|
【结 构 式】 
|
【分子编号】39738 【品名】2-phenyl-3-butenenitrile 【CA登记号】 |
【 分 子 式 】C10H9N 【 分 子 量 】143.1882 【元素组成】C 83.88% H 6.34% N 9.78% |
合成路线1
该中间体在本合成路线中的序号：(I)The alkylation of 2-phenyl-4-pentenenitrile (I) with 2-(trimethylsilyl)ethoxymethyl chloride (II) in the presence of LDA afforded (III), which was reduced to aldehyde (IV) by means of DIBAL. Reductive amination of (III) with methylamine and NaBH(OAc)3 produced amine (V) and subsequent condensation with benzenesulfonyl chloride (VI) yielded sulfonamide (VII). A two-step oxidation of (VII) with osmium tetroxide and N-methylmorpholine-N-oxide, followed by sodium periodate cleavage of the resulting diol (VIII) generated aldehyde (IX). Further reductive amination of (IX) with piperidine derivative (X) gave adduct (XI). The (trimethylsilyl)ethoxy protecting group of (XI) was finally cleaved by means of trifluoroacetic acid to furnish the title compound.
| 【1】 Cladwell, C.G.; Chen, P.; Donnelly, K.F.; et al.; Discovery of potent human CCR5 antagonists for the treatment of HIV-1 infection-IV. 219th ACS Natl Meet (March 26 2000, San Francisco) 2000, Abst MEDI 120. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 39738 | 2-phenyl-3-butenenitrile | C10H9N | 详情 | 详情 | |
| (II) | 27243 | [2-(chloromethoxy)ethyl](trimethyl)silane | 76513-69-4 | C6H15ClOSi | 详情 | 详情 |
| (III) | 39739 | 2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]-3-butenenitrile | C16H23NOSi | 详情 | 详情 | |
| (IV) | 39740 | 2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]-4-pentenal | C17H26O2Si | 详情 | 详情 | |
| (V) | 39741 | N-methyl-N-(2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]-4-pentenyl)amine; N-methyl-2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]-4-penten-1-amine | C18H31NOSi | 详情 | 详情 | |
| (VI) | 14713 | benzenesulfonyl chloride | 98-09-9 | C6H5ClO2S | 详情 | 详情 |
| (VII) | 39742 | N-methyl-N-(2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]-4-pentenyl)benzenesulfonamide | C24H35NO3SSi | 详情 | 详情 | |
| (VIII) | 39743 | N-(4,5-dihydroxy-2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]pentyl)-N-methylbenzenesulfonamide | C24H37NO5SSi | 详情 | 详情 | |
| (IX) | 39744 | N-methyl-N-(4-oxo-2-phenyl-2-[[2-(trimethylsilyl)ethoxy]methyl]butyl)benzenesulfonamide | C23H33NO4SSi | 详情 | 详情 | |
| (X) | 39745 | benzyl ethyl(4-piperidinyl)carbamate | C15H22N2O2 | 详情 | 详情 | |
| (XI) | 39746 | benzyl ethyl[1-(4-[methyl(phenylsulfonyl)amino]-3-phenyl-3-[[2-(trimethylsilyl)ethoxy]methyl]butyl)-4-piperidinyl]carbamate | C38H55N3O5SSi | 详情 | 详情 |