2749-94-2

Usage

Uses

Used in Flavor and Fragrance Industry:
Benzene, 1-Methoxy-4-(1-propyn-1-yl)is used as an intermediate in the synthesis of Cis-Anethole (A653355), an organic compound that is widely used as a flavoring substance. Benzene, 1-Methoxy-4-(1-propyn-1-yl)is a derivative of phenylpropene, a type of aromatic compound that occurs widely in nature, particularly in essential oils. The unique properties of 1-Methoxy-4-(1-propyn-1-yl)benzene make it a valuable component in the creation of various fragrances and flavors, enhancing the sensory experience of consumer products.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, compounds like Benzene, 1-Methoxy-4-(1-propyn-1-yl)-, due to their aromatic nature and synthetic potential, can also be used in the pharmaceutical industry. They may serve as precursors for the development of new drugs or be involved in the synthesis of active pharmaceutical ingredients (APIs) that target specific biological pathways or receptors.
Used in Chemical Synthesis:
Benzene, 1-Methoxy-4-(1-propyn-1-yl)can be utilized in various chemical synthesis processes, particularly in the creation of complex organic molecules. Its unique structure allows for further functionalization and modification, making it a versatile building block for the development of novel compounds with specific applications in various industries, such as materials science, agrochemicals, and more.

Upstream product

• 112534-59-5 4-(2-chloro-propenyl)-anisole 
• 1201-60-1 4-((1RS,2SR)-1,2-dibromo-propyl)-anisole 
• 1201-60-1 1-(1,2-dibromopropyl)-4-methoxybenzene 
• 121-69-7 N,N-dimethyl-aniline 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 18295-60-8 propargyl magnesium bromide 
• 66823-57-2 C₁₈H₂₂N₂O₃S₂ 
• 917-54-4 methyllithium 
• 77-78-1 dimethyl sulfate 
• 768-60-5 4-methoxyphenylacetylen 
• 75-11-6 diiodomethane 
• 104-46-1 anethole 
• 106-98-9 1-butylene 
• 36233-77-9 (E)-1-Bromo-1-(4-methoxyphenyl)-1-propene 

Downstream Products

• 13029-44-2 dienestrol 
• 18826-57-8 2-(4-methoxyphenyl)-3-methyl-2-cyclopropene-1-carboxylic acid 
• 73569-57-0 E-1,2-bismethylthio-1-(4-methoxyphenyl)propene 
• 73569-58-1 Z-1,2-bismethylthio-1-(4-methoxyphenyl)propene 
• 36233-77-9 (E)-1-Bromo-1-(4-methoxyphenyl)-1-propene 
• 36233-78-0 (Z)-1-Bromo-1-(4-methoxyphenyl)-1-propene 
• 25679-28-1 cis-Anethole 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 121-97-1 4-Methoxypropiophenone 
• 85157-85-3 (Z)-1-chloro-1-(4-methoxyphenyl)-1-propene 
• 85157-84-2 (E)-1-chloro-1-(4-methoxyphenyl)-1-propene 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 170651-15-7 4-(prop-1-yn-1-yl)phenol 

Relevant academic research and scientific papers

Gold(I)-catalysed tandem cyclization of propargyl acetals and alkynes

To expand the understanding of the chemistry of propargyl acetals, their gold(I) catalysed cycloaddition reactions with alkynes have been investigated. We hereby report a novel tandem reaction that allows the construction of a new type of polysubstituted

A Convenient Procedure for Sonogashira Reactions Using Propyne

A modified Sonogashira coupling of aryl iodides and propyne was achieved using only two equivalents of propyne in THF from 78 °C to room temperature.

Atom-Economical Thiocyanation-Amination of Alkynes with N-Thiocyanato-Dibenzenesulfonimide

A highly regioselective protocol for intermolecular thiocyanation-amination of alkynes by N-thiocyano-dibenzenesulfonimide (NTSI) as the SCN and nitrogen sources has been developed. A C-S bond and C-N bond are simultaneously constructed in only one step. The reaction under simple mild conditions features a broad substrate scope, atom economy, high yields (up to 94%), and excellent functional group tolerance.

An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis

The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. Here we report Z-selective semihydrogenation of alkynes with ethanol via a coordination-induced ionic monohydride mechanism. The EtOH-coordination-driven Cl- dissociation in a pincer Ir(III) hydridochloride complex (NCP)IrHCl (1) forms a cationic monohydride, [(NCP)IrH(EtOH)]+Cl-, that reacts selectively with alkynes over the corresponding Z-alkenes, thereby overcoming competing thermodynamically dominant alkene Z-E isomerization and overreduction. The challenge for establishing a catalytic cycle, however, lies in the alcoholysis step; the reaction of the alkyne insertion product (NCP)IrCl(vinyl) with EtOH does occur, but very slowly. Surprisingly, the alcoholysis does not proceed via direct protonolysis of the Ir-C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl- ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)-H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting the alcoholysis. The 1-amine-EtOH catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility, as demonstrated by Z-selective reduction of all alkyne classes, including challenging enynes and complex polyfunctionalized molecules. Comparison with a cationic monohydride complex bearing a noncoordinating BArF- ion elucidates the beneficial role of the Cl- ion in controlling the stereoselectivity, and comparison between 1-amine-EtOH and 1-NaOtBu-EtOH underscores the fact that this base variable, albeit in catalytic amounts, leads to different mechanisms and consequently different stereoselectivity.

Regio- And stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides

An electrooxidative direct difunctionalization of internal alkynes with sulfonyl hydrazides has been developed for the construction of sulfonated enethers. In this transformation, metal catalysts or stoichiometric amount of oxidants are not required and molecular nitrogen and hydrogen are the sole byproducts, providing a simple and green approach for preparing various sulfonyl tetrasubstituted alkenes. Notably, the protocol could be efficiently scaled up and the follow-up procedures of the corresponding functionalized alkenes demonstrate the practicality of the electrochemical synthesis.

Regio- and Diastereoselective Copper-Catalyzed Carbomagnesiation for the Synthesis of Penta- and Hexa-Substituted Cyclopropanes

Despite the highly strained nature of cyclopropanes possessing three vicinal quaternary carbon stereocenters, the regio- and diastereoselective copper-catalyzed carbomagnesiation reaction of cyclopropenes provides an easy and efficient access to these novel persubstituted cyclopropyl cores with a complete regio- and diastereoselectivity.

Total Synthesis of Indolizidine Alkaloids via Nickel-Catalyzed (4 + 2) Cyclization

A Ni-catalyzed (4 + 2) cycloaddition of alkynes and azetidinones toward piperidinones was used as key reaction in the enantioselective synthesis of naturally occurring indolizidine alkaloids. The reaction benefits from the use of an easily accessible azet

Br?nsted acid/visible-light-promoted Markovnikov hydroamination of vinylarenes with arylamines

A Br?nsted acid/visible-light-promoted Markovnikov hydroamination of vinylarenes with arylamines in the presence of TPT and CF3CO2H has been developed. This transformation provides a green approach to alpha-amino-substituted arylalkanes under metal-free conditions.

Rh-Catalyzed Asymmetric Hydrogenation of α,β- and β,β-Disubstituted Unsaturated Boronate Esters

A highly enantioselective hydrogenation of α,β-unsaturated boronate esters catalyzed by Rh-(S)-DTBM-Segphos complex has been developed. Both (Z)-α,β- and β,β-disubstituted substrates can be successfully hydrogenated to afford chiral boronates with excellent enantioselectivities, up to 98 % ee. Furthermore, the obtained chiral boronate esters, as important versatile synthetic intermediates are successfully transformed to the corresponding chiral alcohols, amines and other important derivatives with maintained enantioselectivities.

Palladium-catalyzed methylation of terminal alkynes

In this communication, a palladium-catalyzed procedure for the methylation of terminal alkynes has been developed. With N,N,N-trimethylbenzenaminium trifluoromethanesulfonate as the methyl source, various desired products were obtained in moderate to good yields. Both aromatic and aliphatic alkynes are applicable.