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【结 构 式】 
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【分子编号】16565 【品名】2-bromo-4-methoxy-3-methyl-1-naphthyl methyl ether; 2-bromo-1,4-dimethoxy-3-methylnaphthalene 【CA登记号】 |
【 分 子 式 】C13H13BrO2 【 分 子 量 】281.14902 【元素组成】C 55.54% H 4.66% Br 28.42% O 11.38% |
合成路线1
该中间体在本合成路线中的序号：(XII)3) The condensation of 2-bromo-1,4-dimethoxy-3-methylnaphthalene (XII) with 3,7,11,15-tetramethyl-2(E),6(E),10(E),14-hexadecatetraenal (XIII) by means of butyllithium in ethyl ether gives the corresponding secondary alcohol (XIV), which is selectively reduced (previous silylation) by means of Li in THF to afford the alkylated dimethoxynaphthalene (XV). Finally, this compound is oxidized to the corresponding quinone with ceric ammonium nitrate in acetonitrile/water. 4) By laser beam irradiation (435 nm) of cis-vitamin K2 in diisopropyl ether at 25 C.
| 【1】 Graul, A.; Castañer, J.; Menatetrenone. Drugs Fut 1996, 21, 6, 615. |
| 【2】 Garcías, X.; Ballester, P.; Capó, M.; Saá, J.M.; 2DELTA-Stereocontrolled entry to (E)- or (Z)-prenyl aromatics and quinones. Synthesis of menaquinone-4. J Org Chem 1994, 59, 17, 5093-6. |
| 【3】 Ichino, T.; Nakano, K.; Murakami, K.; Narabe, Y.; Imai, A.; Takahashi, K.; Udagawa, T.; Kusaba, Y.; Muramatsu, T.; Katayama, A. (Eisai Co., Ltd.); Manufacturing method for trans-vitamin K2. JP 1988162649 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XII) | 16565 | 2-bromo-4-methoxy-3-methyl-1-naphthyl methyl ether; 2-bromo-1,4-dimethoxy-3-methylnaphthalene | C13H13BrO2 | 详情 | 详情 | |
| (XIII) | 16566 | (2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenal | C20H32O | 详情 | 详情 | |
| (XIV) | 16567 | (2E,6E,10E)-1-(1,4-dimethoxy-3-methyl-2-naphthyl)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraen-1-ol | C33H46O3 | 详情 | 详情 | |
| (XV) | 16568 | (2E,6E,10E)-1-(1,4-dimethoxy-3-methyl-2-naphthyl)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene; 4-methoxy-2-methyl-3-[(2E,6E,10E)-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl]-1-naphthyl methyl ether | C33H46O2 | 详情 | 详情 |