Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, Angewandte Chemie, International Edition called Copper-Catalyzed and Proton-Directed Selective Hydroxymethylation of Alkynes with CO2, Author is Wang, Mei-Yan; Jin, Xin; Wang, Xiaofei; Xia, Shumei; Wang, Yue; Huang, Shouying; Li, Ying; He, Liang-Nian; Ma, Xinbin, which mentions a compound: 57399-11-8, SMILESS is C#CC1=CC=C(C2=CC=C(Cl)C=C2)C=C1, Molecular C14H9Cl, COA of Formula: C14H9Cl.
An intriguing strategy for copper-catalyzed hydroxymethylation of alkynes with CO2 and hydrosilane was developed. Switched on/off a proton source, for example, t-BuOH, direct hydroxymethylation and reductive hydroxymethylation could be triggered selectively, delivering a series of allylic alcs. and homobenzylic alcs., resp., with high levels of Z/E, regio- and enantioselectivity. Such a selective synthesis is attributed to the differences in response of vinylcopper intermediate to proton and CO2. The protonation of vinylcopper species is demonstrated to be prior to hydroxymethylation, thus allowing a diversion from direct alkyne hydroxymethylation to reductive hydroxymethylation in the presence of a suitable proton source.
In addition to the literature in the link below, there is a lot of literature about this compound(4-Chloro-4′-ethynyl-1,1′-biphenyl)COA of Formula: C14H9Cl, illustrating the importance and wide applicability of this compound(57399-11-8).
Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem