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【结 构 式】

【分子编号】44295

【品名】2-phenyl-4-penten-1-ol

【CA登记号】

【 分 子 式 】C11H14O

【 分 子 量 】162.23156

【元素组成】C 81.44% H 8.7% O 9.86%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(X)

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
Extended Information