38276-72-1

Usage

Molecular Structure

A benzene ring with a methoxy group at the first position and an allyloxy group at the fourth position.

Explanation

The core structure of the compound is a benzene ring, which is a hexagonal ring with alternating single and double bonds. The methoxy group (-OCH3) is attached to the first carbon atom of the ring, and the allyloxy group ((E)-3-phenyl-allyloxy) is attached to the fourth carbon atom.

Explanation

The allyloxy group is attached to the benzene ring in a trans configuration, meaning that the phenyl group and the allyl group are on opposite sides of the ring. This arrangement is indicated by the "(E)" notation in the compound's name.

Explanation

Due to its unique structure and reactivity, 1-METHOXY-4-((E)-3-PHENYL-ALLYLOXY)-BENZENE is a valuable intermediate in organic synthesis. It can be used to create complex molecules for use in pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.

Explanation

The compound's structure and reactivity make it an important building block in the field of medicinal and agricultural chemistry. Its ability to form complex molecules allows for the development of new therapeutic agents and agrochemicals, ultimately benefiting both human health and agriculture.

Allyloxy Group Configuration

Trans (denoted by "(E)" in its name)

Usage in Organic Synthesis

Commonly used as a building block for the production of various pharmaceuticals and agrochemicals.

Relevance in Medicinal and Agricultural Chemistry

Valuable for the creation of complex molecules.

InChI:InChI=1/C16H16O2/c1-17-15-9-11-16(12-10-15)18-13-5-8-14-6-3-2-4-7-14/h2-12H,13H2,1H3/b8-5+

Upstream product

• 150-76-5 4-methoxy-phenol 
• 4392-24-9 Cinnamyl bromide 
• 673-32-5 1-Phenylprop-1-yne 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 21040-45-9 Cinnamyl acetate 
• 591-50-4 iodobenzene 
• 13391-35-0 allyl (4-methoxyphenyl) ether 
• 108-86-1 bromobenzene 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 4392-24-9 3-bromo-1-phenyl-1-propenyl bromide 
• 77134-01-1 (Z)-cinnamyl acetate 
• 300-57-2 allylbenzene 

Downstream Products

• 139139-75-6 4-methoxy-4-(3-phenyl-prop-2-enyloxy)-2,5-cyclohexanedione 
• 1442524-66-4 6-methoxy-3,4-dihydro-4-phenyl-2H-chromene 
• 20442-73-3 (1E)-3-(4-methoxyphenyl)-1-phenylpropene 
• 62056-42-2 (E)-3-[(4-N,N-dimethylaminophenyl)]-1-phenylpropene 
• 485844-19-7 1-fluoro-4-[(2E)-3-phenyl-2-propen-1-yl]benzene 
• 5751-29-1 1-[(2E)-3-phenyl-2-propen-1-yl]naphthalene 
• 18916-11-5 (E)-1-methyl-2-(3-phenyl-2-propen-1-yl)benzene 
• 133039-10-8 1-cinnamyl-2,4,6-trimethylbenzene 
• 3412-44-0 (1E)-1,3-diphenylpropene 
• 62056-38-6 (E)-1-phenyl-3-p-tolylpropene 
• 876309-34-1 (Z)-3-(4-methoxyphenoxy)-1-phenylpropene 
• 38276-84-5 2-(α-Phenyl-allyl)-4-methoxy-phenol 

Relevant academic research and scientific papers

Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation

A method for the catalytic, enantioselective, carbosulfenylation of alkenes to construct 3,4-disubstituted chromans is described. Alkene activation proceeds through the intermediacy of enantioenriched, configurationally stable thiiranium ions generated from catalytic, Lewis base activation of an electrophilic sulfenylating agent. The transformation affords difficult-to-generate, enantioenriched, 3,4-disubstituted chromans in moderate to high yields and excellent enantioselectivities. A variety of substituents are compatible including electronically diverse functional groups as well as several functional handles such as aryl halides, esters, anilines, and phenols. The resulting thioether moiety is amenable to a number of functional group manipulations and transformations. Notably, the pendant sulfide was successfully cleaved to furnish a free thiol which readily provides access to most sulfur-containing functional groups which are present in natural products and pharmaceuticals.

Selective Synthesis of Z-Cinnamyl Ethers and Cinnamyl Alcohols through Visible Light-Promoted Photocatalytic E to Z Isomerization

A photocatalytic E to Z isomerization of alkenes using an iridium photosensitizer under mild reaction conditions is disclosed. This method provides scalable and efficient access to Z-cinnamyl ether and allylic alcohol derivatives in high yields with excellent stereoselectivity. Importantly, this method also provides a powerful strategy for the selective synthesis of Z-magnolol and honokiol derivatives possessing potential biological activity.

Cross-coupling reaction of allylic ethers with aryl Grignard reagents catalyzed by a nickel pincer complex

A cross-coupling reaction of allylic aryl ethers with arylmagnesium reagents was investigated using β-aminoketonato- and β-diketiminato-based pincer-type nickel(II) complexes as catalysts. An β-aminoketonato nickel(II) complex bearing a diphenylphosphino group as a third donor effectively catalyzed the reaction to afford the target cross-coupled products, allylbenzene derivatives, in high yield. The regioselective reaction of a variety of substituted cinnamyl ethers proceeded to give the corresponding linear products. In contrast, α- and γ-alkyl substituted allylic ethers afforded a mixture of the linear and branched products. These results indicated that the coupling reaction proceeded via a π-allyl nickel intermediate.

Palladium-Catalyzed Aerobic Oxygenation of Allylarenes

An efficient and practical protocol for the synthesis of (E)-allylethers from readily available olefins with alcohols or phenols was developed. This aerobic oxidative allylic C-H oxygenation protocol features mild conditions, broad substrate scope, and hi

Co-Catalyzed Hydroarylation of Unactivated Olefins

A mild, general, scalable, and functional group tolerant intramolecular hydroarylation of unactivated olefins using a Co(salen) complex, a N-fluoropyridinium salt, and a disiloxane reagent was reported. This method, which was carried out at room temperature, afforded six-membered benzocyclic compounds from mono-, 1,1- or trans-1,2-di, and trisubstituted olefins.

Polymeric β-alanine incarcerated Pd(ii) catalyzed allylic etherification in water: A mild and efficient method for the formation of C(sp3)-O bonds

A new heterogeneous palladium(ii) catalyst has been developed through a convenient and economic way. The catalyst was synthesized by confining palladium metal with a polystyrenal β-alanine-imine network and characterized by FT-IR spectroscopy, thermogravimetric analysis, field emission scanning electron microscopy, energy dispersive X-ray, and elemental analysis. Polymeric imine can be prepared easily from chloromethylated polystyrene and β-alanine. Using this polymer incarcerated palladium(ii) catalyst a useful and efficient procedure for stereospecific synthesis of allyl-aryl ethers has been developed. The benzylic, aromatic, and heteroaromatic phenols react with various substituted allyl acetates by this procedure to furnish a library of allyl-aryl and allyl-hetero-aryl ethers in high yields. The catalyst could be recovered easily and reused five times without any considerable loss of its catalytic activity.

Homogeneous Pd-catalyzed transformation of terminal alkenes into primary allylic alcohols and derivatives

Synthesis of primary alcohols from terminal alkenes is an important process in both bulk and fine chemical syntheses. Herein, a homogeneous Pd-complex-catalyzed transformation of terminal alkenes into primary allylic alcohols, by using 5 mol % [Pd(PPh3)4] as a catalyst, and H2O, CO2, and quinone derivatives as reagents, is reported. When alcohols were used instead of H2O, allylic ethers were obtained. A proposed mechanism includes the addition of oxygen nucleophiles at the less-hindered terminal position of π-allyl Pd intermediates.

From precursor to catalyst: The involvement of [Ru(η5-Cp?)Cl2]2 in highly branch selective allylic etherification of cinnamyl chlorides

(RuCp?Cl2)2, a general entry into Cp?Ru sandwich and half-sandwich chemistry was first used as a precatalyst in allylic etherification of cinnamyl chlorides with up to 98:2 regioselectivity (19 examples). Both the solvent effect and the exsiccant reaction condition are crucial to the reactivity and selectivity. Preliminary mechanism studies and the demonstration of Fluoxetine synthesis were presented in this work as well.

An efficient palladium-catalyzed synthesis of cinnamyl ethers from aromatic halides, phenols, and allylic chloride

A one-pot, two-step catalytic protocol for the preparation of cinnamyl ethers from simple and readily available aryl halides, phenols and allyl chloride is reported for the first time. This simple and highly efficient palladium nanoparticles catalytic system shows good regio- and stereoselectivities and affords the desired products in good to high yields (49-85%) from aryl iodides. Furthermore, less reactive aryl bromides can also give the cinnamyl ethers in moderate yields (24-72%).

Nickel(0) triethyl phosphite complex-catalyzed allylic substitution with retention of regio- and stereochemistry

(Chemical Equation Presented) Nickel(0) triethyl phosphite complex-promoted reaction of allylic acetates with thiols produced allylic sulfides with retention of configuration without allylic rearrangement. A similar reaction of allylic acetates with alcohols and phenols also proceeded with retention of regio- and stereochemistry.