166757-00-2

Upstream product

• 40230-91-9 [(2-methoxyphenyl)ethynyl]trimethylsilane 
• 529-28-2 4-iodoanisol 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 5159-41-1 2-iodobenzyl alcohol 

Downstream Products

• 1448450-08-5 4-((Z)-((Z)-3-(2-methoxybenzylidene)isobenzofuran-1(3H)-ylidene)methyl)-N,N-dimethylaniline 

Relevant academic research and scientific papers

Synthesis of dibenzocyclohepta[1,2-a]naphthalene derivatives from phenylacetaldehyde and alkynyl benzyl alcoholsviasequential electrophilic addition and double Friedel-Crafts reactions

A simple methodology has been developed for the synthesis of substituted 9H-dibenzo[3,4:6,7]-cyclohepta[1,2-a]naphthalenes from phenylacetaldehydes andortho-alkynyl benzyl alcohols in the presence of a Lewis acid in moderate to good yields within a short reaction time. Interestingly, the reaction proceeds through a highly regioselective electrophilic addition followed by double Friedel-Crafts reaction to form uncommon dibenzo-fused seven-membered carbocycles.

Regioselective synthesis and evaluation of 3-alkylidene-1, 3-dihydroisobenzofurans as potential antidepressant agents

3-Alkylidene-1,3-dihydroisobenzofurans exhibited moderate antidepressant activity as evaluated by forced swim and tail suspension test methods. Virtual screening was carried out by docking the designed compounds into the serotonin binding sites of arabinase protein to predict the analogue binding mode of the compounds to the SSRIs. [Figure not available: see fulltext.]

An Unusual Example of a 6-Endo-Dig Addition to an Unactivated Carbon-Carbon Triple Bond

Methyl 2-ethynyl>benzoate was prepared as an intermediate for subsequent conversion to an α-diazo ketone.Under the basic conditions used to hydrolyze the methyl ester, the neighboring hydroxyl functionality underwent reaction with the unactivated acetylenic group, producing a benzopyranyl-substituted α-diazoacetophenone.Treatment of this diazocarbonyl compound with a catalytic quantity of rhodium(II) mandelate afforded a novel dibenzocyclononenone derivative.The reaction proceeds via an initially formed oxonium ylide which rearranges further by means of a 1,2-alkyl shift.A prime factor in determining the direction of internal cyclization to the triple bond is the presence of the carbomethoxy group in the ortho position of the β-phenyl ring.Thus, in contrast with related systems which exhibit a clear preference for 5-exo-dig cyclization at the acetylenic center, the 6-endo-dig addition is the preferred pathway for the o-formyl- and o-carbomethoxy-substituted alkynyl alcohols.Careful monitoring of the reaction actually showed that the reaction proceeds by initial formation of the 5-exo-dig product followed by a novel rearrangement to the 6-endo product.