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【结 构 式】 
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【分子编号】40482 【品名】2-([4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl)-2,5,7,8-tetramethyl-2H-chromen-6-yl acetate 【CA登记号】 |
【 分 子 式 】C26H27NO6S 【 分 子 量 】481.56952 【元素组成】C 64.85% H 5.65% N 2.91% O 19.93% S 6.66% |
合成路线1
该中间体在本合成路线中的序号：(IX)A new short synthesis of troglitazone has been described: Condensation of the bromoacetal (I) with 4-hydroxybenzaldehyde (II) by means of K2CO3 and NaI in refluxing acetone gives the unsaturated ether (III), which is cyclized with trimethylhydroquinone (IV) by means of bis(trifluoromethylsulfonyl)imide in dichloromethane to yield the 6-hydroxybenzopyran (V). Acylation of (V) with acetic anhydride and DMAP in THF affords the expected acetoxybenzopyran (VI), which is condensed with thiazolidine-2,4-dione (VII) by means of piperidine in toluene to provide the 6-benzylidene-thiazolidine (VIII). The hydrogenation of (VIII) with H2 over Pd/C in methanol gives the corresponding benzyl derivative (IX), which is finally deacetylated with AcOH/HCl/water (3:1:1) in MeOH.
| 【1】 Cossy, J.; et al.; A short synthesis of troglitazone: An antidiabetic drug for treating insulin resistance. Bioorg Med Chem Lett 1999, 9, 24, 3439. |
| 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) | 40477 | (E)-4-bromo-1-methoxy-3-methyl-2-butenyl methyl ether; (E)-4-bromo-1,1-dimethoxy-3-methyl-2-butene | C7H13BrO2 | 详情 | 详情 | |
| (II) | 13433 | 4-Hydroxybenzaldehyde; p-Hydroxybenzaldehyde | 123-08-0 | C7H6O2 | 详情 | 详情 |
| (III) | 40478 | 4-[[(E)-4,4-dimethoxy-2-methyl-2-butenyl]oxy]benzaldehyde | C14H18O4 | 详情 | 详情 | |
| (IV) | 26357 | 2,3,5-trimethyl-1,4-benzenediol | 700-13-0 | C9H12O2 | 详情 | 详情 |
| (V) | 40479 | 4-[(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-yl)methoxy]benzaldehyde | C21H22O4 | 详情 | 详情 | |
| (VI) | 40480 | 2-[(4-formylphenoxy)methyl]-2,5,7,8-tetramethyl-2H-chromen-6-yl acetate | C23H24O5 | 详情 | 详情 | |
| (VII) | 10883 | 1,3-Thiazolane-2,4-dione; 2,4-Thiazolidinedione | 2295-31-0 | C3H3NO2S | 详情 | 详情 |
| (VIII) | 40481 | 2-([4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]methyl)-2,5,7,8-tetramethyl-2H-chromen-6-yl acetate | C26H25NO6S | 详情 | 详情 | |
| (IX) | 40482 | 2-([4-[(2,4-dioxo-1,3-thiazolidin-5-yl)methyl]phenoxy]methyl)-2,5,7,8-tetramethyl-2H-chromen-6-yl acetate | C26H27NO6S | 详情 | 详情 |