903512-06-1

Upstream product

• 108-24-7 acetic anhydride 
• 115085-22-8 1-(4-methylphenyl)-2-heptyn-1-ol 
• 104-87-0 4-methyl-benzaldehyde 
• 693-02-7 hex-1-yne 

Downstream Products

• 100765-40-0 (E)-1-(4-methylphenyl)-1-heptene-3-one 
• 1225432-43-8 C₁₄H₁₇BrO 
• 1225432-55-2 (Z)-2-bromo-1-p-tolyl-n-hept-1-en-3-one 
• 1225432-47-2 (E)-2-iodo-1-p-tolyl-n-hept-1-en-3-one 
• 1225432-58-5 (Z)-2-iodo-1-p-tolyl-n-hept-1-en-3-one 
• 1599479-61-4 1-methyl-4-(3-(trifluoromethyl)hepta-1,2-dien-1-yl)benzene 

Relevant academic research and scientific papers

Titanocene-catalyzed metallation of propargylic acetates in homopropargyl alcohol synthesis

The titanium-catalyzed metallation and subsequent carbonyl addition of propargylic acetates enable the direct formation of homopropargylic alcohols in good yields. The corresponding products were obtained as single regioisomers without the corresponding a

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.