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【结 构 式】 
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【分子编号】59165 【品名】ethyl 5-bromo-4-oxopentanoate 【CA登记号】 |
【 分 子 式 】C7H11BrO3 【 分 子 量 】223.06654 【元素组成】C 37.69% H 4.97% Br 35.82% O 21.52% |
合成路线1
该中间体在本合成路线中的序号：(XXXIX)The bromination of ethyl acetylsuccinate (XXXIV) produced initially the beta-bromo derivative (XXXV), which upon standing for further 12 hours in the presence of the HBr generated in the reaction underwent rearrangement to the delta-bromo isomer (XXXVI). Hydrolysis and decarboxylation of (XXXVI) in the presence of HCl produced the expected delta-bromolevulinic acid (XXXVII) along with the chloro analogue (XXXVIII). Esterification of this mixture of acids with ethanol and sulfuric acid led to the respective ethyl esters (XXXIX) and (XL). Condensation of halo esters (XXXIX) and (XL) with potassium phthalimide (XXVII) furnished ethyl delta-phthalimidolevulinate (XLI), which was finally converted to the title compound by acidic hydrolysis.
| 【1】 Lartillot, S.; Baron, C.; New route to delta-aminolevulinic and application to the synthesis of its alpha- and beta-methylated derivatives. Bull Soc Chim Fr 1966, 12, 3798. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXVII) | 27890 | Potassium phthalimide | 1074-82-4 | C8H4KNO2 | 详情 | 详情 |
| (XXXIV) | 59161 | Acetonyl succinic acid diethylester; Diethyl acetylsuccinate | 1115-30-6 | C10H16O5 | 详情 | 详情 |
| (XXXV) | 59162 | diethyl 2-acetyl-2-bromosuccinate | C10H15BrO5 | 详情 | 详情 | |
| (XXXVI) | 59163 | diethyl 2-(2-bromoacetyl)succinate | C10H15BrO5 | 详情 | 详情 | |
| (XXXVII) | 59164 | 5-bromo-4-oxopentanoic acid | C5H7BrO3 | 详情 | 详情 | |
| (XXXVIII) | 59168 | 5-chloro-4-oxopentanoic acid | C5H7ClO3 | 详情 | 详情 | |
| (XXXIX) | 59165 | ethyl 5-bromo-4-oxopentanoate | C7H11BrO3 | 详情 | 详情 | |
| (XL) | 59166 | ethyl 5-chloro-4-oxopentanoate | C7H11ClO3 | 详情 | 详情 | |
| (XLI) | 59167 | ethyl 5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4-oxopentanoate | C15H15NO5 | 详情 | 详情 |