15332-37-3

Upstream product

• 931-49-7 1-ethenylcyclohexene 
• 75618-25-6 butyl triflate 
• 42930-39-2 n-butylzinc chloride 
• 108-94-1 cyclohexanone 
• 32359-01-6 hexenylmagnesium bromide 
• 693-02-7 hex-1-yne 
• 71321-23-8 Methanesulfonic acid 1-trimethylsilanylethynyl-cyclohexyl ester 
• 17962-22-0 1-((trimethylsilyl)ethynyl)cyclohexanol 
• 111-71-7 heptanal 
• 916155-49-2 (1-cyclohexylidenehex-1-en-2-yl)trimethylsilane 
• 15332-33-9 1-(hex-1-ynyl)cyclohexanol 

Downstream Products

• 30857-55-7 1-(cyclohex-1-enyl)hexan-1-one 
• 317845-82-2 2-(2-Hydroxy-cyclohexylidenemethylene)-hexanoic acid methyl ester 
• 1228117-85-8 (E)-2-(1-cyclohexenylhex-1-en-2-yl)-N,N-dimethyl-1H-indole-1-carboxamide 
• 1275466-84-6 methyl 1-acetyl-4-butyl-5-(cyclohex-1-enyl)-1H-pyrrole-2-carboxylate 
• 1400915-20-9 C₂₀H₃₀OSi 
• 1400915-05-0 C₂₃H₄₃BO₃Si 
• 1426536-63-1 C₁₄H₂₆OSi 
• 1426536-38-0 C₁₄H₂₆OSi 
• 85437-90-7 (Z)-1-(1-cyclohexenyl)-1-hexene 
• 1644258-05-8 4-(4-bromophenyl)-2-butyl-1-(cyclohex-1-en-1-yl)spiro[4.5]deca-1,3,7,9-tetraen-6-one 

Relevant academic research and scientific papers

Alkylation of Terminal Alkynes under Zinc Lewis Acid Catalysis and Its Mechanistic Studies

With a zinc Lewis acid catalyst and proton sponge in toluene, terminal alkynes were found to undergo the alkylation by alkyl triflates to provide unsymmetrical internal alkynes. This is the first example that a simple alkyl chain other than benzylic and norbornyl units can be introduced onto the alkynyl carbon atom under Lewis acid catalysis. Mechanistic studies revealed that the activation of the alkyne by the zinc Lewis acid and proton sponge is the trigger of the reaction to give a monoalkynylzinc species, which successively reacts with the alkyl triflate to afford the internal alkyne. A radical pathway is unlikely in this system. (Figure presented.).

The vinyl moiety as a handle for regiocontrol in the preparation of unsymmetrical 2,3-aliphatic-substituted indoles and pyrroles

Rho-Rho-Rho your boat: A rhodium catalyst effects the regioselective oxidative coupling of enynes with N-aryl ureas (X=NR2) and N-vinylacetamides (X=C(O)Me), affording the corresponding 2-alkenylindoles and 2-alkenylpyrroles in good yield. Simple hydrogenation delivers the C2/C3-aliphatic-substituted indole or pyrrole (see scheme).

Palladium-catalyzed aerobic oxidative cross-coupling reactions of terminal alkynes with alkylzinc reagents

Chemical Equation Represented With air as the oxidant, terminal alkynes can be directly cross-coupled with alkylzinc reagents in the presence of a Pd catalyst at room temperature. CO was found to be critical in gaining high chemical yields and selectivities. A wide range of alkynes and alkylzinc reagents were tested, and good to excellent yields were obtained. Copyright

Silver(I)-catalyzed cascade: Direct access to furans from alkynyloxiranes

(Chemical Equation Presented) Functionalized furans are conveniently formed by a new silver(I)-catalyzed reaction of alk-1-ynyl oxiranes in the presence of p-toluenesulfonic acid and methanol. Evidence supported a cascade mechanism.

Mechanistic studies and improvement of coinage metal-catalyzed transformation of alkynyloxiranes to furans: An alcohol addition-cyclization- elimination cascade

(Chemical Equation Presented) In the presence of alcohol Ag or Au salts or complexes catalyze the conversion of alkynyloxiranes to substituted furans. Both catalysts are effective, and a large furan diversity can be obtained in high yield with one or the

Palladium-catalyzed diastereoselective coupling of propargylic oxiranes with terminal alkynes

A diastereoselective coupling of propargylic oxiranes with terminal alkynes has been developed with use of a palladium catalyst. The stereochemistries of the resulting 4-alkynyl-substituted 2,3-allenols have been altered depending on the palladium catalyst. An optically active antf-substituted aliene was synthesized from the reaction of an enantiomerically enriched propargylic oxirane without loss of chirality.

Synthesis of propargylic fluorides from allenylsilanes

Allenylsilanes reacted at room temperature in acetonitrile with Selectfluor, an electrophilic fluorinating reagent, to give secondary propargylic fluorides in moderate to good yields; mechanistically, a side-product resulting from a 1,2-silyl shift testifies to the presence of a cationic intermediate. The Royal Society of Chemistry 2006.

Reaction of α-(N-carbamoyl)alkylcuprates with propargyl substrates: Synthetic route to α-amino allenes and Δ3-pyrrolines

(Chemical Equation Presented) Carbamate deprotonation followed by treatment with CuCN·2LiCl affords α-(N-carbamoyl)-alkylcuprates which react with propargyl halides, mesylates, tosylates, phosphates, acetates, and epoxides to give α-(N-carbamoyl) allenes via an anti-SN2′ substitution process. Propargyl halides, sulfonates, and phosphates give good yields of carbamoyl allenes, while the acetates afford low yields. Propargyl substrates undergo regiospecific SN2′ substitution in the absence of severe steric hindrance. The α-(N-carbamoyl) allenes can be cyclized to 2-oxazolidinones or deprotected to afford the free amines which can be cyclized to Δ3-pyrrolines with either AgNO3 or Ru3(CO)12.