181280-06-8

Usage

Functional Groups

Benzaldehyde derivative
Allyl group ( \textCH2=\textCH-)
Alkoxy group ( \textO- )

Chlorine Atoms

Two chlorine atoms

Common Uses

Synthesis of organic compounds
Pharmaceuticals

Properties

Antimicrobial
Antifungal

Applications

Pharmaceuticals
Agriculture

Versatility

Due to its allyloxy group, it serves as a versatile building block for organic synthesis.

Upstream product

• 106-95-6 allyl bromide 
• 90-60-8 3,5-dichlorosalicyclaldehyde 
• 556-56-9 allyl iodid 
• 865-47-4 potassium tert-butylate 

Downstream Products

• 181280-14-8 2-Allyloxy-3,5-dichloro-benzaldehyde oxime 

Relevant academic research and scientific papers

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.

Synthesis of Chromenoisoxazolidines from Substituted Salicylic Nitrones via Visible-Light Photocatalysis

This effort reports the first redox-neutral visible-light photocatalytic intramolecular dipolar cycloaddition for the diastereoselective synthesis of chromenoisoxazolidines. The authors have found that alkenylphenyl nitrones with a diverse substitution pattern on the aromatic ring and the alkenyl substituent undergo visible-light-promoted cycloadditions in the presence of catalytic amounts of Ru(bpy)3Cl2 in high yields and selectivities. Evidence indicates that the proposed redox-neutral pathway is the predominant photoredox mechanism for this transformation.

Silver-Catalyzed Radical Cascade Cyclization toward 1,5-/1,3-Dicarbonyl Heterocycles: An Atom-/Step-Economical Strategy Leading to Chromenopyridines and Isoxazole-/Pyrazole-Containing Chroman-4-Ones

A novel and convenient silver-catalyzed radical cascade cyclization toward a large variety of 1,5-/1,3-dicarbonyl heterocycles containing a chroman-4-one, indanone, or 2,3-dihydroquinolin-4(1H)-one moiety was developed, by reacting various 2-functionalized benzaldehydes, including 2-allyloxy benzaldehydes, 2-allyl benzaldehyde, and 2-N(Ts)CH2-CH CH2 substituted benzaldehyde, with 1,3-dicarbonyl compounds in the presence of AgNO3/K2S2O8 in one pot under mild reaction conditions. The newly obtained 1,5-/1,3-dicarbonyl-containing heterocycles were further used directly to synthesize more structurally diverse polyheterocycles, mainly including chromenopyridines as well as isoxazole- or pyrazole-containing chroman-4-ones.

Optimization of a binding fragment targeting the “enlarged methionine pocket” leads to potent Trypanosoma brucei methionyl-tRNA synthetase inhibitors

Potent inhibitors of Trypanosoma brucei methionyl-tRNA synthetase were previously designed using a structure-guided approach. Compounds 1 and 2 were the most active compounds in the cyclic and linear linker series, respectively. To further improve cellular potency, SAR investigation of a binding fragment targeting the “enlarged methionine pocket” (EMP) was performed. The optimization led to the identification of a 6,8-dichloro-tetrahydroquinoline ring as a favorable fragment to bind the EMP. Replacement of 3,5-dichloro-benzyl group (the EMP binding fragment) of inhibitor 2 using this tetrahydroquinoline fragment resulted in compound 13, that exhibited an EC50 of 4?nM.

Aldehydes as Carbon Radical Acceptors: Silver Nitrate Catalyzed Cascade Decarboxylation and Oxidative Cyclization toward Dihydroflavonoid Derivatives

Silver nitrate-catalyzed cascade decarboxylation and oxidative cyclization of α-oxocarboxylic acids, alkenes, and aldehydes is demonstrated for the first time. With ammonium persulfate as the oxidant, the cascade reactions afford dihydroflavonoid derivatives as products in moderate to good yields, exhibiting a broad substrate tolerance. Control experiments indicated that the mechanism includes a radical pathway with aldehydes as the carbon radical acceptors. (Figure presented.).

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.

N-(4- carbamimidoyl-phenyl) -glycine derivatives

The invention is concerned with novel N-(4-carbamimidoyl-phenyl)-glycine derivatives of the formula: wherein R1, E, X1 to X4 and G1 and G2 are as defined in the description and the claims, as well as hydrates or solvates and physiologically usable salts thereof.

An efficient synthesis of benzopyrano-2-isoxazolines

A series of benzopyrono-2-isoxazoline compounds have been prepared efficiently by three-step synthesis from corresponding salicylaldehyde derivatives.