【结 构 式】 |
【分子编号】57437 【品名】dimethyl 4-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-1-(methoxymethoxy)-2,3-naphthalenedicarboxylate 【CA登记号】 |
【 分 子 式 】C27H30O11 【 分 子 量 】530.5286 【元素组成】C 61.13% H 5.7% O 33.17% |
合成路线1
该中间体在本合成路线中的序号:(III)In an alternative procedure, the known hydroxynaphthalene dicarboxylate (I) is protected as the methoxymethyl ether (III) using chloromethyl methyl ether (II) and diisopropyl ethylamine. Subsequent partial hydrolysis of diester (III) with KOH leads to acid (IV). Removal of the methoxymethyl protecting group of (IV) to produce naphthol (V) is accomplished by treatment with in situ generated iodotrimethylsilane. Hydroxy acid (V) is then converted to the dioxinone derivative (VI) employing diiodomethane and CsF in hot DMF. Finally, addition of the Grignard reagent (VII) to the lactone function of (VI) yields the desired 2-ethylbutyl ketone.
【1】 Mori, S.; Takechi, S.; Kida, S.; Mizui, T.; Ichihashi, T. (Shionogi & Co. Ltd.); Lignan analog, production thereof, and hypolipidemic drug. EP 0597107; EP 0701991; JP 1993310634; US 5731455; WO 9308155 . |
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) | 57436 | dimethyl 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxy-2,3-naphthalenedicarboxylate | C25H26O10 | 详情 | 详情 | |
(II) | 18319 | Chloro(methoxy)methane; Chloromethyl methyl ether | 107-30-2 | C2H5ClO | 详情 | 详情 |
(III) | 57437 | dimethyl 4-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-1-(methoxymethoxy)-2,3-naphthalenedicarboxylate | C27H30O11 | 详情 | 详情 | |
(IV) | 57438 | 4-(3,4-dimethoxyphenyl)-5,6,7-trimethoxy-3-(methoxycarbonyl)-1-(methoxymethoxy)-2-naphthoic acid | C26H28O11 | 详情 | 详情 | |
(V) | 57439 | 4-(3,4-dimethoxyphenyl)-1-hydroxy-5,6,7-trimethoxy-3-(methoxycarbonyl)-2-naphthoic acid | C24H24O10 | 详情 | 详情 | |
(VI) | 57440 | methyl 6-(3,4-dimethoxyphenyl)-7,8,9-trimethoxy-4-oxo-4H-naphtho[1,2-d][1,3]dioxine-5-carboxylate | C25H24O10 | 详情 | 详情 | |
(VII) | 57441 | bromo(2-ethylbutyl)magnesium | C6H13BrMg | 详情 | 详情 |