86774-84-7

Upstream product

• 85381-13-1 2-phenylcarbamoyl-1-(2-hydroxyphenyl)-1-α,2α,2aβ,8bβ-tetrahydro-3H-cyclobuta--chromen-3-one 
• 614-60-8 o-Coumaric acid 
• 62-53-3 aniline 
• 2210-24-4 N-acryloylaniline 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C?H Functionalization

o-Alkenylation of unprotected phenols has been developed by direct C?H functionalization catalyzed by PdII. This work features phenol group as a directing group and realizes highly site-selective C?H bond functionalization of phenols to achieve the corresponding products in moderate to excellent yields at 60 °C. The advantages of this reaction include unprecedented C?H functionalization using phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C?H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under this catalytic system in good yields. Furthermore, this novel method enables a late-stage modification of complex phenol-containing bioactive molecules toward a diversity-oriented drug discovery.

A photo-sensitive protecting group for amines based on coumarin chemistry

There is a continuing need for the development of new protecting groups for amines which can be cleaved under conditions that are mild and fundamentally different from what are already available. In this paper, we report our studies in using o-hydroxy-trans-cinnamic acid as a photo- sensitive protecting group for amines. The design takes advantage of the trans-cis photo-isomerization and the ensuing facile lactonization of o- hydroxy-cis-cinnamic acid and derivatives. We have found that both the protection and deprotection can be carried out in high yields for a variety of amines with different structural features. The deprotection reaction uses low intensity UV light (365 nm), which is fundamentally different from the conditions used for the deprotection of other commonly used amino-protecting groups. Therefore, the method complements other available methods in allowing for selective manipulation of different functional groups in a complex organic molecule.

Symmetric and Asymmetric Photocleavage of the Cyclobutane Rings in Head-to-head Coumarin Dimers and Their Lactone-opened Derivatives

The photochemical behaviour of fifteen derivatives of head-to-head coumarin demers has been investigated.The photocleavage of the cyclobutane rings in these compounds in solution occurs on irradiation with light of wavelenght 277 +/- 10 nm to give two molecules of coumarin derivatives via symmetric fission and/or 2,2'-dihydroxystilbene and fumaric (and maleic) acid derivatives via asymmetric fission.The direction of these photofissions is primarily affected by the basic structure of the coumarin dimer derivative, the photocleavage proceeding exclusively with retention of the ring structure when the derivative has a stable five- or six-membered ring fused to its cyclobutane ring.A secondary influence is the steric repulsion between the substituents attached to the cyclobutane ring.