2216-21-9Relevant articles and documents
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Wollenberg,R.H.,Miller,S.J.
, p. 3219 - 3222 (1978)
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Synthesis of 1-Palmitoyl-2-((E)-9- and (E)-10-nitrooleoyl)- sn -glycero-3-phosphatidylcholines
Dietz, Ulrich,Frank, Andrea,Lehr, Alexander,Münch, Winfried,Nubbemeyer, Udo
supporting information, p. 3295 - 3304 (2019/08/28)
Extensive investigation of nitrated phospholipids in connection with various biologically important processes requires reliable access to suitable material. A selective chemical synthesis introducing a defined nitrofatty acid at the sn -2 position of a 2-lyso sn -glycero-3-phosphatidylcholine was developed. Given that the nitroalkene moiety of both reactant nitrofatty acid derivative and the product esters is characterised by particular sensitivity to nucleophile addition and, depending on the intermediate, subsequent olefin isomerisation and retro-Henry-type reaction, a reliable two-step ester formation was introduced. The activation of the nitrofatty acid succeeded after reaction with trichlorobenzoyl chloride, and the mixed anhydride could be isolated via extractive work-up. Subsequent reaction with 1-palmitoyl-2-lyso- sn -glycero-3-phosphatidylcholine enabled the sn -2 esterification to be achieved with high yield by using a minimum of reagents, avoiding the formation of side products and facilitating final isolation and purification.
Continuous-flow synthesis using a column reactor packed with heterogeneous catalysts: A convenient production of nitroolefins by using amino-functionalized silicagel
Ishitani, Haruro,Furiya, Yuichi,Kobayashi, Shū
supporting information, p. 6229 - 6232 (2017/09/30)
A continuous-flow synthesis of β-nitroolefins by using heterogeneous base catalysts has been developed. Although the use of an excess amount of nitro-donor such as nitromethane is required in conventional methods, nearly equimolar amounts of nitro-donors and carbonyl compounds are sufficient for high-yielding production of nitroolefins. Catalysts for this flow protocol are inexpensive and abundant, and high durability and high productivity were also realized by using an appropriate second support.