4361-27-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Propynoic acid, 3-cyclohexylis used as an intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Polymer Industry:
2-Propynoic acid, 3-cyclohexylis utilized as a monomer or a building block in the production of polymers. Its incorporation into polymer structures can enhance properties such as strength, flexibility, and durability.
Used in Organic Synthesis:
2-Propynoic acid, 3-cyclohexylis used as a reactant in various organic synthesis processes. Its reactivity and functional groups make it suitable for the formation of complex molecules and materials.
Used in Research:
2-Propynoic acid, 3-cyclohexylserves as a valuable research tool for chemists studying the properties and reactions of propynoic acid derivatives and cyclohexyl-containing compounds. It can provide insights into the development of new synthetic methods and applications.

Upstream product

• 931-48-6 2-cyclohexylacetylene 
• 42134-54-3 3-cyclohexyl-2-propyn-1-ol 
• 2043-61-0 cyclohexanecarbaldehyde 
• 60754-49-6 1,1-dibromo-2-cyclohexylethene 
• 131292-27-8 (α-cyclohexylcarbonyl-α-ethoxycarbonylmethylene)triphenylphosphorane 
• 2719-27-9 cyclohexanylcarbonyl chloride 
• 124-38-9 carbon dioxide 
• 33547-94-3 cyclohexyl-propynoic acid ethyl ester 

Downstream Products

• 42134-55-4 (E)-3-cyclohexyl-2-propen-1-ol 
• 33542-59-5 cyclohexylpropynoic acid N-hydroxy-anilide 
• 42134-60-1 cyclohexylpropynoic acid methyl ester 
• 929704-60-9 (Z)-S-2-acetamidoethyl 3-cyclohexylprop-2-enethioate 
• 1394233-05-6 3-cyclohexylpropynoic acid (3,5-dimethoxybenzyl)naphthalen-1-ylamide 
• 1431959-87-3 C₂₁H₂₅N₅O₂ 
• 1431961-15-7 TH₀₄₃₀₃-040 
• 1431961-14-6 TH₀₄₃₀₃-013 
• 78659-22-0 1-cyclohexyl-3,3,3-trifluoropropan-1-one 

Relevant academic research and scientific papers

CO2-Folded Single-Chain Nanoparticles as Recyclable, Improved Carboxylase Mimics

Emulating the function of natural carboxylases to convert CO2 under atmospheric condition is a great challenge. Herein we report a class of CO2-folded single-chain nanoparticles (SCNPs) that can function as recyclable, function-intensified carboxylase mimics. Lewis pair polymers containing bulky Lewis acidic and basic groups as the precursor, can bind CO2 to drive an intramolecular folding into SCNPs, in which CO2 as the folded nodes can form gas-bridged bonds. Such bridging linkages highly activate CO2, which endows the SCNPs with extraordinary catalytic ability that can not only catalyze CO2-insertion of C(sp3)-H for imitating the natural enzyme's function, it can also act on non-natural carboxylation pathways for C(sp2 and sp)-H substrates. The nanocatalysts are of highly catalytic efficiency and recyclability, and can work at room temperature and near ambient CO2 condition, inspiring a new approach to sustainable C1 utilization.

Semireduction of alkynoic acids via a transition metal-free α borylation-protodeborylation sequence

A method for the semi-reduction of alkynoic acids through an α-borylation and subsequent protodeborylation mechanism has been developed. The transition metal-free protocol is achieved through the activation of bis(pinacolato)diboron by an in situ generated carboxylate moiety yielding aryl acrylic acids. Our studies demonstrate an unprecedented dual role for the carboxylate anion that involves the activation of the diboron reagent and a directing effect in the α-borylation.

Core-shell metal-organic frameworks and metal functionalization to access highest efficiency in catalytic carboxylation

A core-shell metal-organic frameworks (MOF@MOF) based on the Zr-MOFs assembly from core-structure UiO-66 combined with shell-structure UiO-67-BPY were explored. The synthesized materials were characterized via XRD, FTIR, SEM, TEM, and surface area analysis, etc. indicating the presence of a core-shell structure of UiO-66@UiO-67-BPY. Furthermore, incorporation of the bipyridinic (BPY) group in the linker used to construct the shell layer (UiO-67-BPY) could coordinate with active metal species and thus create an advantage for site-selective metal incorporation in the core-shell structure. Silver (Ag) was selected for the selective metal incorporation and an excellent Ag-dispersion via coordination with the bipyridinic groups in the UiO-67-BPY layer of the core-shell material was obtained. The synthesized material (UiO-66@UiO-67-BPY-Ag) was successfully applied as a heterogeneous catalyst for the CO2 fixation via carboxylation of terminal alkynes. The catalytic material showed excellent yields using at a low Ag-loading under mild reaction condition (50 °C, 1 bar). Moreover, the catalyst can be recycled for at least 5 times maintaining a stable catalytic performance. Interestingly, the high catalytic activity of the synthesized material demonstrated clearly the beneficial advantage of the metalated core-shell structure over the reported routes to synthesize silver catalysts such as encapsulated Ag nanoparticles (AgNP@MOF) or Ag-bidentately coordinated on traditional MOFs applying the same reaction model.

Sequential protocol for C(sp)–H carboxylation with CO2: KOtBu-catalyzed C(sp)–H silylation and KOtBu-mediated carboxylation

CO2 incorporation into C–H bonds is an important and interesting topic. Herein a sequential protocol for C(sp)–H carboxylation by employing a metal-free C–H activation/catalytic silylation reaction in conjunction with KOtBu-mediated carboxylation with CO2 was established, in which KOtBu catalyzes silylation of terminal alkynes to form alkynylsilanes at low temperature, and simultaneously mediates carboxylation of the alkynesilanes with atmospheric CO2. Importantly, the carboxylation further promotes the silylation, which makes the whole reaction proceed very rapidly. Moreover, this methodology is simple and scalable, which is characterized by short reaction time, wide substrate scope, excellent functional-group tolerance and mild reaction conditions, affording a range of corresponding propiolic acid products in excellent yields in most cases. In addition, it also allows for a convenient 13C-labeling through the use of 13CO2.

Method for preparing propiolic acid and derivatives thereof under mild condition

The invention provides a novel method for preparing propiolic acid compounds through a domino reaction. The method comprises a step of subjecting terminal alkyne compounds, hydrosilane and CO2 to thedomino reaction under the catalysis action of Lewis base so as to obtain propiolic acid compounds. According to the invention, common Lewis base is used as a promoter, and corresponding propiolic acidcompounds containing different function groups can be efficiently produced through a reaction of the terminal alkyne compounds with hydrosilane and normal-pressure CO2 under a mild condition (a temperature of 40 DEG D). According to the method, CO2 is used as a raw material; the cheap Lewis base is used as the promoter; usage of precious metals is avoided; the domino reaction is employed; purification and separation of intermediates are not needed; and reaction conditions are mild. Thus, the method is an efficient cheap green synthetic method and has good industrial application value.

Carboxylation of Terminal Alkynes with Carbon Dioxide Catalyzed by an In Situ Ag2O/N-Heterocyclic Carbene Precursor System

A carboxylation of terminal alkynes with carbon dioxide (CO2) at ambient conditions was developed in situ using a series of N-heterocyclic carbene (NHC) precursors and Ag2O. The unique structure of NHCs largely increases the solubility of active Ag species and meanwhile activates CO2 by forming the NHC–CO2 adduct. This novel catalytic system demonstrated quite low Ag loading, very high activities, wide substrate generality and excellent tolerance for a variety of functionalities. In addition, avoiding cumbersome synthesis procedures, processing, and reserving of the photosensitive Ag complex, this system could be stored and operated as straightforward as the inorganic Ag salt catalysts.

Cis -1,2-Bis(diphenylphosphino)ethylene copper(i) catalyzed C-H activation and carboxylation of terminal alkynes

The reaction of cis-1,2-bis(diphenylphosphino)ethylene (dppet) with CuX (X = CN, SCN) in 1:1 M molar ratio in DCM-MeOH (50:50 V/V) under refluxing conditions gave two dimeric Cu(i) complexes, viz. [Cu2(μ-CN)2(κ2-P,P-dppet)2] (1) and [Cu2(μ2-SCN)2(κ2-P,P-dppet)2] (2). These complexes have been characterized by elemental analyses, IR, 1H and 31P NMR, and electronic absorption spectroscopies, and ESI-MS. The molecular structure of 2 was confirmed by single crystal X-ray diffraction, which indicated that 2 exists as a centrosymmetric dimer in which the two copper centers are bonded to two dppet ligands and two bridging thiocyanate groups in a μ2-manner. The electrochemical properties of 1 and 2 were studied by cyclic voltammetry. Both the complexes exhibited strong luminescence properties in the solution state at ambient temperature. Both the complexes were found to be efficient catalysts for the conversion of terminal alkynes into propiolic acids with CO2. Owing to their excellent catalytic activity, the reactions proceed at atmospheric pressure and ambient temperature (25 °C). The catalytic products were obtained in excellent yields (90-97%) by using the complex loading of 1 mol%.

Development of Gold-catalyzed [4+1] and [2+2+1]/[4+2] Annulations between Propiolate Derivatives and Isoxazoles

Two new gold-catalyzed annulations of isoxazoles with propiolates have been developed. Most isoxazoles follow an initial O attack on the alkyne to afford a [4+1] annulation product. This process results in a remarkable alkyne cleavage of initial propiolates. Unsubstituted isoxazoles proceed through an N attack step to yield formal [2+2+1]/[4+2] annulation products. These two annulation products arise initially from two seven-membered heterocyclic intermediates, which then lead to products.

1,1′-Bis(di-tert-butylphosphino)ferrocene copper(i) complex catalyzed C-H activation and carboxylation of terminal alkynes

Four copper(i) complexes, [CuBr(dtbpf)] (1), [CuI(dtbpf)] (2), [Cu4(μ2-I)2(μ3-I)2(μ-dtbpf)2] (3) and [Cu6(μ3-I)6(μ-dtbpf)2]·2CH3CN (4), were prepared using CuX (X = Br, I) and 1,1′-bis(di-tert-butylphosphino)ferrocene (dtbpf). These complexes have been characterized by elemental analyses, IR, 1H and 31P NMR, ESI-MS and electronic absorption spectroscopy. Molecular structures of the complexes 2 and 4 were determined crystallographically. Complex 2 is the first monomeric isolated Cu(i) complex of dtbpf with the largest P-Cu-P bite angle (120.070(19)°) to date. Complex 4 shows a centrosymmetrical dimeric unit with two [Cu3(μ3-I)3] motifs bridged by two bidentate dtbpf ligands in the κ1-manner. Each [Cu3(μ3-I)3] motif unites to form a pyramid with one copper atom at the apex and one of the triangular faces capped by an iodine atom. All the complexes were found to be efficient catalysts for the conversion of terminal alkynes into propiolic acids with CO2. Owing to the excellent catalytic activity, the reactions proceeded at atmospheric pressure and ambient temperature (25 °C). The catalytic products were obtained in moderate to good yields (80-96%) by using complex loading to 2 mol%. To the best of our knowledge, this is the first example of an active ferrocenyl diphosphine Cu(i) catalyst for the carboxylation of terminal alkynes with CO2.

Benzannulation of triynes to generate functionalized arenes by spontaneous incorporation of nucleophiles

The thermal reaction of ester-tethered 1,3,8-triynes provides novel benzannulation products with concomitant incorporation of a nucleophile. Evidence suggests that this reaction proceeds via an allene-enyne intermediate generated by an Alder-ene reaction in the first step. Depending on the substituent of the alkyne moiety on the allene-enyne intermediate, the subsequent transformation can take one of two different paths, each leading to discrete aromatization products. The benzannulation of a silane-substituted 1,3,8-triynes provides arene products with a nucleophile incorporated onto the newly formed benzene core, whereas an aryl substituent leads to nucleophile trapping at the benzylic carbon atom connected to the aryl substituent. The formation of these two different products results from the involvement of two regioisomeric allene-enyne intermediates.