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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
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