19530-43-9

Usage

Uses

Used in Organic Synthesis:
2-(Allyloxy)-1-naphthaldehyde is utilized as a reagent in organic synthesis for its ability to react with a range of nucleophiles, which is crucial in the production of pharmaceuticals and fine chemicals. Its versatility in forming new chemical entities makes it an indispensable component in the development of novel compounds with potential therapeutic or industrial applications.
Used in Biochemical Research:
In the field of biochemical research, 2-(allyloxy)-1-naphthaldehyde serves as a fluorescent probe, enabling researchers to study biological processes and interactions at the molecular level. Its fluorescence properties are harnessed for applications in fluorescence-based sensing and imaging techniques, which are vital for detecting and visualizing specific biomolecules or cellular structures.
Used in Pharmaceutical Production:
2-(ALLYLOXY)-1-NAPHTHALDEHYDE is also used as a key intermediate in the production of pharmaceuticals, where its reactivity with nucleophiles is leveraged to create new drug candidates. This contributes to the advancement of medicine by facilitating the discovery and development of innovative therapeutic agents.
Used in Chemical Research:
2-(Allyloxy)-1-naphthaldehyde's potential applications extend to the broader field of chemical research, where it aids in the exploration of new chemical reactions and mechanisms. Its use as a fluorescent probe in this context can provide insights into reaction dynamics and help in the optimization of synthetic pathways.

Upstream product

• 107-05-1 3-chloroprop-1-ene 
• 708-06-5 2-hydroxynaphthalene-1-carbaldehyde 
• 106-95-6 allyl bromide 

Downstream Products

• 104057-32-1 2-Allyloxy-1-naphthaldehyd-tosylhydrazon 
• 176910-00-2 (3aR,11cS)-1-((R)-1-Phenyl-ethyl)-1,3a,4,11c-tetrahydro-3H-2,5-dioxa-1-aza-cyclopenta[c]phenanthrene 
• 177019-99-7 (3aS,11cR)-1-((R)-1-Phenyl-ethyl)-1,3a,4,11c-tetrahydro-3H-2,5-dioxa-1-aza-cyclopenta[c]phenanthrene 
• 436806-96-1 (2R)-1-[(Z)-{[2-(allyloxy)-1-naphthyl]methylene}(oxido)amino]-2-phenylethanol 
• 65103-48-2 2-phenyl-4H-3,3a-dihydropyrazolo<2,3-d>benzopyran 
• 104057-37-6 5-(2'-Allyloxy-1'-naphthyl)-2-phenyltetrazol 
• 135522-23-5 (E)-2-allyloxynaphthalene-1-carbaldehyde oxime 
• 321574-22-5 N-[(1R,2R)-2-(hydroxymethyl)-2,3-dihydro-1H-benzo[f]chromen-1-yl]-N-methyl-N'-[3-(trifluoromethyl)phenyl]thiourea 
• 436807-00-0 (2R)-2-((3aS,11cR)-3a,11c-dihydro-3H-benzo[5,6]chromeno[4,3-c]isoxazol-1(4H)-yl)-2-phenylethanol 
• 436807-20-4 (3aS,11cR)-1,3a,4,11c-tetrahydro-3H-benzo[5,6]chromeno[4,3-c]isoxazole 
• 90587-89-6 (2RS,3aRS,11cSR)-2-phenyl-4H-2,3,3a,11-tetrahydropyrrolo<2,3-d>naphtho<2,1-b>pyran 

Relevant academic research and scientific papers

An efficient synthesis of some thiopyranopyrazole-heterocycles via domino reaction in a Bronsted acidic ionic liquid

The thiopyrazole gave many new polycyclic thiopyranopyrazole-heterocycles when it was assembled with a variety of O-alkenylated/alkynylated salicylaldehydes and naphthaldehydes in Bronsted acidic ionic liquid, [Hmim]HSO4, via domino/Knoevenagel-hetero-Diels-Alder (DKHDA) reaction. The reaction is highly stereoselective and the work-up procedure required no chromatography of products in many cases.

Adjustment of the solid fluorescence of a chalcone derivative through controlling steric hindrance

We designed and synthesized a chalcone derivative, ANPEO, which exhibits weak emission in the solution state but high fluorescence efficiency in the solid state (66%) because ANPEO shows a coplanar conformation with a dihedral angle 1.58° and a loose pattern with a mean interlayer distance of approximately 4.21 ?.

New one-step procedure for the synthesis of 6H-chromeno[4,3-b]quinolines and 8a,9,14,14a-tetrahydro-8H-benzo[5,6]chromeno[4,3-b]quinolines

Schiff bases generated in situ from substituted anilines and 2-allyloxybenzaldehyde underwent acid-catalyzed intramolecular Diels-Alder reaction followed by dehydrogenation to give 6H-chromeno[4,3-b]-quinolines. Under analogous conditions, derivatives of 2-allyloxynaphthalene-1-carbaldehyde were converted into 8a,9,14,14a-tetrahydro-8H-benzo[5,6]chromeno[4,3-b] quinolines. Possible dehydrogenation mechanisms are discussed.

tert-Butyl Hydroperoxide-Initiated Radical Cyclization of 1-(Allyloxy)-2-(1-Arylvinyl)Benzenes with Sulfinic Acids to Access Sulfonated Benzoxepines

A tert-butyl hydroperoxide-initiated radical cyclization of 1-(allyloxy)-2-(1-arylvinyl)benzenes with sulfinic acids for the construction of sulfonated benzoxepines is developed. This reaction involves a radical pathway and offers a straightforward route to the formation of seven-membered ring via sulfonylation/cyclization process. This methodology features mild reaction conditions, a broad substrate scope and good functional group tolerance. (Figure presented.).

Metal-free synthesis of phosphinoylchroman-4-ones via a radical phosphinoylation–cyclization cascade mediated by K2S2O8

A variety of chroman-4-ones bearing phosphine oxide motifs were conveniently synthesized from readily available diphenylphosphine oxides and alkenyl aldehydes via a metal-free tandem phosphinoylation/cyclization protocol. The reaction utilizes K2S2O8 as oxidant and proceeds in DMSO/H2O at environmentally benign conditions with a broad substrate scope and afforded the title compounds in moderate yields.

Visible-Light-Promoted Cascade Radical Cyclization: Synthesis of 1,4-Diketones Containing Chroman-4-One Skeletons

A visible-light-induced cascade radical cyclization of aroyl chlorides with 2-(allyloxy)-benzaldehyde derivatives has been developed. The method takes advantages of unactivated C=C bonds as the acyl radical acceptors and offers a mild and green approach for the synthesis of 1,4-diketones bearing biologically important chroman-4-one skeletons with moderate to good yields.

Catalytic Intramolecular Cycloaddition Reactions by Using a Discrete Molecular Architecture

A discrete tetragonal tube-shaped complex (MT-1) has been synthesised by coordination-driven self-assembly of a carbazole-based tetraimidazole donor L and a Pd(II) 90° acceptor, that is, [cis-(dppf)Pd(OTf)2] (dppf=diphenylphosphinoferrocene, OTf=CF3SO3?). Complex MT-1 was characterised by multinuclear NMR, ESI-MS and single-crystal X-ray diffraction analysis (SCXRD), which showed its symmetrical tetrafacial tube-shaped architecture possessing a large cavity described by four aromatic walls. This coordination cage was successfully utilised as a molecular vessel to perform intramolecular cycloaddition reactions of O-allylated benzylidinebarbituric acid derivatives inside its confined nanospace. The presence of a catalytic amount of MT-1 promoted [4+2] cycloaddition reactions in a regio- and stereoselective manner, yielding the corresponding penta/tetracyclouracil derivatives in good yields under mild reaction conditions. This protocol is interesting compared with the literature reports for the synthesis of similar chromenopyran pyrimidinedione derivatives under high-temperature reflux conditions or solid-state melt reactions (SSMRs).

The Synthesis of 5-Amino-dihydrobenzo[b]oxepines and 5-Amino-dihydrobenzo[b]azepines via Ichikawa Rearrangement and Ring-Closing Metathesis

The combination of Ichikawa's rearrangement and a ring-closing metathesis reaction of allyl carbamates is presented as a method for the preparation of 5-amino-substituted 2,5-dihydro-benzo[b]oxepines, 2,5-dihydro-benzo[b]azepines, and 2,5-dihydro-benzo[b]thiepins. It was demonstrated that the use of nonracemic allyl carbamates enables the synthesis of enantioenriched benzo-fused seven-membered heterocycles. Finally, it was shown that further functionalization of the obtained structures allows access to pharmacologically active 5-amino-substituted 2,3,4,5-tetrahydro-1-benzo[b]oxepine scaffolds.

Silaborative Carbocyclizations of 1,7-Enynes. Diastereoselective Preparation of Chromane Derivatives

Palladium(0)-catalyzed carbocyclization of 1,7-enynes mediated by (chlorodimethylsilyl)pinacolborane proceeds with 1,8-addition of the silicon and boron functions to give functionalized cyclohexane derivatives with boron attached to the exocyclic olefin. A variety of chromane dervatives are accessible by this method. In contrast to the analogous reactions with 1,6-enynes, the configuration of the newly formed stereogenic center is controlled by a stereogenic center present in the substrate.

Straightforward synthesis of functionalized chroman-4-ones through cascade radical cyclization-coupling of 2-(allyloxy)arylaldehydes

A novel and direct approach to synthesize a series of phosphonate, azide and hydroxy functionalized chroman-4-ones has been developed. The cascade transformation appears to proceed through an intramolecular addition of an in situ generated acyl radical onto the alkene, followed by a selective nucleophilic radical-electrophilic radical cross coupling.