4469-89-0Relevant academic research and scientific papers
Fatty Alcohols Through Hydroxylation of Symmetrical Alkenes with Selenium Dioxide/tert.-Butylhydroperoxide
Knothe, G.,Bagby, M. O.,Weisleder, D.
, p. 1021 - 1026 (1995)
Several symmetrical alkenes were reacted with the selenium dioxide/tert.-butylhydroperoxide system to give three hydroxylated products each.These products were those of allylic mono- and dihydroxylation (meso and threo dihydroxy compounds) of the double bond.Some dihydroxy products were hydrogenated to give saturated 1,4-diols.The compounds were characterized by nuclear magnetic resonance.The products have potential for application in commercial products, such as biodiesel, lubricants, greases, and cosmetics. - Keywords: Hydroxylation; nuclear magnetic resonance; selenium dioxide; symmetrical alkene, tert.-butylhydroperoxide.
Biocatalytic synthesis of non-vicinal aliphatic diols
Ebrecht, Ana C.,Aschenbrenner, Jasmin C.,Smit, Martha S.,Opperman, Diederik J.
supporting information, p. 439 - 445 (2021/01/29)
Biocatalysts are receiving increased attention in the field of selective oxyfunctionalization of C-H bonds, with cytochrome P450 monooxygenases (CYP450s), and the related peroxygenases, leading the field. Here we report on the substrate promiscuity of CYP505A30, previously characterized as a fatty acid hydroxylase. In addition to its regioselective oxyfunctionalization of saturated fatty acids (ω-1-ω-3 hydroxylation), primary fatty alcohols are also accepted with similar regioselectivities. Moreover, alkanes such as n-octane and n-decane are also readily accepted, allowing for the production of non-vicinal diols through sequential oxygenation. This journal is
Decane autoxidation: Precursors of gamma lactones and other minor products
Goosen, Andre,Kindermans, Sybrandus
, p. 9 - 13 (2007/10/03)
Autoxidation of decane produces the following minor products in decreasing yields, viz. 2,5-, 3,6- and 4,7-decanediones and diols. Addition of 3-decanone to a decane autoxidation enhances the production of octanal, heptanal, octanoic and heptanoic acids. 3-Decanol initially inhibits the autoxidation reaction prior to being oxidized to 3-decanone. γ-Octanoic and γ-heptanoic lactone formation in the autoxidation of decane is promoted by the addition of 3- and 4-decyl hydroperoxides, respectively. These lactones are formed when tert-butoxy radicals react with 3,6- and 4,7-decane diols in the presence of oxygen. The nature of the intermediates in the formation of the minor products and the inhibition by alcohols are discussed.
