27975-78-6

Usage

Uses

Used in Chemical Synthesis:
1-PHENYL-1-PENTYN-3-OL is used as a reactant in the heterogeneously catalyzed etherification of glycerol. This process involves the reaction of glycerol with an alcohol or phenol in the presence of a catalyst to form ethers, which are valuable intermediates in the chemical industry.
Used in Organic Chemistry:
1-PHENYL-1-PENTYN-3-OL is also utilized in the Fritsch-Wiechell rearrangement of 1-chlorovinyl sulfoxides. This rearrangement is a chemical reaction that involves the conversion of 1-chlorovinyl sulfoxides to α-chloro carbonyl compounds, which are important building blocks for the synthesis of various organic compounds.

InChI:InChI=1/C11H12O/c1-2-11(12)9-8-10-6-4-3-5-7-10/h3-7,11-12H,2H2,1H3

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 925-90-6 ethylmagnesium bromide 
• 27975-81-1 (+/-)-(3-bromopent-1-ynyl)benzene 
• 123-38-6 propionaldehyde 
• 62459-78-3 9-Phenylethynyl-9-bora-bicyclo[3.3.1]nonane 
• 4250-81-1 1-phenyl-1-pentyne 
• 123-72-8 butyraldehyde 
• 536-74-3 phenylacetylene 
• 136121-38-5 (3R)-2-Chloro-1-phenyl-1-penten-3-ol 
• 31552-04-2 (Z)-1-phenyl-3-penten-1-yne 
• 116386-53-9 (-)-1-Chloroethyl-2-phenylethyl p-tolyl sulfoxide 
• 134905-02-5 C₂₃H₂₂Se₂ 
• 128867-15-2 2-Benzenesulfinyl-2-chloro-1-phenyl-ethanol 
• 7205-94-9 chloromethyl phenyl sulfoxide 

Downstream Products

• 117983-72-9 chloromethyl 1-phenyl-1-pentyn-3-yl ether 
• 15295-30-4 5,5-Diphenyl-penten-⁽⁴⁾-ol-⁽³⁾ 
• 104581-57-9 5,5-diphenylpent-4-en-3-one 
• 104581-54-6 (Z)-1,2-Diphenyl-pent-1-en-3-ol 
• 93247-40-6 (1-tert-Butyl-penta-1,2-dienyl)-benzene 
• 75031-47-9 2-phenyl-2,3-hexadiene 
• 124974-83-0 2-Ethyl-4-phenyl-3-butynenitrile 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 105836-17-7 (R)-1-phenyl-3-pentanol 
• 71747-37-0 (S)-1-phenylpentan-3-ol 
• 93247-39-3 (1-Cyclohexyl-penta-1,2-dienyl)-benzene 
• 93247-41-7 (1-Allyl-penta-1,2-dienyl)-benzene 
• 27975-78-6 (S)-1-phenylpent-1-yn-3-ol 
• 104662-02-4 (1R)-1-phenylpent-1-yn-3-ol 

Relevant academic research and scientific papers

Cascade Radical Cyclization on Alkynyl Vinylogous Carbonates for the Divergent Synthesis of Tetrasubstituted Furans and Dihydrofurans

A single alkynyl vinylogous carbonate was elaborated to tetrasubstituted furan or dihydrofuran via a cascade inter-intramolecular radical reaction by changing the radical being added. The strategy could be used in the synthesis of polycyclic heterocycles as well as bis-furan exhibiting atropisomerism. Installation of a new furan motif on the existing one was feasible by iteration. Stannyl dihydrofuran derivative was used in Stille coupling, whereas intramolecular Friedel-Crafts acylation on the furan gave furanonaphthol.

Iron-Catalyzed Cross-Coupling of Propargyl Ethers with Grignard Reagents for the Synthesis of Functionalized Allenes and Allenols

Herein we disclose an iron-catalyzed cross-coupling reaction of propargyl ethers with Grignard reagents. The reaction was demonstrated to be stereospecific and allows for a facile preparation of optically active allenes via efficient chirality transfer. Various tri- and tetrasubstituted fluoroalkyl allenes can be obtained in good to excellent yields. In addition, an iron-catalyzed cross-coupling of Grignard reagents with α-alkynyl oxetanes and tetrahydrofurans is disclosed herein, which constitutes a straightforward approach towards fully substituted β- or γ-allenols, respectively.

A boron-oxygen transborylation strategy for a catalytic midland reduction

The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transb

Benzene-1,3,5-triyl Triformate (TFBen)-Promoted Palladium-Catalyzed Carbonylative Synthesis of 2-Oxo-2,5-dihydropyrroles from Propargyl Amines

In this letter, we developed a palladium-catalyzed procedure for the cyclocarbonylation of propargyl amines. Benzene-1,3,5-triyl triformate (TFBen) has been explored as the CO source and also as the key promotor. Various substituted 2-oxo-dihydropyrroles were produced in a facile manner in good yields (up to 90%).

Catalytic Ynone-Amidine Formal [4 + 2]-Cycloaddition for the Regioselective Synthesis of Tricyclic Azepines

A Ca(OTf)2- and self-promoted ynone-amidine atom-economic formal [4 + 2]-cycloaddition of various ynones with amidines is reported for the construction of highly functionalized tricyclic azepines. High reaction rate, ease of operation, and high product se

Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes

Rh(III)-catalyzed meta-C-H functionalization reactions are still rare. Herein, we report the first example of Rh(III)-catalyzed meta-C-H alkenylation with disubstituted alkynes directed by a U-shaped nitrile template. Exclusive regio-selectivity has been achieved using unsymmetrical aryl and alkyl-disubstituted alkynes to afford synthetically valuable trisubstituted olefins. Propargyl alcohols are also compatible, affording complex allylic alcohols. Notably, transition metal-catalyzed meta-alkenylation with alkynes has not been successful with Pd catalysts.

Transition-metal-free C-C σ-bond activation of α-aryl ketones and subsequent Zn-catalyzed intramolecular cyclization: synthesis of tetrasubstituted furans

A highly atom-economical protocol for the synthesis of tetrasubstituted furans has been developed. This process is realized through the tandem reactions of Cs2CO3 promoted C-C σ-bond activation of α-aryl ketones followed by Zn-cataly

Phosphine-Catalyzed Intermolecular Annulations of Fluorinated ortho-Aminophenones with Alkynones – The Switchable [4+2] or [4+2]/[3+2] Cycloaddition

A phosphine-catalyzed intermolecular annulation reaction of functionalized ortho-aminoacetophenones with alkynones has been disclosed in this paper. A variety of 2-alkynylquinolines and benzo-fused indolizine were selectively afforded in moderate to good yields at different reaction temperatures and with different phosphine catalysts via the in situ generated zwitterionic intermediate derived from alkynone and phosphine. (Figure presented.).

Asymmetric Propargylic Radical Cyanation Enabled by Dual Organophotoredox and Copper Catalysis

The first asymmetric propargylic radical cyanation was realized through a dual photoredox and copper catalysis. An organic photocatalyst serves to both generate propargyl radicals and oxidize Cu(I) species to Cu(II) species. A chiral Cu complex functions as an efficient organometallic catalyst to resemble the propargyl radical and cyanide in an enantio-controlled manner. Thus, a diverse range of optically active propargyl cyanides were produced with high reaction efficiency and enantioselectivities (28 examples, 57-97% yields and 83-98% ee). Moreover, mechanistic investigations including experiments and density functional theory calculations were performed to illustrate on the reaction pathway and stereochemical results.

Palladium(II)/Lewis acid cocatalyzed oxidative annulation of 2-alkenylanilines and propargylic esters: An access to benzo[ b]azepines

An attractive approach to valuable yet synthetically challenging benzo[b]azepines was established via palladium(II)/Lewis acid cocatalyzed oxidative [5 + 2] annulation of readily available 2-alkenylanilines and propargylic esters. The protocol features mild reaction conditions and good functional group tolerance, constituting an array of benzo[b]azepines in yields of 30-75%.