1966-65-0

Usage

Uses

Used in Organic Synthesis:
1-PHENYL-4-METHYL-1-PENTYN-3-OL is used as a reagent in organic synthesis for the preparation of various chemical compounds due to its ability to undergo reactions such as oxidation, reduction, and addition.
Used in Pharmaceutical Industry:
1-PHENYL-4-METHYL-1-PENTYN-3-OL is used as an intermediate in the production of various drugs and pharmaceuticals, contributing to the development of new medications.
Used in Materials Science:
1-PHENYL-4-METHYL-1-PENTYN-3-OL has potential applications in the field of materials science, such as in the production of polymers and other advanced materials, due to its unique chemical properties.

InChI:InChI=1/C12H14O/c1-10(2)12(13)9-8-11-6-4-3-5-7-11/h3-7,10,12-13H,1-2H3

Upstream product

• 19307-74-5 1-phenyl-pent-1-yn-3-one 
• 536-74-3 phenylacetylene 
• 78-93-3 butanone 
• 6738-06-3 phenylethynylmagnesium bromide 
• 6804-29-1 1-Phenylaethinyl-1-<2-hydroxyaethoxy>-cyclopentan 
• 591-50-4 iodobenzene 
• 77-75-8 meparfynol 

Downstream Products

• 536-74-3 phenylacetylene 
• 78-93-3 butanone 
• 20125-66-0 1-phenyl-3-methyl-3-(triethylsilyl)oxy-1-pentyne 
• 20125-68-2 3-methyl-1-phenyl-3-(triethylsilyl)oxypentane 
• 10415-87-9 3-methyl-1-phenylpentan-3-ol 
• 1067324-31-5 3-methyl-1-phenylpenta-1,2-dien-1-yl diphenyl phosphine oxide 
• 1221071-49-3 (3-ethoxy-3-methylpent-1-ynyl)benzene 
• 1228390-89-3 (3-methyl-1-phenylpent-1-yn-3-yl)(propyl)sulfane 
• 40036-62-2 (3-methylpent-1-ynyl)benzene 
• 1373883-83-0 3-ethyl-3,4-dimethyl-7-nitro-1-phenyl-3,4-dihydrocyclopenta[b]indole 
• 1413919-04-6 (E)-2-iodo-3-methyl-1-phenylpent-2-en-1-one 
• 1413919-05-7 (Z)-2-iodo-3-methyl-1-phenylpent-2-en-1-one 
• 1515868-41-3 μ-η2-(3-methyl-1-phenyl-1-pentyn-3-ol)dicobalthexacarbonyl 
• 1515868-42-4 μ-η2-(3-methoxy-3-methyl-1-phenyl-1-pentyne)dicobalthexacarbonyl 

Relevant academic research and scientific papers

Dual Palladium/Copper-Catalyzed anti-Selective Intermolecular Allenylsilylation of Terminal Alkynes: Entry to (E)-Silyl Enallenes

A palladium-/copper-cocatalyzed three-component trans-allenylsilylation of terminal alkynes with propargyl acetates and PhMe2SiBpin is described, which is driven by the regioselective allenylation of the alkyne with propargyl acetates and then silylation. This method allows the simultaneous incorporation of an allene and silicon across the CC bond and provides a highly chemo-, regio-, and stereoselective alkyne difunctionalization route to the synthesis of valuable (E)-silyl enallenes. The utility of this method is highlighted by late-stage derivatization of bioactive compounds.

Ru(ii)-catalyzed allenylation and sequential annulation of: N -tosylbenzamides with propargyl alcohols

We hereby report Ru(ii)-catalyzed C(sp2)-H allenylation of N-tosylbenzamides to access multi-substituted allenylamides. Furthermore, the allenylamides were converted to the corresponding isoquinolone derivatives via base mediated annulation. The current protocol features low catalyst loading, mild reaction conditions, high functional group compatibility and desired scalability. The unique functionality of the afforded allenes allowed further transformations to expand the practicality of the protocol. This journal is

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%).

Synthesis of 4-Oxoisoxazoline N-Oxides via Pd-Catalyzed Cyclization of Propargylic Alcohols with tert-Butyl Nitrite

A cyclization of propargylic alcohols with tert-butyl nitrite at room temperature in air was achieved using Pd(OAc)2 as catalyst. The first reported 4-oxoisoxazoline N-oxides could be directly accessed from a range of multisubstituted propargylic alcohols in moderate to excellent yields under mild conditions. Density functional theory calculations indicated that the reaction proceeds through a palladium-catalyzed NO2 addition that efficiently generates a ketoxime radical, which eventually produces 4-oxoisoxazoline N-oxide.

Flow rhodaelectro-catalyzed alkyne annulations by versatile C-H Activation: Mechanistic support for rhodium(III/IV)

A flow-metallaelectro-catalyzed C-H activation was realized in terms of robust rhodaelectro-catalyzed alkyne annulations. To this end, a modular electro-flow cell with a porous graphite felt anode was designed to ensure efficient turnover. Thereby, a variety of C-H/N-H functionalizations proved amenable for alkyne annulations with high levels of regioselectivity and functional group tolerance, viable in both an inter- or intramolecular manner. The electro-flow C-H activation allowed easy scale up, while in-operando kinetic analysis was accomplished by online flow-NMR spectroscopy. Mechanistic studies suggest an oxidatively induced reductive elimination pathway on rhodium(III) in an electrocatalytic regime.

Metal-Free Regioselective Chloroazidation of Internal Alkynes

A metal-free, room temperature protocol for the regioselective chloroazidation of internal alkynes is disclosed. The reactions of internal alkynes with trimethylsilyl azide (TMSN3) in the presence of 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) afforded the corresponding chloroazidoalkenes in good yields. This reaction has good functional group tolerance and is operationally simple.

DBU-promoted carbonylative synthesis of 1,3-oxathiolan-2-ones from propargylic alcohols with TFBen as the CO source

A DBU-promoted carbonylative cyclization of propargylic alcohols with sulfur was developed. Various 1,3-oxathiolan-2-ones were produced in 61-98% yields under mild conditions in the absence of metal catalysts. TFBen (benzene-1,3,5-triyl triformate) as an efficient and solid CO surrogate and S8 as an ideal sulfur source were employed and incorporated.

Palladium(II)/N-Heterocyclic Carbene-Catalyzed Regioselective Heteroannulation of Tertiary Propargyl Alcohols and o-Haloanilines to form 2-Alkenylindoles

Monometallic and bimetallic palladium(II)/N-heterocyclic carbene complexes appended with naphthalimide or bisnaphthalimide moieties were designed, synthesized, and characterized. Employment of these catalysts brings about the step-economic and regioselective heteroannulation of tertiary propargyl alcohols with o-haloanilines resulting in biologically and pharmaceutically relevant 2-alkenylindoles. Basis for the regioselective heteroannulation is unraveled by coordination of the propargylic hydroxy moiety to palladium during insertion. Embracing this methodology, a single regioisomer of unsymmetrical 2,3-disubstituted indoles could be achieved through late-stage modification. The role of the naphthalimide or bisnaphthalimide appended to the NHC on the catalytic efficiency has been studied. (Figure presented.).

Highly Efficient Synthesis of Multi-Substituted Allenes from Propargyl Acetates and Organoaluminum Reagents Mediated by Palladium

A simple and mild catalytic S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents is reported. The S N 2′ substitution reaction of propargyl acetates with organoaluminum reagents mediated by Pd(PhP 3) 2 Cl 2 (1 mol%)/PPh 3 (2 mol%)/K 2 CO 3 in tetrahydrofuran at 60 °C for 3-4 hours afforded the corresponding multi-substituted allenes in good yields (up to 94%) with high selectivities (up to 99%). The process was simple and easily performed, which offers an efficient method to synthesize the multi-substituted allene derivatives.

Asymmetric Intermolecular Heck Reaction of Propargylic Acetates and Cycloalkenes to Access Fused Cyclobutenes

An asymmetric Heck annulation of propargylic acetates with several types of cyclic olefins affords highly strained cyclobutenes in high enantioselectivity.