5876-69-7

Usage

Uses

Used in Organic Chemistry:
2,4-DIPHENYL-3-BUTYN-2-OL is used as a synthetic intermediate for the preparation of various organic compounds. Its aromatic properties and functional groups make it a versatile building block in the synthesis of complex molecules.
Used in Pharmaceutical Industry:
2,4-DIPHENYL-3-BUTYN-2-OL is used as a key component in the development of pharmaceuticals. Its unique structure allows for the creation of novel drug candidates with potential therapeutic applications.
Used in Materials Science:
2,4-DIPHENYL-3-BUTYN-2-OL is utilized in the research and development of new materials with specific properties. Its reactivity and functional groups contribute to the design of advanced materials for various applications, such as sensors, catalysts, and polymers.

Upstream product

• 536-74-3 phenylacetylene 
• 98-86-2 acetophenone 
• 6738-06-3 phenylethynylmagnesium bromide 
• 1004-22-4 (phenylethynyl)sodium 
• 14161-76-3 1,1-Dichlor-3-methyl-2,3-diphenyl-cyclopropan 
• 160685-76-7 Trimethyl-(1-methyl-1,3-diphenyl-prop-2-ynyloxy)-silane 
• 7338-94-5 1,3-diphenyl-2-propynone 
• 4440-01-1 lithium phenylacetylide 
• 932-88-7 1-iodo-2-phenylethyne 
• 127-66-2 2-Phenyl-3-butyn-2-ol 
• 591-50-4 iodobenzene 
• 5075-59-2 diethyl(phenylethynyl)aluminum 
• 1007-47-2 (phenylethynyl)dimethylaluminum 
• 932-87-6 1-Bromo-2-phenylacetylene 

Downstream Products

• 116575-96-3 2-furyl-4-methyl-3-benzoylchromane 
• 116575-95-2 2-cinnamyl-4-methyl-3-benzoylchromane 
• 62676-20-4 3-methoxy-1,3-diphenyl-1-butyne 
• 62676-19-1 2,4-diphenylbut-1-en-3-yne 
• 100556-40-9 (Z)-iodo-2,4-diphenylbut-3-en-2-one 
• 1243327-71-0 C₂₄H₁₈BrN 
• 1243327-77-6 C₂₅H₂₁NO 
• 1243327-65-2 C₃₁H₂₅N 
• 1263145-87-4 3,9-dimethyl-1,3-diphenyl-3H-pyrrolo[1,2-a]indole 
• 1263146-08-2 2-(1,3-diphenylbuta-1,2-dienyl)-3-methyl-1H-indole 
• 1367363-55-0 C₁₆H₁₂I₂ 
• 1520-44-1 1,3-diphenylbutane 
• 1434146-77-6 3-(1,3-dithiolan-2-ylidene)-6-methyl-4,6-diphenyl-1,6-dihydropyridin-2(3H)-one 
• 1434146-78-7 3-(1,3-dithiolan-2-ylidene)-6-methyl-4,6-diphenyl-3,6-dihydro-2H-pyran-2-one 

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.

Rhodium-Catalyzed and Chiral Zinc Carboxylate-Assisted Allenylation of Benzamides via Kinetic Resolution

Enantioenriched allenes are important building blocks. While they have been accessed by other coupling methodologies, enantioenriched allenes have been rarely obtained via C-H activation. In this work, kinetic resolution of tertiary propargyl alcohols as an allenylating reagent has been realized via rhodium(III)-catalyzed C-H allenylation of benzamides. The reaction proceeded efficiently under mild conditions, and both the allenylated products and the propargyl alcohols were obtained in high enantioselectivities with an s-factor of up to 139. The resolution results from bias of the two propargylic substituents and is assisted by a chiral zinc carboxylate additive.

Method for preparing ethynylnaphthalene derivatives by [4 + 2] cyclization reaction with water as solvent

The invention discloses a [4 + 2] cyclization reaction with water as a solvent to prepare a naphthalene derivative and application thereof. The synthesis method comprises the following steps: taking an alkyne compound and butyne diacid diester as a reacti

Rhodium-Catalyzed Annulation of Phenacyl Ammonium Salts with Propargylic Alcohols via a Sequential Dual C-H and a C-C Bond Activation: Modular Entry to Diverse Isochromenones

Given their omnipresence in natural products and pharmaceuticals, isochromenone congeners are one of the most privileged scaffolds to synthetic chemists. Disclosed herein is a dual (ortho/meta) C-H and C-C activation of phenacyl ammonium salts (acylammonium as traceless directing group) toward annulation with propargylic alcohols to accomplish rapid access for novel isochromenones by means of rhodium catalysis from readily available starting materials. This operationally simple protocol features broad substrate scope and wide functional group tolerance. Importantly, the protocol circumvents the need of any stoichiometric metal oxidants and proceeds under aerobic conditions.

Calcium-Catalyzed Intramolecular Hydroamination-Deacylation Reaction of in situ formed β-Amino Allenes

We have developed a simple, One-Pot, three-component reaction of tert-propargyl alcohols, primary amines and acyl ketones to synthesize fully substituted pyrroles and pyridine derivatives in good to excellent yields with large substrate diversity. An eco-friendly calcium catalyst catalyzes the reaction to form the key intermediate β-amino allene that undergoes subsequent Thorpe-Ingold effect assisted hydroamination and aromaticity driven deacylation reaction to yield fully substituted five and six-membered azacyclic compounds. (Figure presented.).

Alcohol Dehydrogenases and N-Heterocyclic Carbene Gold(I) Catalysts: Design of a Chemoenzymatic Cascade towards Optically Active β,β-Disubstituted Allylic Alcohols

The combination of gold(I) and enzyme catalysis is used in a two-step approach, including Meyer–Schuster rearrangement of a series of readily available propargylic alcohols followed by stereoselective bioreduction of the corresponding allylic ketone intermediates, to provide optically pure β,β-disubstituted allylic alcohols. This cascade involves a gold N-heterocyclic carbene and an enzyme, demonstrating the compatibility of both catalyst types in aqueous medium under mild reaction conditions. The combination of [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene][bis(trifluoromethanesulfonyl)-imide]gold(I) (IPrAuNTf2) and a selective alcohol dehydrogenase (ADH-A from Rhodococcus ruber, KRED-P1-A12 or KRED-P3-G09) led to the synthesis of a series of optically active (E)-4-arylpent-3-en-2-ols in good yields (65–86 %). The approach was also extended to various 2-hetarylpent-3-yn-2-ol, hexynol, and butynol derivatives. The use of alcohol dehydrogenases of opposite selectivity led to the production of both allyl alcohol enantiomers (93->99 % ee) for a broad panel of substrates.

Br?nsted Acid Promoted Thermal-Ring-Rearrangement of Fluorenopyrans to 2-(1H-Inden-3-yl)-9H-fluoren-3-ols Bearing Two All-Carbon-Quaternary Centres

4-Aryl-fluorenopyrans bearing quaternary centre at C2 and C6 positions underwent a thermal-ring-rearrangement with a catalytic amount of pTsOH to furnish 2-(1H-inden-3-yl)-9H-fluoren-3-ols with two all carbon-quaternary centres, in which one is retained a

Organocatalytic Formal (3 + 2) Cycloaddition toward Chiral Pyrrolo[1,2- a]indoles via Dynamic Kinetic Resolution of Allene Intermediates

We report the chiral phosphoric acid catalyzed formal (3 + 2) cycloaddition of 3-substituted 1H-indoles and propargylic alcohols containing a functional directing group (p-NHAc or p-OH). This work represents a straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter. The reaction proceeds smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93percent yield and 98percent ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives.

Fluorescent dye containing phenylacetylene naphthalene as well as preparation method and application of fluorescent dye

The invention relates to a fluorescent dye containing phenylacetylene naphthalene, a preparation method and an application thereof, the chemical structural formula of the fluorescent dye containing phenylacetylene naphthalene is shown in the specification

Copper-Catalyzed Radical 1,4-Difunctionalization of 1,3-Enynes with Alkyl Diacyl Peroxides and N-Fluorobenzenesulfonimide

Many reactions involving allenyl ion species have been studied, but reactions involving allenyl radicals are less well understood, perhaps because of the inconvenience associated with the generation of short-lived allenyl radicals. We describe here a versatile method for the generation of allenyl radicals and their previously unreported applications in the intermolecular 1,4-carbocyanation and 1,4-sulfimidocyanation of 1,3-enynes. With the assistance of the trifunctional reagents, alkyl diacyl peroxides or N-fluorobenzenesulfonimide, a range of synthetically challenging multisubstituted allenes can be prepared with high regioselectivity. These multisubstituted allenes can be easily transformed into synthetically useful structures such as fluorinated vinyl cyanides, lactones, functionalized allenyl amides, 1-aminonaphthalenes, and pyridin-2(1H)-ones, and several novel transformations are reported. The results of radical scavenger and radical clock experiments are consistent with the proposed allenyl radical pathway. Density functional theory (DFT) and IR spectroscopy studies suggest the formation of an isocyanocopper(II) species in the ligand exchange step. On the basis of the results of IR, DFT, and diastereoselectivity studies, an isocyanocopper(II)/copper(I) catalytic cycle is proposed, which differs from the previously considered Cu(III) mechanism in cyanation reactions.