87688-90-2

Usage

InChI:InChI=1/C18H18O2/c1-3-5-14-7-10-16(11-8-14)20-18-13-15(6-4-2)9-12-17(18)19/h3-4,7-13,19H,1-2,5-6H2

Upstream product

• 501-92-8 4-(prop-2-enyl)phenol 
• 140-67-0 Estragole 

Relevant academic research and scientific papers

Development of the radical C–O coupling reaction of phenols toward the synthesis of natural products comprising a diaryl ether skeleton

Compounds comprising a diaryl ether skeleton exist among natural phenols. The diaryl ether skeleton is thought to be biosynthesized through the coupling of two or more phenols. It is an important structural feature in medicines and agrochemicals, and it is imperative to develop methods for constructing such skeletons in organic synthesis. However, by the synthesis method through the coupling of phenols, coupling occurs preferentially at the ortho-substituted carbon atom of phenols. In this study, various radical-generating reagents and conditions were investigated with the aim of developing a short-step construction method of the diaryl ether skeleton by the radical homo-coupling of two phenol molecules. In addition, cross-coupling reactions between radicals of 2,4,6-tri-tert-butylphenol and p-substituted phenol were conducted to synthesize eight C (ortho)–O coupling products. Based on the results, a computational chemical approach was employed to verify the cause of C (ortho)–O bond formation.

Cytotoxic neolignans: An SAR study

The cytotoxic effects of different neolignans with the structure 1 were studied. The neolignans, magnolol 1 and honokiol 2 have been reported to inhibit the growth of several tumor cell lines in vitro and in vivo. The chemical structure of magnolol and honokiol consists of biphenyl skeleton with phenolic and allylic functionalities. Analogs of 1 and 2 containing different substitution have been studies for their effect on the growth of Hep-G2 and their structure-activity relationships were reported in this work.

Biomimetic Synthesis of Illicium Oligomeric Neolignans

Six products have been isolated from the oxidative coupling of 4-allylphenol in the presence of FeIII; the distribution of products suggests that oligomeric neolignans associated with the family Illicium may also be non-enzymic products of oxidative coupling.