4378-23-8

Usage

Uses

Used in Pharmaceutical Synthesis:
1-PHENYL-BUT-3-YN-2-OL is used as a building block in the pharmaceutical industry for the synthesis of organic molecules and pharmaceuticals. Its unique structure and functional groups contribute to the development of new drugs with potential therapeutic applications.
Used in Antioxidant Applications:
1-PHENYL-BUT-3-YN-2-OL is used as an antioxidant in various applications, including food preservation, cosmetics, and pharmaceuticals. Its ability to neutralize free radicals and prevent oxidative damage makes it a valuable component in these industries.
Used in Antimicrobial Applications:
1-PHENYL-BUT-3-YN-2-OL is used as an antimicrobial agent in industries such as healthcare, food processing, and cosmetics. Its potential to inhibit the growth of bacteria, fungi, and viruses contributes to the development of products with enhanced safety and efficacy.
Used in Materials Science:
1-PHENYL-BUT-3-YN-2-OL is used in the field of materials science for the development of polymers and other advanced materials. Its unique structure and properties make it a promising candidate for the creation of innovative materials with improved performance characteristics.
Used in Research and Development:
1-PHENYL-BUT-3-YN-2-OL is used as a research compound in various scientific disciplines, including chemistry, biology, and materials science. Its diverse applications and potential for further exploration make it a valuable tool for researchers seeking to advance their understanding of chemical reactions, biological processes, and material properties.

Upstream product

• 122-78-1 phenylacetaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 1301222-87-6 3-bromo-1-phenyl-3-buten-2-ol 
• 40339-20-6 buta-2,3-dienyl-benzene 
• 1066-54-2 trimethylsilylacetylene 
• 108-05-4 vinyl acetate 
• 135663-97-7 1-phenylbut-3-yn-2-ol 
• 31739-46-5 1-phenylbut-3-yn-2-one 
• 103-82-2 phenylacetic acid 
• 60-12-8 2-phenylethanol 
• 65032-27-1 ethynylmagnesium chloride 
• 4039-82-1 Benzyl propargyl ether 
• 61077-69-8 4-(trimethylsilyl)-1-phenylbut-3-yn-2-ol 
• 1066-26-8 sodium acetylide 

Downstream Products

• 67647-94-3 1-n-Butyl-4-phenylbutadien-1,2 
• 4161-46-0 8-Hydroxy-9-phenyl-nona-4,6-diinsaeure 
• 67647-95-4 1-Cyclohexyl-4-phenyl-1,2-butadien 
• 4378-23-8 (S)-4-phenyl-1-butyn-3-ol 
• 135664-08-3 (R)-1-phenylbut-3-yn-2-yl acetate 
• 135664-08-3 (S)-1-phenylbut-3-yn-2-yl acetate 
• 108054-33-7 3-methylene-1-phenylpent-4-en-2-ol 
• 874338-30-4 1-phenyl-4-(thien-2-yl)but-3-yn-2-ol 
• 874338-28-0 1-[4-(3-hydroxy-4-phenylbut-1-ynyl)phenyl]ethanone 
• 874338-26-8 4-(4-methoxyphenyl)-1-phenylbut-3-yn-2-ol 
• 40339-20-6 buta-2,3-dienyl-benzene 
• 952591-30-9 ethyl 6-(3-hydroxy-4-phenylbut-1-ynyl)-5-iso-butylpyridazine-3-carboxylate 
• 31739-46-5 1-phenylbut-3-yn-2-one 
• 5355-63-5 3-hydroxy-4-phenyl-2-butanone 

Relevant academic research and scientific papers

Rhodium(I)-Catalyzed Three-Component [4+2+1] Cycloaddition of Two Vinylallenes and CO

Transition metal-catalyzed [4+2+1] reactions of dienes (or diene derivatives such as vinylallenes), alkynes/alkenes, and CO (or carbenes) are expected to be the most straightforward approach to synthesize challenging seven-membered ring compounds, but so far only limited successes have been realized. Here, an unexpected three-component [4+2+1] reaction between two vinylallenes and CO was discovered to give highly functionalized tropone derivatives under mild conditions, where one vinylallene acts as a C4 synthon, the other vinylallene as a C2 synthon, and CO as a C1 synthon. It was proposed that this reaction occurred via oxidative cyclization of the diene part of one vinylallene molecule, followed by insertion of the terminal alkene part of the allene moiety in another vinylallene, into the Rh?C bond of five-membered rhodacycle. Then, CO insertion and reductive elimination gave the [4+2+1] cycloadduct. Further experimental exploration of why ene/yne-vinylallenes and CO gave monocyclic tropone derivatives instead of 6/7-bicyclic ring products were reported here.

Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases

The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.

Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.

A novel synthesis of N-hydroxy-3-aroylindoles and 3-aroylindoles

A straightforward indole synthesis via annulation of C-nitrosoaromatics with conjugated terminal alkynones was realised achieving a simple, highly regioselective, atom- and step economical access to 3-aroylindoles in moderate to good yields. Further functionalizations of indole scaffolds were investigated and an easy way to JWH-018, a synthetic cannabinoid, was achieved.

Well-Defined Chiral Gold(III) Complex Catalyzed Direct Enantioconvergent Kinetic Resolution of 1,5-Enynes

The development of a gold(III) catalyzed direct enantioconvergent 1,5-enyne cycloisomerization and kinetic resolution reaction is described. The transformation results in highly enantioenriched bicyclo[3.1.0]hexenes at all levels of conversion, with no racemization or symmetrization taking place during the course of the reaction, and simultaneously affords optically enriched 1,5-enynes. This report marks the first highly enantioselective transformation catalyzed by a well-defined cationic gold(III) catalyst and demonstrates the unique potential of gold(III) complexes in enantioselective catalysis.

Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel-Crafts alkylation and dehydration to tricyclic benzo[f] isochromenes

A three-step domino reaction between 1-aryl-3-hexyne-2,6-diol derivatives and aldehydes is used to construct tricyclic 1,4-dihydro-2H-benzo[f]isochromenes. The cascade is initiated by BF3·OEt2 and involves alkynyl-Prins cyclization, Friedel-Crafts alkenylation, and dehydration/aromatization to create a new, central aromatic ring and eliminate 2 equiv. of water. Electron-donating substituents on the aryl ring of the 1-aryl-3-hexyne-2,6-diols significantly increase overall yields as do electron-rich aldehyde reaction partners. For 2,4-disubstituted 2H-benzo[f]isochromene products, diastereoselectivities in the alkynyl-Prins reaction are ～1.4:1 in favor of the cis-diastereomer. The stereochemistry of one cis-product was verified by X-ray crystallographic analysis and a second structure was also verified by X-ray analysis.

Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.

Catalytic Nucleophilic Fluorination of Secondary and Tertiary Propargylic Electrophiles with a Copper-N-Heterocyclic Carbene Complex

A catalytic method for the nucleophilic fluorination of propargylic electrophiles is described. Our protocol involves the use of a Cu(NHC) complex as the catalyst and is suitable for the preparation of secondary and tertiary propargylic fluorides without

Synthesis of 2-tetralone derivatives by Bi(OTf)3-catalyzed intramolecular hydroarylation/isomerization of propargyl alcohols

Compared to 1-tetralones, 2-tetralones are expensive, less stable, and difficult to synthesize. A concise Bi-catalyzed method was developed for the synthesis of 2-tetralones from 5-phenylpent-1-yn-3-ol derivatives. Diverse 2-tetralones were obtained in moderate to good yields under mild conditions.