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【结 构 式】 
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【分子编号】32292 【品名】1-[7-(2-oxiranylmethoxy)-1-benzofuran-2-yl]-1-ethanone 【CA登记号】 |
【 分 子 式 】C13H12O4 【 分 子 量 】232.23588 【元素组成】C 67.23% H 5.21% O 27.56% |
合成路线1
该中间体在本合成路线中的序号：(II)Compound can be prepared in several different ways: 1) The reaction of 2-acetyl-7-hydroxybenzofuran (I) with epichlorohydrin by means of piperidine hydrochloride (A) at 105 C gives 2-acetyl-7-(2,3-epoxypropoxy)benzofuran (II), which is then condensed with isopropylamine (B) in refluxing ethanol. 2) By reaction of (I) with 1-chloro-3-isopropylamino-2-propanol (C) by means of NaOH at 80 C in a sealed tube. 3) By reductocondensation of 2-[1,1-(ethylenedioxy)ethyl]-7-[2-oxo-3-(hydroxyimino)propoxy]benzofuran (III) with acetone by means of H2 and PtO2 in ethanol, followed by hydrolysis of the reduced product with HCl in ethanol. 4) The reaction of 2-[1,1-(ethylenedioxy)ethyl]-7-glyoxylmethoxybenz-furan (IV) with isopropylamine (B) in ethanol gives the corresponding Schiff base (V), which is then reduced with NaBH4 and hydrolyzed with HCl in ethanol. 5) By hydrolysis of 3-isopropyl-5-(2-acetyl-7-benzofuryloxymethyl)oxazolidinone (VI) with aqueous refluxing NaOH. 6) By reaction of 2-acetyl-7-(2-hydroxy-3-aminopropoxy)benzofuran (VII) with isopropyl bromide (D) in ethanol at 100 C.
| 【1】 Ito, K.; Ikemoto, M.; Kimura, K.; Uchida, K.; Nakanishi, T.; JP 7436664 . |
| 【2】 Ito, K.; Ikemoto, M.; Kimura, K.; Uchida, K.; Nakanishi, T.; JP 7442664 . |
| 【3】 Ito, K.; Ikemoto, M.; Kimura, K.; Uchida, K.; Nakanishi, T.; JP 7441358 . |
| 【4】 Ito, K.; Ikemoto, M.; Kimura, K.; Nakanishi, T.; JP 7443960 . |
| 【5】 Ito, K.; Ikemoto, M.; Kimura, K.; Uchida, K.; Nakanishi, T.; JP 7443961 . |
| 【6】 Ito, K.; Ikemoto, M.; Kimura, K.; Nakanishi, T. (Kaken Pharmaceutical Co., Ltd.); 2-Substittuted-(2-hydroxy-3-lower alkalinopropoxy)benzofurans. DE 2223184; FR 2137901; JP 7242747; US 3853923 . |
| 【7】 Castaner, J.; Blancafort, P.; Weetman, D.F.; Serradell, M.N.; Befunolol. Drugs Fut 1981, 6, 10, 601. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (A) | 10146 | Epichlorohydrin; 2-(Chloromethyl)oxirane | 106-89-8 | C3H5ClO | 详情 | 详情 |
| (B) | 23933 | 2-Propanamine; Isopropylamine | 75-31-0 | C3H9N | 详情 | 详情 |
| (D) | 32658 | 2-bromopropane | 75-26-3 | C3H7Br | 详情 | 详情 |
| (I) | 32291 | 1-(7-hydroxy-1-benzofuran-2-yl)-1-ethanone | 40020-87-9 | C10H8O3 | 详情 | 详情 |
| (II) | 32292 | 1-[7-(2-oxiranylmethoxy)-1-benzofuran-2-yl]-1-ethanone | C13H12O4 | 详情 | 详情 | |
| (III) | 32293 | 3-[[2-(2-methyl-1,3-dioxolan-2-yl)-1-benzofuran-7-yl]oxy]-2-oxopropanal oxime | C15H15NO6 | 详情 | 详情 | |
| (IV) | 32294 | 3-[[2-(2-methyl-1,3-dioxolan-2-yl)-1-benzofuran-7-yl]oxy]-2-oxopropanal | C15H14O6 | 详情 | 详情 | |
| (V) | 32295 | 1-(isopropylimino)-3-[[2-(2-methyl-1,3-dioxolan-2-yl)-1-benzofuran-7-yl]oxy]acetone | C18H21NO5 | 详情 | 详情 | |
| (VI) | 32296 | 5-[[(2-acetyl-1-benzofuran-7-yl)oxy]methyl]-3-isopropyl-1,3-oxazolidin-2-one | C17H19NO5 | 详情 | 详情 | |
| (VII) | 32297 | 1-[7-(3-amino-2-hydroxypropoxy)-1-benzofuran-2-yl]-1-ethanone | C13H15NO4 | 详情 | 详情 | |
| (C) | 32298 | 1-chloro-3-(isopropylamino)-2-propanol | C6H14ClNO | 详情 | 详情 |