28075-50-5

Usage

Uses

Used in Chemical Synthesis:
1-Cyclohexen-1-yl trifluoromethanesulfonate is used as a reactant for the regioselective preparation of phenylpyrrolidines via C-H functionalization of amines with aryl halides. This application is significant in the synthesis of complex organic molecules and pharmaceutical compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-cyclohexen-1-yl trifluoromethanesulfonate is used as a key intermediate in the synthesis of various drugs and drug candidates. Its ability to participate in C-H functionalization and other chemical reactions makes it a valuable component in the development of new medications.
Used in Material Science:
1-Cyclohexen-1-yl trifluoromethanesulfonate may also find applications in material science, particularly in the development of new polymers and materials with specific properties. Its involvement in various chemical reactions can lead to the creation of novel materials with improved characteristics.
Used in Research and Development:
As a compound with unique chemical properties, 1-cyclohexen-1-yl trifluoromethanesulfonate is used in research and development for exploring new reaction pathways, understanding reaction mechanisms, and developing innovative synthetic methods. This can contribute to the advancement of chemical science and technology.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 277, 1986 DOI: 10.1021/jo00352a039

InChI:InChI=1/C7H9F3O3S/c8-7(9,10)14(11,12)13-6-4-2-1-3-5-6/h4H,1-3,5H2

Upstream product

• 358-23-6 trifluoromethylsulfonic anhydride 
• 108-94-1 cyclohexanone 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 456-64-4 phenyl trifluoromethanesulfonamide 
• 109-72-8 n-butyllithium 
• 120-92-3 cyclopentanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 1493-13-6 trifluorormethanesulfonic acid 

Downstream Products

• 148730-31-8 (R)-2-cyclohex-1'-en-1'-yl-2,3-dihydrofuran 
• 118716-31-7 1-(1-butoxyethenyl)cyclohexene 
• 140706-08-7 (S)-2-[(Cyclohex-1-enecarbonyl)-amino]-3-hydroxy-propionic acid methyl ester 
• 2044-08-8 1-bromocyclohex-1-ene 
• 108-94-1 cyclohexanone 
• 92610-64-5 1,1-Bis(2,2,2-trifluorethoxy)cyclohexan 
• 119472-68-3 2-((E)-2-Cyclohex-1-enyl-dec-2-enyl)-malonic acid dimethyl ester 
• 119472-69-4 2-((Z)-2-Cyclohex-1-enyl-dec-2-enyl)-malonic acid dimethyl ester 
• 125952-13-8 2-ethoxy-1-cyclohex-1-enylprop-2-en-1-one 
• 141889-70-5 ethyl 2-(N-acetyl)-5-(cyclohex-1-en-1-yl)pent-4-ynoate 
• 118716-32-8 1-(1-ethoxyethenyl)cyclohexene 
• 22767-95-9 1-methylethyl 3-phenylpropionoate 
• 127977-28-0 (S)-2-tert-Butoxycarbonylamino-3-cyclohex-1-enyl-propionic acid benzyl ester 
• 4452-32-8 diethylcyclohexenylphosphate 

Relevant academic research and scientific papers

A Stepwise Annulation for the Transformation of Cyclic Ketones to Fused 6 and 7-Membered Cyclic Enimines and Enones

The efficient construction of functionalized polycyclic structures is an important objective in organic synthesis. Herein, we disclose a three-step “[2 + n]” annulation method for the transformation of cyclic ketones to fused enimines and enones. The method relies on the Suzuki coupling reaction and the amide reductive alkenylation reaction. A series of fused bicyclic (6/6, 6/7, 8/7) and tricyclic (6/6/6; 6/6/7, 6/5/7) ring systems bearing an α,β-enimine or an α,β-enone functionality have been synthetized in good overall yields.

A short and convenient preparation of (E)-3-(1-cyclohexenyl)-2- propenoic acid using a palladium(II) complex-catalyzed olefination

A convenient, three-step preparation of (E)-3-(1-cyclohexenyl)-2- propenoic acid (1) from cyclohexanone was developed, which exploited the palladium(II) complex-catalyzed olefination of the triflate 3 as a key step.

2,4,6-Tri-tert-butylpyrimidine (TTBP): A cost effective, readily available alternative to the hindered base 2,6-di-tert-butylpyridine and its 4-substituted derivatives in glycosylation and other reactions

It is reported that 2,4,6-tri-tert-butylpyrimidine (TTBP), a highly sterically hindered base available through an efficient, cost-effective one pot sequence, is a replacement for 2,6-di-tert-butylpyridine and its 4-substituted analogs in glycosylation rea

Alkenylation and Arylation of Peptides via Ni-Catalyzed Reductive Coupling of α- C-Tosyl Peptides with Csp2Triflates/Halides

A Ni-catalyzed reductive cross-coupling between α-C-tosyl peptides and Csp2 triflates/halides has been developed. This protocol enables the formation of various unnatural di- and tripeptides containing vinyl and aryl side chains, and it expands the applications of Ni-catalyzed reductive cross-coupling in late-stage diversification of peptides.

Electrochemical Deoxygenative Thiolation of Preactivated Alcohols and Ketones

This work describes an electrochemically promoted nickel-catalyzed deoxygenative thiolation of alcohols and ketones under mild conditions. Excellent substrate tolerance and good chemical yields can be achieved by graphene/nickel foam electrodes in an undivided cell. Further study to gain mechanistic insight into this electrochemical cross-coupling has been carried out.

Visible-Light Photoredox Catalyzed Dehydrogenative Synthesis of Allylic Carboxylates from Styrenes

The visible-light photoredox/[Co(III)] cocatalyzed dehydrogenative functionalization of cyclic and acyclic styryl derivatives with carboxylic acids is documented. The methodology enables the chemo- and regioselective allylic functionalization of styryl compounds, leading to allylic carboxylates (32 examples) under stoichiometric acceptorless conditions. Intermolecular as well as intramolecular variants are documented in high yields (up to 82%). A mechanistic rationale is also proposed on the basis of a combined experimental and spectroscopic investigation.

Three-Component Difunctionalization of Cyclohexenyl Triflates: Direct Access to Versatile Cyclohexenes via Cyclohexynes

Difunctionalization of strained cyclic alkynes presents a powerful strategy to build richly functionalized cyclic alkenes in an expedient fashion. Herein we disclose an efficient and flexible approach to achieve carbohalogenation, dicarbofunctionalization, aminohalogenation and aminocarbonation of readily available cyclohexenyl triflates. We have demonstrated the novel use of zincate base/nucleophile system for effective formation of key cyclohexyne intermediates and selective addition of various carbon and nitrogen nucleophiles. Importantly, leveraging the resulting organozincates enables the incorporation of a broad range of electrophilic partners to deliver structurally diverse cyclohexene motifs. The importance and utility of this method is also exemplified by the modularity of this approach and the ease in which even highly complex polycyclic scaffolds can be accessed in one step.

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

Sequential Suzuki-Miyaura Coupling/Lewis Acid-Catalyzed Cyclization: An Entry to Functionalized Cycloalkane-Fused Naphthalenes

Functionalized angular cycloalkane-fused naphthalenes were prepared using a two-step process involving a Pd-catalyzed Suzuki-Miyaura coupling of aryl pinacol boronates and vinyl triflates followed by a boron trifluoride etherate-catalyzed cycloaromatization.

Metal-Free 1,2,3-Triazole Synthesis in Deep Eutectic Solvents

The metal-free regioselective preparation of 1,5- and 1,4-disubstituted triazoles is reported through a cycloaddition-elimination sequence. Reactions were carried out in environmentally friendly deep eutectic solvent (DES) and pure products were isolated