methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate -Drug Synthesis Database

【结构式】

【分子编号】59540

【品名】methyl 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoate

【CA登记号】

【分子式】C₂₉H₃₀O₃

【分子量】426.5554

【元素组成】C 81.66% H 7.09% O 11.25%

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：(VII)

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).

参考文献中间体

合成目标

【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