【结 构 式】 |
【分子编号】59538 【品名】[3-(1-adamantyl)-4-methoxyphenyl](bromo)magnesium 【CA登记号】 |
【 分 子 式 】C17H21BrMgO 【 分 子 量 】345.56214 【元素组成】C 59.09% H 6.13% Br 23.12% Mg 7.03% O 4.63% |
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:(V)Friedel-Crafts condensation of 4-bromophenol (I) with 1-adamantanol (II) in the presence of H2SO4 yielded the adamantyl phenol (III). Subsequent alkylation of the sodium phenoxide of (III) with iodomethane produced the methyl ether (IV). The Grignard reagent (V), prepared from aryl bromide (IV), was converted to the organozincate derivative, and then subjected to a nickel-catalyzed cross-coupling with methyl 6-bromo-2-naphthoate (VI) to furnish adduct (VII). The target carboxylic acid was finally obtained by saponification of the methyl ester (VII).
【1】 Charpentier, B.; et al.; Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes. J Med Chem 1995, 38, 26, 4993. |
【2】 Shroot, B.; Eustache, J.; Bernardon, J.M. (Laboratoires Galderma SA); Benzonaphthalenic acid derivs., process for their preparation and their use in pharmacy and cosmetics. AU 9047961; EP 0199636; US 4717720; US 5098895; US 5183889 . |
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) | 25313 | 4-bromophenol | 106-41-2 | C6H5BrO | 详情 | 详情 |
(II) | 52642 | 1-Adamantanol; 1-Hydroxyadamantane; Tricyclo[3.3.1.1]decan-1-ol | 768-95-6 | C10H16O | 详情 | 详情 |
(III) | 59536 | 2-(1-adamantyl)-4-bromophenol | C16H19BrO | 详情 | 详情 | |
(IV) | 59537 | 1-(5-bromo-2-methoxyphenyl)adamantane; 2-(1-adamantyl)-4-bromophenyl methyl ether | C17H21BrO | 详情 | 详情 | |
(V) | 59538 | [3-(1-adamantyl)-4-methoxyphenyl](bromo)magnesium | C17H21BrMgO | 详情 | 详情 | |
(VI) | 59539 | 6-Bromo-2-naphthoic acid methyl ester; Methyl 6-bromo-2-naphthoate | 33626-98-1 | C12H9BrO2 | 详情 | 详情 |
(VII) | 59540 | methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate | C29H30O3 | 详情 | 详情 |
Extended Information