15447-62-8

Upstream product

• 14918-21-9 5-hexynonitrile 
• 591-51-5 phenyllithium 
• 116385-36-5 3-iodo-1-trimethylsiloxy-1-phenylpropene 
• 106-96-7 propargyl bromide 
• 768-03-6 Phenyl vinyl ketone 
• 38771-21-0 4-bromobut-1-yne 
• 98-86-2 acetophenone 
• 109459-28-1 3-(trifluoromethanesulfonyloxy)-2-cyclohexen-1-one 
• 15288-81-0 1-phenyl-hex-5-yn-1-ol 
• 100-52-7 benzaldehyde 
• 101-02-0 triphenyl phosphite 
• 771-98-2 1-Phenylcyclohexene 
• 87258-30-8 6-oxo-6-phenylhexanal 
• 2396-63-6 hepta-1,6-diyne 

Downstream Products

• 15289-04-0 1-phenyl-dec-5-yn-1-one 
• 15289-08-4 8-Diaethylamino-1-phenyl-octin-⁽⁵⁾-on-⁽¹⁾ 
• 15288-93-4 1,1-Diphenyl-hexin-⁽⁵⁾-ol-⁽¹⁾ 
• 13983-46-5 6-Dimethylamino-1-benzoyl-hexin-⁽⁴⁾ 
• 13983-40-9 1-Dimethylamino-2-benzoyl-hexin-⁽⁵⁾ 
• 13983-43-2 1-Diaethylamino-2-benzoyl-hexin-⁽⁵⁾ 
• 15288-91-2 2-Hydroxy-2-methyl-8-phenyl-octin-⁽³⁾-on-⁽⁸⁾ 
• 22524-25-0 1-phenylhex-5-en-1-one 
• 87258-30-8 6-oxo-6-phenylhexanal 
• 1313885-32-3 6-cyclopentenyl-1-phenylhex-5-yn-1-one 
• 6303-82-8 1-phenylhexane-1,5-dione 

Relevant academic research and scientific papers

Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark

The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.

Copper-Catalyzed Oxidative Fragmentation of Alkynes with NFSI Provides Aryl Ketones

A copper-catalyzed oxidative cleavage reaction of alkynes using NFSI and TBHP was described. Various terminal and internal alkyne substrates were employed to render quick access to aryl ketone products in moderate to good yields. NFSI not only functioned as N-centered radical precursors but also engaged in the aryl group migration. Mechanistic studies also suggested the important role of water in the title reactions.

Asymmetric Construction of Alkaloids by Employing a Key ω-Transaminase Cascade

An ω-transaminase-triggered intramolecular aza-Michael reaction has been employed for the preparation of cyclic β-enaminones in good yield and excellent enantio- and diastereoselectivity, starting from easily accessible prochiral ketoynones and commercially available enzymes. The powerful thermodynamic driving force associated with the spontaneous aza-Michael reaction effectively displaces the transaminase reaction equilibrium towards product formation, using only two equivalents of isopropylamine. To demonstrate the potential of this methodology, this biocatalytic aza-Michael step was combined with annulation chemistry, affording unique stereo-defined fused alkaloid architectures.

Alkynylation of Tertiary Cycloalkanols via Radical C-C Bond Cleavage: A Route to Distal Alkynylated Ketones

An efficient Na2S2O8-promoted radical coupling of tertiary cycloalkanols with alkynyl hypervalent iodide reagents via C-C bond cleavage was developed. This tandem ring-opening/alkynylation procedure showed some advantages,

Tandem nucleophilic addition/fragmentation of vinylogous acyl nonaflates for the synthesis of functionalized alkynes, with new mechanistic insight

Vinylogous acyl nonaflates, like the corresponding triflates, are subject to nucleophile-triggered fragmentation as part of a tandem process for generating functionalized alkynes. Advantages to the use of nonaflates in lieu of triflates include cost and s

Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation - Base catalyzed elimination sequence

Keto aldehydes were selectively converted to non-conjugated alkynyl ketones possessing an unsubstituted alkyne terminus using one-pot nonaflation - base catalyzed elimination reaction sequences. Consecutive one-pot nonaflation of keto aldehydes with perfluorobutane-1-sulfonyl fluoride and elimination of the nonaflyl group using the P1 phosphazene base resulted in the formation of a terminal CC triple bond with the keto group remaining intact. Careful optimization of the reaction conditions enabled a highly chemoselective conversion of the aldehyde function in the presence of unprotected keto groups exploiting a minor difference in acidity of their α-hydrogen atoms. Scope and limitations of the protocol as well as possible implementation of these substrates in Sonogashira coupling were explored.

Synthesis of pyridines and pyrazines using an intramolecular hydroamination-based reaction sequence

A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). ρ-Toluenesulfonic acid (2 mol%) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redoxneutral aromatization step to occur.

Stereoselective synthesis of medium-sized cyclic compounds through the intramolecular michael-type reaction utilizing alkyne-hexacarbonyldicobalt complex formation

Alkyne-hexacarbonyldicobalt complexes having silyl enol ether and electron-deficient alkene moieties on opposite ends were treated with MeAlCl2 in the presence of 2,6-di-t-butylpyridine in CH 2Cl2 to give synthetically use

Tandem nucleophilic addition/fragmentation reactions and synthetic versatility of vinylogous acyl triflates

A thorough analysis of the chemistry of vinylogous acyl triflates provides insight into important chemical processes and opens new directions in synthetic technology. Tandem nucleophilic addition/C-C bond cleaving fragmentation reactions of cyclic vinylogous acyl triflates 1 yield a variety of acyclic acetylenic compounds. Full details are disclosed herein. A wide array of nucleophiles, such as organolithium and Grignard reagents, lithium enolates and their analogues, hydride reagents, and lithium amides, are applied. The respective reactions produce ketones 2, 1,3-diketones and their analogues 3, alcohols 4, and amides 5. The present reactions are proposed to proceed through a 1,2-addition of the nucleophile to the carbonyl group of starting triflates 1 to form tetrahedral alkoxide intermediates C, followed by Grob-type fragmentation, which effects C-C bond cleavage to yield acyclic acetylenic compounds 2-5 and 7. The potent nucleofugacity of the triflate moiety is channeled through the σ-bond framework of 1, providing direct access to the fragmentation pathway without denying other typical reactions of cyclic vinylogous esters. The synthetic versatility of vinylogous acyl triflates, including functionalization reactions of the cyclic enone core (1 → 6 or 8), is also illustrated.

Unexpected double benzylation of acetophenone under phase transfer catalysis conditions, acidity or π-π interaction effect?

A π-π interaction in the transition state of the benzylation of 1,3-diphenyl-1-propanone, the monobenzylation product of acetophenone, is proposed according to chemical, kinetic and theoretical approaches. Evidence for the existence of this kind of interaction in a transition state has been provided for the first time. The results obtained cannot be explained solely by the increased acidity but by considering the existence of a π-π interaction.