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【结 构 式】 
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【分子编号】18358 【品名】ethyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-5-methylhexanoate 【CA登记号】 |
【 分 子 式 】C18H23NO4 【 分 子 量 】317.38496 【元素组成】C 68.12% H 7.3% N 4.41% O 20.16% |
合成路线1
该中间体在本合成路线中的序号：(X)Substitution on dibromobutene (I) by potassium phthalimide (II) provided bromobutenyl phthalimide (III). Further treatment with sodium acetate afforded acetate (IV) which, after hydrolysis, gave phthalimidobutenol (V). Reaction with refluxing ethyl orthoacetate in the presence of a trace of butyric acid generated the intermediate ketene acetal (VI), which experienced a Claisen rearrangement to give pentenoate ester (VII). Ozonolysis of the olefinic double bond of (VII) yielded aldehyde (VIII). Then, Wittig reaction of aldehyde (VIII) with (isopropylidene)triphenylphosphorane in cold THF provided olefin (IX), which was hydrogenated in the presence of Pd/C to give the isobutyl compound (X). Finally, hydrolysis of both ester and phthalimide groups in refluxing 6 N HCl provided the GABA analogue.
| 【1】 Serfass, L.; Casara, P.J.; General synthesis of 3-substituted alkenyl GABA as potential anticonvulsants. Bioorg Med Chem Lett 1998, 8, 18, 2599. |
| 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) | 18349 | (E)-1,4-dibromo-2-butene；trans-1,4-dibromo-2-butene | 821-06-7 | C4H6Br2 | 详情 | 详情 |
| (II) | 10926 | (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)potassium | C8H4KNO2 | 详情 | 详情 | |
| (III) | 18351 | 2-[(E)-4-bromo-2-butenyl]-1H-isoindole-1,3(2H)-dione | C12H10BrNO2 | 详情 | 详情 | |
| (IV) | 18352 | (E)-4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-butenyl acetate | C14H13NO4 | 详情 | 详情 | |
| (V) | 18353 | 2-[(E)-4-hydroxy-2-butenyl]-1H-isoindole-1,3(2H)-dione | C12H11NO3 | 详情 | 详情 | |
| (VI) | 18354 | 2-[(E)-4-[(1-ethoxyvinyl)oxy]-2-butenyl]-1H-isoindole-1,3(2H)-dione | C16H17NO4 | 详情 | 详情 | |
| (VII) | 18355 | ethyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-4-pentenoate | C16H17NO4 | 详情 | 详情 | |
| (VIII) | 18356 | ethyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-formylbutanoate | C15H15NO5 | 详情 | 详情 | |
| (IX) | 18357 | ethyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-5-methyl-4-hexenoate | C18H21NO4 | 详情 | 详情 | |
| (X) | 18358 | ethyl 3-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-5-methylhexanoate | C18H23NO4 | 详情 | 详情 |