19115-30-1

Usage

Uses

Used in Regulatory and Monitoring Applications:
1'-hydroxy-2',3'-dehydroestragole is used as a target for regulation and monitoring in food and consumer products to ensure safety and minimize potential health risks associated with its genotoxic and carcinogenic properties.
Used in Research and Development:
1'-hydroxy-2',3'-dehydroestragole is used as a subject of ongoing research to better understand its effects and develop strategies to mitigate its potential harm. This includes exploring ways to reduce its presence in food products or finding alternatives to estragole that do not carry the same risks.

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 1066-26-8 sodium acetylide 
• 2386-64-3 ethylmagnesium chloride 
• 1066-54-2 trimethylsilylacetylene 
• 108-05-4 vinyl acetate 
• 16469-68-4 1-(4-methoxyphenyl)-2-propyn-1-one 
• 74-86-2 acetylene 
• 624-67-9 Propargylic aldehyde 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 65032-27-1 ethynylmagnesium chloride 
• 156-60-5 trans-1,2-dichloroethylene 
• 159351-36-7 1-(4-methoxyphenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 41786-37-2 2-(4-methoxyphenyl)-6-methyl-2H-chromene 
• 121507-55-9 C₁₇H₁₆O₂ 
• 94501-18-5 p-methoxyphenyl(benzofuran-2-yl)methanol 
• 99520-55-5 3-acetoxy-3-(4-methoxyphenyl)prop-1-yne 
• 121507-62-8 6-methoxy-2-(4-methoxyphenyl)-2H-chromene 
• 121507-57-1 C₁₇H₁₆O₃ 
• 180693-07-6 1-(2-acetoxyethoxy)methyl-5-(3-hydroxy-3-p-methoxyphenylprop-1-ynyl)uracil 
• 2004-63-9 ethyl 6‐(4‐methoxyphenyl)‐2‐methylnicotinate 

Relevant academic research and scientific papers

Mono-Gold(I)-Catalyzed Enantioselective Intermolecular Reaction of Ynones with Styrenes: Tandem Diels–Alder and Ene Sequence

Gold-catalyzed intermolecular reaction leading to dihydronaphthalene derivatives in one pot from two equivalents of ynones with respect to styrene is uncovered. The [4+2] Diels–Alder cycloaddition of ynones and styrenes is catalyzed by a mono-gold(I) complex and the conjugated acid to provide an unstable 3,8a-dihydronaphthalene to subsequently undergo an intermolecular ene-type reaction with the π-activated ynone to afford multi-component coupling dihydronaphthalene products. Linear relationships between chiral ligand-gold complexes and chiral dihydronaphthalene products proves mono-gold catalysis that triggers an asymmetric tandem Diels–Alder and ene reaction sequence.

Allenylidene Induced 1,2-Metalate Rearrangement of Indole-Boronates: Diastereoselective Access to Highly Substituted Indolines

A process to achieve 1,2-metalate rearrangements of indole boronate as a way to access substituted indolines in high diastereoselectivities is presented. The reaction involves the generation of a Cu–allenylidene, which is sufficiently electrophilic to induce the 1,2-metalate rearrangement. The scope of the reaction is evaluated as well as further transformations of the product.

Enantioselective [3 + 2] annulation of 4-isothiocyanato pyrazolones and alkynyl ketones under organocatalysis

An asymmetric [3 + 2] annulation reaction of 4-isothiocyanato pyrazolones with alkynyl ketones in the presence of an organic catalyst derived from a cinchona alkaloid under mild conditions is realized. This protocol provides unprecedented expeditious access to a wide range of optically active spiro[pyrroline-pyrazolones] with various electronic properties in high yields with good to excellent enantioselectivities.

Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross-Linking

The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol–yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol–yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.

Gold-Catalyzed Iminations of Terminal Propargyl Alcohols with Anthranils with Atypical Chemoselectivity for C(1)-Additions and 1,2-Carbon Migration

This work reports gold-catalyzed iminations of terminal propargyl alcohols with anthranils or isoxazoles to yield E-configured α-amino-2-en-1-ones and -1-als with complete chemoselectivity. These catalytic iminations occur exclusively with C(1)-nucleophilic additions on terminal alkynes, in contrast to a typical C(2)-route. For 3,3-dialkylprop-1-yn-3-ols, a methyl substituent is superior to long alkyl chains as the 1,2-migration groups toward α-imino gold carbenes. For secondary prop-1-yn-3-ols, phenyl, vinyl, and cyclopropyl substituents are better than hydrogen as the migrating groups, obviating typical gold carbene reactions. DFT calculations have been performed to rationalize the observed C(1)-regioselectivity and the preferable cyclopropyl migration based on gold carbene pathways.

Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases

The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

A sustainable access to ynones through laccase/TEMPO-catalyzed metal- and halogen-free aerobic oxidation of propargylic alcohols in aqueous medium

Tuning laccase/TEMPO-catalyzed aerobic oxidation of secondary propargylic alcohols in aqueous media was accomplished in order to efficiently synthesize ynones. This study led to the formulation of an effective and sustainable catalytic method for the preparation of mono- and bis-substituted ynones compared with traditional oxidative methods.

Synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by a palladium-catalyzed three-component reaction

A synthesis of (Z)-alkene-containing linear conjugated dienyl homoallylic alcohols by using a palladium-catalyzed three-component reaction has been developed. This method shows good functional-group compatibility and generality, with high diastereoselectivity. Additionally, in many cases, the present method controls the alkene stereochemistry of the newly formed C-C bond and overcomes the inherent preference for (E)-alkene formation, giving (Z, E)- and (Z, Z)-products.

Allylic and Allenylic Dearomatization of Indoles Promoted by Graphene Oxide by Covalent Grafting Activation Mode

The site-selective allylative and allenylative dearomatization of indoles with alcohols was performed under carbocatalytic regime in the presence of graphene oxide (GO, 10 wt percent loading) as the promoter. Metal-free conditions, absence of stoichiometric additive, environmentally friendly conditions (H2O/CH3CN, 55 °C, 6 h), broad substrate scope (33 examples, yield up to 92 percent) and excellent site- and stereoselectivity characterize the present methodology. Moreover, a covalent activation model exerted by GO functionalities was corroborated by spectroscopic, experimental and computational evidences. Recovering and regeneration of the GO catalyst through simple acidic treatment was also documented.