7342-10-1

Basic information

• Product Name: 1-(4-chlorophenyl)prop-2-yn-1-yl acetate
• Synonyms: 1-(4-chlorophenyl)prop-2-yn-1-yl acetate
• CAS NO: 7342-10-1
• Molecular Weight: 208.644
• Mol File: 7342-10-1.mol

Chemical Properties

• CAS DataBase Reference: 1-(4-chlorophenyl)prop-2-yn-1-yl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-chlorophenyl)prop-2-yn-1-yl acetate(7342-10-1)
• EPA Substance Registry System: 1-(4-chlorophenyl)prop-2-yn-1-yl acetate(7342-10-1)

Safety Data

• Hazardous Substances Data: 7342-10-1(Hazardous Substances Data)

Upstream product

• 29805-11-6 1-(4-chlorophenyl)prop-2-yn-1-ol 
• 108-24-7 acetic anhydride 
• 1041849-95-9 1-(4-chlorophenyl)-3-(trimethylsilyl)prop-2-yn-1-ol 
• 104-88-1 4-chlorobenzaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 64-19-7 acetic acid 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 1041175-28-3 4-chloro-N-methyl-N-[1-(4-chlorophenyl)-2-propynyl]aniline 
• 1041175-19-2 N-methyl-N-[1-(4-chlorophenyl)-2-propynyl]aniline 
• 1186338-34-0 C₁₂H₉ClF₂O₂ 
• 1240238-96-3 C₁₆H₁₃Cl₂N 
• 1240238-82-7 (S)-N-[1-(4-chlorophenyl)-2-propynyl]-4-trifluoromethyl-N-methylaniline 
• 1240238-69-0 N-[(S)-1-(4-chlorophenyl)prop-2-ynyl]-N-methylbenzenamine 
• 56955-39-6 1-(4-chlorophenyl)-2-oxopropyl acetate 
• 1526920-95-5 2-[1-(4-chlorophenyl)prop-2-ynyl]-2-methylcyclohexane-1,3-dione 

Relevant articles and documents

One-pot synthesis of polyfunctionalized quinolines: Via a copper-catalyzed tandem cyclization

An efficient one-pot approach for the synthesis of polyfunctionalized quinolines was developed via a sequence of copper-catalyzed coupling reaction/propargyl-allenyl isomerization/aza-electrocyclization. Easily available starting materials, mild conditions, and a wide substrate scope make this approach potentially useful.

Convenient synthesis of allenylphosphoryl compounds: Via Cu-catalysed couplings of P(O)H compounds with propargyl acetates

A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism involving the nucleophilic interception of the Cu-allenylidene intermediates is proposed.

Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives

A highly efficient cascade sequence for syntheses of 2,3-disubstituted imidazo[1,2-a]pyridines with exclusive regioselectivity in moderate to excellent yields has been developed. This cascade was initiated through propargylation of 2-aminopyridines at pyridine-nitrogen with propargyl alcohol derivatives using Cu(II)-Pybox as catalyst and followed by an intramolecular cyclization and isomerization. Besides 2-aminopyridine, less reactive 2-aminopyrimidine, 2-aminopyrazine and 3-aminopyridazine were also suitable in this cascade.

Diastereo- and enantioselective propargylation of benzofuranones catalyzed by pybox-copper complex

Diastereo- and enantioselective preparation of 2,2-disubstituted benzofuran-3(2H)-one has been realized by a pybox-copper catalyzed reaction between 2-substituted benzofuran-3(2H)-one and propargyl acetate. The utility of this method was demonstrated by further transformation of the terminal alkyne into a methyl ketone without loss of enantiomeric purity.

Stereocontrol in palladium-catalyzed propargylic substitutions: Kinetic resolution to give enantioenriched 1,5-enynes and propargyl acetates

Kinetic resolution during the catalytic allyl-propargyl cross-coupling with chiral starting materials can be accomplished with a chiral palladium catalyst. These reactions offer ready access to enantiomerically enriched enyne products from simple, readily

Silver(I)-catalyzed reaction between pyrazole and propargyl acetates: Stereoselective synthesis of the scorpionate ligands (E)-allyl-gem-dipyrazoles (ADPs)

The reaction between readily accessible pyrazole and propargyl acetates in the presence of Ag(I) catalyst yielded a new class of (E)-allyl-gem-dipyrazole scorpionate ligands: 1-aryl-2-N-pyrazolyl allyl acetates and 1,3-dipyrazolyl-3-arylpropene. The reaction showed broad substrate scope, and various functional and protecting groups were tolerated under the reaction conditions. The palladium(II) scorpionate complex could thus be easily prepared and successfully employed in Suzuki-Miyaura cross-couplings in water.

Construction of 1,5-enynes by stereospecific Pd-catalyzed allyl-propargyl cross-couplings

The palladium-catalyzed cross-coupling of chiral propargyl acetates and allyl boronates delivers chiral 1,5-enynes with excellent levels of chirality transfer and can be applied across a broad range of substrates.

Gold-catalyzed regioselective hydration of propargyl acetates assisted by a neighboring carbonyl group: Access to α-acyloxy methyl ketones and synthesis of (±)-actinopolymorphol B

A general atom-economical approach for the synthesis of α-acyloxy methyl ketone is demonstrated through regioselective hydration of a wide range of propargyl acetates. Readily available catalyst comprising of 1% Ph 3PAuCl and 1% AgSbF6 in dioxane-H2O efficiently hydrolyzes the terminal alkynes of the propargyl acetate in the absence of acid promoters at ambient temperature within a short time. Effective regioselective hydration is facilitated by the neighboring carbonyl group as demonstrated through 18O-labeling study. Compatibility of functional moieties and tolerance to various acid-labile protecting groups are observed. The catalytic condition is also suitable to perform hydration of TMS-substituted propargyl acetates, even though it requires prolonged reaction time for completion. Stereointegrity of the propargylic acetate is preserved during the hydration. The robustness of the system is successfully demonstrated through gram scale preparation of the product in nearly quantitative yield. The common α-acyloxy methyl ketone is transformed to 1,2-diol and 1,2-amino alcohol derivatives. Synthesis of actinopolymorphol B is achieved for the first time involving hydration of the propargyl acetate as the key step.

Copper-catalyzed enantioselective propargylic amination of propargylic esters with amines: Copper-allenylidene complexes as key intermediates

The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles for this catalytic reaction to give the corresponding propargylic amines with a high enantioselectivity. The results of some stoichiometric and catalytic reactions indicate that the catalytic amination proceeds via copper-allenylidene complexes formed in situ, where the attack of amines to the electrophilic γ-carbon atom in the allenylidene complex is an important step for the stereoselection. Investigation of the relative rate constants for the reaction of several para-substituted propargylic acetates with N-methylanilines reveals that the formation of the copper-allenylidene complexes is involved in the rate-determining step. The result of the density functional theory calculation on a model reaction also supports the proposed reaction pathway involving copper-allenylidene complexes as key intermediates. The catalytic procedure presented here provides a versatile and direct method for the preparation of a variety of chiral propargylic amines.

Asymmetrie copper-catalyzed propargylic substitution reaction of propargylic acetates with enamines

Enamines served as carbon-nucleophiles for the first time In the Cu-catalyzed asymmetric propargylic substitution reaction of propargylic acetates, providing corresponding chiral β-ethynyl-substituted ketones In high yields and In good to high enantioselectivity.