Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas was written by Scattolin, Thomas;Bouayad-Gervais, Samir;Schoenebeck, Franziska. And the article was included in Nature (London, United Kingdom) in 2019.Electric Literature of C14H11NOS This article mentions the following:
Amides and related carbonyl derivatives are of central importance across the phys. and life sciences1,2. As a key biol. building block, the stability and conformation of amides affect the structures of peptides and proteins as well as their biol. function. In addition, amide-bond formation is one of the most frequently used chem. transformations3,4. Given their ubiquity, a technol. that is capable of modifying the fundamental properties of amides without compromising on stability may have considerable potential in pharmaceutical, agrochem. and materials science. In order to influence the phys. properties of organic mols.-such as solubility, lipophilicity, conformation, pKa and (metabolic) stability-fluorination approaches have been widely adopted5-7. Similarly, site-specific modification with isosteres and peptidomimetics8, or in particular by N-methylation9, has been used to improve the stability, phys. properties, bioactivities and cellular permeabilities of compounds However, the N-trifluoromethyl carbonyl motif-which combines both N-methylation and fluorination approaches-has not yet been explored, owing to a lack of efficient methodol. to synthesize it. Here the authors report a straightforward method to access N-trifluoromethyl analogs of amides and related carbonyl compounds The strategy relies on the operationally simple preparation of bench-stable carbamoyl fluoride building blocks, which can be readily diversified to the corresponding N-CF3 amides, carbamates, thiocarbamates and ureas. This method tolerates rich functionality and stereochem., and the authors present numerous examples of highly functionalized compounds-including analogs of widely used drugs, antibiotics, hormones and polymer units. In the experiment, the researchers used many compounds, for example, 3-Benzyloxyphenylisothiocyanate (cas: 206559-36-6Electric Literature of C14H11NOS).
3-Benzyloxyphenylisothiocyanate (cas: 206559-36-6) belongs to esters. Esters are widespread in nature and are widely used in industry. In nature, fats are in general triesters derived from glycerol and fatty acids. Esters are responsible for the aroma of many fruits, including apples, durians, pears, bananas, pineapples, and strawberries. Esters contain a carbonyl center, which gives rise to 120° C–C–O and O–C–O angles. Unlike amides, esters are structurally flexible functional groups because rotation about the C–O–C bonds has a low barrier. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Electric Literature of C14H11NOS
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics