146801-59-4Relevant academic research and scientific papers
Micellar Effects in the Nitrous Acid Deamination Reaction of (R)-2H>-1-Octanamine
Brosch, Daniel,Kirmse, Wolfgang
, p. 1118 - 1121 (1993)
The nitrous acid deamination of 1-octanamine (1) afforded mixtures of isomeric octenes, octanols, and octyl nitrites.The aggregation of 1*HClO4 in micelles induced the formation of dioctyl ethers and of 1-nitrooctane as additional products.In homogeneous solution (submicellar aqueous conditions or HOAc), 2H>-1-octanol was obtained from 2H>-1 with ca. 95 percent inversion of configuration.Above the critical micelle concentration, the enantiomeric purity of 2H>-1-octanol decreased while 2H>-1-nitrooctane was formed with ca. 90 percent retention of configuration. 1-Octyl..NO2 radical pairs, rather than ion pairs, are likely to intervene on the retentive route to 1-nitrooctane and 1-octyl nitrite.Equilibration, via NO exchange, of (R)-2H>-1-octyl nitrite with the more abundant (S)-2H>-1-octanol is thought to account for the diminished ee of both products.
Enantioselective synthesis of (R)-and (S)-1-2H-1-octanol and their corresponding amines
Balkenende, Diederik W.R.,Cantekin, Seda,Duxbury, Christopher J.,Van Genderen, Marcel H.P.,Meijer,Palmans, Anja R.A.
, p. 563 - 573 (2011/12/15)
Both enantiomers of 1-2H-1-octanol were obtained by the enzymatic reduction of deuterated octanal in the presence of alcohol dehydrogenases (ADH) (ADH-T or ADH-LB) as the biocatalyst in good yield, purity, and enantiomeric excess (2H-1-octanol in good yields (80%) and good enantiomeric excess (～97%). The (S)-alcohols were converted to their corresponding (R)-amines, which showed ee's around 90%. Taylor & Francis Group, LLC.
Topological study of mechanistic diversity in conjugated fatty acid biosynthesis
Bhar, Palash,Reed, Darwin W.,Covello, Patrick S.,Buist, Peter H.
supporting information; experimental part, p. 6686 - 6690 (2012/08/27)
Variations on an oxidative theme: The precision with which FAD2-type desaturases carry out C-H activation reactions on flexible lipidic substrates is astonishing. The conformational space available within the active site of these enzymes has been explored using deuterium-labeled substrates, and evidence for a novel quasi-eclipsed conformer has been uncovered. The scheme shows some prototypical substrate conformations. Copyright
