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【结 构 式】 
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【分子编号】59195 【品名】(Z)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxo-2-pentenoic acid 【CA登记号】 |
【 分 子 式 】C13H9NO5 【 分 子 量 】259.2182 【元素组成】C 60.24% H 3.5% N 5.4% O 30.86% |
合成路线1
该中间体在本合成路线中的序号：(LXXIII)A related method was based on the oxidation of N-furfuryl phthalimide (LXXI) under irradiation by light in the presence of oxigen gas and a sensitizer, such as Rose Bengal, to afford the 2,5-dihydrofuranone (LXXII) along with its ring-opened isomer (LXXIII). Subsequent catalytic hydrogenation provided phthalimidolevulinic acid (XI), which was then subjected to acidic hydrolysis. Butenolide (LXXII) was also obtained by the photooxygenation of 5-phthalimidomethyl)furfural (LXXIV). Reduction of (LXXII) to phthalimidolevulinic acid (XI) was accomplished using zinc dust in HOAc under sonication.
| 【1】 Cottier, L.; et al.; Syntheses of gamma-oxo acids or gamma-oxo esters by photooxygenation of furanic compounds and reduction under ultrasound: Application to the synthesis of 5-aminolevulinic acid hydrochloride. Synthesis (Stuttgart) 1995, 3, 303. |
| 【2】 Shimizu, T.; Takeya, H.; Ueki, H.; Process for preparing 5-aminolevulinic acid. US 5380935 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XI) | 59147 | 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoic acid | C13H11NO5 | 详情 | 详情 | |
| (LXXI) | 59193 | 2-(2-furylmethyl)-1H-isoindole-1,3(2H)-dione | C13H9NO3 | 详情 | 详情 | |
| (LXXII) | 59194 | 2-[(2-hydroxy-5-oxo-2,5-dihydro-2-furanyl)methyl]-1H-isoindole-1,3(2H)-dione | C13H9NO5 | 详情 | 详情 | |
| (LXXIII) | 59195 | (Z)-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxo-2-pentenoic acid | C13H9NO5 | 详情 | 详情 | |
| (LXXIV) | 59196 | 5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]-2-furaldehyde | C14H9NO4 | 详情 | 详情 |