35556-63-9

Usage

Physical state

yellow to light brown solid at room temperature

Primary uses

organic synthesis and pharmaceutical research

Potential applications

drug and agrochemical development

Studied properties

potential anti-cancer and anti-inflammatory effects, activity as a ligand for receptors in the central nervous system
Versatile and important compound in medicinal chemistry and drug development.

Upstream product

• 637-87-6 1-Chloro-4-iodobenzene 
• 3923-52-2 1,1-diphenyl-2-propyn-1-ol 
• 873-73-4 4-n-chlorophenylacetylene 
• 119-61-9 benzophenone 
• 91-01-0 1,1-Diphenylmethanol 

Downstream Products

• 943034-09-1 C₂₆H₂₅ClOSi 
• 1192167-55-7 3-(4-chlorophenyl)-5,7-dimethyl-1,1-diphenyl-1H-inden-6-ol 
• 1192167-72-8 4-(1-(4-chlorophenyl)-3-phenyl-1H-inden-1-yl)-2,6-diisopropylphenol 
• 1192167-70-6 4-(1-(4-chlorophenyl)-3-phenyl-1H-inden-1-yl)phenol 
• 106552-38-9 1-(4-chlorophenyl)-3,3-diphenylprop-2-en-1-one 
• 1242072-93-0 4-benzhydryl-5-(4-chlorophenyl)-2-methylthiazole 
• 1263098-41-4 4-benzhydryl-5-(4-chlorophenyl)-2-phenyloxazole 
• 1418213-80-5 C₃₂H₂₂ClNO₃ 
• 1616101-37-1 4-(4-chlorophenyl)-1,2-diphenyl-9H-carbazole 

Relevant academic research and scientific papers

Gold-catalyzed tandem annulations of pyridylhomopropargylic alcohols with propargyl alcohols

A gold-catalyzed tandem annulation of propargylic alcohols and pyridylhomopropargylic alcohols is achieved, providing an atom-economical approach to a diverse set of polycyclic dihydrobenzofurans in good yields. The reaction proceeds via the 5-endo-dig cyclization/Meyer?Schuster rearrangement/Friedel?Crafts-type pathway. In this way, three C?C bonds and one C? O bond form to give a polycyclic skeleton in a one-pot process. Moreover, the products exhibit unique optical properties, which reveal their potential application value.

Lewis-Acid-Catalyzed Tandem Cyclization by Ring Expansion of Tertiary Cycloalkanols with Propargyl Alcohols

A new method for the efficient synthesis of hexahydro-1H-fluorene and octahydrobenzo[a]azulene derivatives through a ring-expansion strategy is reported. With an appropriate combination of thulium(III) trifluoromethanesulfonate and 13X molecular sieves, a range of unsaturated polycyclic compounds were obtained in good yields. Mechanism studies reveal that the reaction is more likely to undergo Meyer–Schuster rearrangement, ring expansion, and Friedel–Crafts-type pathways, which provide a conceptually different strategy for the ring opening of tertiary cycloalkanols.

Synthesis of 1H-Pyrrolo[1,2-a]indoles via Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with 2-Ethynylanilines

A novel highly efficient, environmentally benign Lewis acid-catalyzed, and protection-free protocol for the construction of valuable polycyclic products bearing a 1H-pyrrolo[1,2-a]indole scaffold is described, starting from readily available propargylic alcohols and 2-ethynylanilines. The one-pot transformation entails the cleavage of one C?O bond, and the construction of two C?N bonds and one C?C double bond. This unique operationally simple method is performed under mild conditions and in air, producing water as the only byproduct; it is scalable and demonstrates good functional group compatibility and broad scope.

Br?nsted Acid-Mediated Formal [3+3] Annulation Between Propargylic Alcohols and 1,3-Diketones

A Br?nsted acid-mediated formal [3+3] cascade annulation of propargylic alcohols with 1,3-diketones proceeds through a sequential Meyer?Schuster rearrangement/1,2-addition. This protocol, which has a wide scope and is conducted under an ambient atmosphere

Lewis Acid-Catalyzed Formal [3+3] Annulation of Propargylic Alcohols with 4-Hydroxy-2H-chromen-2-ones

A Lewis acid-catalyzed formal [3+3] cascade annulation strategy for the formation of diverse tricyclic compounds possessing functionalized pyrano[3,2-c]chromen-5(2H)-one fragments has been developed using propargylic alcohols and 4-hydroxy-2H-chromen-2-on

Lewis Acid-Catalyzed Annulation of Propargylic Alcohols with (Z)-2-Styryl-1H-Indoles

A novel copper(II) trifluoromethanesulfonate-catalyzed intermolecular cascade annulation strategy for the construction of a great variety of pentacyclic compounds possessing valuable carbazole fragments was developed employing propargylic alcohols and (Z)-2-styryl-1H-indoles as the initial substrates. This protocol, which entails a sequential Meyer-Schuster rearrangement/isomerization/-cyclization cascade, enables facile and atom-economical access to various pentacyclic compounds with broad functional-group tolerance in good yields under mild conditions. The conversion could be efficiently scaled up to gram quantities, accentuating a potential application of this work. (Figure presented.).

Transition-Metal-Free, Br?nsted Acid-Mediated Cascade Sequence in the Reaction of Propargyl Alcohols with Sulfonamido-indoles/-indolines: Highly Substituted δ- And α-Carbolines

Br?nsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/-indolines under mild conditions affords highly substituted δ- or α-carbolines in good to excellent yields. This protocol involves cascade reaction seque

Lewis Acid-Catalyzed [4+2] Annulation between Propargylic Alcohols with Benzo[d]isoxazoles

An unprecedented copper(II) trifluoromethanesulfonate-catalyzed [4+2] cascade annulation of propargylic alcohols with benzo[d]isoxazoles proceeds through a sequential ring opening/Meyer–Schuster rearrangement/intermolecular cyclization. This protocol, whi

Lewis Acid Catalyzed Cyclization of Propargylic Alcohols with 2-Vinylphenol

An unprecedented Lewis acid catalyzed, protection-free, and high-efficiency synthesis of valuable 3,4-dihydro-2H-2,4-methanochromans via cycloaddition of propargylic alkynols with 2-vinylphenol is described. This cycloaddition protocol, which tolerates a

TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide

A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.