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【结 构 式】 
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【分子编号】49951 【品名】3-(1-hydroxy-2-propenyl)-4-nitrophenol 【CA登记号】 |
【 分 子 式 】C9H9NO4 【 分 子 量 】195.1748 【元素组成】C 55.39% H 4.65% N 7.18% O 32.79% |
合成路线1
该中间体在本合成路线中的序号：(XXIV)The precursor aminopropiophenone (XXVII) was synthesized as follows: 3-Amino-1-propanol (XX) was converted to the N-Boc derivative (XXI) and subsequently sulfonylated with p-toluenesulfonyl chloride to afford tosylate (XXII). Addition of vinylmagnesium bromide to 5-hydroxy-2-nitrobenzaldehyde (XXIII) provided the allyl alcohol (XXIV). The phenolic hydroxyl of (XXIV) was then alkylated with tosylate (XXII), yielding ether (XXV). The oxidation of the OH group of (XXV) with MnO2 gave the unsaturated ketone (XXVI). Catalytic hydrogenation of the olefin and nitro groups of (XXVI) provided the aminopropiophenone (XXVII).
| 【1】 Tsujihara, K.; Kawaguchi, T.; Okuno, S.; Yano, T. (Tanabe Seiyaku Co., Ltd.); Camptothecin derivs.. CA 2182244; EP 0757049; JP 1998072467; US 5837673 . |
| 【2】 Nomura, S.; Tsujihara, K.; Kawaguchi, T. (Tanabe Seiyaku Co., Ltd.); S type 2-substd. hydroxy-2-indolidinylbutyric ester cpds. and process for preparation thereof. US 6277992 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XX) | 18522 | 3-amino-1-propanol | 156-87-6 | C3H9NO | 详情 | 详情 |
| (XXI) | 10260 | tert-butyl N-(3-hydroxypropyl)carbamate | 58885-58-8 | C8H17NO3 | 详情 | 详情 |
| (XXII) | 49950 | 3-[(tert-butoxycarbonyl)amino]propyl 4-methylbenzenesulfonate | C15H23NO5S | 详情 | 详情 | |
| (XXIII) | 14942 | 5-hydroxy-2-nitrobenzaldehyde | 42454-06-8 | C7H5NO4 | 详情 | 详情 |
| (XXIV) | 49951 | 3-(1-hydroxy-2-propenyl)-4-nitrophenol | C9H9NO4 | 详情 | 详情 | |
| (XXV) | 49952 | tert-butyl 3-[3-(1-hydroxy-2-propenyl)-4-nitrophenoxy]propylcarbamate | C17H24N2O6 | 详情 | 详情 | |
| (XXVI) | 49953 | tert-butyl 3-(3-acryloyl-4-nitrophenoxy)propylcarbamate | C17H22N2O6 | 详情 | 详情 | |
| (XXVII) | 49954 | tert-butyl 3-(4-amino-3-propionylphenoxy)propylcarbamate | C17H26N2O4 | 详情 | 详情 |