35194-39-9Relevant academic research and scientific papers
PALLADIUM-CATALYZED DECARBONYLATION OF FATTY ACID ANHYDRIDES FOR THE PRODUCTION OF LINEAR ALPHA OLEFINS
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Page/Page column, (2014/06/23)
The present invention is directed to methods of forming olefins, especially linear alpha olefins from fatty acids or anhydrides, each method comprising: contacting an amount of precursor carboxylic acid anhydride with a palladium catalyst comprising a bidentate bis-phosphine ligand in a reaction mixture so as to form an olefin in a product with the concomittant formation and removal of CO and water from the reaction mixture, either directly or indirectly, wherein the reaction mixture is maintained with a sub-stoichiometric excess of a sacrificial carboxylic acid anhydride, an organic acid, or both, said sub-stoichiometric excess being relative to the amount of the precursor carboxylic acid anhydride. The precursor carboxylic acid anhydride may be added to the reaction mixture directly or formed in situ by the reaction between at least one precursor carboxylic acid with a stoichiometric amount of the sacrificial acid anhydride.
Enantioselective allylic hydroxylation of w-alkenoic acids and esters by P450 BM3 monooxygenase
Neufeld, Katharina,Henssen, Birgit,Pietruszka, J?rg
, p. 13253 - 13257 (2015/02/19)
Chiral allylic alcohols of w-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. The direct enantioselective C-H oxidation of linear terminal olefins offers the shortest route toward these compounds, but known synthetic methods are limited and suffer from low selectivities. Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo- and enantioselectivities providing the desirable secondary alcohols.
Palladium-catalyzed decarbonylative dehydration of fatty acids for the production of linear alpha olefins
Liu, Yiyang,Kim, Kelly E.,Herbert, Myles B.,Fedorov, Alexey,Grubbs, Robert H.,Stoltz, Brian M.
supporting information, p. 130 - 136 (2014/03/21)
A highly efficient palladium-catalyzed decarbonylative dehydration reaction of carboxylic acids is reported. This method transforms abundant and renewable even-numbered natural fatty acids into valuable and expensive odd-numbered alpha olefins. Additionally, the chemistry displays a high functional group tolerance. The process employs a low loading of palladium catalyst and proceeds under solvent-free and relatively mild conditions.
Chemical synthesis and biological evaluation of second-generation palmerolide a analogues
Ravu, Vengala Rao,Leung, Gulice Y. C.,Lim, Chek Shik,Ng, Sin Yee,Sum, Rong Ji,Chen, David Y.-K.
supporting information; experimental part, p. 463 - 468 (2011/04/17)
In this communication, second-generation analogues of palmerolide A, a recently reported cytotoxic agent against melanoma cancer cells, were rationally designed, synthesized, and biologically evaluated. Structural variations of the enamide side chain and the C1-C8 segment of palmerolide A revealed a narrow structure-activity relationship window of the newly synthesized compounds. In addition, mechanistic and pharmacological studies were performed to assess the therapeutic potential of palmerolide A. Synthesis and biological evaluation of second-generation palmerolide A analogues are reported. This study focused on further modification of the enamide side chain, and the C1-C8 carbon backbone of palmerolide A. Structure-activity relationship, mechanistic, and pharmacological investigations of the palmerolide compounds pave the foundation for the ensuing in vivo studies.
Preparation of ω-hydroxynonanoic acid and its ester derivatives
Kula, Jozef,Smigielski, Krzysztof,Quang, Thuat B.,Grzelak, Iwona,Sikora, Magdalena
, p. 811 - 817 (2007/10/03)
Methyl ricinoleate was ozonized in methanol or in acetic acid and the intermediate hydroperoxides were reduced electrochemically on Pb-cathode to give 9-hydroxynonanoic acid 1 in high yields. The acid 1 was also prepared by direct castor oil ozonolysis in methanol followed by sodium borohydride reduction of the intermediate hydroperoxides. The cost of the electricity for the electroreduction was at least 30 times lower as compared with sodium borohydride consumption. 9-Hydroxynonanoic acid was then transformed to alkyl 9-acetoxynonanoates 3a-3d, for which 1H nuclear magnetic reasonance, mass, and infrared spectra are given. Esterification of the hydroxy acid 1 with boric acid and pyrolysis of the resultant orthoborates produced 8-nonenoic acid 4 in a 45% yield. Reaction of 4 with lower aliphatic alcohols in presence of Amberlyst 15 produced alkyl 8-noneates 5a-5d along with some amounts of a cis/trans mixture of alkyl 7-noneates.
A significant effect of triflic acid on the hypervalent λ(n)-iodane- mediated fragmentation of the tertiary cyclopropanol system
Kirihara, Masayuki,Yokoyama, Satoshi,Momose, Takefumi
, p. 1947 - 1956 (2007/10/03)
Trifluoromethanesulfonic acid enhanced the ring cleavage in the reaction of silyl tertiary cyclopropyl ethers with phenyliodine(III) diacetate in a catalytic amount.
