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【结 构 式】 
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【药物名称】 【化学名称】2-Hydroxy-N-(2-hydroxyethyl)-N,N-dimethyl-1-hexadecanaminium bromide 【CA登记号】86579-60-4, 126150-49-0 (acetate), 85006-12-8 (cation), 84643-53-8 (chloride), 124591-63-5 (iodide), 85006-13-9 (phosphate) 【 分 子 式 】C20H44BrNO2 【 分 子 量 】410.48318 |
【开发单位】Eastern Virginia Medical School (Originator), Virginia Tech (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY, Contraceptives, Disorders of Sexual Function and Reproduction, Treatment of, ENDOCRINE DRUGS, Female Contraceptives, Vaginal Spermicides |
合成路线1
Treatment of 1,2-epoxyhexadecane (I) with concentrated HBr at 65 C gives rise to bromohydrin (II). This is then condensed with N,N-dimethyl ethanolamine (III) to produce the title ammonium salt.
| 【1】 Rutzen, H. (Henkel KgA); Process for preparing quaternary ammonium cpds.. DE 3136628; EP 0075066; JP 1983046043; US 4480126 . |
合成路线2
In a related procedure, halogenation of 1-hexadecene (I) with N-bromosuccinimide in THF/H2O leads to a mixture of regioisomeric bromohydrins (II) and (III). Refluxing of this mixture of bromohydrins with N,N-dimethyl ethanolamine (IV) in MeOH gives rise to the title ammonium salt as the only isomer.
| 【1】 Wong, Y.-L.; et al.; Spermicidal, anti-HIV, and micellar properties of di- and trihydroxylated cationic surfactants. Tetrahedron 2002, 58, 1, 45. |