27648-87-9Relevant articles and documents
The synthesis of macrocyclic diamides and tetramides containing phenol units
Gryko, Daniel T.,Piatek, Piotr,Jurczak, Janusz
, p. 7957 - 7966 (1997)
Thirteen new macrocyclic diamides and tetramides have been synthesized by reaction of methyl phenoxyacetates (readily obtained from various phenols) with α,ω-diamines in methanol as a solvent. Relationship between structure of esters and ratio of diamides to tetraamides has been investigated.
Synthesis of benzodioxepinone analogues via a novel synthetic route with qualitative olfactory evaluation
Drevermann, Britta,Lingham, Anthony R.,Huegel, Helmut M.,Marriott, Philip J.
, p. 1006 - 1027 (2008/02/04)
Marine odorants represent a minor yet diverse class of substances within the fragrance industry, of which 7-methyl-2H-1,5-benzodioxepin-3(4H)-one (1) is commercially known as Calone 1951, a synthetic first in the area of marine-fragrance chemistry. To determine the extent to which the characteristic marine odor of Calone 1951 corresponds to the substitution at the benzo portion of the molecule, a variety of aromatic substituents were incorporated into the benzodioxepinone structure (Scheme 1, Table 3). In light of the difficulty experienced in applying patented literature to deriving the analogues 12-18, particularly those with electron-withdrawing substituents, an alternative synthetic scheme was implemented for the construction of all analogues in favorable yields (Scheme 4, Table 3). Formation of the hydroxy-protected dihalo alkylating agent 24 via epoxide cleavage of epichlorohydrin (Scheme 3) allowed etherification favoring dihalo displacement and subsequent intramolecular ring closure (-→26a-g). THP Deprotection followed by oxidation of the alcohols 27a-g to the ketones 12-18 provided a general pathway to the benzodioxepinone products. The influence of the substituent nature on odor activity revealed a diverse scope of olfactory character (Table 4).
Iodinated biaryls synthesized by the direct dehydrodimerization of iodoarenes using phenyliodine(III) bis(trifluoroacetate) (PIFA)
Mirk, Daniela,Willner, Alexander,Froehlich, Roland,Waldvogel, Siegfried R.
, p. 675 - 681 (2007/10/03)
Multiply iodinated biaryls can be prepared in yields up to 75% by direct oxidative coupling reaction of the iodinated arenes. The PIFA-mediated dehydrodimerization is superior to all other known methods. The developed protocol is reliable and easy to perform.