3,5-dimethoxyphenol -Drug Synthesis Database

【结构式】

【分子编号】22390

【品名】3,5-dimethoxyphenol

【CA登记号】500-99-2

【分子式】C₈H₁₀O₃

【分子量】154.1656

【元素组成】C 62.33% H 6.54% O 31.13%

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：(VI)

Friedel Crafts condensation of p-dimethoxybenzene (I) with dichloromaleic anhydride (II) in a molten mixture of AlCl3 and NaCl yielded dichloronaphthazarin (III). Subsequent methylation of (III) with CH3I in the presence of Ag2O in CHCl3 gave a mixture of dimethoxy naphthoquinones (IV) and (V), from which the desired isomer (IV) was isolated by recrystallization from CHCl3-CCl4. Finally, treatment of (IV) with 3,5-dimethoxyphenol (VI) and Na2CO3 in DMSO at room temperature furnished the target compound.

参考文献中间体

合成目标

【1】 Chang, H.-X.; Chou, T.C.; Savaraj, N.; Liu, L.F.; Yu, C.; Cheng, C.C.; Design of antineoplastic agents based on the "2-phenylnaphthalene-type" structural pattern. 4. Synthesis and biological activity of 2-chloro-3-(substituted phenoxy)-1,4-naphthoquinones and related 5,8-dihydroxy-1,4-naphthoquinones. J Med Chem 1999, 42, 3, 405.

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)	21946	1,4-dimethoxybenzene; 4-methoxyphenyl methyl ether	150-78-7	C₈H₁₀O₂	详情	详情
(II)	21947	3,4-dichloro-2,5-furandione	1122-17-4	C₄Cl₂O₃	详情	详情
(III)	21948	2,3-dichloro-5,8-dihydroxynaphthoquinone	14918-69-5	C₁₀H₄Cl₂O₄	详情	详情
(IV)	21951	2,3-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(V)	21950	6,7-dichloro-5,8-dimethoxynaphthoquinone		C₁₂H₈Cl₂O₄	详情	详情
(VI)	22390	3,5-dimethoxyphenol	500-99-2	C₈H₁₀O₃	详情	详情

Extended Information