1719-19-3

Usage

Uses

Used in Pharmaceutical Industry:
2-METHYL-4-PHENYL-3-BUTYN-2-OL is used as an intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicines. Its role in this industry is crucial for the production of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 2-METHYL-4-PHENYL-3-BUTYN-2-OL serves as an intermediate, playing a significant part in the creation of pesticides and other agricultural chemicals that are essential for crop protection and enhancement of agricultural productivity.
Used in Organic Chemistry:
2-METHYL-4-PHENYL-3-BUTYN-2-OL also has potential applications as a synthetic building block in organic chemistry. It is utilized in the synthesis of complex organic molecules, facilitating the development of novel compounds with diverse applications in various fields.

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

Upstream product

• 917-64-6 methyl magnesium iodide 
• 60-29-7 diethyl ether 
• 2216-94-6 phenylpropynoic acid ethyl ester 
• 22965-96-4 (Z)-3-bromo-4-phenyl-3-buten-2-one 
• 917-54-4 methyllithium 
• 30665-96-4 2-phenylethynyl phenyl selenide 
• 67-64-1 acetone 
• 108-86-1 bromobenzene 
• 115-19-5 2-methyl-but-3-yn-2-ol 
• 591-50-4 iodobenzene 
• 4440-01-1 lithium phenylacetylide 
• 13329-40-3 4-Iodoacetophenone 
• 628-21-7 1,4-Diiodobutane 
• 102921-26-6 (1,2-dibromoethyl)benzene 

Downstream Products

• 61423-02-7 ethyl 1,1-dimethyl-3-phenylpropargyl acetate 
• 1463-04-3 (3-methylbut-3-en-1-ynyl)benzene 
• 103-05-9 4-phenyl-2-methyl-2-butanol 
• 3355-29-1 1,1-dimethyl-3-phenylprop-2-ynyl chloride 
• 63257-87-4 methyl 1,1-dimethyl-3-phenylprop-2-ynyl ether 
• 66294-45-9 (1-tert-Butyl-3-methyl-buta-1,2-dienyl)-benzene 
• 17530-18-6 1-(4-methylpenta-2,3-dien-2-yl)benzene 
• 66294-44-8 (1-Isopropyl-3-methyl-buta-1,2-dienyl)-benzene 
• 30979-53-4 1,1'-(3-methyl-1,2-butadienylidene)bisbenzene 
• 61065-28-9 1-phenyl-2-(dimethylamino)-3-(diethoxymethoxy)-3-methylbutene 
• 27298-56-2 [1-(Dicyclohexyl-phosphinoyl)-3-methyl-buta-1,2-dienyl]-benzene 
• 82454-03-3 2-(4-Chloro-phenylselanyl)-3-methyl-1-phenyl-but-2-en-1-one 
• 68727-84-4 5,5-dimethyl-3-phenylfuran-2(5H)-one 
• 1612-03-9 3-methyl-1-phenyl-but-1-yne 

Relevant academic research and scientific papers

Sonogashira-Hagihara and Buchwald-Hartwig cross-coupling reactions with sydnone and sydnone imine derived catalysts

Seven different palladium complexes of sydnones and sydnone imines and a co-catalyst system consisting of lithium sydnone-4-carboxylate and Pd(PPh3)4 catalyzed Sonogashira-Hagihara reactions between (hetero)- aromatic bromides and 2-methylbut-3-yn-2-ol (52 examples, up to 100% yield). The co-catalyst system and a sydnone Pd complex were also tested in Buchwald-Hartwig reactions (9 examples, up to 100% yield). (Equation Presented).

Synthesis and Utility of 2,2-Dimethyl-2 H-pyrans: Dienes for Sequential Diels-Alder/Retro-Diels-Alder Reactions

The practical use of 2,2-dimethyl-2H-pyrans as electron-rich dienes in sequential Diels-Alder/retro-Diels-Alder (DA/rDA) domino processes to generate aromatic platforms has been demonstrated. Different polysubstituted alkyl 2-naphthoates have been synthesized by the DA/rDA reaction of benzynes and 2,2-dimethyl-2H-pyrans. The use of other activated alkynes allows the access of substituted alkyl benzoate derivatives.

Palladium(II)-Catalyzed Reaction of Lawsones and Propargyl Carbonates: Construction of 2,3-Furanonaphthoquinones and Evaluation as Potential Indoleamine 2,3-Dioxygenase Inhibitors

An efficient reaction utilizing propargyl carbonates through Claisen rearrangement to synthesize furanonaphthoquinones is described. The remarkable transformation exhibits excellent functional group tolerance, affording the target furanonaphthoquinones in

Synthesis and Photochemistry of a New Photolabile Protecting Group for Propargylic Alcohols

A new and efficient thiochromenone S,S-dioxide-based photolabile protecting group for propargylic alcohols is described. Robust protection reactions were developed through copper (II)-catalyzed substitution of propargylic alcohols. Subsequent photodeprote

Hollow palladium-cobalt bimetallic nanospheres as an efficient and reusable catalyst for Sonogashira-type reactions

The synthesis and characterization of hollow Pd-Co bimetallic nanospheres are reported. During Sonogashira-type coupling reactions between aryl halides and terminal alkynes in aqueous medium, these hollow materials exhibited much higher activity than the solid counterpart nanoparticles. Moreover, the catalytic activity could be adjusted via changing the catalyst composition. The enhanced activity was attributed to both the hollow chamber structure and the promotional effect of Co-dopants, which provided more Pd active sites for the reactants. The Royal Society of Chemistry 2010.

Efficient synthesis of substituted 3-azabicyclo[3.1.0]hexan-2-ones from 2-iodocyclopropanecarboxamides using a copper-free Sonogashira coupling

The copper-free Sonogashira coupling between N-substituted cis- 2-iodocyclopropanecarboxamides and terminal aryl-, heteroaryl-alkynes or enynes, followed by 5-exo-dig cyclization of the nitrogen amide onto the carbon-carbon triple bond, provides a remarkably efficient access to a variety of substituted 4-methylene-3-azabicyclo[3.1.0]hexan-2-ones in excellent yields. Protonation of these latter enamides generates bicyclic N-acyliminium ions that can be involved in Pictet-Spengler cyclizations leading to new 3-azabicyclo[3.1.0]hexan-2-ones, possessing a quaternary stereocenter at C4, with high diastereoselectivities. This strategy constitutes an attractive complementary alternative to the classical route that relies on the addition of organometallic reagents to cyclopropyl imides. A copper-free Sonogashira coupling between cis-2-iodocyclopropanecarboxamides and terminal aryl-, heteroaryl-alkynes or enynes followed by 5-exo-dig cyclization provides an efficient access to substituted 4-methylene-3-azabicyclo[3.1.0]hexan-2-ones (see scheme). Protonation of these enamides generates N-acyliminium ions, which can be involved in Pictet-Spengler cyclizations leading to new 3-azabicyclo[3.1.0] hexan-2-ones containing a quaternary stereocenter at C4 with high diastereoselectivities. Copyright

Rhodium-catalyzed oxidative coupling of benzoic acids with propargyl alcohols: An efficient access to isocoumarins

An efficient protocol of Rh(III)-catalyzed oxidative cyclization of benzoic acids with propargyl alcohols to give substituted isocoumarins under mild conditions was reported. A variety of substrates were applied in this reaction in yields up to 89%.

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.

An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis

The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. Here we report Z-selective semihydrogenation of alkynes with ethanol via a coordination-induced ionic monohydride mechanism. The EtOH-coordination-driven Cl- dissociation in a pincer Ir(III) hydridochloride complex (NCP)IrHCl (1) forms a cationic monohydride, [(NCP)IrH(EtOH)]+Cl-, that reacts selectively with alkynes over the corresponding Z-alkenes, thereby overcoming competing thermodynamically dominant alkene Z-E isomerization and overreduction. The challenge for establishing a catalytic cycle, however, lies in the alcoholysis step; the reaction of the alkyne insertion product (NCP)IrCl(vinyl) with EtOH does occur, but very slowly. Surprisingly, the alcoholysis does not proceed via direct protonolysis of the Ir-C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl- ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)-H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting the alcoholysis. The 1-amine-EtOH catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility, as demonstrated by Z-selective reduction of all alkyne classes, including challenging enynes and complex polyfunctionalized molecules. Comparison with a cationic monohydride complex bearing a noncoordinating BArF- ion elucidates the beneficial role of the Cl- ion in controlling the stereoselectivity, and comparison between 1-amine-EtOH and 1-NaOtBu-EtOH underscores the fact that this base variable, albeit in catalytic amounts, leads to different mechanisms and consequently different stereoselectivity.

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