145126-90-5Relevant articles and documents
Ring-closing metathesis of vinyl fluorides towards α-fluorinated α,β-unsaturated lactams and lactones
Marhold, Michael,Stillig, Christian,Fr?hlich, Roland,Haufe, Günter
supporting information, p. 5777 - 5785 (2014/10/15)
Ring-closing olefin metathesis reactions (RCM) using Grubbs II or Hoveyda's catalysts have been applied to a series of N-alkenyl-N-benzyl-α-fluoroacrylamides. α-Fluoro-α,β-unsaturated γ- or δ-lactams incorporating a fluorinated double bond were obtained in moderate to good yields, depending on the nature of substituents on the benzyl ring. The corresponding seven- and eight-membered lactams were not formed under similar conditions. When the N-benzyl group was replaced by an N-tosyl group, the corresponding ε-lactam was also formed in 38% yield. When N-(2-fluoroallyl) derivatives were used instead of fluoroacryloyl derivatives, six-, seven-, and eight-membered N-heterocycles were obtained in low yields. This method was also used to synthesize fluorinated α,β-unsaturated analogues of pyrrolizidine and indolizidine alkaloids from prolinol, and also to synthesize N-benzyl-3-fluoroquinolone in three steps from commercially available 2-vinylaniline in 44% overall yield. Also 3-fluorocoumarin and 3-fluorochromene were prepared from ovinylphenol, and 3-fluoro-benzoxepine was available from o-allylphenol.
Mild nonepimerizing N -alkylation of amines by alcohols without transition metals
Guerin, Claire,Bellosta, Veronique,Guillamot, Gerard,Cossy, Janine
supporting information; experimental part, p. 3534 - 3537 (2011/08/10)
A one-pot two-step sequence involving an oxidation/imine-iminium formation/reduction allowed the N-alkylation of amines by alcohols without any epimerization when optically active alcohols and amines are involved in the process.
Low background FRET-substrates for lipases and esterases suitable for high-throughput screening under basic (pH 11) conditions
Yang, Yongzheng,Babiak, Peter,Reymond, Jean-Louis
, p. 1746 - 1754 (2008/03/11)
FRET-based fluorogenic substrates for lipases and esterases were prepared in four steps from commercially available building blocks. The substrates are pyrenebutyric acid monoesters of aliphatic 1,2-diols bearing a dinitrophenylamino group as a quencher. The most enzyme-reactive substrate is ester 2a. The substrates do not show any measurable background reaction in the absence of enzyme even at pH 11, but react fast and specifically with lipases and esterases. These substrates offer an unprecedented and practical solution to the long-standing problem of a simple yet efficient high-throughput screening tool for lipase activities under basic conditions. The Royal Society of Chemistry 2006.
