新产品编号:57461
Chemical Name: 3-[4-(2-Tridecynyloxymethyl)phenyl]propionic acid
CAS No. 152124-63-5
项目整合开发状态: Biological Testing
项目研究机构: Vanderbilt University (Originator), Wayne State University (Originator)
合成路线:The sodium salt prepared from 2-tridecyn-1-ol (I) and sodium hydride in THF was O-alkylated with 4-bromobenzyl bromide to afford ether (II).Then,2-(carboethoxy)ethylzinc iodide (IV),(obtained from ethyl 3-iodopropanoate (III) and an excess of zinc-copper couple),was condensed with this bromoether (II) in the presence of a triphenylphosphine palladium (0) catalyst in a refluxing mixture of toluene and N,N-dimethyl acetamide.Finally,the resulting 3-(phenyl)propanoic ester (V) was hydrolyzed with NaOH in methanol-water.
📌 参考资料/链接：
参考文献标题:Aryl aliphatic acids
文献作者:Johnson,C.R.; Gorins,G.; Honn,K.V.; Marnett,L.J.(Vanderbilt University; Wayne State University)
参考来源:US 5238832
📄 详细内容
合成路线:The sodium salt prepared from 2-tridecyn-1-ol (I) and sodium hydride in THF was O-alkylated with 4-bromobenzyl bromide to afford ether (II).Then,2-(carboethoxy)ethylzinc iodide (IV),(obtained from ethyl 3-iodopropanoate (III) and an excess of zinc-copper couple),was condensed with this bromoether (II) in the presence of a triphenylphosphine palladium (0) catalyst in a refluxing mixture of toluene and N,N-dimethyl acetamide.Finally,the resulting 3-(phenyl)propanoic ester (V) was hydrolyzed with NaOH in methanol-water.
参考文献标题:(Carboxyalkyl)benzyl propargyl ethers as selective inhibitors of leukocyte-type 12-lipoxygenases
文献作者:Gorins,G.; Kuhnert,L.; Johnson,C.R.; Marnett,L.J.
参考来源:J Med Chem 1996,39(25),4871