2227-57-8

Usage

Uses

Used in Chemical Synthesis:
3-(4-methoxyphenyl)-2-propynoic acid (SALTDATA: FREE) is used as a reagent for the preparation of bis(phenylethynyl)benzenes. Its unique structure allows for the formation of these complex organic molecules, which have potential applications in various fields such as materials science, pharmaceuticals, and chemical research.

InChI:InChI=1/C10H8O3/c1-13-9-5-2-8(3-6-9)4-7-10(11)12/h2-3,5-6H,1H3,(H,11,12)

Upstream product

• 91089-40-6 2,3-dibromo-3-(4-methoxyphenyl)propionic acid methyl ester 
• 90772-66-0 2-bromo-3-(4-methoxy-phenyl)-acrylic acid 
• 91059-50-6 3-(4-Methoxyphenyl)-cyano-propiolsaeure-anhydrid 
• 124-38-9 carbon dioxide 
• 91585-32-9 ((4-methoxyphenyl)ethynyl)(phenyl)selane 
• 157019-58-4 2,3-dibromo-3-(4-methoxyphenyl)propionic acid ethyl ester 
• 7515-17-5 methyl 3-(4-methoxyphenyl)propynoate 
• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 
• 768-60-5 4-methoxyphenylacetylen 
• 696-62-8 para-iodoanisole 
• 471-25-0 Propiolic acid 
• 5720-07-0 4-methoxyphenylboronic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 832-01-9 methyl p-methoxycinnamate 

Downstream Products

• 15828-76-9 1-(4-methoxyphenyl)-7-methoxy-2,3-naphthalenedicarboxylic anhydride 
• 768-60-5 4-methoxyphenylacetylen 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 119003-61-1 5,6,7-Trimethoxy-4-(4-methoxyphenyl)coumarin 
• 131292-14-3 3-(4-methoxyphenyl)propioloyl chloride 
• 81423-94-1 (E)-1-carboxy-2-(p-methoxyphenyl)vinylsulfonic Acid 
• 74877-32-0 (Z)-3-(4-Methoxy-phenyl)-3-phenylsulfanyl-acrylic acid 
• 53060-07-4 1-methoxy-4-(1,2,2-triiodovinyl)benzene 
• 53178-57-7 p-Methoxy-trans-α.β-diiodzimtsaeure 
• 226383-14-8 3,4-methylenedioxycinnamyl 4'-methoxyphenylpropiolate 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 61926-37-2 1-(iodoethynyl)-4-methoxybenzene 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 90772-66-0 2-bromo-3-(4-methoxy-phenyl)-acrylic acid 

Relevant academic research and scientific papers

An efficient nanoscale heterogeneous catalyst for the capture and conversion of carbon dioxide at ambient pressure

Silver nanoparticles were successfully supported on the zeolite-type metal-organic framework MIL-101 to yield Ag@MIL-101 by a simple liquid impregnation method. For the first time, the conversion of terminal alkynes into propiolic acids with CO2 was achieved by the use of the Ag@MIL-101 catalysts. Owing to the excellent catalytic activity, the reaction proceeded at atmospheric pressure and low temperature (50 8C). The Ag@MIL-101 porous material is of outstanding bifunctional character as it is capable of simultaneously capturing and converting CO2 with low energy consumption and can be recovered easily by centrifugation.

Gold-Catalyzed Post-Ugi Cascade Transformation for the Synthesis of 2-Pyridones

A gold-catalyzed post-Ugi cascade transformation for the synthesis of 2-pyridones is described. The process involves furan–alkyne cyclization followed by furan ring-opening and cleavage of the isocyanide-originated fragment. The initially formed cis double bond can isomerize into a more stable trans double bond upon prolonged exposure to a strong Br?nsted acid. Thus, the overall strategy provides a viable access towards two types of 2-pyridones.

Composite System of Ag Nanoparticles and Metal-Organic Frameworks for the Capture and Conversion of Carbon Dioxide under Mild Conditions

The materials Ag@MIL-100(Fe) and Ag@UIO-66(Zr) are obtained for the capture and transformation of CO2 into alkynyl carboxylic acids, which are environmental friendly, facile to synthesize, and exhibit excellent efficiency and reusability. The influence on the catalytic activity of such Ag@MOF systems by metal-organic frameworks' (MOFs) surface area, thermal, and chemical stability, especially the acid-base characteristics of the pores, are compared and discussed systematically.

An efficient Ag/MIL-100(Fe) catalyst for photothermal conversion of CO2 at ambient temperature

The conversion of CO2 under mild condition is of great importance because these reactions involving CO2 can not only produce value-added chemicals from abundant and inexpensive CO2 feedstock but also close the carbon cycle. However, the chemical inertness of CO2 requires the development of high-performance catalysts. Herein, Ag nanoparticles/MIL-100(Fe) composites were synthesized by simple impregnation-reduction method and employed as catalysts for the photothermal carboxylation of terminal alkynes with CO2. MIL-100(Fe) could stabilize Ag nanoparticles and prevent them from aggregation during catalytic process. Taking the advantages of photothermal effects and catalytic activities of both Ag nanoparticles and MIL-100(Fe), various aromatic alkynes could be converted to corresponding carboxylic acid products (86%–92% yields) with 1 atm CO2 at room temperature under visible light irradiation when using Ag nanoparticles/MIL-100(Fe) as photothermal catalysts. The catalysts also showed good recyclability with almost no loss of catalytic activity for three consecutive runs. More importantly, the catalytic performance of Ag nanoparticles/MIL-100(Fe) under visible light irradiation at room temperature was comparable to that upon heating, showing that the light source could replace conventional heating method to drive the reaction. This work provided a promising strategy of utilizing solar energy for achieving efficient CO2 conversion to value-added chemicals under mild condition.

Hierarchically porous covalent organic frameworks assembled in ionic liquids for highly effective catalysis of C-C coupling reactions

Although significant progress has been made in the synthesis of covalent organic frameworks (COFs) in recent years, the construction of hierarchical pores in such materials remains a great challenge. Herein, we report a facile synthesis of hierarchically porous COFs (HP-COFs) under mild conditions in ionic liquids 1-alkyl-3-methylimidazolium tetrafluoroborates ([Cnmim][BF4], n = 4, 6, 10). It has been found that apart from the inherent micropores, a large mesoporous structure has been produced in the COFs in which the size of pores can be simply tuned by adjusting the alkyl chain length of the ionic liquids. These mesopores have been confirmed by N2 sorption and electron microscopy techniques. Importantly, this approach is applicable for the preparation of various HP-COFs, such as imine and hydrazone based COFs, which are quite difficult to acquire through traditional methods. In addition, these HP-COFs show highly effective catalytic performance for C-C bond formation, especially for large size molecule based C-C coupling reactions in comparison with uni-pore COFs.

Cobalt-Mediated Decarboxylative/Desilylative C?H Activation/Annulation Reaction: An Efficient Approach to Natural Alkaloids and New Structural Analogues

A Co(II)-mediated decarboxylative/desilylative C?H activation/annulation reaction for the efficient synthesis of 3-arylisoquinolines has been developed. Using alkynyl carboxylic acid and alkynyl silane as terminal alkyne precursors, providing straightforw

Acetylenic Replacement of Albicidin's Methacrylamide Residue Circumvents Detrimental E/Z Photoisomerization and Preserves Antibacterial Activity

The natural product albicidin is a highly potent inhibitor of bacterial DNA gyrase. Its outstanding activity, particularly against Gram-negative pathogens, qualifies it as a promising lead structure in the search for new antibacterial drugs. However, as we show here, the N-terminal cinnamoyl moiety of albicidin is susceptible to photochemical E/Z isomerization. Moreover, the newly formed Z isomer exhibits significantly reduced antibacterial activity, which hampers the development and biological evaluation of albicidin and potent derivatives thereof. Hence, we synthesized 13 different variants of albicidin in which the vulnerable para-coumaric acid moiety was replaced; this yielded photostable analogues. Biological activity assays revealed that diaryl alkyne analogues exhibited virtually undiminished antibacterial efficacy. This promising scaffold will therefore serve as a blueprint for the design of a potent albicidin-based drug.

Enantioselective hydroesterificative cyclization of 1,6-enynes to chiral γ-lactams bearing a quaternary carbon stereocenter

A palladium-catalyzed asymmetric hydroesterification-cyclization of 1,6-enynes with CO and alcohol was developed to efficiently prepare a variety of enantioenriched γ-lactams bearing a chiral quaternary carbon center and a carboxylic ester group. The approach featured good to high chemo-, region-, and enantioselectivities, high atom economy, and mild reaction conditions as well as broad substrate scope. The correlation between the multiple selectivities of such process and the N-substitutes of the amide linker in the 1,6-enyne substrate has been depicted by the crystallographic evidence and control experiments.

Access to Triazolopiperidine Derivatives via Copper(I)-Catalyzed [3+2] Cycloaddition/Alkenyl C?N Coupling Tandem Reactions

A copper-catalyzed [3+2] cylcoaddition/ alkenyl C?N coupling tandem reaction was demonstrated. It provided a method for the formation of triazolopiperidine skeletons. (Figure presented.).

Organocatalytic Strategy for the Fixation of CO2via Carboxylation of Terminal Alkynes

An organocatalytic strategy for the direct carboxylation of terminal alkynes with CO2 has been developed. The combined use of a bifunctional organocatalyst and Cs2CO3 resulted in a robust catalytic system for the preparation of a range of propiolic acid derivatives in high yields with broad substrate scope using CO2 at atmospheric pressure under mild temperatures (60 °C). This work has demonstrated that this organocatalytic method offers a competitive alternative to metal catalysis for the carboxylation of terminal alkynes and CO2. In addition, this protocol was suitable for the three-component carboxylation of terminal alkynes, alkyl halides, and CO2.