66684-39-7

Usage

Uses

Used in Pharmaceutical Industry:
(bromoethynyl)cyclohexane is utilized as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and medications. Its alkyne group facilitates essential reactions that enable the formation of complex molecular structures required for therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, (bromoethynyl)cyclohexane serves as a key component in the production of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties allow for the creation of effective compounds that protect crops and enhance agricultural productivity.
Used in Fine Chemicals Production:
(bromoethynyl)cyclohexane is also employed in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including cosmetics, fragrances, and specialty chemicals. Its versatility in organic synthesis makes it a valuable asset in the development of high-quality and specialized products.
Safety Precautions:
It is crucial to handle (bromoethynyl)cyclohexane with care, as it is potentially hazardous. Direct contact with the skin and eyes can cause irritation, necessitating the use of appropriate protective equipment and safety measures during its manipulation and storage.

Upstream product

• 931-48-6 2-cyclohexylacetylene 
• 506-68-3 bromocyane 
• 60754-49-6 1,1-dibromo-2-cyclohexylethene 

Downstream Products

• 112043-61-5 7-cyclohexyl-(E)-6-hepten-1-ol 
• 106924-77-0 ((E)-2-Bromo-hex-1-enyl)-cyclohexane 
• 91219-55-5 Thiophosphoric acid S-cyclohexylethynyl ester O,O'-diethyl ester 
• 60754-49-6 1,1-dibromo-2-cyclohexylethene 
• 67404-69-7 (Z)-1-iodo-2-cyclohexyl-1-ethene 
• 67478-59-5 (E)-1-bromo-2-cyclohexyl-1-ethene 
• 112330-88-8 Thiophosphoric acid S-cyclohexylethynyl ester O,O'-dimethyl ester 
• 56077-28-2 Bromomethyl cyclohexyl ketone 
• 1121746-89-1 C₁₈H₂₃NO₂S 
• 1221576-82-4 2-cyclohexylethynyl-5-methylbenzoxazole 
• 1221577-02-1 2-(1-cyclohexyl)ethynyl-4,4-dimethyloxazoline 
• 1429308-91-7 N-allyl-N-(tert-butoxycarbonyl)cyclohexylethynylamine 
• 1422721-79-6 methyl cyclohexylethynyl(phenyl)carbamate 
• 1422721-73-0 (E)-methyl 2-cyclohexyl-1-iodovinyl(phenyl)carbamate 

Relevant academic research and scientific papers

Diastereo- and Enantioselective 1,4-Difunctionalization of Borylenynes by Catalytic Conjunctive Cross-Coupling

Enantioselective conjunctive cross-coupling of enyne-derived boronate complexes occurs with 1,4 addition of the electrophile and migrating group across the π system. This reaction pathway furnishes α-boryl allenes as the reaction product. In the presence of a chiral catalyst, both the central and axial chirality of the product can be controlled during product formation.

Palladium-Catalyzed Carbonylation in the Synthesis of N-Ynonylsulfoximines

Palladium-catalyzed carbonylation reactions with Cr(CO)6 as carbonyl source are key for the preparation of N-ynonylsulfoximines from NH-sulfoximines and bromoalkynes. The couplings proceed at room temperature with a wide range of substrate combinations affording the corresponding products in good yields. (Figure presented.).

Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides

In this paper we are reporting the first regio- and stereoselective silylformylation of ynamides. This reaction is tolerant to a wide range of functional groups around the ynamides. The substitution of CO by an isocyanide makes this reaction safer and mor

A Micellar Catalysis Strategy for Amidation of Alkynyl Bromides: Synthesis of Ynamides in Water

Copper-catalyzed amidation of alkynyl bromides can be carried out in water for the first time, which is made possible by a micellar catalysis strategy using rosin-based surfactant APGS-550-M. The surfactant can be easily prepared from natural abundant biomass, resin acids. Studies as to substrate scope and reaction aqueous medium recycling showcase the ease and sustainability of this technology.

Gold Catalyzed Photoredox C1-Alkynylation of N-Alkyl-1,2,3,4- tetrahydroisoquinolines by 1-Bromoalkynes with UVA LED Light

A synthetic method that combines [Au2(m-dppm)2]Cl2 (dppm=bis(diphenylphosphanyl)methane) and UVA LED (LED=light emitting diode) light (365 nm) to catalyze the regioselective C1-alkynylation of N-alkyl-1,2,3,4-tetrahydroisoquinolines (THIQs) with alkynyl bromides is described. The reaction mechanism was delineated to involve a reductive quench pathway to generate the two posited radical species of the nitrogen-containing heterocycle and organic halide. In contrast, radical formation via an oxidative quench pathway was suggested to be operative in analogous control experiments with a 1-iodoalkyne. The usefulness of this carbon-carbon bond forming strategy was also exemplified by its application to the formal synthesis of the opioid analgesic drug methopholine and synthesis of a protoberberine alkaloid derivative.

Nickel-Catalyzed Reductive 1,2-Dialkynylation of Alkenes Bearing an 8-Aminoquinoline Directing Group

An unprecedented nickel-catalyzed reductive 1,2-dialkynylation of alkenes bearing an 8-aminoquinoline directing group has been developed. This method proceeded through a migratory insertion/reductive-coupling process under mild conditions with a wide substrate scope and good functional group tolerance, providing direct access to the synthetically flexible 1,5-diynes. Moreover, the 1,2-dialkynylation products could be further converted to borate-ester- or azide-functionalized 1,5-dienes, ditriazole, β-diyne primary amide, and trisubstituted benzene.

Copper-mediated synthesis of N-vinyl ynamides from N-vinyl carbamates

Ynamides are versatile 3-atoms building blocks for organic synthesis as they participate in a variety of ionic, radical and pericyclic processes. Converting ynamides into 5-atom building blocks, such as the yet unreported N-vinyl ynamides, would open new avenues in this fascinating chemistry. We describe herein our efforts towards such goal and demonstrate that the cross-coupling between N-vinyl carbamates and bromo-alkynes using copper(I) thiophene carboxylate, 1,10-phenanthroline and tBuOK in DMSO is a reactive system with an improved profile compared to the classical ynamides syntheses. The advantages and limitations of this copper-mediated reaction are discussed.

A Stereoselective Synthesis of the Carbon Backbone of Phoslactomycin B

A convergent synthesis of the entire carbon framework of phoslactomycin B is disclosed. An initial route aimed to create the C-8 tetrasubstituted stereocentre through regioselective intermolecular coupling between an internal alkyne and an allyl silyl ether, adopting Trost's protocol, followed by [2,3] sigmatropic rearrangement. But this was not successful. In a second approach, a propargylic sulfide was rearranged to give an unsaturated ketone. This was then treated with lithio acetonitrile to create the C-8 stereocentre selectively. The C-4 and C-5 stereocentres were introduced by a non-Evans syn-aldol reaction using Crimmins's protocol. The C-9 and C-11 carbinol centres were created by asymmetric transfer hydrogenation. The (Z,Z)-diene moiety was introduced by partial reduction of a diyne following Hansen's modification of the Boland reduction reaction.

Borane-catalyzed selective hydrosilylation of internal ynamides leading to β-silyl (Z)-enamides

We have developed a borane-catalyzed regioand stereoselective hydrosilylation of internal ynamides for the first time. The scope of ynamide substrates and silane reactants was broad under mild reaction conditions, affording synthetically versatile β-silyl (Z)-enamide products. The observed stereoselectivity was reasoned to be due to the β-silicon effect on a postulated ketene iminium intermediate.

Cobalt(II)-catalyzed electrophilic alkynylation of 1,3-dicarbonyl compounds to form polysubstituted furans via π-π Activation

Polysubstituted furans were obtained with excellent yields via the electrophilic alkynylation of 1,3-dicarbonyl compoundsws with phenyl- or ester-substituted brominated alkynes. The reaction is catalyzed by the inexpensive and readily available catalyst, cobalt(II) chloride, and has a wide substrate scope. The C(sp)-C(sp3) coupling occurs under mild conditions with short reaction times and does not require an inert atmosphere or ligands. It is proposed that the reaction proceeds through a chelation complex of cobalt(II) with the deprotonated 1,3-dicarbonyl compound.