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【结 构 式】 
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【分子编号】52123 【品名】[3-(methoxymethoxy)phenoxy]methyl methyl ether; 1,3-bis(methoxymethoxy)benzene 【CA登记号】 |
【 分 子 式 】C10H14O4 【 分 子 量 】198.21876 【元素组成】C 60.59% H 7.12% O 32.29% |
合成路线1
该中间体在本合成路线中的序号：(I)Lithiation of 1,3-bis(O-methoxymethyl)resorcinol (I) by means of n-butyllithium, followed by acylation with acetyl chloride, gave the protected acetophenone (II). Subsequent acid hydrolysis of the methoxymethyl protecting groups furnished diol (III). The 4-hydroxybenzofuran derivative (VI) was prepared by monoalkylation of (III) with ethyl bromoacetate (IV), followed by base-catalyzed cyclization of the resulting keto ester (V). Alkylation of the hydroxybenzofuran (VI) with 1,3-dibromopropane (VII) gave the bromopropyl ether (VIII). This was finally condensed with 3-picolylamine (IX) to produce the title compound.
| 【1】 Masubuchi, M.; et al.; Design and synthesis of novel benzofurans as a new class of antifungal agents targeting fungal N-myristoyltransferase. Part 1. Bioorg Med Chem Lett 2001, 11, 14, 1833. |
| 【2】 Fujii, T.; Tsujii, S.; Liu, P.; Ohtsuka, T.; Ebiike, H.; Masubuchi, M.; Aoki, Y.; Kawasaki, K. (F. Hoffmann-La Roche AG); Novel bicyclic cpds.. US 6376491; WO 0037464 . |
| 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) | 52123 | [3-(methoxymethoxy)phenoxy]methyl methyl ether; 1,3-bis(methoxymethoxy)benzene | C10H14O4 | 详情 | 详情 | |
| (II) | 52124 | 1-[2,6-bis(methoxymethoxy)phenyl]-1-ethanone | C12H16O5 | 详情 | 详情 | |
| (III) | 27511 | 1-(2,6-dihydroxyphenyl)-1-ethanone | 699-83-2 | C8H8O3 | 详情 | 详情 |
| (IV) | 16640 | Ethyl 2-bromoacetate; Ethyl bromoacetate | 105-36-2 | C4H7BrO2 | 详情 | 详情 |
| (V) | 52125 | ethyl 2-(2-acetyl-3-hydroxyphenoxy)acetate | C12H14O5 | 详情 | 详情 | |
| (VI) | 52126 | ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate | C12H12O4 | 详情 | 详情 | |
| (VII) | 12581 | 1,3-Dibromopropane | 109-64-8 | C3H6Br2 | 详情 | 详情 |
| (VIII) | 52127 | ethyl 4-(3-bromopropoxy)-3-methyl-1-benzofuran-2-carboxylate | C15H17BrO4 | 详情 | 详情 | |
| (IX) | 18731 | 3-pyridinylmethanamine; 3-pyridinylmethylamine | 3731-52-0 | C6H8N2 | 详情 | 详情 |