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Usage

Uses

Used in Perfumery Industry:
Chavicol is utilized as a fragrance ingredient in the perfumery industry for its sweet, floral odor, contributing to the creation of various scent profiles in perfumes and other fragranced products.
Used in Flavoring Industry:
In the flavoring industry, chavicol serves as a key component in the formulation of food and beverage flavorings, enhancing the taste and aroma of these products due to its distinctive scent.
Used in Pharmaceutical Industry:
Chavicol is employed in the pharmaceutical industry for its antimicrobial and anti-inflammatory properties, making it a valuable asset in the development of medications and treatments for various conditions.
Used in Traditional Medicine:
In traditional medicine, chavicol is used for its therapeutic properties, including its ability to combat microbial infections and reduce inflammation, thus playing a role in the treatment of diverse ailments.
Used as a Natural Insecticide and Repellent:
Chavicol has demonstrated potential as a natural insecticide and repellent, making it a candidate for use in agricultural and environmental applications to control pests and insects without the use of synthetic chemicals.

Upstream product

• 36854-32-7 (E)-α-(3',4'-dimethoxyphenylmethylene)benzeneacetic acid 
• 1100-88-5 benzyltriphenylphosphonium chloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 100-39-0 benzyl bromide 
• 100-52-7 benzaldehyde 
• 7016-55-9 benzyl-triethylphosphonium bromide 
• 1666-17-7 benzaldehyde p-toluenesulfonylhydrazone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 140-29-4 phenylacetonitrile 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 770-09-2 benzyltrimethylsilane 
• 27895-67-6 N-(3,4-dimethoxybenzylidene)aniline 
• 6380-23-0 3,4-dimethoxystyrene 
• 71-43-2 benzene 

Downstream Products

• 131475-32-6 (2,2-Diethoxy-ethyl)-[2-(3,4-dimethoxy-phenyl)-1-phenyl-ethyl]-amine 
• 100-52-7 benzaldehyde 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 3892-93-1 1-(3,4-dimethoxyphenyl)-2-phenylethane 
• 3391-75-1 2-methoxy-4-((E)-phenylethenyl)phenol 
• 143207-84-5 (Z)-1-(3,4-dimethoxyphenyl)-2-phenyl-ethene 
• 76306-71-3 4-((1S,2R)-1,2-Dichloro-2-phenyl-ethyl)-1,2-dimethoxy-benzene 
• 19826-29-0 (E)-3,4-dihydroxystilbene 

Relevant academic research and scientific papers

Tandem Acceptorless Dehydrogenative Coupling-Decyanation under Nickel Catalysis

The development of new catalytic processes based on abundantly available starting materials by cheap metals is always a fascinating task and marks an important transition in the chemical industry. Herein, a nickel-catalyzed acceptorless dehydrogenative coupling of alcohols with nitriles followed by decyanation of nitriles to access diversely substituted olefins is reported. This unprecedented C=C bond-forming methodology takes place in a tandem manner with the formation of formamide as a sole byproduct. The significant advantages of this strategy are the low-cost nickel catalyst, good functional group compatibility (ether, thioether, halo, cyano, ester, amino, N/O/S heterocycles; 43 examples), synthetic convenience, and high reaction selectivity and efficiency.

Aza-peterson olefinations: Rapid synthesis of (E)-alkenes

An aza-Peterson olefination methodology to access 1,3-dienes and stilbene derivatives from the corresponding allyl- or benzyltrimethylsilane is described. Silanes can be deprotonated using Schlosser's base and added to N -phenyl imines or ketones to directly give the desired products in high yields.

Non-Chelate-Assisted Palladium-Catalyzed Aerobic Oxidative Heck Reaction of Fluorobenzenes and Other Arenes: When Does the C?H Activation Need Help?

The pyridone fragment in the ligand [2, 2’-bipyridin]-6(1H)-one (bipy-6-OH) enables the oxidative Heck reaction of simple arenes with oxygen as the sole oxidant and no redox mediator. Arenes with either electron-donating or electron-withdrawing groups can be functionalized in this way. Experimental data on the reaction with toluene as the model arene shows that the C?H activation step is turnover limiting and that the ligand structure is crucial to facilitate the reaction, which supports the involvement of the pyridone fragment in the C?H activation step. In the case of fluoroarenes, the alkenylation of mono and 1,2-difluoro benzenes requires the presence of bipy-6-OH. In contrast, this ligand is detrimental for the alkenylation of 1,3-difluoro, tri, tetra and pentafluoro benzenes which can be carried out using just [Pd(OAc)2]. This correlates with the acidity of the fluoroarenes, the most acidic undergoing easier C?H activation so other steps of the reaction such as the coordination-insertion of the olefin become kinetically important for polyfluorinated arenes. The use of just a catalytic amount of sodium molybdate as a base proved to be optimal in all these reactions. (Figure presented.).

Synthesis of Stilbenes by Rhodium-Catalyzed Aerobic Alkenylation of Arenes via C-H Activation

Arene alkenylation is commonly achieved by late transition metal-mediated C(sp2)-C(sp2) cross-coupling, but this strategy typically requires prefunctionalized substrates (e.g., with halides or pseudohalides) and/or the presence of a directing group on the arene. Transition metal-mediated arene C-H activation and alkenylation offers an alternative method to functionalize arene substrates. Herein, we report a rhodium-catalyzed oxidative arene alkenylation from arenes and styrenes to prepare stilbene and stilbene derivatives. The reaction is successful with several functional groups on both the arene and the olefin including fluoride, chloride, trifluoromethyl, ester, nitro, acetate, cyanide, and ether groups. Reactions of monosubstituted arenes are selective for alkenylation at the meta and para positions, generally with approximately 2:1 selectivity, respectively. Resveratrol and (E)-1,2,3-trimethoxy-5-(4-methoxystyryl)benzene (DMU-212) are synthesized by this single-step approach in high yield. Comparison with palladium catalysis showed that rhodium catalysis is more selective for meta-functionalization for monosubstituted arenes and that the Rh catalysis has better tolerance of halogen groups.

Nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones with the liberation of H2

A nickel(ii)-catalyzed direct olefination of benzyl alcohols with sulfones to access various terminal and internal olefins with the liberation of hydrogen gas is reported.

Preparation of dihydroxy polycyclic aromatic hydrocarbons and activities of two dioxygenases in the phenanthrene degradative pathway

Dihydroxy phenanthrene, fluoranthene, and pyrene derivatives are intermediates in the bacterial catabolism of the corresponding parent polycyclic aromatic hydrocarbon (PAH). Ring-opening of the dihydroxy species followed by a series of enzyme-catalyzed re

Decarboxylative Arylation of α,β-Unsaturated Carboxylic Acids Using Aryl Triazenes by Copper/Ionic Liquid Combination in PEG-400

A practical method for the construction of stilbene derivatives has been developed via catalytic cross-coupling of cinnamic acids with aryl triazenes. The methodology offers high stereoselectivity and is endowed with broad substrate scope, high yield, and significant functional group tolerance.

O -Iodoxybenzoic acid mediated generation of aryl free radicals: Synthesis of stilbenes through C-C cross-coupling with β-nitrostyrenes

The generation of an aryl free radicals in the presence of nitrostyrenes through a combination of aryl hydrazines and o-iodoxybenzoic acid led to the synthesis of stilbenes by forming a new carbon-carbon bond after subsequent elimination of a nitrosyl radical. The symmetrical and unsymmetrical stilbenes with excellent E-selectivity were synthesized in good yields, with advantages of broad substrate scope and transition metal free, mild reaction conditions, under an open atmosphere in a short reaction time. A free radical mediated mechanism was postulated and supported by radical trapping experiments. Application of the developed methodology is demonstrated through a simple, two step synthesis of resveratrol, a valuable stilbenoid for anticancer and neurological studies via its prodrug E-1,3-dimethoxy-5-(4-methoxystyryl)benzene.

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn

Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using-NO2 as a leaving group

The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.