of up to 6 carbon atoms or aroyl of up to 11 carbon atoms; R3 and R4 are H, F, Cl or Br and n is 0 or 1, and physiologicaly acceptable metals salts thereof, have antiinflammatory activity. These compounds can be made from compounds of the formula STR2 wherein Q is a functionally-modified hydroxy and R1, R3, R4 and n are as above by treatment with a solvolyzing agent.