220649-65-0

Usage

Molecular Structure

Consists of a benzene ring with an aldehyde group and a propynyl group attached to it.

Propynyl Group

Substituted with a methoxy group, which consists of a methylene group connected to an oxygen atom.

Reactivity

Commonly used in organic synthesis and chemical reactions due to its reactive aldehyde and propynyl groups.

Building Block

Can be used as a building block in the synthesis of various pharmaceuticals, agrochemicals, and advanced materials.

Applications

May have applications in the fields of fragrance and flavor compounds due to its aromatic and functional group properties.

Upstream product

• 26260-02-6 2-iodobenzaldehyde 
• 627-41-8 propargyl alcohol methyl ether 
• 220650-26-0 3-(2-[1,3]dioxolan-2-yl)phenyl-2-propyn-1-ol 
• 152302-84-6 2-iodobenzaldehyde ethylene glycol ketal 
• 89-98-5 2-chloro-benzaldehyde 
• 6630-33-7 ortho-bromobenzaldehyde 
• 220650-27-1 2-[2-(3-methoxy-prop-1-ynyl)-phenyl]-[1,3]dioxolane 

Downstream Products

• 1422184-67-5 C₁₆H₁₈N₂O₂ 
• 1265917-71-2 C₁₅H₁₆O₃ 
• 864910-25-8 2-[2-(3-methoxyprop-1-ynyl)phenyl]cyclobutanone 

Relevant academic research and scientific papers

A Transient-Directing-Group Strategy Enables Enantioselective Reductive Heck Hydroarylation of Alkenes

Metal-coordinating directing groups have seen extensive use in the field of transition-metal-catalyzed alkene functionalization; however, their waste-generating installation and removal steps limit the efficiency and practicality of reactions that rely on their use. Inspired by developments in asymmetric organocatalysis, where reactions rely on reversible covalent interactions between an organic substrate and a chiral mediator, we have developed a transient-directing-group approach to reductive Heck hydroarylation of alkenyl benzaldehyde substrates that proceeds under mild conditions. Highly stereoselective migratory insertion is facilitated by in situ formation of an imine from catalytic amounts of a commercially available amino acid additive. Computational studies reveal an unusual mode of enantioinduction by the remote chiral center in the transient directing group.

Synthesis of Functionalized 1H-Isochromene Derivatives via a Au-Catalyzed Domino Cycloisomerization/Reduction Approach

A Au-catalyzed versatile and efficient access to 1H-isochromenes is reported. The efficiency of the [AuCl2(Pic)] complex (1-5 mol %) was demonstrated and allowed a domino cycloisomerization/reduction reaction process starting from a wide range of functionalized ortho-alkynylbenzaldehydes and one example of ortho-alkynylpyridinylaldehyde. The smooth reaction conditions were amenable to aryl- and alkyl-substituted alkynyl derivatives, as well as functionalized halogen and ether moieties, leading to a chemo- and regioselective 6-endo-cyclization with good to excellent yields.

Synthesis and SAR study of novel tricyclic pyrazoles as potent phosphodiesterase 10A inhibitors

Novel pyrazolo[5,1-f][1,6]naphthyridines, pyrazolo[5,1-a][2,6] naphthyridines, pyrazolo[5,1-a][2,7]naphthyridines and pyrazolo[5,1-a] isoquinolines phenylimidazole/benzimidazole ethylene-linked were designed and synthesized for PDE10A interaction. An AgOTf and proline-cocatalyzed multicomponent methodology based on use of o-alkynylaldehydes, tosylhydrazide and ketones was developed and proved to be a convenient route for assembly of most of the novel tricyclic pyrazoles synthesized. Pyrazolo[5,1-f][1,6] naphthyridine 43 and 59, pyrazolo[5,1-a][2,6]naphthyridine 66, and pyrazolo[5,1-a][2,7]naphthyridine 42 showed the highest affinity for PDE10A enzyme (IC50 = 40, 42, 40, 55 nM, respectively).

Silver-catalyzed domino hydroarylation/cycloisomerization reactions of ortho-alkynylbenzaldehydes: An entry to functionalized isochromene derivatives

A Ag-catalyzed versatile and efficient access to 1H,1-arylisochromenes is reported. Starting from ortho-alkynylbenzaldehydes bearing various substitution patterns on the benzaldehyde and alkynyl units, the use of silver triflate (10 mol %) allowed a domino hydroarylation/cycloisomerization reaction process, leading to aryl-functionalized 1H-isochromene (>10 compounds, 80-98% yields). Notably, the reaction conditions were also compatible with benzaldehydes bearing an aliphatic-substituted alkynyl moiety with modest to good yields (34-88%, 10 compounds).

A one-pot conversion of ortho-alkynyl benzaldehydes into indolo[2,1-a]isoquinolines

The conversion of readily available 2-halobenzaldehydes into indolo[2,1-a]isoquinolines in two operations represents a very direct entry to this class of molecules.

Silver(I)-catalyzed addition-cyclization of alkyne-functionalized azomethines

AgOTf can catalyze an addition-cyclization tandem between alkyne-azomethine and a nucleophile such as ketone, nitroalkane, water, and terminal alkyne to give a polycyclic amide via six-exo-trig selectivity.

Novel platinum-catalyzed tandem reaction: An efficient approach to construct naphtho[l,2-b]furan

An efficient approach to synthesize naphtho[1,2-b]furan has been developed via platinum-catalyzed tandem reaction. This new tandem catalysis induces a cycloisomerization of allenyl ketone, followed by a 6Π-electrocyclization- type reaction of carbene intermediate. The metal carbene proved to be an effective intermediate in the 6π-electrocyclization-type reaction.

Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: A versatile access to furoquinoline and pyranoquinoline cores

An efficient and versatile tandem process of acetalization and cycloisomerization reactions has been developed for the reactions of 1-alkynyl-2-carbonyl-quinoline substrates. The reaction occurs thanks to Au 1 and Ag1 catalysis. Silver(I) catalysis has been extensively studied (11 different silver species) on a broad range of quinoline derivatives (variation of alkyne substituent, of carbonyl function and of nucleophiles), leading to a variety of furoquinoline and pyranoquinoline moieties. An insight is given for the presumed mechanism along with DFT-B3LYP/6-31G** calculations to address the 6-endo and 5-exo regioselectivities observed.

Synthesis of seven-membered-ring ketones by arylative ring expansion of alkyne-substituted cyclobutanones

(Chemical Equation Presented) Ever-increasing circles: Seven-membered-ring ketones are constructed by a rhodium(I)-catalyzed arylative ring-expansion reaction of alkyne-substituted aryl cyclobutanones, in which two C-C bond-forming and one C-C bond-cleavi

Synthesis of 3-substituted 4-aroylisoquinolines via Pd-catalyzed carbonylative cyclization of 2-(1-alkynyl)benzaldimines

A number of 3-substituted 4-aroylisoquinolines have been prepared in good yields by treating N-tert-butyl-2-(1-alkynyl)benzaldimines with aryl halides in the presence of CO and a palladium catalyst. Synthetically the methodology provides a simple and convenient route to isoquinolines containing an aryl, alkyl, or vinylic group at C-3 and an aroyl group at C-4 of the isoquinoline ring. The reaction is believed to proceed via cyclization of the alkyne containing a proximate nucleophilic center promoted by an acylpalladium complex.