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【结 构 式】 
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【分子编号】44294 【品名】2-phenyl-4-pentenoic acid 【CA登记号】 |
【 分 子 式 】C11H12O2 【 分 子 量 】176.21508 【元素组成】C 74.98% H 6.86% O 18.16% |
合成路线1
该中间体在本合成路线中的序号：(IX)Alkylation of phenylacetic acid (VII) with allyl bromide (VIII) using lithium bis(trimethylsilyl)amide furnished 2-phenyl-4-pentenoic acid (IX). Reduction of the carboxylate group of (IX) by means of LiAlH4 and AlCl3 gave rise to alcohol (X), which was subsequently converted to triflate (XI). The triflate group of (XI) was then displaced with benzimidazole (XII) to produce adduct (XIII). Dihydroxylation of the double bond of (XIII) with N-methylmorpholine-N-oxide in the presence of OsO4, followed by oxidative cleavage with NaIO4, yielded aldehyde (XIV). Finally, aldehyde (XIV) was reductively condensed with piperidine (VI) in the presence of sodium triacetoxyborohydride.
| 【1】 Kim, D.; Wang, L.; Caldwell, C.G.; et al.; Design, synthesis, and SAR of heterocycle-containing human CCR5 antagonists for the treatment of HIV-1 infection. 220th ACS Natl Meet (Aug 20 2000, Washington DC) 2000, Abst MEDI 84. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VI) | 43905 | 4-nitrobenzyl allyl(4-piperidinyl)carbamate | C16H21N3O4 | 详情 | 详情 | |
| (VII) | 16148 | Benzeneacetic acid; 2-Phenylacetic acid; Phenyl Acetic Acid | 103-82-2 | C8H8O2 | 详情 | 详情 |
| (VIII) | 11463 | 3-Bromo-1-propene; 3-Bromopropene；allyl bromide | 106-95-6 | C3H5Br | 详情 | 详情 |
| (IX) | 44294 | 2-phenyl-4-pentenoic acid | C11H12O2 | 详情 | 详情 | |
| (X) | 44295 | 2-phenyl-4-penten-1-ol | C11H14O | 详情 | 详情 | |
| (XI) | 44296 | 2-phenyl-4-pentenyl trifluoromethanesulfonate | C12H13F3O3S | 详情 | 详情 | |
| (XII) | 44297 | 1H-benzimidazole | 51-17-2 | C7H6N2 | 详情 | 详情 |
| (XIII) | 44298 | 1-(2-phenyl-4-pentenyl)-1H-benzimidazole | C18H18N2 | 详情 | 详情 | |
| (XIV) | 44299 | 4-(1H-benzimidazol-1-yl)-3-phenylbutanal | C17H16N2O | 详情 | 详情 |