ABSTRACT
Although interest in cyclotriveratrylene and its analogues has been significant, limitations in the ability to adjust its structure fully have hampered studies into their complete range of properties. A unique strategy to synthesize a previously unobtainable cyclotriveratrylene analogue and a procedure which adjusts the inner methylene bridges of that material to a triketone is reported. A second triketone synthesis and computational studies indicate the parameters needed for success.
Subject(s)
Ketones/chemistry , Polycyclic Compounds/chemistry , Polycyclic Compounds/chemical synthesis , Molecular Structure , Stereoisomerism , Structure-Activity RelationshipABSTRACT
Explorations into a series of different approaches for 9-membered carbocycle formation have afforded the first reported example of a 9-exo-dig ring closure via a Au(III)-promoted reaction between an alkyne and an aryl ring as well as several additional, unique Friedel-Crafts-type cyclizations. Analyses of the factors leading to the success of these transformations are provided, with the application of one of the developed 9-membered ring closures affording an efficient and scalable synthesis of the bioactive resveratrol trimer caraphenol A. That synthesis proceeded with an average yield of 89% per step (7.8% overall yield) and has provided access to more than 600 mg of the target molecule.
Subject(s)
Phenols/chemical synthesis , Stilbenes/chemical synthesis , Biological Products , Catalysis , Cyclization , Molecular Structure , Phenols/chemistry , Resveratrol , Stereoisomerism , Stilbenes/chemistryABSTRACT
It has been shown that compounds containing the p-N,N,-dialkylaminobenzylidene cyanoacetate motif can serve as fluorescent non-mechanical viscosity sensors. These compounds, referred to as molecular rotors, belong to a class of fluorescent probes that are known to form twisted intramolecular charge-transfer complexes in the excited state. In this study we present the synthesis and spectroscopic characterization of these compounds as viscosity sensors. The effects of the molecular structure and electronic density of these rotors to the emission wavelength, fluorescence intensity and viscosity sensitivity are discussed.
