Trichlorfon, Metriphonate, Metrifonate, Bayer-L-1359, Bay-a-9826, Bilarcil, Memobay, ProMem

敌百虫Chemical Name: (2,2,2-Trichloro-1-hydroxyethyl)phosphonic acid dimethyl ester
CAS No. 52-68-6
项目整合开发状态: Launched-1971
项目研究机构: Bayer (Originator)
合成路线:Metrifonate is easily synthesized in a one-step spontaneous exothermic condensation of equimolar amounts of chloral hydrate with dimethylhydrogenphosphite,which in turn is accessible by reacting PCl3 with methanol.Contrary to similar reactions described earlier (1950-1952) in two Soviet papers and a U.S.process patent,no catalyst is needed if the aldehyde compound is chloral.Therefore,metrifonate can be readily crystallized directly from the reaction mixture.

合成路线:Metrifonate is totally unique among the acetylcholinesterase inhibitors currently used or proposed for the treatment of Alzheimer's disease because it is an inactive prodrug.The active compound dichlorvos,(2,2-dichlorovinyl dimethylphosphate; DDVP),is formed in a nonenzymatic reaction by hydrolysis and elimination of HCl followed by rearrangement of an intermediate according to Scheme.