76925-79-6

Basic information

• Product Name: 2-Propynoic acid, 3-(1-hydroxycyclohexyl)-, ethyl ester
• CAS NO: 76925-79-6
• Molecular Formula: C11H16O3
• Molecular Weight: 196.246
• Mol File: 76925-79-6.mol

Chemical Properties

• CAS DataBase Reference: 2-Propynoic acid, 3-(1-hydroxycyclohexyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propynoic acid, 3-(1-hydroxycyclohexyl)-, ethyl ester(76925-79-6)
• EPA Substance Registry System: 2-Propynoic acid, 3-(1-hydroxycyclohexyl)-, ethyl ester(76925-79-6)

Safety Data

• Hazardous Substances Data: 76925-79-6(Hazardous Substances Data)

Upstream product

• 64-17-5 ethanol 
• 25294-58-0 3-(1-hydroxycyclohexyl)propiolic acid 
• 78-27-3 1-Ethynylcyclohexan-1-ol 
• 108-94-1 cyclohexanone 
• 623-47-2 propynoic acid ethyl ester 

Downstream Products

• 27338-44-9 3-(cyclohex-1-en-1-yl)propionic acid 
• 65173-43-5 ethyl 3-(cyclohex-1-en-1-yl)propionate 
• 74120-62-0 ethyl 3-(1'-hydroxycyclohexyl)propionate 
• 1062140-80-0 C₁₅H₂₄O₄ 
• 126491-76-7 3-(1-hydroxy-1-cyclohexyl)-2-propynamide 
• 25294-58-0 3-(1-hydroxycyclohexyl)propiolic acid 

Relevant articles and documents

Molecular Hybridization of Potent and Selective γ-Hydroxybutyric Acid (GHB) Ligands: Design, Synthesis, Binding Studies, and Molecular Modeling of Novel 3-Hydroxycyclopent-1-enecarboxylic Acid (HOCPCA) and trans-γ-Hydroxycrotonic Acid (T-HCA) Analogs

γ-Hydroxybutyric acid (GHB) is a neuroactive substance with specific high-affinity binding sites. To facilitate target identification and ligand optimization, we herein report a comprehensive structure-affinity relationship study for novel ligands targeting these binding sites. A molecular hybridization strategy was used based on the conformationally restricted 3-hydroxycyclopent-1-enecarboxylic acid (HOCPCA) and the linear GHB analog trans-4-hydroxycrotonic acid (T-HCA). In general, all structural modifications performed on HOCPCA led to reduced affinity. In contrast, introduction of diaromatic substituents into the 4-position of T-HCA led to high-affinity analogs (medium nanomolar Ki) for the GHB high-affinity binding sites as the most high-affinity analogs reported to date. The SAR data formed the basis for a three-dimensional pharmacophore model for GHB ligands, which identified molecular features important for high-affinity binding, with high predictive validity. These findings will be valuable in the further processes of both target characterization and ligand identification for the high-affinity GHB binding sites.

Rhodium-Catalyzed Cascade Reactions of Indoles with 4-Hydroxy-2-Alkynoates for the Synthesis of Indole-Fused Polyheterocycles

Herein, an efficient and regioselective Rh(III)-catalyzed [4+2] annulation/lactonization cascade of indoles with 4-hydroxy-2-alkynoates at room temperature to access the furo[3′,4′:4,5]pyrimido[1,6-a]indole-1,5(3H,4H)-diones is described. This method feat

Synthesis of γ-acetoxy β-keto esters through regioselective hydration of γ-acetoxy-α,β-alkynoates

The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are selectively hydrated to the corresponding β-keto esters. The reaction tolerates a wide variety of other carboxylates, such as benzoates, propionates, acrylates, and pivalates, including chiral carboxylates with retention of the configuration. The broad substrate scope, including the derivatization of complex natural products and neutral and open air conditions, makes this atom economical approach very practical. 18O labeling experiments disclose that the oxygen transposition occurs from the carboxylate group to the triple bond, not from water.

Microwave-Assisted Organocatalyzed Rearrangement of Propargyl Vinyl Ethers to Salicylaldehyde Derivatives: An Experimental and Theoretical Study

The microwave-assisted imidazole-catalyzed transformation of propargyl vinyl ethers (PVEs) into multisubstituted salicylaldehydes is described. The reaction is instrumentally simple, scalable, and tolerates a diverse degree of substitution at the propargylic position of the starting PVE. The generated salicylaldehyde motifs incorporate a broad range of topologies, spanning from simple aromatic monocycles to complex fused polycyclic systems. The reaction is highly regioselective and takes place under symmetry-breaking conditions. The preparative power of this reaction was demonstrated in the first total synthesis of morintrifolin B, a benzophenone metabolite isolated from the small tree Morinda citrifolia L. A DFT study of the reaction was performed with full agreement between calculated values and experimental results. The theoretically calculated values support a domino mechanism comprising a propargyl Claisen rearrangement, a [1,3]-H shift, a [1,7]-H shift (enolization), a 6π electrocyclization, and an aromatization reaction.

Gold(I)-catalyzed tandem alkoxylation/lactonization of γ-hydroxy- α,β-acetylenic esters

The formation of 4-alkoxy-2(5H)-furanones was achieved via tandem alkoxylation/lactonization of γ-hydroxy-α,β-acetylenic esters catalyzed by 2 mol% of [2,6-bis(diisopropylphenyl)imidazol-2-ylidine]gold bis(trifluoromethanesulfonyl)imidate [Au(IPr)(NTf2)]. The economic and simple procedure was applied to a series of various secondary propargylic alcohols allowing for yields of desired product of up to 95%. In addition, tertiary propargylic alcohols bearing mostly cyclic substituents were converted into the corresponding spiro derivatives. Both primary and secondary alcohols reacted with propargylic alcohols at moderate temperatures (65-80 °C) in either neat reactions or using 1,2-dichloroethane as a reaction medium allowing for yields of 23-95%. In contrast to [Au(IPr)(NTf2)], reactions with cationic complexes such as [2,6-bis(diisopropylphenyl)imidazol-2-ylidine] (acetonitrile)gold tetrafluoroborate [Au(IPr)(CH3CN)][BF4] or (μ-hydroxy)bis{[2,6-bis(diisopropylphenyl)imidazol-2-ylidine]gold} tetrafluoroborate or bis(trifluoromethanesulfonyl)imidate - [{Au(IPr)} 2(μ-OH)][X] (X=BF4, NTf2) - mostly stop after the alkoxylation. Analysis of the intermediate proved the exclusive formation of the E-isomer which allows for the subsequent lactonization. Copyright

Gold-catalyzed one-step practical synthesis of oxetan-3-ones from readily available propargylic alcohols

A general solution for the synthesis of various oxetan-3-ones is developed. This reaction uses readily available propargylic alcohols as substrates and proceeds without the exclusion of moisture or air ("open flask"). Notably, oxetan-3-one, a highly valuable substrate for drug discovery, can be prepared in one step from propargyl alcohol in a fairly good yield. The facile formation of the strained oxetane ring provides strong support for the intermediacy of α-oxo gold carbenes. This safe and efficient generation of gold carbenes via intermolecular alkyne oxidation offers a potentially general entry into α-oxo metal carbene chemistry without using hazardous diazo ketones.

Catalytic alkynylation of ketones and aldehydes using quaternary ammonium hydroxide base

Catalytic alkynylation of diverse ketones and aldehydes using nonmetallic benzyltrimethylammonium hydroxide or a basic resin of the hydroxide type in DMSO is described. Aliphatic or alicyclic carbonyl partners gave satisfactory results, whereas aromatic o