111833-50-2

Upstream product

• 100-52-7 benzaldehyde 
• 693-02-7 hex-1-yne 
• 73922-80-2 1-phenylhept-2-yn-1-ol 
• 108-24-7 acetic anhydride 

Downstream Products

• 141503-07-3 4-phenyldec-5-yn-2-one 
• 34877-79-7 phenyl 2-phenyl-3-octynyl ketone 
• 1163687-55-5 (E)-1,2-diphenylhept-1-en-3-one 
• 1140505-07-2 5-pentyl-2,4-diphenyloxazole 
• 19184-21-5 (E)-1-phenylhept-1-en-3-one 
• 1181227-24-6 (E)-2-iodo-1-phenyl-n-hept-1-en-3-one 
• 1181227-15-5 (Z)-2-iodo-1-phenyl-n-hept-1-en-3-one 
• 1225432-42-7 (E)-2-bromo-1-phenyl-n-hept-1-en-3-one 
• 1225432-54-1 (Z)-2-bromo-1-phenyl-n-hept-1-en-3-one 
• 903512-24-3 1-phenylhepta-1,2-dien-3-yl acetate 
• 4071-84-5 1-phenyl-hept-1-en-3-one 
• 1383536-82-0 ((1E,3Z)-3-methylhepta-1,3-dien-1-yl)benzene 
• 1383536-81-9 ((1E,3E)-3-methylhepta-1,3-dien-1-yl)benzene 
• 1902-95-0 ethyl-(1-phenyl-hept-2-ynyl)-ether 

Relevant academic research and scientific papers

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

Highly efficient synthesis of allenes from trimethylaluminum reagent and propargyl acetates mediated by a palladium catalyst

A series of propargyl acetates were prepared and used as propargyl electrophiles for coupling reactions with trimethylaluminum. The simple catalytic system of palladium(II) acetate (1 mol-%) and tri(o-tolyl)phosphine (2 mol-%) worked efficiently for a wide variety of aromatic and aliphatic propargyl acetates, producing the substituted allenes in good to excellent yields of up to 94% in tetrahydrofuran. The process was simple and easily performed, and it provides an efficient method for the synthesis of substituted allene derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions

We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.

Iron-catalyzed C-O bond activation for the synthesis of propargyl-1,2,3-triazoles and 1,1-bis-triazoles

(Equation Presented). The FeCl3-catalyzed triazole propargylation was developed. This transformation was suitable for a large scope of substituted propargyl alcohols, giving the corresponding propargyl triazoles in excellent yields (up to 96%). Further derivatization produced the 1,1-bis-triazoles in excellent yields and regioselectivity, which could be applied as potential transition metal ligands or new reagents.

Efficient synthesis of e -α-haloenones through chemoselective alkyne activation over allene with triazole-Au catalysts

Figure presented The E-α-haloenones were prepared through a triazole-Au complex (TriA-Au) catalyzed propargyl acetate rearrangement and sequential allene halogenation. The reactions proceeded with only 1% catalyst loading, giving the challenging kinetic p

[(NHC)AuI]-catalyzed formation of conjugated enones and enals: An experimental and computational study

The [(NHC)AuI]-catalyzed (NHC = N-heterocyclic carbene) formation of α,β-unsaturated carbonyl compounds (enones and enals) from propargylic acetates is described. The reactions occur at 60°C in 8 h in the presence of an equimolar mixture of [(NHC)AuCl] and AgSbF6 and produce conjugated enones and enals in high yields. Optimization studies revealed that the reaction is sensitive to the solvent, the NHC, and, to a lesser extent, to the silver salt employed, leading to the use of [(ItBu)AuCl]/ AgSbF6 in THF as an efficient catalytic system. This transformation proved to have a broad scope, enabling the stereoselective formation of (E)-enones and -enals with great structural diversity. The effect of substitution at the propargylic and acetylenic positions has been investigated, as well as the effect of aryl substitution on the formation of cinnamyl ketones. The presence or absence of water in the reaction mixture was found to be crucial. From the same phenylpropargyl acetates, anhydrous conditions led to the formation of indene compounds via a tandem [3,3] sigmatropic rearrangement/intramolecular hydroarylation process, whereas simply adding water to the reaction mixture produced enone derivatives cleanly. Several mechanistic hypotheses, including the hydrolysis of an allenol ester intermediate and SN2′ addition of water, were examined to gain an insight into this transformation. Mechanistic investigations and computational studies support [(NHC)AuOH], produced in situ from [(NHC)AuSbF6] and H 2O, instead of cationic [(NHC)AuSbF6] as the catalytically active species. Based on DFT calculations performed at the B3LYP level of theory, a full catalytic cycle featuring an unprecedented transfer of the OH moiety bound to the gold center to the C≡C bond leading to the formation of a gold-allenolate is proposed.

AuI-catalyzed tandem [3,3] rearrangement-intramolecular hydroarylation: Mild and efficient formation of substituted indenes

(Chemical Equation Presented) Dignified auration: The rearrangement of phenylpropargyl acetates to substituted indenes is catalyzed by [Au 1(NHC)] complexes (see scheme, NHC = N-heterocyclic carbene) under extremely mild reaction conditions. This chemoselective transformation involves 1,3-migration of the acetate group and is proposed to proceed through an allene intermediate. TMS = trimethylsilyl, TBS = tert-butyldimethylsilyl.

TiCl4-mediated nucleophilic substitution of propargylic esters

Direct displacement reactions of propargylic esters are reported. 10 mol% of TiCl4 were used to carry out a nucleophilic substitution. Scope and limitation of this novel reaction are described. (C) 2000 Elsevier Science Ltd.